3256. Dimethyl Sulfate

Nomenclature

CAS number: 77-78-1
Sulfuric acid dimethyl ester; DMS.
C2H6O4S; mol wt 126.13.
C 19.04%, H 4.79%, O 50.74%, S 25.42%.
(CH3)2SO4.

Description and references

Prepn by distillation of a mixture of oleum and methanol: Guyot, Simon, Compt. Rend. 169, 796 (1919). Technical production from dimethyl ether and SO3: BIOS Final Report No. 986, p 176. Review: C. M. Suter, The Organic Chemistry of Sulfur (John Wiley, New York, 1944) p 49-61. Use as methylating agent: L. Fieser, M. Fieser, Reagents for Organic Synthesis (John Wiley, New York, 1967) pp 293-295. Toxicity data: Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951). Review of toxicology: E. Browning, Toxicity and Metabolism of Industrial Solvents (Elsevier, New York, 1965) pp 713-721; of carcinogenicity studies: IARC Monographs 4, 271-276 (1974); of mutagenicity studies: G. R. Hoffmann, Mutat. Res. 75, 63-129 (1980).

Properties

Colorless oily liq. Poisonous. Corrosive. bp ≈188° (with dec); bp15 76°. mp -27°. d420 1.3322. nD20 1.3874. Flash pt 182°F (83°C). Soly in water 2.8 g/100 ml at 18°. Hydrolysis is rapid at or above this temp. Vapor density 4.35. Sol in ether, dioxane, acetone, aromatic hydrocarbons. Sparingly sol in carbon disulfide, aliphatic hydrocarbons. LD50 orally in rats: 440 mg/kg (Smyth).

Caution

Vapors and liquid can be absorbed through the skin or respiratory tract, causing local and systemic toxicity. Potential symptoms of overexposure are irritation of eyes and nose; conjunctivitis; eye and skin burns; headache; giddiness; delerium; photophobia; periorbital edema; dysphonia, aphonia, dysphagia; cough, chest pain; dyspnea; cyanosis; vomiting; diarrhea, dysuria; analgesia; fever; albuminuria, hematuria. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 116; P. Grandjean, “Skin Penetration: Hazardous Chemicals at Work” (Taylor & Francis, New York, 1990) pp 173-174. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-109.

Use

Methylating agent in the manuf of many organic chemicals. War gas.