993-13-5

Basic information

• Product Name: METHYLPHOSPHONIC ACID
• Synonyms: Phosphonic acid, methyl-;METHYLPHOSPHONIC ACID;METHANEPHOSPHONIC ACID;Methylphosphonicacid,98%;Methanephosphonic acid,98%;Methylphosphonic acid ,97.5%;Methanephosphonic acid, 98% 25GR;Methanephosphonic acid, 98% 5GR
• CAS NO: 993-13-5
• Molecular Formula: CH₅O₃P
• Molecular Weight: 96.02
• EINECS: 237-027-4
• Product Categories: Organic Building Blocks;Phosphonic/Phosphinic Acids;Phosphorus Compounds
• Mol File: 993-13-5.mol
• Article Data: 48

Chemical Properties

• Melting Point: 105-107 °C(lit.)
• Boiling Point: 265.2 °C at 760 mmHg
• Flash Point: 114.2 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.495 g/cm³
• Vapor Pressure: 0.00269mmHg at 25°C
• Refractive Index: 1.431
• Storage Temp.: ?20°C
• Solubility: H2O: soluble2.88 g in 30 mL, clear, colorless
• PKA: pK1:2.38;pK2:7.74 (25°C)
• Water Solubility: Soluble in water and alcohol.
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• BRN: 1739372
• CAS DataBase Reference: METHYLPHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLPHOSPHONIC ACID(993-13-5)
• EPA Substance Registry System: METHYLPHOSPHONIC ACID(993-13-5)

Safety Data

• Hazard Codes: C,T,F
• Statements: 22-34-39/23/24/25-23/24/25-11
• Safety Statements: 26-36/37/39-45-36/37-16-7
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 993-13-5(Hazardous Substances Data)

Usage

Uses

Methylphosphonic acid is used to produce methyl-phosphonic acid dichloride by chlorination.

Flammability and Explosibility

Notclassified

Purification Methods

Methylphosphonic acid [993-13-5] M 96.0, m 104-106o, 105-107o, 108o, pK 1 2.12, pK 2 7.29. If it tests for Cl-, then add H2O and evaporate to dryness, repeat several times till free from Cl-. The residue solidifies to a wax-like solid. Alternatively, dissolve the acid in the minimum volume of H2O, add charcoal, warm, filter and evaporate to dryness in a vacuum over P2O5. [Kosolapoff J Am Chem Soc 75 3379 1953.] The di-Na salt is prepared from 24g of acid in 50mL of dry EtOH, and a solution of 23g Na dissolved in 400mL EtOH is added. A white precipitate is formed, but the mixture is refluxed for 30minutes to complete the reaction. Filter off the solid and recrystallise it from 50% EtOH. Dry the crystals in a vacuum desiccator. [Thompson J Chem Soc 3292 1952, Beilstein 4 IV 3498.]

InChI:InChI=1/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4)

Synthetic route

dimethyl methane phosphonate (756-79-6) → methylphosphonic acid (993-13-5)

Conditions	Yield
With hydrogenchloride for 3h; Hydrolysis; Heating;	96%
With trifluorormethanesulfonic acid In water at 140℃; for 24h; Sealed tube; Schlenk technique;	93%
With hydrogenchloride	88%

chloromethylphosphonic acid (2565-58-4) + iminodiacetic acid (142-73-4) → methylphosphonic acid (993-13-5)

Conditions	Yield
With sodium hydroxide; copper In water at 95℃; for 1.2h;	15.3%

chloromethylphosphonic acid (2565-58-4) + iminodiacetic acid (142-73-4) → GI + methylphosphonic acid (993-13-5) + tri-sodium salt of N-phosphonomethylglycine (34494-03-6, 40465-64-3, 40465-65-4, 70393-85-0, 102413-71-8)

Conditions	Yield
With sodium hydroxide; copper In water at 95℃; for 17 - 65h;	A 3 - 6 %Spectr. B 15.3% C 2.7 - 4 %Spectr.
With sodium hydroxide; copper(II) hydroxide In water at 95℃; for 20h;	A 90.3 %Spectr. B 4.5 %Spectr. C 4.6 %Spectr.

