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Dimethyl methylphosphonate

CAS No.
756-79-6
Chemical Name:
Dimethyl methylphosphonate
Synonyms
DMMP;Fyrol dmmp;DIMETHYL METHANEPHOSPHONATE;Metaran;pyroldmmp;NSC 62240;fyroldmmp;NCI-C54762;Pyrol DMMP;Reoflam DMMP
CBNumber:
CB8418753
Molecular Formula:
C3H9O3P
Molecular Weight:
124.08
MDL Number:
MFCD00008349
MOL File:
756-79-6.mol
MSDS File:
SDS
Last updated:2023-05-15 10:43:23

Dimethyl methylphosphonate 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)
pka pKa (20°) in water: 2.37
form Liquid
color Clear colorless
Specific Gravity 1.16
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 constant 2.37 at 20℃
CAS DataBase Reference 756-79-6(CAS DataBase Reference)
FDA UNII 20Z996230U
NIST Chemistry Reference Phosphonic acid, methyl-, dimethyl ester(756-79-6)
EPA Substance Registry System Dimethyl methylphosphonate (756-79-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H319-H340-H361f
Precautionary statements  P201-P305+P351+P338-P308+P313
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
Toxicity LD50 in rats, mice (mg/kg): 10190, >6810 orally (Rowland)
NFPA 704
2
3 0

Dimethyl methylphosphonate Chemical Properties,Uses,Production

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

77-99-6
121-45-9
756-79-6
Synthesis of Dimethyl methylphosphonate from Trimethylolpropane and Trimethyl phosphite
Furan tf 2000 fyroldmmp Metaran methyl-phosphonicacidimethylester NCI-C54762 o,o-Dimethyl methylphosphonate Phosphonicacid,methyl-,dimethylester Pyrol DMMP NSC 62240 Reoflam DMMP pyroldmmp METHYLPHOSPHONIC ACID DIMETHYL ESTER DIMETHYL METHYLPHOSPHONATE METHANEPHOSPHONIC ACID DIMETHYL ESTER Dimethylmethylphosphonate,97% Methylphosphonsuredimethylester Dimethyl ester methylphosphonic acid (Methoxy-methylphosphoryl)oxymethane Phosphonic acid,P-Methyl-, diMethyl ester DiMethyl Methylphosphonate 97% Dimethyl ester of methylphosphonic acid dimethylmethanephosphate Dimethoxymethylphosphine oxide dimethoxymethylphosphineoxide Dimethyl Methylphosphonate,>98% Fyrol dmmp DIMETHYL METHANEPHOSPHONATE DMMP Travoprost Impurity 40 Rivastigmine Impurity 4 L-Tartrate(Rivastigmine EP Impurity D L-Tartrate) Dimethyl methylphosphonate(97.85%) 756-79-6 C3H9O3P CH3O2POCH3 CH3POOCH32 Synthetic Reagents Olefination Horner-Wadsworth-Emmons Reagents C-C Bond Formation Horner-Emmons Reaction Wittig & Horner-Emmons Reaction organophosphorus compound C-C Bond Formation Horner-Wadsworth-Emmons Reagents Olefination Miscellaneous Horner-Emmons Reaction Synthetic Organic Chemistry Wittig & Horner-Emmons Reaction