Product Name

  • Name

    Dimethyl methylphosphonate

  • EINECS 212-052-3
  • CAS No. 756-79-6
  • Article Data127
  • CAS DataBase
  • Density 1.079 g/cm3
  • Solubility >=10 g/100 mL at 21 ºC
  • Melting Point <50°
  • Formula C3H9O3P
  • Boiling Point 181 °C at 760 mmHg
  • Molecular Weight 124.076
  • Flash Point 68.9 °C
  • Transport Information UN No 199
  • Appearance colourless liquid
  • Safety 53-26-45
  • Risk Codes 36-46
  • Molecular Structure Molecular Structure of 756-79-6 (Dimethyl methylphosphonate)
  • Hazard Symbols ToxicT
  • 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;
  • PSA 45.34000
  • LogP 1.10210

Synthetic route

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

methyl iodide
74-88-4

methyl iodide

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
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%
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
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%
1,1,1-tri(hydroxymethyl)propane
77-99-6

1,1,1-tri(hydroxymethyl)propane

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
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%
methylphosphonic acid dichloroanhydride
676-97-1

methylphosphonic acid dichloroanhydride

methanol
67-56-1

methanol

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With aluminum oxide at 20℃;95%
With triethylamine80%
benzyl bromide
100-39-0

benzyl bromide

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

dimethyl benzylphosphonate
773-47-7

dimethyl benzylphosphonate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
at 120℃; for 9h;A 95%
B 144 g
...Expand
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

A

dimethyl (2-bromobenzyl)phosphonate
103474-07-3

dimethyl (2-bromobenzyl)phosphonate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
A 93%
B n/a
...Expand
ethyl 4-(acetoxymethyl)-2-(bromomethyl)-5-tert-butylfuran-3-carboxylate

ethyl 4-(acetoxymethyl)-2-(bromomethyl)-5-tert-butylfuran-3-carboxylate

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

B

ethyl 4-(acetoxymethyl)-5-tert-butyl-2-(dimethoxyphosphorylmethyl)furan-3-carboxylate

ethyl 4-(acetoxymethyl)-5-tert-butyl-2-(dimethoxyphosphorylmethyl)furan-3-carboxylate

Conditions
ConditionsYield
at 100 - 140℃; for 0.2h; Arbuzov reaction;A n/a
B 90%
...Expand
methanol
67-56-1

methanol

methylphosphonic acid
993-13-5

methylphosphonic acid

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
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%
1,2,2,2-tetrachloro-1-isocyanato-ethane
15145-29-6

1,2,2,2-tetrachloro-1-isocyanato-ethane

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

2,2-dichloro-1-(dimethoxyphosphinyl)vinyl isocyanate
85978-66-1

2,2-dichloro-1-(dimethoxyphosphinyl)vinyl isocyanate

B

2,2,2-trichloro-1-(dimethoxyphosphinyl)ethyl isocyanate
85978-65-0

2,2,2-trichloro-1-(dimethoxyphosphinyl)ethyl isocyanate

C

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
at 100℃; for 1h;A 7%
B n/a
C 81%
...Expand
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

Benzyl bromoacetate
5437-45-6

Benzyl bromoacetate

A

benzyl 2-(dimethoxyphosphoryl)acetate
57443-18-2

benzyl 2-(dimethoxyphosphoryl)acetate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
at 85℃; for 60h;A 81%
B n/a
...Expand
iodobenzene
591-50-4

iodobenzene

Dimethyl phosphite
868-85-9

Dimethyl phosphite

A

dimethyl phenylphosphonate
2240-41-7

dimethyl phenylphosphonate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; palladium diacetate; triphenylphosphine In acetonitrile at 70℃; for 4h; Title compound not separated from byproducts;A 80%
B n/a
...Expand
Dimethyl phosphite
868-85-9

