4-Nitrotoluene

4-Nitrotoluene

4-Nitrotoluene

Chemical compound

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

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Synthesis and reactions

Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene,[4] commonly using titanium(IV) nitrate.[5] It undergoes the reactions typical for nitrobenzene derivatives, e.g. hydrogenation gives p-toluidine.

Oxidation of the methyl substituent of 4-nitrotoluene has been extensively investigated. Depending on the conditions, oxidation yields 4-nitrobenzaldehyde diacetate,[6] 4-nitrobenzenoic acid,[7] and 4,4'-dinitrobibenzyl.[8] Treatment of 4-nitrotoluene with bromine gives the 4-nitrobenzyl bromide.[9]

Applications

The principal application involves its sulfonation to give the 4-nitrotoluene-2-sulfonic acid (with the –SO3H group adjacent to methyl). This species can be oxidatively coupled to produce stilbene derivatives,[10] which are used as dyes.[11] Representative derivatives include the molecular and salt forms of 4,4'-dinitroso- and the 4,4'-dinitro-2,2'-stilbenedisulfonic acids, e.g. disodium 4,4'-dinitrostilbene-2,2'-disulfonate.[12]

Safety

Evidence exists for toxicity and carcinogenicity in mice.[13]

References

  1. [1]
    NIOSH Pocket Guide to Chemical Hazards. "#0464". National Institute for Occupational Safety and Health (NIOSH).
  2. [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. [3]
    "Nitrotoluene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. [4]
    Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
  5. [5]
    Amos, D.W.; D.A. Baines, G.W. Flewett (1973). "Nitration by titanium (IV) nitrate". Tetrahedron Letters. 14 (34): 3191–3194. doi:10.1016/S0040-4039(00)79808-X. ISSN 0040-4039.
  6. [6]
    Tamio Nishimura (1956). "o- and p-Nitrobenzaldiacetate". Organic Syntheses. 36: 58. doi:10.15227/orgsyn.036.0058.
  7. [7]
    O. Kamm, A. O. Matthews (1922). "p-Nitrobenzoic Acid". Organic Syntheses. 2: 53. doi:10.15227/orgsyn.002.0053.
  8. [8]
    Herbert O. House (1954). "p,p'-Dinitrobibenzyl". Organic Syntheses. 34: 35. doi:10.15227/orgsyn.034.0035.
  9. [9]
    G. H. Coleman, G. E. Honeywell (1936). "p-Nitrobenzyl Bromide". Organic Syntheses. 16: 54. doi:10.15227/orgsyn.016.0054.
  10. [10]
    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. New York: D. Van Nostrand Company. p. 314.
  11. [11]
    Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN 978-3527306732.
  12. [12]
    Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
  13. [13]
    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.
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