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3-Nitrotoluene

Summary

3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is one of three isomers of nitrotoluene. A yellow liquid, it is used in the manufacture of meta-toluidine, which is an intermediate in the production of various dyes.[3]

3-Nitrotoluene
Names
Preferred IUPAC name
1-Methyl-3-nitrobenzene
Other names
m-Nitrotoluene
Identifiers
  • 99-08-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:39931
ChemSpider
  • 21106146
ECHA InfoCard 100.002.480 Edit this at Wikidata
  • 7422
UNII
  • 29A9W826KQ checkY
  • DTXSID5021831 Edit this at Wikidata
  • InChI=1S/C7H7NO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3
  • O=[N+]([O-])c1cccc(C)c1
Properties
C7H7NO2
Molar mass 137.138 g·mol−1
Appearance yellow liquid[1]
Odor mild, aromatic[1]
Density 1.1581 g·cm−3 @ 20°C [2]
Melting point 15.5 °C (59.9 °F; 288.6 K)[2]
Boiling point 232 °C (450 °F; 505 K)[2]
0.05% (20°C)[1]
Vapor pressure 0.1 mmHg (20°C)[1]
-72.71·10−6 cm3/mol
Hazards
Flash point 106 °C; 223 °F; 379 K[1]
Explosive limits 1.6%-?[1]
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).
Infobox references

Synthesis and reactions edit

It is made by nitrating toluene. This reaction mainly affords a 2:1 mixture of 2-nitro and 4-nitro isomers, but after removal of the 2-isomer, the 3-nitrotoluene can be purified by distillation. It is a precursor to toluidine, which is used in producing azo dyes.[3]

References edit

  1. ^ a b c d e f g h i NIOSH Pocket Guide to Chemical Hazards. "#0463". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ 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.
  3. ^ a b Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.

External links edit

  • CDC - NIOSH Pocket Guide to Chemical Hazards - m-Nitrotoluene