Benzyl carbamate

Benzyl carbamate
Names
	Other names Carbamic acid, phenylmethyl ester
Identifiers
CAS Number	621-84-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2259788;
ChemSpider	11638;
ECHA InfoCard	100.009.738
EC Number	210-710-4;
PubChem CID	12136;
UNII	7890Q001S7;
CompTox Dashboard (EPA)	DTXSID00211159 ;
	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

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

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.
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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[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.