chloromethylphosphonic acid (2565-58-4) + iminodiacetic acid (142-73-4) → GI + methylphosphonic acid (993-13-5)

Conditions	Yield
With sodium hydroxide; copper In water at 95℃; for 6h;	A 84.9 %Spectr. B 15.1%
With sodium hydroxide; copper In water at 95℃; for 6h;	A 92.3 %Spectr. B 7.7%
With sodium hydroxide; copper In water at 95℃; for 1.5h;	A 90.4 %Spectr. B 6.2%

di-(4-methoxy-1-naphthyl) methylphosphate (173313-25-2) → methylphosphonic acid (993-13-5) + 4,4'-dimethoxy-1,1'-binaphthyl (19817-09-5)

Conditions	Yield
With dichloro-acetic acid In acetonitrile Quantum yield; Rate constant; Mechanism; Irradiation;	A 12% B 7%
With dichloro-acetic acid In tetrahydrofuran for 1h; Quantum yield; Further Variations:; Reagents; Elimination; Irradiation;

di-1-naphthyl methylphosphate (173313-35-4) → methylphosphonic acid (993-13-5) + 1,1'-bisnaphthalene (604-53-5)

Conditions	Yield
With dichloro-acetic acid In acetonitrile Quantum yield; Rate constant; Mechanism; Irradiation;	A 10% B 7%
With dichloro-acetic acid In tetrahydrofuran for 1h; Quantum yield; Further Variations:; Reagents; Elimination; Irradiation;

methylphosphonic acid dichloroanhydride (676-97-1) → methylphosphonic acid (993-13-5)

Conditions	Yield
With water

methylphosphine (593-54-4) → methylphosphonic acid (993-13-5)

Conditions	Yield
With nitric acid

dibutyl methylphosphonate (2404-73-1) → methylphosphonic acid (993-13-5)

Conditions	Yield
With hydrogenchloride

chloroacetic acid ethyl ester (105-39-5) → methylphosphonic acid (993-13-5)

Conditions	Yield
With sodium hypophosphite; ethanol Oxydation des Reaktionsprodukts mit KMnO4 in Wasser;

triphenyl phosphite (101-02-0) + methyl iodide (74-88-4) → methylphosphonic acid (993-13-5)

Conditions	Yield
man schuettelt das Reaktionsprodukt mit verd. Natronlauge und verseift den Ester durch Alkohol Kalilauge oder rauchende Salpetersaeure. Entsteht der Diphenylester.;

phosphorous acid dicyclohexyl ester-methyl ester (854728-09-9) + methyl iodide (74-88-4) → methylphosphonic acid (993-13-5) + cyclohexene (110-83-8)

Conditions	Yield
at 200℃;

ethanol (64-17-5) + methylphosphonothioic acid (5994-73-0) → methylphosphonic acid (993-13-5) + ethyl methylphosphonic acid (1832-53-7) + methylphosphinic acid (4206-94-4) + CH5O3PS (128371-71-1) + CH5O3PS (128371-70-0)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid Product distribution;

methylphosphonofluoridic acid (1511-67-7) → methylphosphonic acid (993-13-5)

Conditions	Yield
With hydrogenchloride at 0.4 - 43.2℃; Kinetics; Mechanism; var. HCl and phosphate buffer concn.;

O-isopropyl methylphosphonofluoridate (107-44-8) → methylphosphonic acid (993-13-5)

Conditions	Yield
With water for 672h; Product distribution; other methylphosphonofluoridate;

diisopropyl methanephosphonate (1445-75-6) → propene (187737-37-7) + methylphosphonic acid (993-13-5)

Conditions	Yield
aluminum oxide In solid at 99.9℃; under 1 Torr; Mechanism; decomposition of adsorbed molecule at various temperatures;

O,O-di-4-nitrophenyl methylphosphonate (6395-57-9) → methylphosphonic acid (993-13-5)

Conditions	Yield
With water; N-butylamine at 25℃; Rate constant; Thermodynamic data; other reagents: various amines; E(activ.); other temperatures.;

Bis (4-methoxyphenyl) methylphosphonate (60705-73-9) → methylphosphonic acid (993-13-5) + 4,4'-Dimethoxybiphenyl (2132-80-1)

