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).
N verify (what is YN ?)
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]

gollark: I know! We've had some *fascinating* results under Project UNTRANSLATABLE CONGAS.
gollark: [REDACTED]
gollark: I mean, I never actually checked, but I don't think they are.
gollark: They're not you, probably.
gollark: Common side effects of soul harvesting include paranoia about side effects of soul harvesting, hallucinations of bee noises, reading lists, and complaining about gollark.

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.


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.