Chlorodimethyl Ether

Chlorodimethyl ether is a colorless liquid which decomposes in water and in hot ethyl alcohol. It is soluble in acetone, carbon disulfide ond concentrated hydrochloric ocid. 

This ether is a colorless liquid which is an irritant to the mucous membrones. It is used as a raw material in organic syntheses. 

Constant-boiling mixtures (% by wt.) Ethyl ether 99% Carbon disulfide 1.0% B.P. at 760 mm. 34.5°C. 

Boiling range at 760 mm. Coefficient of exponsion at 20 C. Coefficient of expansion at 55°C. Constant boiling mixture (% by wt.) Dichlorethyl ether Water 

Specific gravity at 20/20 C. Specific heat (at 20-30 C.) Surface tension at 25°C. Solubility in water at 20 C. Solubility of water in dichlorethyl ether at 20°C. 

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The chloromethylation of 2,6-dimethyl- and 2,5-diethyl-thiophene both with chlorodimethyl ether and formaldehyde and hydrochloric acid gives a mixture of mono- and di-chloromethylated product. " The former reagent gives the larger proportion of monochloromethyl-ated product. " If the chloromethylation is carried out in the presence of zinc chloride, (120) and (121) are obtained. ... 

Dichloromethyl methyl ether has been prepared by the chlorination of chlorodimethyl ether in the liquid5-4 or gas phase,5 by the reaction of chlorodimethyl ether with sulfuryl chloride and benzoyl peroxide,6 7 and by the treatment of methyl formate with phosphorus pentachloride.8-10... 

This method fails, however, with bicyclic ketones such as 1-tetralones even in the presence of TsOH, affording only enol trimethylsilyl ethers such as 107 a [114, 115]. A subsequent investigation revealed that cyclohexanone reacts with equivalent amounts of N-trimethylsilyldimefhylamine 463 in the presence of TMSOTf 20 at -30 °C to give the enol silyl ether 107 a, whereas reaction of cyclohexanone, benzaldehyde, and chlorodimethyl ether with 463 and TMSOTf 20 or TCS 14 at 1-20 °C afforded the iminium salts 547, 548, and 549 in high yield [116-118]. Analogously, N-trimethylsilylpyrrolidine 550 and N-trimethylsilylmorphoHne 294 convert aldehydes such as benzaldehyde, at ambient temperature in the presence... 

Retardation of solvolysis by common anions, a characteristic feature of Sifl reaction (Ingold, 1953a), was found to be substantial for 4-methoxy-diphenylmethyl chloride (Bailey ef cU., 1966) but could not be detected when the suWrate was the equally reactive chlorodimethyl ether (Hallas and Kohnstam, unpublished work). As the magnitude of this retardation roughly parallels the reactivity of the substrate (see Bailey et al., 1966), these observations are consistent with the view that the chloro-ether does not undergo entirely Sul solvolysis. 

Beilstein Handbook Reference) BRN 0506943 CCRIS 138 Chlordimethylether Chlorodimethyl ether Chloromethoxymethane Chloromethyl methyl ether a,a-Dichlorodimethyl ether Dimethylchloroether EINECS 203-480-1 Ether, chloromethyl methyl Ether, dimethyl chloro Ether methylique monochlore HSDB 908 Methane, chloromethoxy- Methoxychloromethane Methoxy-methyl chloride Methyl chloromethyl ether Monochlorodimethyl ether Monochloromethyl methyl ether NSC 21208 RCRA waste number U046 UN1239, Liquid mp = -103,5° bp = 59.5° d = 1.063 soluble in EtOH, Et20, Me2CO, CHCI3. 

SYNONYMS Chlorodimethyl ether, chloromethyoxymethane, dimethylchloroether, methylchloromethyl ether, monochlorodimethyl ether. 

SYNONYMS chlorodimethyl ether, chloromethoxymethane, dimethylchloroether, meth-... 

Synonyms/Trade Names Chlorodimethyl ether, Chloromethoxymethane. CMME, Dimethylchloroether, Methylchloromethyl ether ... 

Synonyms chlorodimethyl ether dimethyl-1 1 -dichloroether oxybis(chloromethane) chloro(chloromethoxy)methane... 

Chlowmethylation reactions of the aromatic rings of polystyrene and styrene copolymers are being carried out extensively. Chlorodimethyl ether (a carcinogen) is a good solvent for these... 

DL-2-(p-Chloro-a-2-(dimethylamino) ethylbenzyl) pyridine bimaleate 2-(p-Chloro-a-(2-(dimethylamino) ethyl) benzyl) pyridine maleate (1 1). See Chloropheniramine maleate Chlorodimethyl ether. See Chloromethyl methyl ether... 

Stork and co-workers investigated the use of silyl acetals as tethers for the stereoselective formation of (3-mannosides [56]. Initial studies were performed on primary acceptors of glucose 57 and mannose. Glucosyl acceptor 57 is first converted to its chlorodimethyl ether derivative by treatment with n-butyllithium... 

Stannic chloride is a very effective catalyst for this Friedel-Craft reaction [186]. lodomethylation can also be carried out in the same manner with similar results [179]. When the reactions are carried out on cross-linked styrene copolymers with chlorodimethyl ether and stannic chloride catalyst, they are accompanied by strong morphological changes [187]. If these reactions are carried out with low levels of chloromethylating agents or catalysts, they occur more or less homogeneously. Larger levels... 

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