Naphthalene

Not to be confused with naphtha or naphthene.

but not extensively conjugated to it (at least in the ground

state). As such, naphthalene possesses several resonance
structures.

Naphthalene is an organic compound with formula C

10H
8. It is the simplest polycyclic aromatic hydrocarbon,
and is a white crystalline solid with a characteristic odor
that is detectable at concentrations as low as 0.08 ppm
by mass.* [12] As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings.
Two isomers are possible for mono-substituted naphIt is best known as the main ingredient of traditional
thalenes, corresponding to substitution at an alpha or beta
mothballs.
position. Bicyclo[6.2.0]decapentaene is a structural isomer with a fused 48 ring system.* [17]

History

2.1 Reactions with electrophiles

In the early 1820s, two separate reports described a white

solid with a pungent odor derived from the distillation of
coal tar. In 1821, John Kidd cited these two disclosures
and then described many of this substance's properties
and the means of its production. He proposed the name
naphthaline, as it had been derived from a kind of naphtha
(a broad term encompassing any volatile, ammable liquid hydrocarbon mixture, including coal tar).* [13] Naphthalene's chemical formula was determined by Michael
Faraday in 1826. The structure of two fused benzene
rings was proposed by Emil Erlenmeyer in 1866,* [14]
and conrmed by Carl Grbe three years later.* [15]

In electrophilic aromatic substitution reactions, naphthalene reacts more readily than benzene. For example,
chlorination and bromination of naphthalene proceeds
without a catalyst to give 1-chloronaphthalene and 1bromonaphthalene. Likewise, whereas both benzene and
naphthalene can be alkylated using FriedelCrafts reactions, naphthalene can also be easily alkylated by reaction
with alkenes or alcohols, using sulfuric or phosphoric acid
catalysts.
In terms of regiochemistry, electrophiles attack occurs at
the alpha position. The selectivity for alpha over beta
substitution can be rationalized in terms of the resonance structures of the intermediate: for the alpha substitution intermediate, seven resonance structures can be
drawn, of which four preserve an aromatic ring. For
beta substitution, the intermediate has only six resonance structures, and only two of these are aromatic.
Sulfonation, however, gives a mixture of the alpha
product 1-naphthalenesulfonic acid and thebetaproduct 2-naphthalenesulfonic acid, with the ratio dependent
on reaction conditions. The 1-isomer forms predominantly at 25 C, and the 2-isomer at 160 C. Sulfonation
to give the 1- and 2-sulfonic acid occurs readily:

Structure and reactivity

A naphthalene molecule can be viewed as the fusion of

a pair of benzene rings. (In organic chemistry, rings are
fused if they share two or more atoms.) As such, naphthalene is classied as a benzenoid polycyclic aromatic
hydrocarbon (PAH). There are two sets of equivalent hydrogen atoms: the alpha positions are numbered 1, 4, 5,
and 8 (per diagram in right margin), and the beta positions, 2, 3, 6, and 7.
Unlike benzene, the carboncarbon bonds in naphthalene
are not of the same length. The bonds C1C2, C3C4,
C5C6 and C7C8 are about 1.37 (137 pm) in length,
whereas the other carboncarbon bonds are about 1.42
(142 pm) long. This dierence, established by Xray diraction,* [16] is consistent with the valence bond
model in naphthalene and in particular, with the theorem
of cross-conjugation. This theorem would describe naphthalene as an aromatic benzene unit bonded to a diene

