3-Nitrotoluene

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3-Nitrotoluene
M-Nitrotoluol.svg
Names
Preferred IUPAC name
1-Methyl-3-nitrobenzene
Other names
m-Nitrotoluene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.480 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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
Appearanceyellow 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).

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]

Contents

Synthesis and reactions

It is made by nitrating toluene by conventional mixed acid (acetyl nitrate doesn't produce it [4] ): 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

  1. 1 2 3 4 5 6 7 8 9 NIOSH Pocket Guide to Chemical Hazards. "#0463". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 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. 1 2 Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN   978-3-527-30673-2.
  4. ↑ Amé Pictet; Eug. Khotinsky (January 1907). "Über Acetylnitrat". Berichte der Deutschen Chemischen Gesellschaft (in German). 40 (1): 1163–1166. doi:10.1002/CBER.190704001172. ISSN   0365-9496. Wikidata   Q61714426.
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