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Benzyl carbamate

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Benzyl carbamate
Names
Preferred IUPAC name Benzyl carbamate
Other names Carbamic acid, phenylmethyl ester
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.738 Edit this at Wikidata
EC Number
  • 210-710-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H9NO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)Key: PUJDIJCNWFYVJX-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C=C1)COC(=O)N
Properties
Chemical formula C8H9NO2
Molar mass 151.165 g·mol
Appearance white solid
Melting point 88 °C (190 °F; 361 K)
Solubility in water moderate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
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. 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.

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.
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