Chloromethyl methyl ether

Chemical Properties

Chloromethyl methyl ether is a volatile, highly flammable, corrosive liquid with an ethereal odor.

Uses

Chloromethyl methyl ether (CMME) is usedas a methylating agent in the synthesis ofchloromethylated compounds.

Hazard

Flammable, dangerous fire and explosion risk. Toxic by ingestion and inhalation. TLV: Suspected human carcinogen.

Health Hazard

The acute toxicity of chloromethyl methyl ether is moderate to high. Inhalation of the vapor is severely irritating to the eyes, skin, nose, and respiratory tract, and causes sore throat, fever, chills, and difficulty breathing. Exposure to high concentrations can lead to delayed pulmonary edema, which can be fatal. Eye or skin contact with the liquid can result in severe and painful burns. Ingestion of this substance may lead to severe burns of the mouth and stomach and can be fatal. Chloromethyl methyl ether is regulated by OSHA as a carcinogen (29 CFR 1910.1006) and is listed in IARC Group 1 ("carcinogenic to humans"). This substance is classified as a "select carcinogen" under the criteria of the OSHA Laboratory Standard. Note also that some commercial samples of chloromethyl methyl ether contain up to 7% of highly carcinogenic bis(chloromethyl) ether. Hydrolysis of chloromethyl methyl ether produces HCl and formaldehyde, which can recombine to form bis(chloromethyl) ether. No information is available on the reproductive and developmental toxicity of chloromethyl methyl ether. Odor does not provide adequate warning of the harmful presence of this carcinogenic substance.

Fire Hazard

Chloromethyl methyl ether is highly flammable. Fires involving this substance should be extinguished with carbon dioxide or dry chemical extinguishers.

Flammability and Explosibility

Chloromethyl methyl ether is highly flammable. Fires involving this substance should be extinguished with carbon dioxide or dry chemical extinguishers.

Safety Profile

Confirmed human carcinogen with experimental carcinogenic, tumorigenic, and neoplastigenic data. Poison by inhalation. Moderately toxic by ingestion. Human mutation data reported. A very dangerous fire hazard when exposed to heat or flame. To fight fire, use alcohol foam,water, CO2, or dry chemical. Reaction with dvalent metals forms a very reactive product. When heated to decomposition it emits toxic fumes of Cl-. See also ETHERS and CHLORINATED HYDROCARBONS, ALIPHATIC.

Potential Exposure

Chloromethyl. methyl ether is a highly reactive methylating agent and is used in the chemical industry for synthesis of organic chemicals. Most industrial operations are carried out in closed process vessels so that exposure is minimized.

Carcinogenicity

Technical-grade chloromethyl methyl ether (CMME) are known to be human carcinogens based on sufficient evidence of carcinogenicity from studies in humans.

storage

work with this substance should be conducted in a fume hood to prevent exposure by inhalation, and appropriate impermeable gloves and splash goggles should be worn at all times to prevent skin and eye contact. Chloromethyl methyl ether is also highly flammable and should be used only in areas free of ignition sources; quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers in secondary containers.

Shipping

UN1239 Methyl chloromethyl ether, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquid, Inhalation Hazard Zone A. PGI.

Purification Methods

If suspect (check IR), shake it with saturated aqueous CaCl2 solution, dry over CaCl2 and fractionally distil taking middle fraction. [Marvel & Porter Org Synth Coll Vol I 377 1941, Beilstein 1 H 580, 1 I 304, 1 II 645, 1 III 2587, 1 IV 3046.] VERY TOXIC and CARCINOGENIC.

Incompatibilities

May form explosive mixture with air. May be able to form unstable and explosive peroxides on contact with oxygen. Contact with (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Decomposes on contact with water, forming hydrochloric acid and formaldehyde. Attacks various metals in presence of water.

Waste Disposal

Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced.

Raw materials

Preparation Products