Dimethyl phosphite

methyl iodide
74-88-4

methyl iodide

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
Stage #1: Dimethyl phosphite With sodium hydroxide for 0.25h; Michaelis-Becker reaction; Ionic liquid;
Stage #2: methyl iodide for 12h; Michaelis-Becker reaction; Ionic liquid;		80%
Stage #1: Dimethyl phosphite With sodium In dichloromethane for 40h; Heating;
Stage #2: methyl iodide In dichloromethane for 10h; Michaelis-Becker reaction; Heating;
trimethyl phosphonoformate
31142-23-1

trimethyl phosphonoformate

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
at 295℃; for 6h;A 18%
B 75%
dichloromethane
75-09-2

dichloromethane

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With tetraethylammonium bromide; cyclohexene at 20℃; electrolysis, Pt electrodes;75%
methanol
67-56-1

methanol

methyl hydrogen methylphosphonate
1066-53-1

methyl hydrogen methylphosphonate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With polymer supported sulfonated magnetic resin In toluene at 20 - 70℃; for 0.75h;74%
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

O,O,O-trimethylthiophosphate
152-18-1

O,O,O-trimethylthiophosphate

C

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -95℃;A 25%
B 4%
C 71%
...Expand
carbonic acid bromomethyl ester 1-ethoxy-ethyl ester

carbonic acid bromomethyl ester 1-ethoxy-ethyl ester

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

1-ethoxyethyl O,O-dimethylphosphorylethanoate
749887-15-8

1-ethoxyethyl O,O-dimethylphosphorylethanoate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
at 50 - 60℃; for 2.5h; Arbuzov reaction;A 71%
B 25.9%
...Expand
methanol
67-56-1

methanol

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With phosphorous; tetraethylammonium iodide In acetonitrile at 18℃; electrolysis;A 70%
B 11%
C 3%
With phosphorous; tetraethylammonium iodide In acetonitrile at 18℃; Mechanism; Product distribution; electrolysis; var. nucleophiles; var. temperatures;A 70%
B 11%
C 3%
With phosphorous In acetonitrile at 18℃; Electrolysis;A 70%
B 11%
C 3%
...Expand
methyl phosphite
96-36-6, 868-85-9

methyl phosphite

methyl iodide
74-88-4

methyl iodide

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With potassium carbonate at 25℃; for 4h;70%
With potassium carbonate at 25℃; for 4h; other phosphonates;70%
carbonic acid 1-ethoxy-ethyl ester iodomethyl ester

carbonic acid 1-ethoxy-ethyl ester iodomethyl ester

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

1-ethoxyethyl O,O-dimethylphosphorylethanoate
749887-15-8

1-ethoxyethyl O,O-dimethylphosphorylethanoate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
at 40 - 50℃; for 2h; Arbuzov reaction;A 67.2%
B 27.4%
...Expand
dimethyl (1-methylethyl) phosphite
52956-34-0

dimethyl (1-methylethyl) phosphite

methyl iodide
74-88-4

methyl iodide

A

isopropyl methyl methylphosphonate
690-64-2

isopropyl methyl methylphosphonate

B

diisopropyl methyl phosphonate

diisopropyl methyl phosphonate

C

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
for 2h; Arbusov rearrangement; Heating;A 66%
B 7 % Chromat.
C 3 % Chromat.
...Expand
Dimethyl phosphite
868-85-9

Dimethyl phosphite

MeX (X = Br or I)

MeX (X = Br or I)

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With tetraethylammonium bromide In acetonitrile at 20℃; on a platinum electrode;65%
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

O,O,O-trimethylthiophosphate
152-18-1

O,O,O-trimethylthiophosphate

C

dimethyl sulfate
77-78-1

dimethyl sulfate

D

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -78℃; Product distribution; other trialkyl phosphite,trialkyl phosphine, trialkyl arsines, trialkoxyarsines, var. molar ratio and temperatures;A 22%
B 4%
C 55%
D 19%
With sulfur trioxide In dichloromethane at -78℃;A 48%
B 16%
C 3%
D 9%
...Expand
methanol
67-56-1

methanol

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With phosphorous; tetraethylammonium iodide In acetonitrile at 50℃; electrolysis;A 51%
B 28%
With phosphorous In acetonitrile at 50℃; Electrolysis;A 51%
B 28%
benzophenone
119-61-9

benzophenone

dimethyl α-trimethylsilylmethylphosphonate
13433-42-6

dimethyl α-trimethylsilylmethylphosphonate

A

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

B

dimethyl (2,2-diphenylvinyl)phosphonate
71265-07-1

dimethyl (2,2-diphenylvinyl)phosphonate

C

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With cesium fluorideA 20%
B 30%
C 50%
With cesium fluoride In tetrahydrofuran for 24h; Heating;A 20%
B 30%
C 50%
...Expand
propargyl bromide
106-96-7

propargyl bromide

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

Dimethyl propargylphosphonate
4885-44-3

Dimethyl propargylphosphonate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
for 5h; Heating;A 45%
B n/a
...Expand
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

