| | 24424-99-5 Basic information More.. |
| Product Name: | Di-tert-butyl dicarbonate | | Synonyms: | RARECHEM TB OC 0001;Di-tert-butyl dicarbonate,Diboc;DI-TERT-BUTYL PYROCARBONATE GRADE II;DI-TERT-BUTYL DICARBONATE, 1.0M SOLUTION IN TETRAHYDROFURAN;DI-TERT-BUTYL DICARBONATE, REAGENTPLUS, >=99%;Di-tert-butyl dicarbonate, 99%+ (Phosgene-free);Di-tert-butyldicarbonate,97+%;DI-TERT-BUTYL DICARBONATE (DI-BOC) (BOC-2O) | | CAS: | 24424-99-5 | | MF: | C10H18O5 | | MW: | 218.25 | | EINECS: | 246-240-1 | | Mol File: | 24424-99-5.mol |  |
Use
Di-tert-butyl dicarbonate (Boc2O) and di-tert-butyl tricarbonate ((BocO)2CO) have been used as amine carbonylating reagents to obtain linear or branched aliphatic isocyanates.
most of the known methods for transforming amines into isocyanates are not mild enough and furnish undefined products as a result of uncontrolled side reactions. However, 4-dimethylaminopyridine (DMAP)-catalyzed reaction with activated carbonates as C1 building blocks constitutes a convenient laboratory method for the phosgene-free isocyanation of amines. A procedure has been described whereby alkyl- and arylamines are converted into isocyanates in high yields by reaction with activated carbonates (for example, di-tert-butyl dicarbonate, Boc2O) in the presence of a catalytic amount of a nucleophilic nitrogen base at room temperature.
Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. The reaction of substituted anilines with Boc2O in the presence of a stoichiometric amount of 4-dimethylaminopyridine (DMAP) in an inert solvent (acetonitrile, dichloromethane, ethyl acetate, tetrahydrofuran, toluene) at room temperature leads to aryl isocyanates in almost quantitative yields within 10 min.
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24424-99-5
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