Benzyl chloroformate

Benzyl chloroformate
IUPAC name Benzyloxycarbonyl chloride Benzyl chloroformate
Identifiers
CAS number	501-53-1 Y
PubChem	10387
ChemSpider	9958 Y
Jmol-3D images	Image 1
SMILES ClC(=O)OCc1ccccc1
InChI InChI=1S/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2 Y Key: HSDAJNMJOMSNEV-UHFFFAOYSA-N Y InChI=1/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2 Key: HSDAJNMJOMSNEV-UHFFFAOYAW
Properties
Molecular formula	C8H7ClO2
Molar mass	170.59 g mol−1
Density	1.195 g/cm3
Melting point	0 °C
Boiling point	103 °C (20 Torr)
Hazards
MSDS	External MSDS
EU Index	607-064-00-4
EU classification	C N Xn
R-phrases	R34, R50/53
S-phrases	(S1/2), S26, S45, S60, S61
Flash point	80 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Benzyl chloroformate is the benzyl ester of chloroformic acid. It is also known as benzyl chlorocarbonate and is an oily liquid whose color is anywhere from yellow to colorless. It is also known for its pungent odor. When heated, benzyl chloroformate decomposes into phosgene and if it comes in contact with water it produces toxic, corrosive fumes.

Benzyl chloroformate is used in organic synthesis for the introduction of the carboxybenzyl (Cbz or Z) protecting group for amines:

The newly formed Cbz protecting group can be removed under reductive conditions. Typically hydrogen gas and activated palladium on carbon is used.

External links

• International Chemical Safety Card 0990