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Benzene

Benzene
Skeletal formula detail of benzene
Geometry
Benzene ball-and-stick model
Ball and stick model
Benzene molecule
Space-filling model
Names
Preferred IUPAC name
Benzene
Other names
Benzol
Phene
Phenyl hydride
[6]annulene (not recommended)
Identifiers
71-43-2 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:16716 YesY
ChEMBL ChEMBL277500 YesY
ChemSpider 236 YesY
ECHA InfoCard 100.000.685
EC Number 200-753-7
KEGG C01407 YesY
PubChem 241
RTECS number CY1400000
UNII J64922108F YesY
Properties
C6H6
Molar mass 78.11 g·mol−1
Appearance Colorless liquid
Odor Aromatic, gasoline-like
Density 0.8765(20) g/cm3
Melting point 5.53 °C (41.95 °F; 278.68 K)
Boiling point 80.1 °C (176.2 °F; 353.2 K)
1.53 g/L (0 °C)
1.81 g/L (9 °C)
1.79 g/L (15 °C)
1.84 g/L (30 °C)
2.26 g/L (61 °C)
3.94 g/L (100 °C)
21.7 g/kg (200 °C, 6.5 MPa)
17.8 g/kg (200 °C, 40 MPa)
Solubility Soluble in alcohol, CHCl3, CCl4, diethyl ether, acetone, acetic acid
Solubility in ethanediol 5.83 g/100 g (20 °C)
6.61 g/100 g (40 °C)
7.61 g/100 g (60 °C)
Solubility in ethanol 20 °C, solution in water:
1.2 mL/L (20% v/v)
Solubility in acetone 20 °C, solution in water:
7.69 mL/L (38.46% v/v)
49.4 mL/L (62.5% v/v)
Solubility in diethylene glycol 52 g/100 g (20 °C)
log P 2.13
Vapor pressure 12.7 kPa (25 °C)
24.4 kPa (40 °C)
181 kPa (100 °C)
UV-vismax) 255 nm
-54.8·10−6 cm3/mol
1.5011 (20 °C)
1.4948 (30 °C)
Viscosity 0.7528 cP (10 °C)
0.6076 cP (25 °C)
0.4965 cP (40 °C)
0.3075 cP (80 °C)
Structure
Trigonal planar
0 D
Thermochemistry
134.8 J/mol·K
173.26 J/mol·K
48.7 kJ/mol
3267.6 kJ/mol
Hazards
Main hazards potential occupational carcinogen, flammable
Safety data sheet See: data page
HMDB
GHS pictograms The 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)
GHS signal word Danger
H225, H304, H315, H319, H340, H350, H372
P201, P210, P301+310, P305+351+338, P308+313, P331
Highly Flammable FToxic T
Carc. Cat. 1
Muta. Cat. 2
R-phrases R45, R46, R11, R16, R36/38,R48/23/24/25, R65
S-phrases S53, S45
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −11.63 °C (11.07 °F; 261.52 K)
497.78 °C (928.00 °F; 770.93 K)
Explosive limits 1.2–7.8%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
930 mg/kg (rat, oral)
44,000 ppm (rabbit, 30 min)
44,923 ppm (dog)
52,308 ppm (cat)
20,000 ppm (human, 5 min)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 1 ppm, ST 5 ppm
REL (Recommended)
Ca TWA 0.1 ppm ST 1 ppm
IDLH (Immediate danger)
500 ppm
Related compounds
Related compounds
Toluene
Borazine
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Benzene is an important organic chemical compound with the chemical formula C6H6. The benzene molecule is composed of 6 carbon atoms joined in a ring with 1 hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

Benzene is a natural constituent of crude oil and is one of the elementary petrochemicals. Because of the cyclic continuous pi bond between the carbon atoms, benzene is classed as an aromatic hydrocarbon, the second [n]-annulene ([6]-annulene). It is sometimes abbreviated Ph–H. Benzene is a colorless and highly flammable liquid with a sweet smell, and is responsible for the aroma around petrol stations. It is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced. Because benzene has a high octane number, it is an important component of gasoline.

Because benzene is a human carcinogen, most non-industrial applications have been limited.

The word "benzene" derives historically from "gum benzoin" (benzoin resin), an aromatic resin known to European pharmacists and perfumers since the 15th century as a product of southeast Asia. An acidic material was derived from benzoin by sublimation, and named "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene.Michael Faraday first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name bicarburet of hydrogen. In 1833, Eilhard Mitscherlich produced it by distilling benzoic acid (from gum benzoin) and lime. He gave the compound the name benzin. In 1836, the French chemist Auguste Laurent named the substance "phène"; this word has become the root of the English word "phenol", which is hydroxylated benzene, and "phenyl", the radical formed by abstraction of a hydrogen atom (free radical H•) from benzene.


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Wikipedia

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