Conditions	Yield
In methanol for 1h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given;
In methanol for 1h; Quantum yield; Ambient temperature; Irradiation;

Bis (4-methoxyphenyl) methylphosphonate (60705-73-9) → methylphosphonic acid (993-13-5) + 4,4'-Dimethoxybiphenyl (2132-80-1) + 2,4',5-trimethoxy-1,1'-biphenyl (66731-04-2)

Conditions	Yield
In methanol for 1h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
In methanol for 1h; Product distribution; Quantum yield; Irradiation; photolysis of 4-methoxyphenyl aryl alkylphosphonates, solvent effect;

bis(4-t-butylphenyl) methylphosphonate (60705-72-8) → methylphosphonic acid (993-13-5) + 4,4'-di-tert-butylbiphenyl (1625-91-8)

Conditions	Yield
In methanol for 1h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given;
In methanol for 1h; Quantum yield; Ambient temperature; Irradiation;

methylphosphinic acid (4206-94-4) → methylphosphine (593-54-4) + methylphosphonic acid (993-13-5) + methylidynephosphine (6829-52-3)

Conditions	Yield
at 820℃;

1-methylphosphorane oxide (7187-92-0) → methylphosphonic acid (993-13-5)

bis(4-methylthiophenyl) methylphosphonate (88847-60-3) → methylphosphonic acid (993-13-5) + 4,4'-bis(methylsulfanyl)biphenyl (10075-90-8)

Conditions	Yield
In methanol for 1h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given;
In methanol for 1h; Quantum yield; Ambient temperature; Irradiation;

bis(4-ethoxyphenyl) methylphosphonate (135263-37-5) → methylphosphonic acid (993-13-5) + 4,4'-diethoxybiphenyl (7168-54-9)

Conditions	Yield
In methanol for 1h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given;
In methanol for 1h; Quantum yield; Ambient temperature; Irradiation;

4-chlorophenyl 4-methoxyphenyl methylphosphonate → methylphosphonic acid (993-13-5) + 4-chloro-(4'-methoxybiphenyl) (58970-19-7) + Methyl-phosphonic acid mono-(5-chloro-4'-methoxy-biphenyl-2-yl) ester

Conditions	Yield
In methanol for 1h; Irradiation; Yield given. Title compound not separated from byproducts;
In methanol for 1h; Product distribution; Quantum yield; Irradiation; photolysis of 4-methoxyphenyl aryl alkylphosphonates, solvent effect;

4-cyanophenyl 4-methoxyphenyl methylphosphonate (154196-96-0) → methylphosphonic acid (993-13-5) + 4'-methoxybiphenyl-4-carbonitrile (58743-77-4) + 4-hydroxy-3-(4-methoxyphenyl)benzonitrile (78338-71-3) + Methyl-phosphonic acid mono-(5-cyano-4'-methoxy-biphenyl-2-yl) ester

Conditions	Yield
In methanol for 1h; Irradiation; Yield given. Title compound not separated from byproducts;
In methanol for 1h; Product distribution; Quantum yield; Irradiation; photolysis of 4-methoxyphenyl aryl alkylphosphonates, solvent effect, quenching experiments with oxygen;

3-cyanophenyl 4-methoxyphenyl methylphosphonate → methylphosphonic acid (993-13-5) + 3-cyano-4'-methoxybiphenyl (154197-00-9)

Conditions	Yield
In methanol for 1h; Irradiation; Yield given;
In methanol for 1h; Product distribution; Quantum yield; Irradiation; photolysis of 4-methoxyphenyl aryl alkylphosphonates, solvent effect;

dimethyl methane phosphonate (756-79-6) → methanol (67-56-1) + methylphosphate (812-00-0) + dimethylphosphoric acid (813-78-5) + methylphosphonic acid (993-13-5) + methyl hydrogen methylphosphonate (1066-53-1)

Conditions	Yield
With air; water; Pt/Al2O3 at -23.1℃; oxidative and hydrolytic reaction; var. Pt loading, other temp.;

dimethyl methane phosphonate (756-79-6) → methanol (67-56-1) + methylphosphonic acid (993-13-5)

