Dimethyl Sulfate
Structural Formula Vector Image
Title: Dimethyl Sulfate
CAS Registry Number: 77-78-1
CAS Name: Sulfuric acid dimethyl ester
Additional Names: DMS
Molecular Formula: C2H6O4S
Molecular Weight: 126.13
Percent Composition: C 19.04%, H 4.79%, O 50.74%, S 25.42%
Line Formula: (CH3)2SO4
Literature 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).
Melting point: mp -27°
Boiling point: bp ~188° (with dec); bp15 76°
Flash point: Flash pt 182°F (83°C)
Index of refraction: nD20 1.3874
Density: d420 1.3322
Toxicity data: 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.

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