Dimethyl propargylphosphonate
4885-44-3

Dimethyl propargylphosphonate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With propargyl bromide for 5h; Heating;A 45%
B n/a
methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

methyltrimethoxyphosphonium triflate
64294-66-2

methyltrimethoxyphosphonium triflate

B

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
In chloroform-d1 at 0 - 20℃; for 1h; Time; Inert atmosphere; Schlenk technique;A 45%
B 27 %Spectr.
...Expand
benzaldehyde
100-52-7

benzaldehyde

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl (2-hydroxy-2-phenyl)ethylphosphonate

dimethyl (2-hydroxy-2-phenyl)ethylphosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Metallation;
Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Addition;		100%
With n-butyllithium 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 -> -20 deg C; Yield given. Multistep reaction;
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at -70℃; Inert atmosphere;
Stage #2: benzaldehyde In tetrahydrofuran Inert atmosphere;
(S)-3-(4-Methoxy-benzyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester
231291-83-1

(S)-3-(4-Methoxy-benzyl)-2,2-dimethyl-oxazolidine-4-carboxylic acid methyl ester

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

{2-[(S)-3-(4-Methoxy-benzyl)-2,2-dimethyl-oxazolidin-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester
231291-85-3

{2-[(S)-3-(4-Methoxy-benzyl)-2,2-dimethyl-oxazolidin-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;100%
N-carbobenzoxy-L-phenylalanine methyl ester
35909-92-3

N-carbobenzoxy-L-phenylalanine methyl ester

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl [(3S)-4-phenyl-3-[(benzyloxycarbonyl)amino]-2-oxobutyl]phosphonate
347851-53-0

dimethyl [(3S)-4-phenyl-3-[(benzyloxycarbonyl)amino]-2-oxobutyl]phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: N-carbobenzoxy-L-phenylalanine methyl ester In tetrahydrofuran; hexane Further stages.;		100%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexanes at -78℃; under 760.051 Torr; for 0.333333h;
Stage #2: N-carbobenzoxy-L-phenylalanine methyl ester In tetrahydrofuran; hexanes at -78 - 20℃; under 760.051 Torr; for 1.25h;
Stage #3: With water; acetic acid In tetrahydrofuran; hexanes at 0℃; under 760.051 Torr;		100%
2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate
150765-78-9

2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

1-(dimethylphosphonato)-2-oxo-6-octyne
475467-02-8

1-(dimethylphosphonato)-2-oxo-6-octyne

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h;
Stage #2: 2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate In tetrahydrofuran; hexane at -78 - 60℃; for 1.33333h; Inert atmosphere;		100%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: 2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate In tetrahydrofuran; hexane at -78 - 60℃; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; diethyl ether; hexane Inert atmosphere;		97%
Stage #1: dimethyl methane phosphonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate In tetrahydrofuran at -78 - 60℃; for 1.33333h; Claisen condensation;		21%
Stage #1: dimethyl methane phosphonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate In tetrahydrofuran at -78 - 60℃; Claisen condensation;		21%
Benzyloxymethyl-oxiran
2930-05-4

Benzyloxymethyl-oxiran

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl 4-(benzyloxy)-3-hydroxybutanephosphonate
476310-16-4

dimethyl 4-(benzyloxy)-3-hydroxybutanephosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h;
Stage #2: Benzyloxymethyl-oxiran With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -70℃; for 2h;		100%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: Benzyloxymethyl-oxiran With boron trifluoride diethyl etherate In tetrahydrofuran at -70℃; for 2h;		100%
methyl 3-(adamantan-1-yl)propanoate
29542-59-4

methyl 3-(adamantan-1-yl)propanoate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl 2-oxo-4-(1-adamantyl)butylphosphonate
53273-30-6

dimethyl 2-oxo-4-(1-adamantyl)butylphosphonate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane; water100%
methyl 2-((tert-butyl(diphenyl)silyl)oxy)acetate
154698-92-7

methyl 2-((tert-butyl(diphenyl)silyl)oxy)acetate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl 3-(tert-butyldiphenylsilyl)oxy-2-oxopropylphosphonate
1075244-38-0

dimethyl 3-(tert-butyldiphenylsilyl)oxy-2-oxopropylphosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: methyl 2-((tert-butyl(diphenyl)silyl)oxy)acetate In tetrahydrofuran; hexane for 0.5h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water		100%
1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate
73323-65-6

