2-Nitrotoluene

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.[4]

2-Nitrotoluene
Names
IUPAC name
1-methyl-2-nitro-benzene
Other names
o-Nitrotoluene, o-Methylnitrobenzene, 2-Methylnitrobenzene, ortho-Nitrotoluene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.685
EC Number
  • 201-853-3
KEGG
RTECS number
  • XT3150000
UNII
UN number 1664
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
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H302, H340, H350, H361, H411
P201, P202, P264, P270, P273, P281, P301+312, P308+313, P330, P391, P405, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Flash point 106 °C; 223 °F; 379 K [1]
Explosive limits 2.2%-?[1]
Lethal dose or concentration (LD, LC):
891 mg/kg (oral, rat)
970 mg/kg (oral, mouse)
1750 mg/kg (oral, rabbit)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 5 ppm (30 mg/m3) [skin][1]
REL (Recommended)
 TWA 2 ppm (11 mg/m3) [skin][1]
IDLH (Immediate danger)
 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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Infobox references

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 of 2-nitrotoluene 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]

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References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0462". National Institute for Occupational Safety and Health (NIOSH).
  2. 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.
  3. "Nitrotoluene (o-, m-, p-isomers)". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.


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