Editing Naphthalene (section)

{{Distinguish|naphtha|Cycloalkane{{!}}naphthene|Naphtali}}
{{Chembox
|Verifiedfields = changed
|Watchedfields  = changed
|verifiedrevid  = 477170210
|Name = Naphthalene
|ImageFileL1 = Naphthalene numbering.svg
|ImageSizeL1 = 100px
|ImageNameL1 = Skeletal formula and numbering system of naphthalene
|ImageFileR1 = Naphthalene-from-xtal-3D-balls.png
|ImageSizeR1 = 100px
|ImageNameR1 = Ball-and-stick model of naphthalene
|ImageFile2 = Naphthalene-from-xtal-3D-vdW.png
|ImageSize2 = 150px
|ImageName2 = Spacefill model of naphthalene
|ImageFile3 = Naphthalene-xtal-3D-vdW-B.png
|ImageSize3 = 150px
|ImageName3 = Unit cells of naphthalene
|IUPACName = Naphthalene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The [[Royal Society of Chemistry]] | date = 2014 | location = Cambridge | pages = 13, 35, 204, 207, 221–222, 302, 457, 461, 469, 601, 650 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
|OtherNames = white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes<ref>Naphthalene: trade names</ref>
|Section1 = {{Chembox Identifiers
|CASNo = 91-20-3
|CASNo_Ref = {{cascite|correct|CAS}}
|PubChem = 931
|ChemSpiderID = 906
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|UNII = 2166IN72UN| ChEBI_Ref = {{ebicite|correct|EBI}}
|UNII_Ref = {{fdacite|changed|FDA}}
|EINECS = 214-552-7
|KEGG = C00829
|KEGG_Ref = {{keggcite|correct|kegg}}
|ChEBI = 16482
|ChEMBL = 16293
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|RTECS = QJ0525000
|SMILES = c1c2ccccc2ccc1
|Beilstein = 1421310
|Gmelin = 3347
|InChI = 1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
|InChIKey = UFWIBTONFRDIAS-UHFFFAOYAC
|StdInChI = 1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = UFWIBTONFRDIAS-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2 = {{Chembox Properties
|C=10 | H=8
|Appearance = White solid crystals/ flakes
|Odor = Strong odor of coal tar or mothballs
|Density = 1.145 g/cm<sup>3</sup> (15.5 °C)<ref name=water.epa>{{cite web
|url =http://water.epa.gov/scitech/swguidance/standards/upload/2001_10_12_criteria_ambientwqc_napthalene80.pdf|title = Ambient Water Quality Criteria for Naphthalene|publisher = United States Environmental Protection Agency|access-date = 2014-06-21|date = 2014-04-23}}</ref><br /> 1.0253 g/cm<sup>3</sup> (20 °C)<ref name=crc /><br /> 0.9625 g/cm<sup>3</sup> (100 °C)<ref name=water.epa />
| Solubility = 19 mg/L (10 °C)<br /> 31.6 mg/L (25 °C)<br /> 43.9 mg/L (34.5 °C)<br /> 80.9 mg/L (50 °C)<ref name=crc /><br /> 238.1 mg/L (73.4 °C)<ref name=chemister>{{cite web|last = Anatolievich|first = Kiper Ruslan|website = chemister.ru|url = http://chemister.ru/Database/properties-en.php?dbid=1&id=1005|title = naphthalene|access-date = 2014-06-21}}</ref>