1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

(R)-1-tert-butyl 2-(2-(dimethoxyphosphoryl)acetyl)pyrrolidine-1-carboxylate
1140496-59-8

(R)-1-tert-butyl 2-(2-(dimethoxyphosphoryl)acetyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.5h;
Stage #2: 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate In tetrahydrofuran; hexanes at -78℃; for 3h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexanes		100%
dimethyl (2S)-N-(triphenylmethyl)aspartate
116393-72-7

dimethyl (2S)-N-(triphenylmethyl)aspartate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

methyl (2S)-2-(tritylamino)-4-oxo-5-(dimethoxyphosphoryl)pentanoate
1197335-24-2

methyl (2S)-2-(tritylamino)-4-oxo-5-(dimethoxyphosphoryl)pentanoate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; regioselective reaction;100%
With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;92%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: dimethyl (2S)-N-(triphenylmethyl)aspartate In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;		92%
ethyl 4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate
1309567-74-5

ethyl 4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl (2-(4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-oxoethyl)phosphonate
1309567-75-6

dimethyl (2-(4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-oxoethyl)phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78 - -20℃; for 0.25h; Inert atmosphere;
Stage #2: ethyl 4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate In tetrahydrofuran; hexane at -78 - 0℃; for 0.166667h; Inert atmosphere;		100%
C17H28O4

C17H28O4

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

C19H33O6P

C19H33O6P

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: C17H28O4 In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water at -78℃;		100%
methyl 5-methylpyridine-2-carboxylate
29681-38-7

methyl 5-methylpyridine-2-carboxylate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

C10H14NO4P
1369491-73-5

C10H14NO4P

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: methyl 5-methylpyridine-2-carboxylate In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water		100%
methyl 2,3-O-isopropylidene-α-D-mannopyranoside-4,6-cyclic sulfate
139978-82-8

methyl 2,3-O-isopropylidene-α-D-mannopyranoside-4,6-cyclic sulfate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

[2-((2R,3S,4S,5S,6S)-3,4,5-Trihydroxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-phosphonic acid dimethyl ester
454183-61-0

[2-((2R,3S,4S,5S,6S)-3,4,5-Trihydroxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
Stage #1: methyl-2,3-O-isopropylidene-4,6-cyclic sulfate-α-D-mannopyranoside; dimethyl methane phosphonate With 1,1-Diphenylethylene; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran at -78℃;
Stage #2: In tetrahydrofuran; methanol regioselective reaction;		100%
dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

ethyl 4-iodopent-4-enoate

ethyl 4-iodopent-4-enoate

dimethyl (5-iodo-2-oxohex-5-en-1-yl)phosphonate
1569075-94-0

dimethyl (5-iodo-2-oxohex-5-en-1-yl)phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: ethyl 4-iodopent-4-enoate In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;		100%
methyl 2-(((tert-butoxycarbonyl)oxy)methyl)benzofuran-5-carboxylate

methyl 2-(((tert-butoxycarbonyl)oxy)methyl)benzofuran-5-carboxylate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

tert-butyl ((5-(2-(dimethoxyphosphoryl)acetyl)-1-benzofuran-2-yl)methyl) carbonate

tert-butyl ((5-(2-(dimethoxyphosphoryl)acetyl)-1-benzofuran-2-yl)methyl) carbonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: methyl 2-(((tert-butoxycarbonyl)oxy)methyl)benzofuran-5-carboxylate In tetrahydrofuran; hexane at -78℃; for 2h;		100%
dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

A

methylphosphonic acid dichloroanhydride
676-97-1

methylphosphonic acid dichloroanhydride

B

methylene chloride
74-87-3

methylene chloride

Conditions
ConditionsYield
With thionyl chloride; N-Formylpiperidine for 19h; Heating; various conditions and cactalasts investigated;A 99.2%
B n/a
3-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-propionic acid methyl ester
117625-50-0

3-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-propionic acid methyl ester

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

{4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-2-oxo-butyl}-phosphonic acid dimethyl ester
110828-45-0

