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Basic Information
| CAS No.: | 756-79-6 |
|---|---|
| Name: | Dimethyl methylphosphonate |
| Article Data: | 127 |
| Molecular Structure: | |
|
|
|
| Formula: | C3H9O3P |
| Molecular Weight: | 124.076 |
| Synonyms: | Phosphonicacid, methyl-, dimethyl ester (6CI,8CI,9CI);DMMP;Dimethoxymethyl phosphineoxide;Dimethyl methanephosphonate;Dimethyl methylphosphonate;Fran TF 2000;Fyrol DMMP;Metaran;Methanephosphonic acid dimethyl ester;Methylphosphonicacid dimethyl ester;NSC 62240;O,O-Dimethyl methylphosphonate;Reoflam DMMP; |
| EINECS: | 212-052-3 |
| Density: | 1.079 g/cm3 |
| Melting Point: | <50° |
| Boiling Point: | 181 °C at 760 mmHg |
| Flash Point: | 68.9 °C |
| Solubility: | >=10 g/100 mL at 21 ºC |
| Appearance: | colourless liquid |
| Hazard Symbols: |
 T
|
| Risk Codes: | 36-46 |
| Safety: | 53-26-45 |
| Transport Information: | UN No 199 |
| PSA: | 45.34000 |
| LogP: | 1.10210 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| In neat (no solvent) at 100℃; for 0.138833h; Solvent; Arbuzov Reaction; Flow reactor; | 99% |
| for 1h; Irradiation; | 95% |
| for 0.0833333h; Michaelis-Arbuzov reaction; microwave irradiation; | 95% |
Conditions
| Conditions | Yield |
|---|---|
| With iodine for 24h; Heating; | 99% |
| With trimethylsilyl trifluoromethanesulfonate In chloroform at 60℃; for 18h; Michaelis-Arbuzov rearrangement; | 98% |
| With trimethylsilyl iodide at 50℃; for 6h; Michaelis-Arbuzov rearrangement; | 95% |
- 77-99-6
1,1,1-tri(hydroxymethyl)propane
- 121-45-9
phosphorous acid trimethyl ester
- 756-79-6
dimethyl methane phosphonate
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: 1,1,1-tri(hydroxymethyl)propane; phosphorous acid trimethyl ester at 80 - 120℃; for 4h; Stage #2: With methyl p-toluene sulfonate at 170 - 180℃; for 2h; Reagent/catalyst; Temperature; | 96% |
Conditions
| Conditions | Yield |
|---|---|
| With aluminum oxide at 20℃; | 95% |
| With triethylamine | 80% |
- 100-39-0
benzyl bromide
- 121-45-9
phosphorous acid trimethyl ester
A
- 773-47-7
dimethyl benzylphosphonate
B
- 756-79-6
dimethyl methane phosphonate
Conditions
| Conditions | Yield |
|---|---|
| at 120℃; for 9h; | A 95% B 144 g |
...Expand
- 121-45-9
phosphorous acid trimethyl ester
- 3433-80-5
1-Bromo-2-bromomethyl-benzene
A
- 103474-07-3
dimethyl (2-bromobenzyl)phosphonate
B
- 756-79-6
dimethyl methane phosphonate
Conditions
| Conditions | Yield |
|---|---|
| A 93% B n/a |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| at 100 - 140℃; for 0.2h; Arbuzov reaction; | A n/a B 90% |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| With tetrachlorosilane at 0℃; | 89% |
| With p-TsOH-Celite at 20℃; | 87% |
| Stage #1: methylphosphonic acid With 1H-imidazole; iodine In dichloromethane at 45 - 50℃; for 0.5h; Gareg-Samuelsson reaction; Stage #2: methanol In dichloromethane at 45 - 50℃; for 0.666667h; Gareg-Samuelsson reaction; | 85% |
- 15145-29-6
1,2,2,2-tetrachloro-1-isocyanato-ethane
- 121-45-9
phosphorous acid trimethyl ester
A
- 85978-66-1
2,2-dichloro-1-(dimethoxyphosphinyl)vinyl isocyanate
B
- 85978-65-0
2,2,2-trichloro-1-(dimethoxyphosphinyl)ethyl isocyanate
C
- 756-79-6
dimethyl methane phosphonate
Conditions
| Conditions | Yield |
|---|---|
| at 100℃; for 1h; | A 7% B n/a C 81% |
...Expand
- 121-45-9
phosphorous acid trimethyl ester
- 5437-45-6
Benzyl bromoacetate
A
- 57443-18-2
benzyl 2-(dimethoxyphosphoryl)acetate
B
- 756-79-6
dimethyl methane phosphonate
Conditions
| Conditions | Yield |
|---|---|
| at 85℃; for 60h; | A 81% B n/a |
...Expand
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Dimethyl methylphosphonate
Chemistry
Dimethyl methylphosphonate(756-79-6) is a colorless liquid with chemical formula C3H9O3P or CH3PO(OCH3)2. It is combustible. It emits a distinct odor. It can be found in household radiators, especially those installed in the former Soviet Block. In contact with water it slowly undergoes hydrolysis. May soften some plastics and rubbers.