H
2SO
4+C
10H
8C
10H
7SO
3H + H
2O
1

PRODUCTION

Further sulfonation occurs to give di-, tri-, and tetrasul- practice, distillation of coal tar yields an oil containing
fonic acids.
about 50% naphthalene, along with twelve other aromatic
compounds. This oil, after being washed with aqueous
sodium hydroxide to remove acidic components (chiey
2.2 Lithiation
various phenols), and with sulfuric acid to remove basic
components, undergoes fractional distillation to isolate
Analogous to the synthesis of phenyllithium is the con- naphthalene. The crude naphthalene resulting from this
version of 1-bromonaphthalene to 1-lithionaphthalene, a process is about 95% naphthalene by weight. The chief
lithium-halogen exchange:
impurities are the sulfur-containing aromatic compound
benzothiophene (< 2%), indane (0.2%), indene (< 2%),
and methylnaphthalene (< 2%). Petroleum-derived naphC10 H7 Br + BuLi C10 H7 Li + BuBr
thalene is usually purer than that derived from coal tar.
The resulting lithionaphthalene undergoes a second lithi- Where required, crude naphthalene can be further puriation, in contrast to the behavior of phenyllithium. These ed by recrystallization from any of a variety of solvents,
1,8-dilithio derivatives are precursors to a host of peri- resulting in 99% naphthalene by weight, referred to as 80
C (melting point). Approximately 1.3M tons are pronaphthalene derivatives.* [18]
duced annually.* [19]

2.3

Reduction and oxidation

With alkali metals, naphthalene forms the dark bluegreen radical anion salts such as sodium naphthalenide,
Na* +C10 H8 * -. The naphthalenide salts are strong reducing agents.

In North America, the coal tar producers are Koppers

Inc., Ruetgers Canada Inc. and Recochem Inc., and the
primary petroleum producer is Monument Chemical Inc.
In Western Europe the well-known producers are Koppers, Ruetgers, and Deza. In Eastern Europe, naphthalene is produced by a variety of integrated metallurgy
complexes (Severstal, Evraz, Mechel, MMK) in Russia,
dedicated naphthalene and phenol makers INKOR and
Yenakievsky Metallurgy plant in Ukraine, and ArcelorMittal Temirtau in Kazakhstan.

Naphthalene can be hydrogenated under high pressure in the presence of metal catalysts to give 1,2,3,4tetrahydronaphthalene(C
10H
12), also known as tetralin. Further hydrogenation yields
3.1 Other sources and occurrences
decahydronaphthalene or decalin (C
10H
18).
Aside from coal tar, trace amounts of naphthalene are
produced by magnolias and certain species of deer, as
Oxidation with O
2 in the presence of a vanadium catalyst gives phthalic well as the Formosan subterranean termite, possibly
produced by the termite as a repellant against ants,
anhydride:
poisonous fungi and nematode worms.* [20] Some
strains of the endophytic fungus Muscodor albus proC10 H8 + 4.5 O2 C6 H4 (CO)2 O + 2 CO2 +
duce naphthalene among a range of volatile organic com2 H2 O
pounds, while Muscodor vitigenus produces naphthalene
almost exclusively.* [21]
This reaction is the basis of the main use of naphthalene.
Naphthalene has been found in meteorites: n C
Oxidation can also be eected using conventional stoi10H
chiometric chromate or permanganate reagents.
7SO
3H + n CH
2=O SO
3 Production
3HC
10H
Most naphthalene is derived from coal tar. From the 7(CH
1960s until the 1990s, signicant amounts of naphtha- 2C
lene were also produced from heavy petroleum fractions 10H
during petroleum rening, but today petroleum-derived 7SO
naphthalene represents only a minor component of naph- 3H)
n+nH
thalene production.
2O
Naphthalene is the most abundant single component of
coal tar. Although the composition of coal tar varies
Neutralization step (naphthalene sulfonic acid conwith the coal from which it is produced, typical coal
densate plus sodium hydroxide):
tar is about 10% naphthalene by weight. In industrial

4.2

Niche applications

3.2

Naphthalene
medium

in

the

interstellar cursors for various dyestus, pigments, rubber processing

chemicals and other chemicals and pharmaceuticals.* [19]

Naphthalene has been tentatively detected in the

interstellar medium in the direction of the star Cernis 52
in the constellation Perseus.* [22]* [23] More than 20%
of the carbon in the universe may be associated with polyaromatic hydrocarbons, including naphthalene.* [24]
Protonated cations of naphthalene (C
10H+
9) are the source of part of the spectrum of the
Unidentied Infrared Emissions (UIRs). Protonated
naphthalene diers from neutral naphthalene (e.g. that
used in mothballs) in that it has an additional hydrogen
atom. The UIRs from "naphthalene cation" (C
10H+
8) have been observed by astronomers. This research has
been publicized as mothballs in space.* [25]

Naphthalene sulfonate polymers are produced by treating

naphthalenesulfonic acid with formaldehyde, followed by
neutralization with sodium hydroxide or calcium hydroxide. These products are commercially sold in solution
(water) or dry powder form.

