4-Nitrotoluene

4-Nitrotoluene
Names
IUPAC name
1-Methyl-4-nitrobenzene
Other names
p-Nitrotoluene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.553
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]
−72.06·10−6 cm3/mol
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):
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

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 (with the –SO3H group adjacent to methyl). This species is produced on a large scale since it can be oxidatively coupled to produce stilbene derivatives[5] which are used as dyes.[6] Representative derivatives include the molecular and salt forms of 4,4'-dinitroso- and the 4,4'-dinitro-2,2'-stilbenedisulfonic acids.[4] Arthur Green and André Wahl reported the formation of disodium 4,4'-dinitrostilbene-2,2'-disulfonate in the late nineteenth century using sodium hypochlorite as an oxidising agent,[7][8] and improved processes using air oxidation in liquid ammonia have been developed.[9]

Safety

There is some evidence for toxicity and carcinogenicity in mice.[10]

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 Booth, Gerald (2005). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
  5. ↑ Cumming, William M.; Hopper, I. Vance; Wheeler, T. Sherlock (1926). "Preparation 294.—Dinitro-Stilbene-Disulphonic Acid (Na salt)". Systematic Organic Chemistry: Modern Methods of Preparation and Estimation (PDF). New York: D. Van Nostrand Company. p. 314.
  6. ↑ Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245.
  7. ↑ Green, Arthur G.; Wahl, André R. (1897). "Ueber die Oxydation von Paranitrotoluolsulfosäure" [On the oxidation of para-nitrotoluenesulfonic acid]. Ber. Dtsch. Chem. Ges. (in German). 30 (3): 3097–3101. doi:10.1002/cber.189703003128.
  8. ↑ Green, Arthur G.; Wahl, André R. (1898). "Ueber die Oxydation der Paranitrotoluolsulfosäure" [On the oxidation of para-nitrotoluenesulfonic acid]. Ber. Dtsch. Chem. Ges. (in German). 31 (1): 1078–1080. doi:10.1002/cber.189803101195.
  9. ↑ US patent 5041632, Guglielmetti, Leonardo, "Process for the preparation of 4,4'-dinitrostilbene-2,2-disulfonic acid", published 1991-08-20, issued 1991-08-20, assigned to Ciba-Geigy Corporation
  10. ↑ 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.