Conditions	Yield
aluminum oxide In solid at 99.9℃; under 1 Torr; Mechanism; decomposition of adsorbed molecule, at various temperatures;

N-(O-isopropyl methylphosphonyl)-L-serine methyl ester → methylphosphonic acid (993-13-5) + O-(O-isopropyl methylphosphonyl)-L-serine methyl ester

Conditions	Yield
With 1H-imidazole In butan-1-ol at 40℃; for 16h; Rate constant;

methylphosphonic acid (993-13-5) → methylphosphonyl difluoride (676-99-3)

Conditions	Yield
With trifluoro-[1,3,5]triazine In chloroform at 100℃; for 72h;	100%
With N,N-dimethyl-1-fluoro-2-methylpropenamine In 1,1,2,2-tetrachloroethane at 120℃; for 0.0833333h;	100 % Spectr.

methylphosphonic acid (993-13-5) + tetra-n-butylphosphonium hydroxide (14518-69-5) → tetrabutylphosphonium hydrogenmethylphosphonate (1242169-18-1)

Conditions	Yield
In water for 0.166667h;	100%

methylphosphonic acid (993-13-5) → methylphosphonofluoridic acid (1511-67-7)

Conditions	Yield
With trifluoro-[1,3,5]triazine In chloroform; 1,2-dichloro-ethane at 100℃; for 23h; Inert atmosphere;	100%

aluminum trihydroxide + methylphosphonic acid (993-13-5) → C2H6O5P2(2-)*C2H7O5P2(1-)*Al(3+)

Conditions	Yield
In water for 3h; Inert atmosphere; Heating;	100%

tert-butyldimethylsilanol (18173-64-3) + methylphosphonic acid (993-13-5) → methylphosphonic acid bis(tert-butyldimethylsilyl) ester

Conditions	Yield
In hexane for 2h; Heating;	99%

methylphosphonic acid (993-13-5) + aluminium(III) chloride hexahydrate → tris[methylphosphonic acid] aluminum salt

Conditions	Yield
In sulfolane; water at 60 - 160℃; for 42h;	99%

rubidium carbonate + methylphosphonic acid (993-13-5) + vanadia → Rb(1+)*3VO2(1+)*2CH3PO3(2-)=Rb(VO2)3(CH3PO3)2

Conditions	Yield
In water molar ratio Rb:V:P=1:1:2; Teflon-lined bomb, 180°C, 5 d;	98%
In water molar ratio Rb:V:P=2:3:3; Teflon-lined bomb, 180°C, 5 d;	21%

aluminium oxide hydrate + methylphosphonic acid (993-13-5) → ξ-aluminium methylphosphonate

Conditions	Yield
With NH4OH In water High Pressure; hydrothermal treatment (168°C, 48 h); filtration, washing (H2O), drying; elem. anal.;	97%

cis-dichlorobis(triphenylarsine)platinum(II) (15130-26-4, 16242-55-0, 60873-46-3) + methylphosphonic acid (993-13-5) → {Pt(O2P(O)CH3)((C6H5)3As)2}*H2O

Conditions

Yield

With Ag2O In dichloromethane react. under dry N2, addn. of methylphosphonic acid and an excess of Ag2O to a stirred soln. of cis-PtCl2(AsPh3)2 in CH2Cl2, refluxing for 4 h, cooling; filtration,, evapg. the filtrate to dryness under reduced pressure, oily residue, dissolving the oil in CH2Cl2, addn. of light petroleum, crystn. on standing, recrystn. from CH2Cl2-light petroleum, drying in vac., elem. anal.;

96%

piperazine (110-85-0) + methylphosphonic acid (993-13-5) → 2CH5O3P*C4H10N2

Conditions	Yield
In water at 40 - 85℃; for 3.5h;	95.7%

dichloro(1,5-cyclooctadiene)platinum(ll) (12080-32-9) + methylphosphonic acid (993-13-5) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → {Pt(O2P(O)CH3)((C6H5)2P(CH2)2P(C6H5)2)}*H2O