| Solubility1 = 5 g/100 g (0 °C)<br /> 11.3 g/100 g (25 °C)<br /> 19.5 g/100 g (40 °C)<br /> 179 g/100 g (70 °C)<ref name=sioc>{{cite book|last1 = Seidell|first1 = Atherton|last2 = Linke|first2 = William F.|year = 1919|title = Solubility of Inorganic and Organic Compounds|url = https://archive.org/details/solubilitiesino04seidgoog|publisher = D. Van Nostrand Company|place = New York|edition = 2nd|pages = [https://archive.org/details/solubilitiesino04seidgoog/page/n468 443]–446}}</ref>
|Solvent1 = ethanol
|Solubility2 = 6.8 g/100 g (6.75 °C)<br /> 13.1 g/100 g (21.5 °C)<br /> 31.1 g/100 g (42.5 °C)<br /> 111 g/100 g (60 °C)<ref name=sioc />
|Solvent2 = acetic acid
|Solubility3 = 19.5 g/100 g (0 °C)<br /> 35.5 g/100 g (25 °C)<br /> 49.5 g/100 g (40 °C)<br /> 87.2 g/100 g (70 °C)<ref name=sioc />
|Solvent3 = chloroform
|Solubility4 = 5.5 g/100 g (0 °C)<br /> 17.5 g/100 g (25 °C)<br /> 30.8 g/100 g (40 °C)<br /> 78.8 g/100 g (70 °C)<ref name=sioc />
|Solvent4 = hexane
|Solubility5 = 13.6 g/100 g (6.75 °C)<br /> 22.1 g/100 g (21.5 °C)<br /> 131.6 g/100 g (60 °C)<ref name=sioc />
|Solvent5 = butyric acid
|SolubleOther = Soluble in [[Alcohol (chemistry)|alcohol]]s, liquid [[ammonia]], [[Carboxylic acid]]s, [[Benzene|C<sub>6</sub>H<sub>6</sub>]], [[Sulfur dioxide|SO<sub>2</sub>]],<ref name=chemister /> [[Carbon tetrachloride|CCl<sub>4</sub>]], [[Carbon disulfide|CS<sub>2</sub>]], [[toluene]], [[aniline]]<ref name=sioc />
|MeltingPtC = 78.2
|MeltingPt_notes = <br /> {{convert|80.26|C|F K}}<br /> at 760 mmHg<ref name=crc />
|BoilingPtC = 217.97
|BoilingPt_notes = <br /> at 760 mmHg<ref name=water.epa /><ref name=crc />
|VaporPressure = 8.64 Pa (20 °C)<br /> 23.6 Pa (30 °C)<br /> 0.93 kPa (80 °C)<ref name=chemister /><br /> 2.5 kPa (100 °C)<ref name=nist>{{nist|name=Naphthalene|id=C91203|accessdate=2014-05-24|mask=FFFF|units=SI}}</ref>
|LogP = 3.34<ref name=crc />
|RefractIndex = 1.5898<ref name=crc />
|HenryConstant = 0.42438 L·atm/mol<ref name=crc />
|ThermalConductivity = 98 kPa:<br /> 0.1219 W/m·K (372.22 K)<br /> 0.1174 W/m·K (400.22 K)<br /> 0.1152 W/m·K (418.37 K)<br /> 0.1052 W/m·K (479.72 K)<ref>{{cite web |title = Thermal Conductivity of Naphthalene |url = http://www.ddbst.com/en/EED/PCP/TCN_C123.php |website = DDBST GmbH |access-date = 2014-06-21 |archive-date = 2016-03-04 |archive-url = https://web.archive.org/web/20160304070707/http://www.ddbst.com/en/EED/PCP/TCN_C123.php |url-status = dead }}</ref>
| Viscosity = 0.964 cP (80 °C)<br /> 0.761 cP (100 °C)<br /> 0.217 cP (150 °C)<ref>{{cite web|title = Dynamic Viscosity of Naphthalene|url = http://www.ddbst.com/en/EED/PCP/VIS_C123.php|website = DDBST GmbH|access-date = 2014-06-21|archive-date = 2016-03-04|archive-url = https://web.archive.org/web/20160304104728/http://www.ddbst.com/en/EED/PCP/VIS_C123.php|url-status = dead}}</ref>
|MagSus = −91.9·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3 = {{Chembox Structure
