3039. Di-tert-butyl Tricarbonate

Nomenclature

CAS number: 24424-95-1
Tricarbonic acid bis(1,1-dimethylethyl)ester.
C11H18O7; mol wt 262.26.
C 50.38%, H 6.92%, O 42.70%.

Description and references

Mild reagent which converts most primary amines quantitatively into their corresponding isocyanate. Prepn: C. S. Dean, D. S. Tarbell, Chem. Commun. 1969, 728; B. M. Pope et al., Org. Synth. 57, 45 (1977). Kinetic study: eidem, J. Org. Chem. 43, 2410 (1978). Use in prepn of isocyanates: H. W. I. Peerlings, E. W. Meijer, Tetrahedron Lett. 40, 1021 (1999); of polyurethanes: R. V. Versteegen et al., Angew. Chem. Int. Ed. 38, 2917 (1999).

Chemical structure

Properties

Crystalline solid, mp 64-65° (Dean); also reported as colorless prisms, mp 62-63° (Pope).

Use

In synthesis of polyurethanes.