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Naphthalene

Not to be confused with naphtha, naphthene, or Naphtali.
Naphthalene
Skeletal formula and numbering system of naphthalene
Skeletal formula and numbering system of naphthalene
Ball-and-stick model of naphthalene
Ball-and-stick model of naphthalene
Spacefill model of naphthalene
Unit cells of naphthalene
Names
IUPAC name
Naphthalene[2]
Other names
white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes[1]
Identifiers
3D model (JSmol)
1421310
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.863 Edit this at Wikidata
EC Number
  • 214-552-7
3347
KEGG
RTECS number
  • QJ0525000
UNII
  • InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H checkY
    Key: UFWIBTONFRDIAS-UHFFFAOYSA-N checkY
  • InChI=1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
    Key: UFWIBTONFRDIAS-UHFFFAOYAC
  • c1c2ccccc2ccc1
Properties
C10H8
Molar mass 128.174 g·mol−1
Appearance White solid crystals/ flakes
Odor Strong odor of coal tar or mothballs
Density 1.145 g/cm3 (15.5 °C)[3]
1.0253 g/cm3 (20 °C)[4]
0.9625 g/cm3 (100 °C)[3]
Melting point 78.2 °C (172.8 °F; 351.3 K)
80.26 °C (176.47 °F; 353.41 K)
at 760 mmHg[4]
Boiling point 217.97 °C (424.35 °F; 491.12 K)
at 760 mmHg[3][4]
19 mg/L (10 °C)
31.6 mg/L (25 °C)
43.9 mg/L (34.5 °C)
80.9 mg/L (50 °C)[4]
238.1 mg/L (73.4 °C)[5]
Solubility Soluble in alcohols, liquid ammonia, Carboxylic acids, C6H6, SO2,[5] CCl4, CS2, toluene, aniline[6]
Solubility in ethanol 5 g/100 g (0 °C)
11.3 g/100 g (25 °C)
19.5 g/100 g (40 °C)
179 g/100 g (70 °C)[6]
Solubility in acetic acid 6.8 g/100 g (6.75 °C)
13.1 g/100 g (21.5 °C)
31.1 g/100 g (42.5 °C)
111 g/100 g (60 °C)[6]
Solubility in chloroform 19.5 g/100 g (0 °C)
35.5 g/100 g (25 °C)
49.5 g/100 g (40 °C)
87.2 g/100 g (70 °C)[6]
Solubility in hexane 5.5 g/100 g (0 °C)
17.5 g/100 g (25 °C)
30.8 g/100 g (40 °C)
78.8 g/100 g (70 °C)[6]
Solubility in butyric acid 13.6 g/100 g (6.75 °C)
22.1 g/100 g (21.5 °C)
131.6 g/100 g (60 °C)[6]
log P 3.34[4]
Vapor pressure 8.64 Pa (20 °C)
23.6 Pa (30 °C)
0.93 kPa (80 °C)[5]
2.5 kPa (100 °C)[7]
0.42438 L·atm/mol[4]
-91.9·10−6 cm3/mol
Thermal conductivity 98 kPa:
0.1219 W/m·K (372.22 K)
0.1174 W/m·K (400.22 K)
0.1152 W/m·K (418.37 K)
0.1052 W/m·K (479.72 K)[8]
1.5898[4]
Viscosity 0.964 cP (80 °C)
0.761 cP (100 °C)
0.217 cP (150 °C)[9]
Structure
Monoclinic[10]
P21/b[10]
C5
2h[10]
a = 8.235 Å, b = 6.003 Å, c = 8.658 Å[10]
α = 90°, β = 122.92°, γ = 90°
Thermochemistry
165.72 J/mol·K[4]
167.39 J/mol·K[4][7]
78.53 kJ/mol[4]
201.585 kJ/mol[4]
-5156.3 kJ/mol[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable, sensitizer, possible carcinogen.[12] Dust can form explosive mixtures with air
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard[11]
Danger
H228, H302, H351, H410[11]
P210, P273, P281, P501[11]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 80 °C (176 °F; 353 K)[11]
525 °C (977 °F; 798 K)[11]
Explosive limits 5.9%[11]
10 ppm[4] (TWA), 15 ppm[4] (STEL)
Lethal dose or concentration (LD, LC):
1800 mg/kg (rat, oral)
490 mg/kg (rat, intravenous)
1200 mg/kg (guinea pig, oral)
533 mg/kg (mouse, oral)[14]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 10 ppm (50 mg/m3)[13]
REL (Recommended)
 TWA 10 ppm (50 mg/m3) ST 15 ppm (75 mg/m3)[13]
IDLH (Immediate danger)
 250 ppm[13]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[15] As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is the main ingredient of traditional mothballs.

  1. ^ Naphthalene: trade names
  2. ^ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 13, 35, 204, 207, 221–222, 302, 457, 461, 469, 601, 650. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ a b c "Ambient Water Quality Criteria for Naphthalene" (PDF). United States Environmental Protection Agency. 2014-04-23. Retrieved 2014-06-21.
  4. ^ a b c d e f g h i j k l m n Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  5. ^ a b c Anatolievich, Kiper Ruslan. "naphthalene". chemister.ru. Retrieved 2014-06-21.
  6. ^ a b c d e f Seidell, Atherton; Linke, William F. (1919). Solubility of Inorganic and Organic Compounds (2nd ed.). New York: D. Van Nostrand Company. pp. 443–446.
  7. ^ a b Naphthalene in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-24)
  8. ^ "Thermal Conductivity of Naphthalene". DDBST GmbH. Archived from the original on 2016-03-04. Retrieved 2014-06-21.
  9. ^ "Dynamic Viscosity of Naphthalene". DDBST GmbH. Archived from the original on 2016-03-04. Retrieved 2014-06-21.
  10. ^ a b c d Douglas, Bodie E.; Ho, Shih-Ming (2007). Structure and Chemistry of Crystalline Solids. New York: Springer Science+Business Media, Inc. p. 288. ISBN 978-0-387-26147-8.
  11. ^ a b c d e f Sigma-Aldrich Co., Naphthalene.
  12. ^ Naphthalene carcinogenicity
  13. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0439". National Institute for Occupational Safety and Health (NIOSH).
  14. ^ "Naphthalene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  15. ^ 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 water dilution". J Appl Toxicol. 3 (6): 272–290. doi:10.1002/jat.2550030603. PMID 6376602. S2CID 36525625.

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