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Bis(chloromethyl) ether
IUPAC name	bis(chloromethyl) ether
Other names	bis-CME, chloro-(chloromethoxy)methane, oxybis[chloromethane]
Abbreviations	BCME
Identifiers
CAS number	542-88-1
PubChem	10967
EC number	208-832-8
SMILES	ClCOCCl
InChI	1/C2H4Cl2O/c3-1-5-2-4/h1-2H2
InChI key	HRQGCQVOJVTVLU-UHFFFAOYAN
ChemSpider ID	21106500
Properties
Molecular formula	C2H4Cl2O
Molar mass	114.96 g mol−1
Melting point	-41.5 °C, 232 K, -43 °F
Boiling point	106 °C, 379 K, 223 °F
Hazards
Main hazards
Flash point	38 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Bis(chloromethyl) ether is an organic compound with the chemical formula (CH₂Cl)₂O. It is one of the chloroalkyl ethers. This colourless liquid is used for chloromethylation of aromatic substrates. It is produced industrially from paraformaldehyde and a mixture of chlorosulfonic acid and sulfuric acid.^[1]

Safety

Bis(chloromethyl) ether is carcinogenic.

Synthesis

References

1. ^ Wilhelm Heitmann, Günther Strehlke, Dieter Mayer “Ethers, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a10_023