6650. Nitrotoluene

Nomenclature

Methylnitrobenzene.
C7H7NO2; mol wt 137.14.
C 61.31%, H 5.14%, N 10.21%, O 23.33%.

Description and references

Nitration of toluol by a mixture of HNO3 and H2SO4 yields principally o- and p-nitrotoluol. Prepn of m-nitrotoluene from 3-nitro-4-amino-toluene and NaNO2: Clark, Taylor, Org. Synth. 3, 91 (1923).

Chemical structure

Derivative

m-Nitrotoluene.

Nomenclature

CAS number: 99-08-1
3-Nitrotoluene.

Properties

Liquid. d415 1.1630; d420 1.1581; d459 1.124; d4121 1.063. Solidifies in an ice and salt cooling mixture; mp 15°. bp760 232°; bp100 156.9°; bp40 130.7°; bp20 112.8°; bp10 96.0°; bp5 81.0°; bp1.0 50.2°. nD30 1.5426. Absorption spectrum: Marchlewski, Mayer, Bull. Acad. Polon. [A] 1929, 188. Miscible with alcohol and ether. Sol in benzene. Soly in water at 30° (mg/l): 498. Log P (octanol/water): 2.40.

Derivative

o-Nitrotoluene.

Nomenclature

CAS number: 88-72-2
2-Nitrotoluene.

Description and references

Technical report: NTP Technical Report on the Toxicology and Carcinogenesis Studies of o-Nitrotoluene (NTP TR-504/NIH 02-4438, 2002) 368 pp.

Properties

Yellowish liquid at ordinary temp. d1519 1.1622. mp -9.3°. bp 220.4°. nD20 1.5472. Soly in water at 30° (mg/l): 652. Sol in alcohol, benzene, petr ether. Log P (octanol/water): 2.30.

Derivative

p-Nitrotoluene.

Nomenclature

CAS number: 99-99-0
4-Nitrotoluene.

Description and references

Technical report: NTP Technical Report on the Toxicology and Carcinogenesis Studies of p-Nitrotoluene (NTP TR-498/NIH 02-4432, 2002) 277 pp.

Properties

Yellowish crystals. d 1.286. mp 51.7°. bp 238.3°. Flash pt 106°C. Soly in water at 30° (mg/l): 442. Sol in alcohol, benzene, ether, chloroform, acetone. Log P (octanol/water): 2.37.

Caution

Potential symptoms of overexposure are anoxia, cyanosis; headache, lassitude, dizziness; ataxia; dyspnea; tachycardia; nausea, vomiting. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 2003) p 232.

Use

Manuf of dyes, toluidines, nitrobenzoic acids, agricultural and rubber chemicals.