4.2 Niche applications

Being inexpensive, naphthalene nds many niche uses.

Uses

Naphthalene is used mainly as a precursor to other chemicals. The single largest use of naphthalene is the industrial
production of phthalic anhydride, although more phthalic
anhydride is made from o-xylene. Many azo dyes are produced from naphthalene. The insecticide 1-naphthyl-Nmethylcarbamate (carbaryl). Other useful agrichemicals
include naphthoxyacetic acids.

OH
O

OH
NH2

Nadoxolol is a beta blocker.

4.1

Naphthalene sulfonic acids are used in the manufacture of

naphthalene sulfonate polymer plasticizers (dispersants),
which are used to produce concrete and plasterboard
(wallboard or drywall). They are also used as dispersants
in synthetic and natural rubbers, and as tanning agents
(syntans) in leather industries, agricultural formulations
(dispersants for pesticides), dyes and as a dispersant in
leadacid battery plates.

Naphthalenesulfonic acids and sulfonates

4.2.1 Laboratory uses

Molten naphthalene provides an excellent solubilizing
medium for poorly soluble aromatic compounds. In many
cases it is more ecient than other high-boiling solvents,
such as dichlorobenzene, benzonitrile, nitrobenzene and
durene. The reaction of C60 with anthracene is conveniently conducted in reuxing naphthalene to give
the 1:1 DielsAlder adduct.* [26] The aromatization of
hydroporphyrins has been achieved using a solution of
DDQ in naphthalene.* [27]

4.3 Wetting agent and surfactant

Alkyl naphthalene sulfonates (ANS) are used in many industrial applications as nondetergent wetting agents that
eectively disperse colloidal systems in aqueous media.
The major commercial applications are in the agricultural
chemical industry, which uses ANS for wettable powder
and wettable granular (dry-owable) formulations, and
the textile and fabric industry, which utilizes the wetting
and defoaming properties of ANS for bleaching and dyeing operations.
4.3.1 As a fumigant

Many naphthalenesulfonic acids and sulfonates are useful. Alkyl naphthalene sulfonate are surfactants, The
aminonaphthalenesulfonic acids, naphthalenes substituted with amines and sulfonic acids, are intermediates
in the preparation of many synthetic dyes. The hydrogenated naphthalenes tetrahydronaphthalene (tetralin)
and decahydronaphthalene (decalin) are used as lowvolatility solvents. Naphthalene sulfonic acids are also
used in the synthesis of 1-naphthol and 2-naphthol, pre-

Naphthalene has been used as a household fumigant. It

was once the primary ingredient in mothballs, although its
use has largely been replaced in favor of alternatives such
as 1,4-dichlorobenzene. In a sealed container containing
naphthalene pellets, naphthalene vapors build up to levels
toxic to both the adult and larval forms of many moths
that attack textiles. Other fumigant uses of naphthalene
include use in soil as a fumigant pesticide, in attic spaces

REFERENCES

to repel animals and insects, and in museum storage- 5.1 Regulation

drawers and cupboards to protect the contents from attack
US government agencies have set occupational exposure
by insect pests.
limits to naphthalene exposure. The Occupational Safety
*
*
Naphthalene is a repellent to opossums. [28] [29]
and Health Administration has set a permissible exposure
limit at 10 ppm (50 mg/m3 ) over an eight-hour timeweighted average. The National Institute for Occupational Safety and Health has set a recommended expo4.3.2 Pyrotechnics
sure limit at 10 ppm (50 mg/m3 ) over an eight-hour timeweighted average, as well as a short-term exposure limit
It is used in pyrotechnic special eects such as the gen- at 15 ppm (75 mg/m3 ).* [37]
eration of black smoke and simulated explosions. It is
used to create articial pores in the manufacture of high- Mothballs and other products containing naphthalene
*
*
porosity grinding wheels. In the past, naphthalene was have been banned within the EU since 2008. [38] [39]
administered orally to kill parasitic worms in livestock. In China, the use of naphthalene in mothballs is forbidNaphthalene and its alkyl homologs are the major con- den.* [40] Danger to human health and the common use
stituents of creosote. Naphthalene is used in engineering of natural camphor are cited as reasons for the ban.
to study heat transfer using mass sublimation.

