Naphthalene
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| Names | |||
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| IUPAC name
Naphthalene[2]
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| Other names
white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes[1]
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| Identifiers | |||
CAS Number
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3D model (JSmol)
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Beilstein Reference
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1421310 | ||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.001.863 | ||
| EC Number |
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Gmelin Reference
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3347 | ||
| KEGG | |||
PubChem CID
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| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |||
Chemical formula
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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] | ||
Solubility in water
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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] | ||
Henry's law
constant (kH) |
0.42438 L·atm/mol[4] | ||
Magnetic susceptibility (χ)
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−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] | ||
Refractive index (nD)
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1.5898[4] | ||
| Viscosity | 0.964 cP (80 °C) 0.761 cP (100 °C) 0.217 cP (150 °C)[9] | ||
| Structure | |||
Crystal structure
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Monoclinic[10] | ||
Space group
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P21/b[10] | ||
Point group
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C5 2h[10] | ||
Lattice constant
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a = 8.235 Å, b = 6.003 Å, c = 8.658 Å[10] α = 90°, β = 122.92°, γ = 90°
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| Thermochemistry | |||
Heat capacity (C)
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165.72 J/mol·K[4] | ||
Std molar
entropy (S⦵298) |
167.39 J/mol·K[4][7] | ||
Std enthalpy of
formation (ΔfH⦵298) |
78.53 kJ/mol[4] | ||
Gibbs free energy (ΔfG⦵)
|
201.585 kJ/mol[4] | ||
Std enthalpy of
combustion (ΔcH⦵298) |
−5156.3 kJ/mol[4] | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Flammable, sensitizer, possible carcinogen.[12] Dust can form explosive mixtures with air | ||
| GHS labelling: | |||
Pictograms
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[11] | ||
Signal word
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Danger | ||
Hazard statements
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H228, H302, H351, H410[11] | ||
Precautionary statements
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P210, P273, P281, P501[11] | ||
| NFPA 704 (fire diamond) | |||
| Flash point | 80 °C (176 °F; 353 K)[11] | ||
Autoignition
temperature |
525 °C (977 °F; 798 K)[11] | ||
| Explosive limits | 5.9%[11] | ||
Threshold limit value (TLV)
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10 ppm[4] (TWA), 15 ppm[4] (STEL) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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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)
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TWA 10 ppm (50 mg/m3)[13] | ||
REL (Recommended)
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TWA 10 ppm (50 mg/m3) ST 15 ppm (75 mg/m3)[13] | ||
IDLH (Immediate danger)
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250 ppm[13] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
| |||
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.
- ^ Naphthalene: trade names
- ^ 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.
- ^ a b c "Ambient Water Quality Criteria for Naphthalene" (PDF). United States Environmental Protection Agency. 2014-04-23. Archived from the original (PDF) on May 14, 2011. Retrieved 2014-06-21.
- ^ 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.
- ^ a b c Anatolievich, Kiper Ruslan. "naphthalene". chemister.ru. Retrieved 2014-06-21.
- ^ 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.
- ^ 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)
- ^ "Thermal Conductivity of Naphthalene". DDBST GmbH. Archived from the original on 2016-03-04. Retrieved 2014-06-21.
- ^ "Dynamic Viscosity of Naphthalene". DDBST GmbH. Archived from the original on 2016-03-04. Retrieved 2014-06-21.
- ^ 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.
- ^ a b c d e f Sigma-Aldrich Co., Naphthalene.
- ^ Naphthalene carcinogenicity
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0439". National Institute for Occupational Safety and Health (NIOSH).
- ^ "Naphthalene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ 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.