2-Nitrotoluene
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Names | |||
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IUPAC name
1-methyl-2-nitro-benzene
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Other names
o-Nitrotoluene, o-Methylnitrobenzene, 2-Methylnitrobenzene, ortho-Nitrotoluene
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Identifiers | |||
3D model (JSmol)
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.001.685 | ||
CompTox Dashboard (EPA)
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Properties | |||
C7H7NO2 | |||
Molar mass | 137.138 g·mol−1 | ||
Appearance | yellow liquid[1] | ||
Odor | weak, aromatic[1] | ||
Density | 1.1611 g·cm−3 @ 19°C [2] | ||
Melting point | −10.4 °C (13.3 °F; 262.8 K)[2] | ||
Boiling point | 222 °C (432 °F; 495 K)[2] | ||
0.07% (20°C)[1] | |||
Vapor pressure | 0.1 mmHg (20°C)[1] | ||
-72.28·10−6 cm3/mol | |||
Hazards | |||
Flash point | 106 °C; 223 °F; 379 K [1] | ||
Explosive limits | 2.2%-?[1] | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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891 mg/kg (oral, rat) 970 mg/kg (oral, mouse) 1750 mg/kg (oral, rabbit)[3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 5 ppm (30 mg/m3) [skin][1] | ||
REL (Recommended)
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TWA 2 ppm (11 mg/m3) [skin][1] | ||
IDLH (Immediate danger)
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200 ppm[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that is a versatile intermediate in the production of various dyes.[4]
Synthesis and reactions
It is made by nitrating toluene at above -10 °C. This reaction affords a 2:1 mixture of 2-nitro and 4-nitro isomers.[4]
Chlorination gives two isomers of the chloronitrotoluenes. Similarly nitration gives two isomers of dinitrotoluene.
2-Nitrotolune is mainly consumed in the production of o-toluidine, a precursor to dyes.[4]
References
- ^ a b c d e f g h i NIOSH Pocket Guide to Chemical Hazards. "#0462". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c Lide DR, ed. (2004). CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data (85 ed.). Boca Ratan Florida: CRC Press. ISBN 0-8493-0485-7.
- ^ "Nitrotoluene (o-, m-, p-isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c Gerald Booth (2007). "Nitro Compounds, Aromatic". Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
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