6 See also
5

Health eects

Exposure to large amounts of naphthalene may damage or

destroy red blood cells, most commonly in people with
an underlying G6PD (glucose-6-phosphate dehydrogenase) deciency.* [30] Over 400 million people have an
inherited condition called glucose-6-phosphate dehydrogenase deciency. Humans, in particular children, have
developed this condition, known as hemolytic anemia, after ingesting mothballs or deodorant blocks containing
naphthalene. Symptoms include fatigue, lack of appetite,
restlessness, and pale skin. Exposure to large amounts
of naphthalene may cause confusion, nausea, vomiting,
diarrhea, blood in the urine, and jaundice (yellow coloration of the skin due to dysfunction of the liver).* [31]
When the US National Toxicology Program (NTP) exposed male and female rats and mice to naphthalene vapors on weekdays for two years,* [32] male and female
rats exhibited evidence of carcinogenesis with increased
incidences of adenoma and neuroblastoma of the nose,
female mice exhibited some evidence of carcinogenesis
based on increased incidences of alveolar and bronchiolar
adenomas of the lung, and male mice exhibited no evidence of carcinogenesis.

Camphor
Dialin, Tetralin, Octalin, Decalin
List of interstellar and circumstellar molecules
Mothballs
1-Naphthol, 2-Naphthol
Sodium naphthalenide
Wagner-Jauregg reaction (classic naphthalene synthesis)

7 References
[1] Ambient Water Quality Criteria for Naphthalene
(PDF). United States Environmental Protection Agency.
Retrieved 2014-06-21.
[2] Lide, David R., ed. (2009). CRC Handbook of Chemistry
and Physics (90th ed.). Boca Raton, Florida: CRC Press.
ISBN 978-1-4200-9084-0.
[3] Anatolievich, Kiper Ruslan.naphthalene. chemister.ru.
Retrieved 2014-06-21.

The International Agency for Research on Cancer

(IARC)* [33] classies naphthalene as possibly carcino- [4] Seidell, Atherton; Linke, William F. (1919). Solubilities
genic to humans and animals (Group 2B). The IARC also
of Inorganic and Organic Compounds (2nd ed.). New
points out that acute exposure causes cataracts in humans,
York: D. Van Nostrand Company. pp. 443446.
rats, rabbits, and mice; and that hemolytic anemia (described above) can occur in children and infants after oral [5] Naphthalene in Linstrom, P.J.; Mallard, W.G. (eds.) NIST
Chemistry WebBook, NIST Standard Reference Database
or inhalation exposure or after maternal exposure during
Number 69. National Institute of Standards and Techpregnancy. Under California's Proposition 65, naphthanology, Gaithersburg MD. http://webbook.nist.gov (relene is listed as known to the State to cause cancer
trieved 2014-05-24)
*
. [34] A probable mechanism for the carcinogenic eects
of mothballs and some types of air fresheners containing [6] Thermal Conductivity of Naphthalene. DDBST GmbH.
DDBST GmbH. Retrieved 2014-06-21.
naphthalene has been identied.* [35]* [36]

[7] Dynamic Viscosity of Naphthalene. DDBST GmbH.

DDBST GmbH. Retrieved 2014-06-21.
[8] Douglas, Bodie E.; Ho, Shih-Ming (2007). Structure and
Chemistry of Crystalline Solids. New York: Springer Science+Business Media, Inc. p. 288. ISBN 0-387-261478.

[21] Daisy BH, Strobel GA, Castillo U, et al. (November

2002). Naphthalene, an insect repellent, is produced
by Muscodor vitigenus, a novel endophytic fungus. Microbiology (Reading, Engl.). 148 (Pt 11): 373741.
doi:10.1099/00221287-148-11-3737. PMID 12427963.
[22] Interstellar Space Molecules That Help Form Basic Life
Structures Identied. Science Daily. September 2008.

