Benzyl carbamate

Names
Preferred IUPAC name

Benzyl carbamate

Other names

Carbamic acid, phenylmethyl ester

Identifiers

CAS Number

* 621-84-1

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL2259788

ChemSpider |

* 11638

EC Number |

* 210-710-4

PubChem CID

* 12136

UNII |

* 7890Q001S7

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−1
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 [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

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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*[CID]: Compound ID