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Dimethyl methylphosphonate

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Dimethyl methylphosphonate Basic information

Product Name:
Dimethyl methylphosphonate
Synonyms:
  • Dimethoxymethylphosphine oxide
  • dimethoxymethylphosphineoxide
  • Dimethyl ester of methylphosphonic acid
  • dimethylmethanephosphate
  • Furan tf 2000
  • Fyrol dmmp
  • fyroldmmp
  • Metaran
CAS:
756-79-6
MF:
C3H9O3P
MW:
124.08
EINECS:
212-052-3
Product Categories:
  • organophosphorus compound
  • C-C Bond Formation
  • Miscellaneous
  • Horner-Emmons Reaction
  • Horner-Wadsworth-Emmons Reagents
  • Olefination
  • Synthetic Organic Chemistry
  • Wittig & Horner-Emmons Reaction
Mol File:
756-79-6.mol
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Dimethyl methylphosphonate Chemical Properties

Melting point:
<50°
Boiling point:
181 °C(lit.)
Density 
1.145 g/mL at 25 °C(lit.)
vapor pressure 
<0.1 mm Hg ( 20 °C)
refractive index 
n20/D 1.413(lit.)
Flash point:
156 °F
solubility 
Chloroform, Methanol (Slightly, Heated)
form 
Liquid
pka
pKa (20°) in water: 2.37
Specific Gravity
1.16
color 
Clear colorless
Water Solubility 
>=10 g/100 mL at 21 ºC
Merck 
14,3391
BRN 
878263
Stability:
Stability Combustible. Incompatible with strong oxidizing agents, strong bases. May soften some rubbers or plastics. Hydrolyzes slowly in contact with water.
LogP
-0.61
Dissociation constant
2.37 at 20℃
CAS DataBase Reference
756-79-6(CAS DataBase Reference)
NIST Chemistry Reference
Phosphonic acid, methyl-, dimethyl ester(756-79-6)
EPA Substance Registry System
Dimethyl methylphosphonate (756-79-6)
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Safety Information

Hazard Codes 
T,Xi
Risk Statements 
46-36-62
Safety Statements 
53-26-45
RIDADR 
2810
WGK Germany 
2
RTECS 
SZ9120000
Hazard Note 
Irritant/Toxic
TSCA 
Yes
Hazardous Substances Data
756-79-6(Hazardous Substances Data)
Toxicity
LD50 in rats, mice (mg/kg): 10190, >6810 orally (Rowland)

MSDS

  • Language:English Provider:DMMP
  • Language:English Provider:SigmaAldrich
  • Language:English Provider:ALFA
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Dimethyl methylphosphonate Usage And Synthesis

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

Dimethyl methylphosphonate Preparation Products And Raw materials

Preparation Products

Dimethyl methylphosphonateSupplier