[9] Sigma-Aldrich Co., Naphthalene. Retrieved on 2014-0621.

[23] Iglesias-Groth, S.; et al. (2008-09-20), Evidence

for the Naphthalene Cation in a Region of the In[10] Naphthalene. Immediately Dangerous to Life and
terstellar Medium with Anomalous Microwave EmisHealth. National Institute for Occupational Safety and
sion, The Astrophysical Journal Letters, 685: L55
Health (NIOSH).
L58, arXiv:0809.0778 , Bibcode:2008ApJ...685L..55I,
doi:10.1086/592349 - This spectral assignment has not
[11] NIOSH Pocket Guide to Chemical Hazards #0439
been independently conrmed, and is described by the au. National Institute for Occupational Safety and Health
thors as tentative(page L58).
(NIOSH).
[12] Amoore JE, Hautala E (1983).Odor as an aid to chemical safety: Odor thresholds compared with threshold limit
values and volatiles for 214 industrial chemicals in air and
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doi:10.1002/jat.2550030603.
[13] John Kidd (1821). Observations on Naphthalene, a peculiar substance resembling a concrete essential oil, which
is produced during the decomposition of coal tar, by exposure to a red heat. Philosophical Transactions. 111:
209221. doi:10.1098/rstl.1821.0017.
[14] Emil Erlenmeyer (1866). Studien ber die s. g. aromatischen Suren. Annalen der Chemie und Pharmacie.
137 (3): 327359. doi:10.1002/jlac.18661370309.
[15] C. Graebe (1869) Ueber die Constitution des Naphthalins (On the structure of naphthalene), Annalen der
Chemie und Pharmacie, 149 : 2028.
[16] Cruickshank, D. W. J.; Sparks, R. A. (18 October 1960).
Experimental and Theoretical Determinations of Bond
Lengths in Naphthalene, Anthracene and Other Hydrocarbons. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences. 258 (1293):
270285. doi:10.1098/rspa.1960.0187.
[17] Dieter Cremer; Thomas Schmidt; Charles W. Bock
(1985). Theoretical determination of molecular structure and conformation. 14. Is bicyclo[6.2.0]decapentaene
aromatic or antiaromatic?". J. Org. Chem. 50 (15):
26842688. doi:10.1021/jo00215a018.
[18] van Soolingen, J.; de Lang, R. J.; den Besten, R.;
Klusener, P. A. A.; Veldman, N.; Spek, A. L.; Brandsma,
L., A simple procedure for the preparation of 1,8bis(diphenylphosphino)naphthalene, Synthetic Communications 1995, 25, 1741-1744.
[19] Gerd Collin, Hartmut Hke, Helmut Greim Naphthalene and Hydronaphthalenesin Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim,
2003. doi:10.1002/14356007.a17_001.pub2. Article
Online Posting Date: March 15, 2003.
[20] Termite 'mothball' keep insects at bay. Sci/Tech. BBC
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[24] Hoover, Rachel (February 21, 2014).Need to Track Organic Nano-Particles Across the Universe? NASA's Got
an App for That. NASA. Retrieved February 22, 2014.
[25] Mothballs in Space. Astrobiology Magazine. Retrieved
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[26] K. Komatsua; Y. Murataa; N. Sugitaa; K. Takeuchib;
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selective formation of the 1:1 DielsAlder adduct of C60
with anthracene. Tetrahedron Letters. 34 (52): 8473
8476. doi:10.1016/S0040-4039(00)61362-X.
[27] M.A. Filatov; A.V. Cheprakov (2011).The synthesis of
new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole. Tetrahedron. 67
(19): 35593566. doi:10.1016/j.tet.2011.01.052.
[28] Summary of Possum Repellent Study. Archived from
the original on September 28, 2013.
[29]Removing a possums from your roof, NSW
Department of the Environment and Heritage,
http://www.environment.nsw.gov.au/animals/
RemovingAPossumFromYourRoof.htm
[30] Santucci K, Shah B (Jan 2000). Association of naphthalene with acute hemolytic anemia. Acad Emerg Med.
7 (1): 427. PMID 10894241.
[31] MedlinePlus Encyclopedia Naphthalene poisoning
[32] NTP Technical Reports 410 and 500. NTP Technical
Reports 410 and 500, available from NTP: Long-Term Abstracts & Reports. Archived from the original on October
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[33] IARC Monographs on the Evaluation of Carcinogenic
Risks to Humans. Monographs on the Evaluation of
Carcinogenic Risks to Humans, Some Traditional Herbal
Medicines, Some Mycotoxins, Naphthalene and Styrene,
Vol. 82 (2002) (p. 367). Retrieved December 25, 2008.
[34] Proposition 65, Oce of Environmental Health Hazard
Assessment
[35] Scientists May Have Solved Mystery Of Carcinogenic
Mothballs, Physorg.com, June 20, 2006.

