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Properties of substance:

chloro(chloromethoxy)methane

Synonyms:

bis(chloromethyl)ether

Group of substances:

organic

Physical appearance:

colorless liquid

Empirical formula (Hill's system for organic substances):

C2H4Cl2O

Structural formula as text:

ClCH2OCH2Cl

Molar/atomic mass: 114.9586

Melting point (°C):

-41.3

Boiling point (°C):

102

CAS №: 542-88-1

Solubility (g/100 g of solvent):

organic solvents: soluble [Ref.]
water: insoluble [Ref.]

Synthesis 1:

Reference: Evans, L., & Gray, R. Preparation of Certain Polychlorodimethyl Ethers / Journal of Organic Chemistry. - 1958. - Vol. 23, No. 5 pp. 746 [doi: 10.1021/jo01099a602]


CH3OCH2Cl + Cl2 → ClCH2OCH2Cl + HCl

A 2-liter, 3-necked flask which was equipped with a mechanical stirrer, condenser and ice trap, thermometer, and sintered-glass disk inlet tube was charged with 322 g. (4.0 moles) of chloromethyl methyl ether and 1232 g. (8.0 moles) carbon tetrachloride. The flask was illuminated with a 275-watt ultraviolet bulb. Chlorine was admitted through the sintered disk at a rate of 200 ml./min. until 142 g. (2.0 moles) had been introduced. The heat of reaction maintained the system at reflux. Fractionation of the product produced 163 g. (1.4 moles) bis(chloromethyl) ether; b.p. 103—105°, n(20, D) 1.4421 and 24 g. (0.2 mole) dichloromethyl methyl ether; b.p. 82—84°, n(20, D) 1.4353.

Anal. Calcd. for ClCH2OCH2Cl: Sapon. Equiv., 57.5; Cl, 61.68. Found: Sapon. Equiv., 57.3; Cl, 61.81.

References:

  1. Pohanish R.P. Sittig's Handbook of Toxic and Hazardous Chemicals and Carcinogens. - 6 ed. - Elsivier, 2012. - pp. 388-391
  2. Лос К. Синтетические яды. - М.: ИИЛ, 1963. - pp. 51 [Russian]
  3. Химический энциклопедический словарь. - Под ред. Кнунянц И.Л. - М.: Советская энциклопедия, 1983. - pp. 189 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru