Dichloromethyl methyl ether

Last updated
Dichloromethyl methyl ether
Dichloromethyl methyl ether.svg
Names
Preferred IUPAC name
Dichloro(methoxy)methane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.023.180 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/C2H4Cl2O/c1-5-2(3)4/h2H,1H3
  • ClC(Cl)OC
Properties
C2H4Cl2O
Molar mass 114.95 g·mol−1
Boiling point 85°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dichloromethyl methyl ether (HCl2COCH3) is an organic compound that belongs to the class of ethers with a dichloromethyl group and a methyl group. It can be synthesized from methyl formate and a mixture of phosphorus pentachloride and phosphorus oxychloride [1] or by chlorination of chlorodimethyl ether.

The compound is used in the formylation of aromatic compounds (Rieche formylation) and as a chlorination agent in the formation of acid chlorides. [2]

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Formylation reaction

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Chloromethyl methyl ether Chemical compound

Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. It is a chloroalkyl ether. It is used as an alkylating agent and industrial solvent to manufacture the detergent dodecylbenzyl chloride, water repellents and ion-exchange resins. In organic synthesis, it is used for introducing the methoxymethyl (MOM) protecting group, and is thus often called MOM-Cl or MOM chloride. It also finds application as a chloromethylating agent in some variants of the Blanc chloromethylation.

Rieche formylation is a type of formylation reaction. The substrates are electron rich aromatic compounds, such as mesitylene or phenols, with dichloromethyl methyl ether acting as the formyl source. The catalyst is titanium tetrachloride and the workup is acidic. The reaction is named after Alfred Rieche who discovered it in 1960.

Methylphosphonic acid dichloride Chemical compound

Methyl phosphonic dichloride is an organophosphorus compound. It has a number of potential uses but is most notable as being a precursor to several chemical weapons agents. It is a white crystalline solid, with a low melting point. It hydrolyzes readily and must be handled with care as it is exceedingly toxic.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

References

  1. Organic Syntheses , Coll. Vol. 5, p.365 (1973); Vol. 47, p.51 (1967). link
  2. Organic Syntheses, Coll. Vol. 7, p.467 (1990); Vol. 61, p.1 (1983). Link