Structural Formula Vector Image
Title: Toluidine
Molecular Formula: C7H9N
Molecular Weight: 107.15
Percent Composition: C 78.46%, H 8.47%, N 13.07%
Literature 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).
Derivative Type: m-Toluidine
CAS Registry Number: 108-44-1
Additional Names: 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.
Melting point: mp ~-50°
Boiling point: bp 203-204°
Index of refraction: nD22 1.5711
Density: d2525 0.990
Derivative Type: o-Toluidine
CAS Registry Number: 95-53-4
Additional Names: 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).
Boiling point: bp 200-202°
Flash point: Flash pt, closed cup: 185°F (85°C)
Index of refraction: nD20 1.5688
Density: d2020 1.008
Toxicity data: LD50 orally in rats: 0.94 g/kg (Smyth)
Derivative Type: p-Toluidine
CAS Registry Number: 106-49-0
Additional Names: 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.
Melting point: mp 44-45°
Boiling point: bp 200-201°
Flash point: Flash pt, closed cup: 188°F (86°C)
Index of refraction: nD59 1.5532
Density: d420 1.046
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.

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