Dimethyl methylphosphonate

Dimethyl methylphosphonate Basic information
Product Name:Dimethyl methylphosphonate
Synonyms:Furan tf 2000;fyroldmmp;Metaran;methyl-phosphonicacidimethylester;NCI-C54762;o,o-Dimethyl methylphosphonate;Phosphonicacid,methyl-,dimethylester;Pyrol DMMP
CAS:756-79-6
MF:C3H9O3P
MW:124.08
EINECS:212-052-3
Product Categories:organophosphorus compound;C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination;Miscellaneous;Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction
Mol File:756-79-6.mol
Dimethyl methylphosphonate Structure
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.)
Fp 156 °F
solubility Chloroform, Methanol (Slightly, Heated)
pkapKa (20°) in water: 2.37
form Liquid
color Clear colorless
Specific Gravity1.16
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 constant2.37 at 20℃
CAS DataBase Reference756-79-6(CAS DataBase Reference)
NIST Chemistry ReferencePhosphonic acid, methyl-, dimethyl ester(756-79-6)
EPA Substance Registry SystemDimethyl methylphosphonate (756-79-6)
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 Data756-79-6(Hazardous Substances Data)
ToxicityLD50 in rats, mice (mg/kg): 10190, >6810 orally (Rowland)
MSDS Information
ProviderLanguage
DMMP English
SigmaAldrich English
ALFA English
Dimethyl methylphosphonate Usage And Synthesis
Chemical Propertiescolourless liquid
UsesNMR probe for cell volume. Flame retardant. Simulant for nerve agents.
UsesAs 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
UsesDimethyl 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.
Synthesis Reference(s)Synthetic Communications, 20, p. 239, 1990 DOI: 10.1080/00397919008052289
General DescriptionClear colorless liquid with a pleasant odor.
Air & Water ReactionsHighly flammable. Water soluble. Hydrolyzes slowly upon contact with water.
Reactivity ProfileDimethyl 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 HazardDimethyl methylphosphonate (DMMP) administered to male rats is a reproductive toxicant and carcinogen. Effects in humans are unknown.
Fire HazardDimethyl methylphosphonate is combustible.
Safety ProfileModerately 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 ProductsDIMETHYL 3,3-DIMETHYL-2-OXOHEPTYLPHOSPHONATE-->METHYLPHOSPHONICACIDMETHYL-1-METHYLETHYLESTER-->(4R-cis)-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethylidene)naphthalen-2(3H)-one-->Trimethyl phosphate-->METHYLPHOSPHONIC ACID-->Dimethyl (2-Oxononyl)phosphonate -->PHENYLPHOSPHONIC ACID DIMETHYL ESTER-->Methanol-->Methanesulfonic acid
TrifluoroMethyl Dechloro Travoprost Impurity 19 (R)-4-fluoro-2-((3-methyl-2,4-dioxo-6-(piperidin-3-ylamino)-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (3-TRIFLUOROMETHYLPHENOXY) ACETIC ACID ETHYL ESTER Trelagliptin succinate 2-((6-chloro-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)Methyl)-4-fluorobenzonitrile (-)-Corey aldehyde benzoate (3-TRIFLUOROMETHYL-PHENOXY)-ACETIC ACID 5-Heptenoic acid, 7-[(1S,2S,3S,5R)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoroMethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-, 1-Methylethyl ester, (5Z)- Trelagliptin Impurity YYJ 208114-58-3 Travoprost Impurity 11 Phosphonic acid, ethenyl-, bis(2-chloroethyl) ester, polymer with dimethyl methylphosphonate TRIETHYL PHOSPHONOACETATE phosphorus pentoxide/dimethyl methylphosphonate ethoxylate DIMETHYL TRIMETHYLSILYLMETHYLPHOSPHONATE Dimethyl sebacate TRIMETHYLSILYL DIETHYLPHOSPHONOACETATE

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