Boc Anhydride

Other Names:

Di-tert-butyl dicarbonate

Di-tert-butyl pyrocarbonate

General Information:

Structure:

CAS Number: 24424-99-5

Molecular Weight: 218.25 g/mol

Appearance: Colorless solid

Melting Point: 22-24 C

Boiling Point: 56-57 C

Boc anhydride has a melting point of only 22-24 C. It often starts to melt while being weighed out for a reaction. In order to use boc anhydride as a solid, it should be kept in a refrigerator and weighed out soon after being removed from the refrigerator.

Common Uses:

Reagent in the Boc protection of amines

Procedure excerpt:

To a solution of the SM (15 g, 43 mmol) and (Boc)2O (23 g, 105 mmol) in DCM (150 mL) was added TEA (19 mL, 140 mmol). The reaction mixture was stirred . . .

[full procedure]

Safety:

Boc anhydride causes eye and skin irritation and is harmful if inhaled. Boc anhydride is also a flammable solid. Care should be taken when running boc deprotections because it is a gas forming reaction.

References:

1) Patent Reference: WO2014177977, page 65, (6.0 MB)

2) Wikipedia: Di-tert-butyl dicarbonate (link)

3) www.sigmaaldrich.com: Di-tert-butyl dicarbonate (link)

4) www.alfa.com: A14708 Di-tert-butyl dicarbonate, 97+% (link)