286. Allyl Alcohol

Nomenclature

CAS number: 107-18-6
2-Propen-1-ol; 1-propenol-3; vinyl carbinol.
C3H6O; mol wt 58.08.
C 62.04%, H 10.41%, O 27.55%.

Description and references

Prepd by heating glycerol with formic acid: O. Kamm, C. S. Marvel, Org. Synth. coll. vol. I, 42 (2nd ed., 1941); cf. Delaby, Dubois, Compt. Rend. 188, 710 (1929). Toxicity study: Smyth, Carpenter, J. Ind. Hyg. Toxicol. 30, 63 (1948).

Chemical structure

Properties

Colorless liquid; pungent, mustard-like odor. Flammable, poisonous. Keep tightly closed. d420 0.8540. bp 96-97°. mp 50°. nD20 1.41345. Absorption spectrum: Lüthy, Z. Phys. Chem. 107, 289 (1923). Flash pt 70°F (open cup); 75°F (closed cup); autoignition temp 713°F. 72.3% of the alcohol with 27.7% water forms a constant boiling mixture, bp at 87.5°. Miscible with water, alcohol, chloroform, ether, petr ether. Upon storage for several years allyl alcohol polymerizes and a thick syrup is formed (insol in water, sol in chloroform) which on treatment with ether yields a brittle resinoid mass: Blicke, J. Am. Chem. Soc. 45, 1563 (1923). LD50 orally in rats: 64 mg/kg (Smyth, Carpenter).

Caution

Potential symptoms of overexposure are eye irritation, tissue damage; irritation of upper respiratory system and skin; pulmonary edema. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 10.

Use

Manuf allyl compds, war gas, resins, plasticizers.