4-Nitrotoluene

4-Nitrotoluene
Names
IUPAC name
1-methyl-4-nitrobenzene
Other names
p-Nitrotoluene
Identifiers
99-99-0
ChemSpider 13863774
Jmol interactive 3D Image
PubChem 7473
Properties
C7H7NO2
Molar mass 137.14 g·mol−1
Appearance crystalline solid[1]
Odor weak, aromatic[1]
Density 1.1038 g·cm−3 @ 75°C [2]
Melting point 51.63 °C (124.93 °F; 324.78 K)[2]
Boiling point 238.3 °C (460.9 °F; 511.4 K)[2]
0.04% (20°C)[1]
Vapor pressure 0.1 mmHg (20°C)[1]
Hazards
Flash point 106 °C; 223 °F; 379 K [1]
Explosive limits 1.6%-?[1]
Lethal dose or concentration (LD, LC):
1231 mg/kg (mouse, oral)
1960 mg/kg (rat, oral)
1750 mg/kg (rabbit, oral)[3]
US health exposure limits (NIOSH):
TWA 5 ppm (30 mg/m3) [skin][1]
TWA 2 ppm (11 mg/m3) [skin][1]
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

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. This compound is mainly used to prepare dyes.

Synthesis and reactions

Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene.[4] It undergoes the expected reactions, e.g. hydrogenation gives p-toluidine.

Applications

The principle application involves its sulfonation to give the 4-nitrotoluene-2-sulfonic acid (SO3H group adjacent to methyl). This species is produced on a large scale since it can be coupled to make stilbene derivatives which are used as dyes. Representative derivatives include 4,4'-dinitroso- and the 4,4'-dinitro-2,2'-stilbenedisulfonic acids.[4]

Safety

There is some evidence for toxicity and carcinogenecity in mice.[5]

References

  1. 1 2 3 4 5 6 7 8 9 "NIOSH Pocket Guide to Chemical Hazards #0464". 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. "Nitrotoluene". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 Gerald Booth "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411
  5. National Toxicology, Program (2002). "Toxicology and carcinogenesis studies of p-nitrotoluene (CAS no. 99-99-0) in F344/N rats and B6C3F(1) mice (feed studies)". National Toxicology Program technical report series (498): 1–277. PMID 12118261.

External links


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