Chloromethyl dichloromethyl ether

The adducts 2 of (chloromethoxy)carbene (generated from chloromethyl dichloromethyl ether using alkyllithium as base) are of limited stability. They form stable methoxymethoxycyc-lopropanes 3 on reaction with sodium methoxide. These products do not react with mineral acids." ... 

The reaction of methoxycarbene (generated from chloromethyl dichloromethyl ether using methyllithium as the base) with twelve-membered cycloalkenes, dienes and trienes reveals that the carbene undergoes faster addition across E than Z double bonds, and that Z-configurated double bonds react stereoselectively (see also the example in Houben-Weyl Vol. El 9 b, p 1636), e.g. formation of 4 and 5. 

Chloromethyl dichloromethyl ether, CH2C10CHC12, reacts similarly to di-chloromethyl methyl ether.1123... 

Synonyms BCME Bis(chloromethyl) ether Bis-CME BRN 1679223 CCRIS 90 Chloro-(chloromethoxy)methane Chloromethyl ether Dimethyl-l,l -dichloroether sj/ 3-Dichlorodimeth-yl ether Dichloromethyl ether EINECS 208-832-8 Oxybis(chloroethane) RCRA waste number P016 UN 2249. 

Anticipated products from the reaction of sym-dichloromethyl ether with ozone or OH radicals in the atmosphere, excluding the decomposition products formaldehyde and HCl, are chloromethyl formate and formyl chloride (Cupitt, 1980). 

Chloromethyl methyl ether may contain 1 to 8% 57/ -dichloromethyl ether as an impurity (Environment Canada, 1993a). 

Bis(chloromethyl) ether, see sjm-Dichloromethyl ether Bis(2-chloro-l-methylethyl) ether, see Bis(2-chloroiso-propyl) ether... 

Chloro-3-hydrox34oluene, see p-Chloro-ro-cresol 2-Chloroisopropyl ether, see Bis(2-chloroisopropyl) ether p-Chloroisopropyl ether, see Bis(2-chloroisopropyl) ether Chloromethane, see Methyl chloride (Chloromethyl)benzene, see Benzyl chloride Chloromethyl bromide, see Bromochloromethane Chloromethyl ether, see sym-Dichloromethyl ether (Chloromethyl)ethylene oxide, see Epichlorohydrin (2-Chloro-l-methylethyl) ether, see Bis(2-chloroisoprop-yl)... 

Bis(2-chloroisopropyl) ether Chloromethyl formate, see sjm-Dichloromethyl ether 1 Chloro-2-methylnaphthalene, see 2-Methylnaphthalene... 

Dichloromethyl methyl ether (98%) was purchased from Aldrich Chemical Company, Inc. (listed as a, a-dichloromethyl methyl ether), and used without purification. Better results can be obtained if the material is distilled under nitrogen prior to use. Unlike chloromethyl methyl ether and bis(chloromethyl) ether, dichloromethyl methyl ether is reported to have no significant carcinogenic activity.6 However, as a precaution it should be handled carefully in a well-ventilated hood. 

Chloromethyl methyl ether and bis-chloromethyl ether (CICH2 OCH2Cl) in common with several alkylating agents possess carcinogenic properties in experimental animals and have been listed as assumed human carcinogens similar hazardous properties associated with dichloromethyl methyl ether have not been reported but it would be prudent to handle this compound with due care. 

Chemical Name chloromethyl ether, sym-dichloromethyl ether... 

However, in the particular case of the halogenated methyl ethers it is preferable, especially in their industrial manufacture, to commence with formaldehyde (or its polymers) and the hydrogen halide. In this case the reaction takes place in two stages for instance, in the preparation of dichloromethyl ether, chloromethyl alcohol is formed first ... 

Synonyms BCME sym-Dichloromethyl ether Di-chloromethyl ether... 

Usually chloromethyl or dichloromethyl ethers are the starting materials in the former two methods. Aryloxycyclopropanes have been prepared from aryl chloromethyl ethers, butyl-lithium and an alkene. For the synthesis of alkoxycyclopropanes alkylchloromethyl and alkyidichloromethyl ethers have been utilized. In the second method the use of methyllithium prepared from iodomethane is recommended since it contains iodide ions which facilitate the reaction to substitute the chlorine in the chloro ethers (commercial methyllithium gives... 

Method A chloromethyl ether, base Method B dichloromethyl ether, base. 

Bis(chloromethyl) ether, BCME, dichloromethyl ether, chloromethyl ether, Cici. Colourless liquid, bp 106°C, suffocating odour decomposes in moist air to HC1 and formaldehyde eye and respiratory irritant, acts on labyrinth, producing staggering. Used as a war gas and as a solvent for ethyl dichloroarsine and mustard gas. 

Synonyms/Trade Names BCME, bis-CME, Chloromethyl ether, Dichlorodimethyl ether, Dichloromethyl ether, Oxybis(chloromethane) ... 

Dichloromethyl ether sym-Dichloromethyl ether. See Bis (chloromethyl) ether... 

Several chlorophyll derivatives have been prepared by electrophilic substitution, inter alia by formylation reactions. Adopting methods from corrin chemistry.50 alkylation with chloro-methyl methyl ether (caution toxic),32k chloromethyl methyl sulfide,51 and dichloromethyl methyl ether (caution toxic)52 in the presence of Lewis acids are the methods of choice to introduce carbon residues into the chlorin frame work. The compounds listed below have been prepared by these methods. 

A number of chlorinated poly(ethers) have practical uses. A common compound from this group is polyepichlorohydrin, [-CH(CH2CI)CH20-]n. Polyepichlorohydrin has practical applications as an elastomer and is used in copolymers with propylene oxide, ethylene oxide, allyl glycidyl ether (1-allyloxy-2,3-epoxypropane), etc. Another example is poly oxy[2,2 -bis(chloromethyl)-1,3-propandiyl] or poly[oxy-1,3-(2,2 -dichloromethyl)propylene], CAS 25323-58-4, which can be used as inert lining material for chemical plant equipment, as adhesive, coating material, etc. This macromolecule can be prepared starting with pentaerythritol in the sequence of reactions shown below ... 

Olefin additions Bromine azide. Bromine chloride. Bromine (chlorine) dipyridine nitrate. N-Bromoacetamine. N-Bromoacetamide-DMSO-Water. N-Bromoacetamide-Hydrogen fluoride. n-Butyllithium. Dichloroketene. Dichloromethyl 2-chloromethyl ether. N,N-Dichlorourethane. Dichlorovinylene carbonate. Difluoramine. Ethyl azidoformate. Ethyl bromoacetate. Iodine azide. Iodine isocyanate. Iodine nitrate, lodobenzene dichloride. 1-lodoheptafluoropropane. Mercuric acetate. Nitrosyl chloride. Nitrosyl fluoride. Nitryl iodide. Rhodium trichloride. Silver fluoride. 

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