Benzyl chloroformate

Benzyl chloroformate
Names
	IUPAC names Benzyloxycarbonyl chloride; Benzyl chloroformate
	Other names Z-Chloride
Identifiers
CAS Number	501-53-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	9958 ;
ECHA InfoCard	100.007.205
PubChem CID	10387;
CompTox Dashboard (EPA)	DTXSID9027158 ;
	InChI InChI=1S/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2 Key: HSDAJNMJOMSNEV-UHFFFAOYSA-N ; InChI=1/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2 Key: HSDAJNMJOMSNEV-UHFFFAOYAW;
	SMILES ClC(=O)OCc1ccccc1;
Properties
Chemical formula	C8H7ClO2
Molar mass	170.59 g·mol−1
Density	1.195 g/cm3
Boiling point	103 °C (217 °F; 376 K) (20 Torr)
Hazards
Flash point	80 °C (176 °F; 353 K)
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.

Preparation

It is prepared in the lab by dropping benzyl alcohol into liquid phosgene at −20 °C. Phosgene is used in excess to minimise the production of the carbonate.^[1]

Uses

Benzyl chloroformate is used in organic synthesis for the introduction of the carboxybenzyl (abbreviated 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 are used.

References

^ Hough, L.; Priddle, J. E. (1961). "Carbonate derivatives of methyl α-D-mannopyranoside and of D-mannose". J. Chem. Soc. 1961: 3178–3181. doi:10.1039/JR9610003178.

External links

International Chemical Safety Card 0990

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[1] Hough, L.; Priddle, J. E. (1961). "Carbonate derivatives of methyl α-D-mannopyranoside and of D-mannose". J. Chem. Soc. 1961: 3178–3181. doi:10.1039/JR9610003178.

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