[36] Mothballs, air fresheners and cancer. Environmental

Health Association of Nova Scotia. Environmental Health
Association of Nova Scotia. Retrieved 24 May 2013.
[37] CDC - NIOSH Pocket Guide to Chemical Hazards
[38] Alderson, Andrew (15 Nov 2008). Holy straight bananas now the Eurocrats are banning moth balls. The
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[39] Gray, Kerrina (17 November 2013). Council warned
against use of poisonous moth balls. Your Local
Guardian. Newsquest (London) Ltd. Retrieved 2012-1123.
[40]
199364

External links
NaphthaleneNational Pesticide Information Center
NaphthaleneEPA Air Toxics Web Site
Naphthalene (PIM 363) mostly on toxicity of
naphthalene
Naphthalene CDC NIOSH Pocket Guide to
Chemical Hazards
Naphthalene in the Pesticide Properties DataBase
(PPDB)

EXTERNAL LINKS

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/></a>
Original artist:
This version:Trappist_the_monk (talk) (Uploads)
File:GHS-pictogram-exclam.svg Source: https://upload.wikimedia.org/wikipedia/commons/c/c3/GHS-pictogram-exclam.svg License:
Public domain Contributors: EPS le exclam.eps from UNECE web site converted with ImageMagick convert and with potrace, edited
in inkscape Original artist: Unknown<a href='//www.wikidata.org/wiki/Q4233718' title='wikidata:Q4233718'><img alt='wikidata:
Q4233718'
src='https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/20px-Wikidata-logo.svg.png'
width='20' height='11' srcset='https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/30px-Wikidata-logo.
svg.png 1.5x,
https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/40px-Wikidata-logo.svg.png 2x'
data-le-width='1050' data-le-height='590' /></a>
File:GHS-pictogram-flamme.svg Source:
https://upload.wikimedia.org/wikipedia/commons/6/6d/GHS-pictogram-flamme.svg
License: Public domain Contributors: EPS le amme.eps from UNECE web site converted with ImageMagick convert and
with potrace, edited and ame redrawn in inkscape Original artist: Unknown<a href='//www.wikidata.org/wiki/Q4233718'
title='wikidata:Q4233718'><img
alt='wikidata:Q4233718'
src='https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/
Wikidata-logo.svg/20px-Wikidata-logo.svg.png' width='20' height='11' srcset='https://upload.wikimedia.org/wikipedia/commons/
thumb/f/ff/Wikidata-logo.svg/30px-Wikidata-logo.svg.png
1.5x,
https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/
Wikidata-logo.svg/40px-Wikidata-logo.svg.png 2x' data-le-width='1050' data-le-height='590' /></a>
File:GHS-pictogram-pollu.svg Source: https://upload.wikimedia.org/wikipedia/commons/b/b9/GHS-pictogram-pollu.svg License:
Public domain Contributors: EPS le pollu.eps from UNECE web site converted with ImageMagick convert and with potrace, edited
in inkscape Original artist: Unknown<a href='//www.wikidata.org/wiki/Q4233718' title='wikidata:Q4233718'><img alt='wikidata:
Q4233718'
src='https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/20px-Wikidata-logo.svg.png'
width='20' height='11' srcset='https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/30px-Wikidata-logo.
svg.png 1.5x,
https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/40px-Wikidata-logo.svg.png 2x'
data-le-width='1050' data-le-height='590' /></a>

