12-02092. Cheirolin [Archived]

Nomenclature

CAS number: 505-34-0
1-Isothiocyanato-3-(methylsulfonyl)propane; isothiocyanic acid 3-(methylsulfonyl)propyl ester; γ-isothiocyanopropyl methyl sulfone; methylpropylsulfone mustard oil.
C5H9NO2S2; mol wt 179.26.
C 33.50%, H 5.06%, N 7.81%, O 17.85%, S 35.77%.
CH3SO2(CH2)3NCS.

Description and references

From seed of Cheiranthus cheiri L., Cruciferae: Wagner, Chem. Ztg. 32, 76 (1908); Schneider, Ber. 41, 4466 (1909); 42, 3416 (1910). Structure: idem., Ann. 375, 207 (1910). Synthesis: Kjaer et al., Acta Chem. Scand. 7, 1370 (1953). Prepn by enzymatic hydrolysis of glucocheirolin: Kjaer, Jensen, ibid. 12, 1746 (1958).

Properties

Crystals from ether, mp 47-48°. bp3 200°. Slightly sol in water, ether; freely sol in alcohol, chloroform, ethyl acetate.

Status

This monograph has been retired and is no longer subject to revision or update.