{4-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-2-oxo-butyl}-phosphonic acid dimethyl ester

Conditions
ConditionsYield
With n-butyllithium99%
With n-butyllithium Yield given;
methyl (4Z)-6,6,9-trimethyl-10-(tetrahydropyranyloxy)dec-6-en-2-ynoate
260970-23-8

methyl (4Z)-6,6,9-trimethyl-10-(tetrahydropyranyloxy)dec-6-en-2-ynoate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

(7Z)-1-dimethoxyphosphiryl-7,10,10-trimethyl-11-(tetrahydropyranyloxy)undec-7-en-3-yn-2-one
260970-36-3

(7Z)-1-dimethoxyphosphiryl-7,10,10-trimethyl-11-(tetrahydropyranyloxy)undec-7-en-3-yn-2-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Substitution;99%
Dodecanal
112-54-9

Dodecanal

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl 2-hydroxytridecylphosphonate
88708-59-2

dimethyl 2-hydroxytridecylphosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Metallation;
Stage #2: Dodecanal In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Addition;		99%
(S)-methyl 2-palmitamido-3-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)propanoate
935548-14-4

(S)-methyl 2-palmitamido-3-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)propanoate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

(S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate
935548-32-6

(S)-dimethyl 2-oxo-3-palmitamido-4-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)butylphosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere;
Stage #2: (S)-methyl 2-palmitamido-3-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)propanoate In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere;		99%
Stage #1: dimethyl methane phosphonate With n-butyllithium
Stage #2: (S)-methyl 2-palmitamido-3-(4-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methoxy)phenyl)propanoate at -78℃; for 3h;
C36H54N2O5Si

C36H54N2O5Si

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

C37H56NO7PSi

C37H56NO7PSi

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;99%
dihydro isoquinoline-1-methyl formate

dihydro isoquinoline-1-methyl formate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl 2-(1-isoquinolinyl)-2-oxoethyl phosphonate

dimethyl 2-(1-isoquinolinyl)-2-oxoethyl phosphonate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃; for 2h;99%
butyryl chloride
141-75-3

butyryl chloride

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl (2-oxopentyl)phosphonate
65921-74-6

dimethyl (2-oxopentyl)phosphonate

Conditions
ConditionsYield
99%
ziconium(IV) oxychloride octahydrate
13520-92-8

ziconium(IV) oxychloride octahydrate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

zirconium bis(methylphosphonate)

zirconium bis(methylphosphonate)

Conditions
ConditionsYield
With aq. HCl In water reflux (24 h or 112 h); aq. HBr or H2O alone may also be used; filtration, washing (H2O; acetone), drying (40°C, 18 h, then 200°C, 24 h); elem. anal.;99%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

lithio dimethyl (2-oxo-2-pyridin-3-ylethyl)phosphonate

lithio dimethyl (2-oxo-2-pyridin-3-ylethyl)phosphonate

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran Barbier reaction; Cooling with ice; Inert atmosphere;99%
methyl 4-iodobenzoate
619-44-3

methyl 4-iodobenzoate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

lithio dimethyl [2-(4-iodophenyl)-2-oxoethyl]phosphonate

lithio dimethyl [2-(4-iodophenyl)-2-oxoethyl]phosphonate

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran Barbier reaction; Cooling with ice; Inert atmosphere;99%
N-Ethylimidazole
7098-07-9

N-Ethylimidazole

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

[EMIM] methyl methylphosphonate
1059603-87-0

[EMIM] methyl methylphosphonate

Conditions
ConditionsYield
at 100℃; for 24h; Neat (no solvent);99%
methyl-2-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-3-phenyl-propionate
1439462-50-6

methyl-2-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-3-phenyl-propionate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl-{3-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2-oxo-4-phenyl-butyl}phosphonate
1439462-62-0

dimethyl-{3-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-2-oxo-4-phenyl-butyl}phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: methyl-2-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-3-phenyl-propionate In tetrahydrofuran; hexane at -78 - 0℃; for 5h; Inert atmosphere;		99%

DIMETHYL METHYLPHOSPHONATE Chemical Properties

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 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.

DIMETHYL METHYLPHOSPHONATE 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 .

DIMETHYL METHYLPHOSPHONATE Consensus Reports

Reported in EPA TSCA Inventory.

DIMETHYL METHYLPHOSPHONATE 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 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.

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