|CrystalStruct = [[Monoclinic crystal system|Monoclinic]]<ref name=sccs>{{cite book|url = https://books.google.com/books?id=hYRCAAAAQBAJ&pg=PA288|title = Structure and Chemistry of Crystalline Solids|last1 = Douglas|first1 = Bodie E.|last2 = Ho|first2 = Shih-Ming|publisher = Springer Science+Business Media, Inc.|year = 2007|isbn = 978-0-387-26147-8|place = New York|page = 288}}</ref>
|SpaceGroup = P2<sub>1</sub>/b<ref name=sccs />
|PointGroup = C{{sup sub|5|2h}}<ref name=sccs />
|LattConst_a = 8.235&nbsp;Å
|LattConst_b = 6.003&nbsp;Å
|LattConst_c = 8.658&nbsp;Å<ref name=sccs />
|LattConst_alpha =
|LattConst_beta = 122.92
}}
|Section4 = {{Chembox Thermochemistry
|HeatCapacity = 165.72 J/mol·K<ref name=crc />
|Entropy = 167.39 J/mol·K<ref name=crc /><ref name=nist />
|DeltaHf = 78.53 kJ/mol<ref name=crc />
|DeltaGf = 201.585 kJ/mol<ref name=crc />
|DeltaHc = −5156.3 kJ/mol<ref name=crc />
}}
|Section5 = {{Chembox Hazards
|MainHazards = [[Combustibility and flammability|Flammable]], [[wikt:sensitizer|sensitizer]], possible [[carcinogen]].<ref>Naphthalene carcinogenicity</ref> Dust can form [[explosive]] mixtures with [[Atmosphere of Earth|air]]
|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}{{GHS09}}<ref name="sigma">{{Sigma-Aldrich|id=147141|name=Naphthalene|access-date=2014-06-21}}</ref>
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|228|302|351|410}}<ref name="sigma" />
|PPhrases = {{P-phrases|210|273|281|501}}<ref name="sigma" />
|NFPA-H = 2
|NFPA-F = 2
|NFPA-R = 0
|FlashPtC = 80
|FlashPt_ref = <ref name="sigma" />
|AutoignitionPtC = 525
|AutoignitionPt_ref = <ref name="sigma" />
|ExploLimits = 5.9%<ref name="sigma" />
|TLV-TWA = 10 ppm<ref name=crc>{{CRC90}}</ref>
|TLV-STEL = 15 ppm<ref name=crc />
|LD50 = 1800 mg/kg (rat, oral)<br />490 mg/kg (rat, intravenous)<br />1200 mg/kg (guinea pig, oral)<br />533 mg/kg (mouse, oral)<ref>{{IDLH|91203|Naphthalene}}</ref>
|IDLH = 250 ppm<ref name=PGCH>{{PGCH|0439}}</ref>
|REL = TWA 10 ppm (50 mg/m<sup>3</sup>) ST 15 ppm (75 mg/m<sup>3</sup>)<ref name=PGCH/>
|PEL = TWA 10 ppm (50 mg/m<sup>3</sup>)<ref name=PGCH/>
}}
}}

'''Naphthalene''' is an [[organic compound]] with formula {{chem|[[Carbon|C]]|10|[[Hydrogen|H]]|8}}. It is the simplest [[polycyclic aromatic hydrocarbon]], and is a white [[Crystal|crystalline solid]] with a characteristic odor that is detectable at concentrations as low as 0.08&nbsp;[[Parts-per notation|ppm by mass]].<ref>{{cite journal | title=Odor as an aid to chemical safety: Odor thresholds compared with threshold limit values and volatiles for 214 industrial chemicals in air and water dilution |vauthors=Amoore JE, Hautala E| journal=J Appl Toxicol | volume=3| issue=6| pages=272–290| year=1983| doi=10.1002/jat.2550030603 |pmid=6376602|s2cid=36525625}}</ref> As an [[Aromaticity|aromatic]] hydrocarbon, naphthalene's structure consists of a fused pair of [[benzene]] rings. It is the main ingredient of traditional [[mothball]]s.