9 TEXT AND IMAGE SOURCES, CONTRIBUTORS, AND LICENSES

File:GHS-pictogram-silhouette.svg Source: https://upload.wikimedia.org/wikipedia/commons/2/21/GHS-pictogram-silhouette.svg

License: Public domain Contributors: EPS le silhouete.eps from UNECE web site converted with ImageMagick convert and with potrace,
edited in inkscape Original artist: Unknown<a href='//www.wikidata.org/wiki/Q4233718' title='wikidata:Q4233718'><img alt='wikidata:
Q4233718'
src='https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/20px-Wikidata-logo.svg.png'
width='20' height='11' srcset='https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/30px-Wikidata-logo.
svg.png 1.5x,
https://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/40px-Wikidata-logo.svg.png 2x'
data-le-width='1050' data-le-height='590' /></a>
File:Hazard_N.svg Source: https://upload.wikimedia.org/wikipedia/commons/6/6a/Hazard_N.svg License: Public domain Contributors:
Converted from EPS le at http://forum.cptec.org/index.php?showtopic=368 Original artist: See historic
File:Hazard_X.svg Source: https://upload.wikimedia.org/wikipedia/commons/e/ed/Hazard_X.svg License: Public domain Contributors:
? Original artist: ?
File:Nadoxolol.svg Source: https://upload.wikimedia.org/wikipedia/commons/e/ea/Nadoxolol.svg License: Public domain Contributors:
Own work Original artist: Ed (Edgar181)
File:Naphthalene-from-xtal-3D-balls.png
Source:
https://upload.wikimedia.org/wikipedia/commons/8/81/
Naphthalene-from-xtal-3D-balls.png License: Public domain Contributors: Own work Original artist: Ben Mills
File:Naphthalene-from-xtal-3D-vdW.png
Source:
https://upload.wikimedia.org/wikipedia/commons/6/65/
Naphthalene-from-xtal-3D-vdW.png License: Public domain Contributors: Own work Original artist: Ben Mills
File:Naphthalene-xtal-3D-vdW-B.png Source: https://upload.wikimedia.org/wikipedia/commons/7/75/Naphthalene-xtal-3D-vdW-B.
png License: Public domain Contributors: Own work Original artist: Ben Mills
File:Naphthalene_numbering.svg Source: https://upload.wikimedia.org/wikipedia/commons/5/55/Naphthalene_numbering.svg License: Public domain Contributors: Own work Original artist: Ed (Edgar181)
File:Naphthalene_resonance_structure.svg Source: https://upload.wikimedia.org/wikipedia/commons/0/03/Naphthalene_resonance_
structure.svg License: Public domain Contributors: Own work Original artist: <a href='//commons.wikimedia.org/wiki/User:Asadwarraich'
title='User:Asadwarraich'>Warraich Sahib</a>
File:Nitrous-oxide-3D-balls.png Source: https://upload.wikimedia.org/wikipedia/commons/9/93/Nitrous-oxide-3D-balls.png License:
Public domain Contributors: Own work Original artist: Ben Mills
File:Portal-puzzle.svg Source: https://upload.wikimedia.org/wikipedia/en/f/fd/Portal-puzzle.svg License: Public domain Contributors: ?
Original artist: ?
File:Symbol_book_class2.svg Source: https://upload.wikimedia.org/wikipedia/commons/8/89/Symbol_book_class2.svg License: CC
BY-SA 2.5 Contributors: Mad by Lokal_Prol by combining: Original artist: Lokal_Prol
File:X_mark.svg Source: https://upload.wikimedia.org/wikipedia/commons/a/a2/X_mark.svg License: Public domain Contributors: Own
work Original artist: User:Gmaxwell
File:Yes_check.svg Source: https://upload.wikimedia.org/wikipedia/en/f/fb/Yes_check.svg License: PD Contributors: ? Original artist: ?

9.3

Content license

Creative Commons Attribution-Share Alike 3.0