Conditions

Yield

With Ag2O In dichloromethane react. under dry N2, addn. of Ph2P(CH2)2PPh2, methylphosphonic acid (molar ratio = 1:1) and an excess of Ag2O to a stirred soln. of PtCl2(cycloocta-1,5-diene) in CH2Cl2, refluxing for 4 h, cooling; filtration,, evapg. the filtrate to dryness under reduced pressure, oily residue, dissolving the oil in CH2Cl2, addn. of light petroleum, crystn. on standing, recrystn. from CH2Cl2-light petroleum, drying in vac., elem. anal.;

95%

pentan-1-ol (71-41-0) + methylphosphonic acid (993-13-5) → O,O'-dipentyl methylphosphonate (1000-36-8)

Conditions	Yield
Stage #1: methylphosphonic acid With 1H-imidazole; iodine In dichloromethane at 45 - 50℃; for 0.5h; Gareg-Samuelsson reaction; Stage #2: pentan-1-ol In dichloromethane at 45 - 50℃; for 0.833333h; Gareg-Samuelsson reaction;	94%
With p-TsOH-Celite at 20℃;	87%

dichloro(1,5-cyclooctadiene)platinum(ll) (12080-32-9) + methylphosphonic acid (993-13-5) + 1,3-bis-(diphenylphosphino)propane (6737-42-4) → {Pt(O2P(O)CH3)((C6H5)2P(CH2)3P(C6H5)2)}*CH2Cl2

Conditions

Yield

With CH2Cl2; Ag2O In dichloromethane react. under dry N2, addn. of Ph2P(CH2)3PPh2, methylphosphonic acid (molar ratio = 1:1) and an excess of Ag2O to a stirred soln. of PtCl2(cycloocta-1,5-diene) in CH2Cl2, refluxing for 4 h, cooling; filtration,, evapg. the filtrate to dryness under reduced pressure, oily residue, dissolving the oil in CH2Cl2, addn. of light petroleum, crystn. on standing, recrystn. from CH2Cl2-light petroleum, drying in vac., elem. anal.;

94%

zirconyl chloride + methylphosphonic acid (993-13-5) + 2-naphthyl phosphate monosodium salt (14463-68-4) → zirconium(2-naphthyl phosphate)(methylphosphonate)

Conditions	Yield
With hydrogen fluoride In water for 144h; Reflux; Inert atmosphere;	94%

methylphosphonic acid (993-13-5) + cyclohexanol (108-93-0) → Methylphosphonsaeure-dicyclohexylester (7040-53-1)

Conditions	Yield
With p-TsOH-Celite at 20℃;	93%

dichloro(1,5-cyclooctadiene)platinum(ll) (12080-32-9) + methylphosphonic acid (993-13-5) + 1,4-di(diphenylphosphino)-butane (7688-25-7) → {Pt(O2P(O)CH3)((C6H5)2P(CH2)4P(C6H5)2)} (140889-86-7)

Conditions

Yield

With Ag2O In dichloromethane react. under dry N2, addn. of Ph2P(CH2)4PPh2, methylphosphonic acid (molar ratio = 1:1) and an excess of Ag2O to a stirred soln. of PtCl2(cycloocta-1,5-diene) in CH2Cl2, refluxing for 4 h, cooling; filtration,, evapg. the filtrate to dryness under reduced pressure, oily residue, dissolving the oil in CH2Cl2, addn. of light petroleum, crystn. on standing, recrystn. from CH2Cl2-light petroleum, drying in vac., elem. anal.;

93%

hydrogenchloride (7647-01-0) + zirconyl chloride octahydrate + methylphosphonic acid (993-13-5) + (p-aminobenzyl)phosphonic acid (5424-27-1) → Zr(4+)*1.0O3PCH2C6H4NH3(1-)*1.0Cl(1-)*1.0O3PCH3(2-)=Zr(O3PCH2C6H4NH3Cl)1.0(O3PCH3)1.0

Conditions	Yield
With HF In water dropwise addn. of 4.3 M HCl to stoich. mixt. of phosphonic acids, addn. of ZrOCl2 (in 1 M HCl), refluxing under N2 for 19 d, addn. of HF, stirring and refluxing for 7 d; cooling to room temp., EtOH addn., refrigeration (pptn.), collection (filtration, washing (75% EtOH, Me2CO, ether), drying in air;	93%

