Bis(2-Chloromethyl)Ether CASNO: 542-88-1

Bis(chloromethyl) ether (BCME), is a clear, volatile, colorless liquid with a strong, irritating odor, known for its high reactivity as an alkylating agent, with properties like

a boiling point of ~106°C, a melting point of around -41.5°C, and a density of ~1.33 g/cm³ at room temp, but it’s a potent carcinogen, so it’s handled with extreme caution.

Key Physical Properties 

Appearance: Clear less to slight yellow colored liquid

Odor: Strong, unpleasant, irritating

Molecular Formula:

Molar Mass: 114.95 g/mol

Melting Point: -41.5°C (-42.7°F)

Density: ~1.33 g/cm³ (at 15°C)

Solubility: Readily dissolves in water but degrades rapidly.

Vapor Pressure: Significant, ~30 mmHg at 22°C.

Moisture Content  :0.5%

Boiling Range            :104 – 106°C

Purity by GC :Min 96%

Important Considerations

Carcinogen: Classified as a probable human carcinogen, causing severe respiratory and skin damage.

Reactivity: A powerful alkylating agent, it decomposes in water and reacts with moisture.

Usage: Highly restricted; primarily used in enclosed systems for manufacturing other chemicals.

Uses:

Chemical Intermediate: For manufacturing plastics, ion-exchange resins, polymers, paints, and varnishes.

Alkylating Agent: Used to introduce alkyl groups in organic synthesis.

Crosslinking Agent: In the textile industry and resin production.

Chloromethylation: For adding chloromethyl groups to aromatic compounds.

Lab Reagent: Small amounts used in controlled laboratory settings.

Antidote Synthesis: Historically used in making nerve agent antidotes like obidoxime.

Key Considerations:

Extreme Hazard: BCME is a known human carcinogen, leading to strict regulation and limited production.

Formation: Can form spontaneously from formaldehyde and hydrogen chloride, making it a hazardous impurity.

Current Status: Production is minimal and confined to highly controlled, enclosed systems for synthesizing other compounds.

Key Applications

Polymer & Resin Manufacturing: Used to create plastics, ion-exchange resins, and for crosslinking cellulose.

Chemical Synthesis: Acts as an intermediate for organic synthesis, including the preparation of certain nerve agent antidotes (like obidoxime) and for chloromethylation of aromatic compounds.

Textile Industry: Historically used for flame-retardant fabrics and surface treatments for rubber.

Laboratory Reagent: Used in controlled settings for research.

Important Context

Formation: It can form spontaneously from formaldehyde and hydrogen chloride in warm, moist air, and is often a byproduct in the production of chloromethyl methyl ether (CMME).

Safety: BCME is a known carcinogen, so its production and use are extremely limited, occurring only in closed systems with strict safety measures to prevent inhalation exposure.