9536. Toluidine

C7H9N; mol wt 107.15.
C 78.46%, H 8.47%, N 13.07%.

Description and references

Prepn: J. S. Muspratt, A. W. Hofmann, Ann. 54, 1 (1845); of each isomer: F. Beilstein, A. Kuhlberg, ibid. 156, 66 (1870); P. Kovacic, J. L. Foote, J. Am. Chem. Soc. 83, 743 (1961); P. Kovacic et al., ibid. 84, 759 (1962). Toxicity data: H. F. Smyth, Am. Ind. Hyg. Assoc. J. 23, 95 (1962). GC determn in urine: K. El-Bayoumy et al., Cancer Res. 46, 6064 (1986).

Chemical structure

Derivative

m-Toluidine.

Nomenclature

CAS number: 108-44-1
3-Methylbenzamine; 3-aminotoluene; 3-methylaniline.

Properties

Liquid, mp ≈50°. bp 203-204°. d2525 0.990. nD22 1.5711. Slightly sol in water; sol in alcohol, ether, dil acids.

Derivative

o-Toluidine.

Nomenclature

CAS number: 95-53-4
2-Methylbenzamine; 2-aminotoluene; 2-methylaniline.

Properties

Light yellow liquid becoming reddish brown on exposure to air and light. bp 200-202°. d2020 1.008. nD20 1.5688. Flash pt, closed cup: 185°F (85°C). Slightly sol in water; sol in alcohol, ether, dil acids. Keep well closed and protected from light. LD50 orally in rats: 0.94 g/kg (Smyth).

Derivative

p-Toluidine.

Nomenclature

CAS number: 106-49-0
4-Methylbenzamine; 4-aminotoluene; 4-methylaniline.

Properties

Lustrous plates or leaflets, mp 44-45°. bp 200-201°. d420 1.046. nD59 1.5532. Flash pt, closed cup: 188°F (86°C). Sol in about 135 parts water; freely sol in alcohol, ether, acetone, methanol, carbon disulfide, oils, dil acids.

Caution

Potential symptoms of overexposure to o-toluidine are eye irritation; anoxia, headache, cyanosis; weakness, dizziness, drowsiness; microhematuria; eye burns; dermatitis. Potential symptoms of overexposure to m- or p- toluidine are eye, skin irritation; hematuria, methemoglobinemia; cyanosis, nausea, vomiting, low blood pressure, convulsions; anemia, weakness. p-Toluidine is a potential occupational carcinogen. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 312. o-Toluidine and its hydrochloride are reasonably anticipated to be human carcinogens: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-258.

Use

Manufacture of various dyes and other organic chemicals. o-Isomer also in printing textiles blue black; making colors fast to acids. p-Isomer also as a reagent for lignin, nitrite, phloroglucinol.