Dimethyl methylphosphonate

Chemical Properties

colourless liquid

Uses

As a flame retardant, a preignition additive for gasoline, an antifoam agent, a plasticizer and stabilizer, a textile conditioner, and an antistatic agent; used experimentally to mimic the physical and spectroscopic (but not biological) properties of anticholinesterase agents

Uses

Dimethyl methylphosphonate is used as a catalyst and a reagent in organic synthesis for the conversion of esters to ketophosphonates. It is an additive for the synthesis of unsaturated polyester resin which has flame retardant high phosphorous and UV-cured epoxy acrylate. It finds application as hydraulic fluids as well.

Uses

NMR probe for cell volume. Flame retardant. Simulant for nerve agents.

Synthesis Reference(s)

Synthetic Communications, 20, p. 239, 1990 DOI: 10.1080/00397919008052289

General Description

Clear colorless liquid with a pleasant odor.

Air & Water Reactions

Highly flammable. Water soluble. Hydrolyzes slowly upon contact with water.

Reactivity Profile

Dimethyl methylphosphonate is incompatible with strong oxidizing agents and strong bases. Dimethyl methylphosphonate reacts with organic halides at 302-392° F. When heated to temperatures greater than 302° F, Dimethyl methylphosphonate will act as an alkylating agent with basic nitrogen compounds and phenols. Dimethyl methylphosphonate reacts with enol lactones. Dimethyl methylphosphonate has plasticizing properties and may soften or deteriorate some plastics and elastomers (particularly vinyl-based resins, neoprene and natural rubbers) upon contact.

Health Hazard

Dimethyl methylphosphonate (DMMP) administered to male rats is a reproductive toxicant and carcinogen. Effects in humans are unknown.

Fire Hazard

Dimethyl methylphosphonate is combustible.

Safety Profile

Moderately toxic by intravenous route. Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. An experimental nerve gas stimulant. A flame retardant. When heated to decomposition it emits toxic fumes of POx

Toxics Screening Level

The ITSL for dimethyl methyl phosphonate is 700 μg/m3 based on an annual averaging time.