3376. 1,4-Dithiothreitol

Nomenclature

CAS number: 3483-12-3
(2R,3R)-rel-1,4-Dimercapto-2,3-butanediol; Cleland's reagent; threo-2,3-dihydroxy-1,4-dithiolbutane.
C4H10O2S2; mol wt 154.25.
C 31.15%, H 6.53%, O 20.74%, S 41.58%.

Description and references

Prepn: R. M. Evans et al., J. Chem. Soc. 1949, 253; and use as reagent for protecting SH groups: W. W. Cleland, Biochemistry 3, 480 (1964).

Chemical structure

Properties

Slightly hygroscopic needles from ether, mp 42-43°. Can be sublimed at 37° and 0.005 mm press; bp2 125-130°. Redox potential: -0.33 volts at pH 7. Freely sol in water, ethanol, acetone, ethyl acetate, chloroform, ether.

Use

In organic synthesis as reagent for protection of SH groups.