Benzyl chloromethyl ether

Benzyl chloromethyl ether
Names
	Preferred IUPAC name Chloromethoxymethylbenzene
	Other names BOM chloride; benzyloxymethyl chloride;
Identifiers
CAS Number	3587-60-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	121628;
ECHA InfoCard	100.157.155
EC Number	628-927-1;
PubChem CID	137983;
UNII	9GR9P34HWY;
CompTox Dashboard (EPA)	DTXSID10956786 ;
	InChI InChI=1S/C8H9ClO/c9-7-10-6-8-4-2-1-3-5-8/h1-5H,6-7H2 Key: LADPCMZCENPFGV-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)COCCl;
Properties
Chemical formula	C8H9ClO
Molar mass	156.61 g·mol−1
Density	1.1350
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H318, H331, H334
Precautionary statements	P233, P260, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P321, P330, P332+P317, P342+P316, P362+P364, P403, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Benzyl chloromethyl ether is a chemical compound with the chemical formula C₆H₅CH₂OCH₂Cl. Like similar chloroalkyl ethers, it is an alkylating reagent, and is primarily used to prepare benzyloxymethyl protecting groups for alcohols in organic synthesis.

Preparation

Benzyl chloromethyl ether may be prepared from benzyl alcohol, formaldehyde, and hydrogen chloride in anhydrous conditions.^[1]

Benzyl chloromethyl ether has the typical reactions of a chloroalkyl ether. In particular, it reacts with all types of alcohol in the presence of a weak, sterically hindered base such as N,N-diisopropylethylamine. This reaction yields benzyloxymethyl ethers, a protecting group similar to methoxymethyl ethers but with some properties of benzyl ethers. Like benzyl ethers, benzyloxymethyl ethers can be removed by hydrogenolysis with palladium on carbon or by Birch reduction.^[2]

Like many alkylating agents, benzyl chloromethyl ether is cytotoxic and a probable human carcinogen. Hydrolysis and alcoholysis yield hydrogen chloride.

↑ D. S. Connor, G. W. Klein, G. N. Taylor, R. K. Boeckman, Jr., and J. B. Medwid. (1972). "Benzyl chloromethyl ether". Organic Syntheses. 52: 16{{cite journal}}: CS1 maint: multiple names: authors list (link).
↑ Philip J. Kocienski (2005). Protecting Groups. Georg Thieme Verlag. p. 301. ISBN 3-13-135603-0.