Methallyl Isothiocyanate

Abstract

[41834-90-6] CH2C(CH3)CH2NCS (MW 113.18) InChI = 1S/C5H7NS/c1-5(2)3-6-4-7/h1,3H2,2H3 InChIKey = SFCQVEDGNZVACI-UHFFFAOYSA-N (reagent for conversion of amines to N-methallylthioureas; can be used for the preparation of methallyl-substituted N-,S-containing heterocycles) Alternative Names: 3-isothiocyanato-2-methylprop-1-ene, MAITC. Physical Data: bp 78 °C (25 mmHg),1 97 °C (76 mmHg),2 169–170 °C (760 mmHg)1; n D 21 1.52372; d 0.993 g cm−3. Solubility: soluble in most organic solvents, e.g., acetone, dimethyl sulfoxide, methanol, ethanol, ether, toluene, and chloroform. Insoluble in water. Form Supplied in: methallyl isothiocyanate is commercially available as a colorless liquid. Preparative Methods: the reaction of methallyl chloride with inorganic thiocyanates leads to methallyl thiocyanate, which readily rearranges under heating to the desired methallyl isothiocyanate.1–3 Handling, Storage, and Precaution: MAITC is a lachrymator with a strong garlic-like odor.4 Containers with the reagent must be tightly closed and kept in a dry and well-ventilated place. Recommended storing in a cool place (about 2–8 °C). The substance is moisture sensitive. Use in a fume hood. MAITC causes respiratory tract, skin, and eye irritation if inhaled, swallowed, or in contact with skin or eyes.