Dimethyl methylphosphonate(756-79-6)'s molecular formula is C3H9O3P and its formula weight is 124.08.
The density of dimethyl methylphosphonate(756-79-6) is 1.145 g/mL at 25 °C(lit.) and it has a boiling point of 181 °C(lit.). The refractive index is about 1.413(lit.). Its flash point is 156 °F. The water solubility should be equal to or greater than 10 g/100 mL at 21 oC.
Dimethyl methylphosphonate(756-79-6) has the property of being dissolved in water.
The molecular structure of dimethyl methylphosphonate(756-79-6):
Dimethyl methylphosphonate(756-79-6)'s molecular formula is C3H9O3P and its formula weight is 124.08.
The density of dimethyl methylphosphonate(756-79-6) is 1.145 g/mL at 25 °C(lit.) and it has a boiling point of 181 °C(lit.). The refractive index is about 1.413(lit.). Its flash point is 156 °F. The water solubility should be equal to or greater than 10 g/100 mL at 21 oC.
Dimethyl methylphosphonate(756-79-6) has the property of being dissolved in water.
The molecular structure of dimethyl methylphosphonate(756-79-6):
Uses
Widely used as the additive type flame retardant of polyurethane foam, polyurethane resin, epoxy resin and other materials.
The primary commercial use of dimethyl methylphosphonate(756-79-6) is as a flame retardant. Other commercial uses are a preignition additive for gasoline, anti-foaming agent, plasticizer, stabilizer, textile conditioner, antistatic agent, and an additive for solvents and low-temperature hydraulic fluids. It can be used as a catalyst and a reagent in organic synthesis, as it can generate a highly reactive ylide. The yearly production in the United States varies between 91,000 and 910,000 kilograms.
The primary commercial use of dimethyl methylphosphonate(756-79-6) is as a flame retardant. Other commercial uses are a preignition additive for gasoline, anti-foaming agent, plasticizer, stabilizer, textile conditioner, antistatic agent, and an additive for solvents and low-temperature hydraulic fluids. It can be used as a catalyst and a reagent in organic synthesis, as it can generate a highly reactive ylide. The yearly production in the United States varies between 91,000 and 910,000 kilograms.
Toxicity Data With Reference
| 1. | dlt-mus-orl 65 g/kg/13W-C | MUREAV Mutation Research. 138 (1984),213. | ||
| 2. | cyt-ham:ovr 250 mg/L | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD-A124-785 . | ||
| 3. | orl-mus TDLo:33 g/kg (female 7-14D post):REP | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB85-220143 . | ||
| 4. | orl-rat LD50:8210 mg/kg | TSCAT* Office of Toxic Substances Report. (U.S. Environmental Protection Agency, Office of Toxics Substances, 401M Street SW, Washington, DC 20460) FYI-OTS-0483-0242 . | ||
| 5. | ivn-rat LD50:1050 mg/kg | TSCAT* Office of Toxic Substances Report. (U.S. Environmental Protection Agency, Office of Toxics Substances, 401M Street SW, Washington, DC 20460) FYI-OTS-0483-0242 . | ||
| 6. | orl-mus LD50:>6810 mg/kg | NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-323 ,1987. | ||
| 7. | ivn-mus LD50:912 mg/kg | TSCAT* Office of Toxic Substances Report. (U.S. Environmental Protection Agency, Office of Toxics Substances, 401M Street SW, Washington, DC 20460) FYI-OTS-0483-0242 . |
Consensus Reports
Reported in EPA TSCA Inventory.
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.
Specification
Incompatibilities
Incompatible with strong oxidizing agents and strong bases Reacts with organic halides at 302-392 F Reacts with enol lactones.
Storage
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
Handling
All chemicals should be considered hazardous. Avoid direct physical contact. Use appropriate, approved safety equipment. Untrained individuals should not handle this chemical or its container. Handling should occur in a chemical fume hood.
Incompatible with strong oxidizing agents and strong bases Reacts with organic halides at 302-392 F Reacts with enol lactones.
Storage
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
Handling
All chemicals should be considered hazardous. Avoid direct physical contact. Use appropriate, approved safety equipment. Untrained individuals should not handle this chemical or its container. Handling should occur in a chemical fume hood.