Benzyl carbamate

Chemical compound

Benzyl carbamate is the organic compound with the formula C₆H₅CH₂OC(O)NH₂. The compound can be viewed as the ester of carbamic acid (O=C(OH)(NH₂)) and benzyl alcohol, although it is produced from benzyl chloroformate with ammonia.^[1] It is a white solid that is soluble in organic solvents and moderately soluble in water. Benzyl carbamate is used as a protected form of ammonia in the synthesis of primary amines. After N-alkylation, C₆H₅CH₂OC(O) group is removable with Lewis acids.^[2]

References

1. Meyer, Hartmut; Beck, Albert K.; Sebesta, Radovan; Seebach, Dieter (2008). "Benzyl Isopropoxymethyl Carbamate - an Aminomethylating Reagent for Mannich Reactions of Titanium Enolates". Organic Syntheses. 85: 287. doi:10.15227/orgsyn.085.0287.
2. Sanchez-Sancho, Francisco; Romero, Jose Antonio; Fernandez-Ibanez, M. Angeles (2010). "Benzyl Carbamate". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01206. ISBN 978-0471936237.