Benzyl carbamate

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Benzyl carbamate
Bncarbamate.png
Names
Preferred IUPAC name
Benzyl carbamate
Other names
Carbamic acid, phenylmethyl ester
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.738 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-710-4
PubChem CID
UNII
  • 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
  • C1=CC=C(C=C1)COC(=O)N
Properties
C8H9NO2
Molar mass 151.165 g·mol−1
Appearancewhite solid
Melting point 88 °C (190 °F; 361 K)
moderate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.
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