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4-Nitrotoluene

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4-Nitrotoluene
Names
Preferred IUPAC name 1-Methyl-4-nitrobenzene
Other names p-nitrotoluene
p-mononitrotoluene, p-methylnitrobenzene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.553 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H7NO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3Key: ZPTVNYMJQHSSEA-UHFFFAOYSA-N
SMILES
  • O=()c1ccc(C)cc1
Properties
Chemical formula C7H7NO2
Molar mass 137.138 g·mol
Appearance crystalline solid
Odor weak, aromatic
Density 1.1038 g·cm (75 °C)
Melting point 51.63 °C (124.93 °F; 324.78 K)
Boiling point 238.3 °C (460.9 °F; 511.4 K)
Solubility in water 0.04% (20°C)
Vapor pressure 0.1 mmHg (20°C)
Magnetic susceptibility (χ) −72.06·10 cm/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards moderately toxic
Flash point 106 °C; 223 °F; 379 K
Explosive limits 1.6%–?
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1231 mg/kg (mouse, oral)
1330 mg/kg (rat, oral)
1450 mg/kg (rabbit, oral)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 5 ppm (30 mg/m)
REL (Recommended) TWA 2 ppm (11 mg/m)
IDLH (Immediate danger) 200 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
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.

Synthesis and reactions

Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene, commonly using titanium(IV) nitrate. 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, 4-nitrobenzenoic acid, and 4,4'-dinitrobibenzyl. Treatment of 4-nitrotoluene with bromine gives the 4-nitrobenzyl bromide.

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, which are used as dyes. 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.

Safety

Evidence exists for toxicity and carcinogenicity in mice.

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0464". 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". Immediately Dangerous to Life or 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. ISBN 978-3527306732.
  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. Tamio Nishimura (1956). "o- and p-Nitrobenzaldiacetate". Organic Syntheses. 36: 58. doi:10.15227/orgsyn.036.0058.
  7. O. Kamm, A. O. Matthews (1922). "p-Nitrobenzoic Acid". Organic Syntheses. 2: 53. doi:10.15227/orgsyn.002.0053.
  8. Herbert O. House (1954). "p,p'-Dinitrobibenzyl". Organic Syntheses. 34: 35. doi:10.15227/orgsyn.034.0035.
  9. G. H. Coleman, G. E. Honeywell (1936). "p-Nitrobenzyl Bromide". Organic Syntheses. 16: 54. doi:10.15227/orgsyn.016.0054.
  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. 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. ISBN 3527306730.
  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. 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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