Naphthalene

Naphthalene
Skeletal formula and numbering system of naphthalene
Ball-and-stick model of naphthalene
Spacefill model of naphthalene
Unit cells of naphthalene
Names
Preferred IUPAC name
Naphthalene[1]
Systematic IUPAC name
Bicyclo[4.4.0]deca-1,3,5,7,9-pentaene
Other names
white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes
Identifiers
3D model (JSmol)
1421310
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.001.863
EC Number214-552-7
3347
KEGG
RTECS numberQJ0525000
UNII
Properties
C10H8
Molar mass128.17 g·mol−1
AppearanceWhite solid crystals/ flakes
OdorStrong odor of coal tar
Density1.145 g/cm3 (15.5 °C)[2]
1.0253 g/cm3 (20 °C)[3]
0.9625 g/cm3 (100 °C)[2]
Melting point 78.2 °C (172.8 °F; 351.3 K)
80.26 °C (176.47 °F; 353.41 K)
at 760 mmHg[3]
Boiling point 217.97 °C (424.35 °F; 491.12 K)
at 760 mmHg[2][3]
19 mg/L (10 °C)
31.6 mg/L (25 °C)
43.9 mg/L (34.5 °C)
80.9 mg/L (50 °C)[3]
238.1 mg/L (73.4 °C)[4]
SolubilitySoluble in alcohols, liquid ammonia, carboxylic acids, C6H6, SO2,[4] CCl4, CS2, toluene, aniline[5]
Solubility in ethanol5 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)[5]
Solubility in acetic acid6.8 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)[5]
Solubility in chloroform19.5 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)[5]
Solubility in hexane5.5 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)[5]
Solubility in butyric acid13.6 g/100 g (6.75 °C)
22.1 g/100 g (21.5 °C)
131.6 g/100 g (60 °C)[5]
log P3.34[3]
Vapor pressure8.64 Pa (20 °C)
23.6 Pa (30 °C)
0.93 kPa (80 °C)[4]
2.5 kPa (100 °C)[6]
0.42438 L·atm/mol[3]
-91.9·10−6 cm3/mol
Thermal conductivity98 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)[7]
1.5898[3]
Viscosity0.964 cP (80 °C)
0.761 cP (100 °C)
0.217 cP (150 °C)[8]
Structure
Monoclinic[9]
P21/b[9]
C5
2h
[9]
a = 8.235 Å, b = 6.003 Å, c = 8.658 Å[9]
α = 90°, β = 122.92°, γ = 90°
Thermochemistry
165.72 J/mol·K[3]
167.39 J/mol·K[3][6]
78.53 kJ/mol[3]
201.585 kJ/mol[3]
-5156.3 kJ/mol[3]
Hazards
Main hazardsFlammable, sensitizer, possible carcinogen. Dust can form explosive mixtures with air
GHS pictogramsThe flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[10]
GHS signal wordDanger
H228, H302, H351, H410[10]
P210, P273, P281, P501[10]
NFPA 704
Flash point 80 °C (176 °F; 353 K)[10]
525 °C (977 °F; 798 K)[10]
Explosive limits5.9%[10]
10 ppm[3] (TWA), 15 ppm[3] (STEL)
Lethal dose or concentration (LD, LC):
1800 mg/kg (rat, oral)
490 mg/kg (rat, oral)
1200 mg/kg (guinea pig, oral)
533 mg/kg (mouse, oral)[12]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 10 ppm (50 mg/m3)[11]
REL (Recommended)
TWA 10 ppm (50 mg/m3) ST 15 ppm (75 mg/m3)[11]
IDLH (Immediate danger)
250 ppm[11]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Naphthalene is an organic compound with formula C
10
H
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.[13] As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is best known as the main ingredient of traditional mothballs.

History

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, flammable liquid hydrocarbon mixture, including coal tar).[14] 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,[15] and confirmed by Carl Gräbe three years later.[16]

Other Languages
Afrikaans: Naftaleen
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تۆرکجه: نفتالین
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català: Naftalè
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日本語: ナフタレン
norsk: Naftalen
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português: Naftalina
română: Naftalină
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Simple English: Naphthalene
slovenčina: Naftalén
slovenščina: Naftalen
српски / srpski: Нафтален
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اردو: نفتھلین
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