3,3-dimethyl-2-butanol (464-07-3, 20281-91-8) + methylphosphonic acid (993-13-5) → pinacolyl methylphosphonic acid (616-52-4)

Conditions	Yield
With Celite; dicyclohexyl-carbodiimide at 50 - 60℃; for 1h;	92%
With phenylarsonic acid In toluene Heating;

methylphosphonic acid (993-13-5) + isopropyl alcohol (67-63-0) → diisopropyl methanephosphonate (1445-75-6)

Conditions	Yield
With tetrachlorosilane at 0℃;	92%
With p-TsOH-Celite at 20℃;	92%
Stage #1: methylphosphonic acid With 1H-imidazole; iodine In dichloromethane at 45 - 50℃; for 0.5h; Gareg-Samuelsson reaction; Stage #2: isopropyl alcohol In dichloromethane at 45 - 50℃; Gareg-Samuelsson reaction;	35%

thallium(I) carbonate + methylphosphonic acid (993-13-5) + vanadia → Tl(1+)*3VO2(1+)*2CH3PO3(2-)=Tl(VO2)3(CH3PO3)2

Conditions	Yield
In water molar ratio Tl:V:P=1:1:3; Teflon-lined bomb, 160°C, 5 d; crystn., filtration;	92%

methylphosphonic acid (993-13-5) + aluminum isopropoxide (555-31-7) → tris[methylphosphonic acid] aluminum salt

Conditions	Yield
In sulfolane; water at 90 - 250℃; for 7h; Dean-Stark;	92%

iron(III) oxide + methylphosphonic acid (993-13-5) → C2H6O5P2(2-)*C2H7O5P2(1-)*Fe(3+)

Conditions	Yield
In water at 165℃; for 12h; Inert atmosphere;	92%

methylphosphonic acid (993-13-5) → barium hydrogen methylphosphonate

Conditions	Yield
With barium hydroxide octahydrate; water for 1h;	91.5%

methylphosphonic acid (993-13-5) + butan-1-ol (71-36-3) → dibutyl methylphosphonate (2404-73-1)

Conditions	Yield
With p-TsOH-Celite at 20℃;	91%
With tetrachlorosilane at 0℃;	90%

dichloro(1,5-cyclooctadiene)platinum(ll) (12080-32-9) + methylphosphonic acid (993-13-5) + diphenyl(methyl)phosphine (1486-28-8) → {Pt(O2P(O)CH3)(P(C6H5)2CH3)2}*CH2Cl2

Conditions

Yield

With Ag2O; CH2Cl2 In dichloromethane react. under dry N2, addn. of methyldiphenylphosphine, methylphosphonic acid (molar ratio = 2:1) and an excess of Ag2O to a stirred soln. of PtCl2(cycloocta-1,5-diene) in CH2Cl2, refluxing for 4 h, cooling; filtration,, evapg. the filtrate to dryness under reduced pressure, oily residue, dissolving the oil in CH2Cl2, addn. of light petroleum, crystn. on standing, recrystn. from CH2Cl2-light petroleum, drying in vac., elem. anal.;

91%

methylphosphonic acid (993-13-5) + p-(9-anthroyloxy)phenacyl bromide (94345-04-7) → bis methylphosphonate (106864-22-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 0.5h;	90%

pentan-1-ol (71-41-0) + methylphosphonic acid (993-13-5) → methylphosphonic acid monopentyl ester

Conditions	Yield
With Celite; dicyclohexyl-carbodiimide at 50 - 60℃; for 0.75h;	90%
With phenylarsonic acid In toluene for 28h; Heating;
With phenylarsonic acid

methylphosphonic acid (993-13-5) + butan-1-ol (71-36-3) → methyl-phosphonic acid n-butyl ester (1832-55-9)

Conditions	Yield
With phenylarsonic acid In toluene for 28h; Heating;	90%
With phenylarsonic acid In toluene for 15h; Reflux;	43.9%
With phenylarsonic acid In toluene for 28h; Heating;
With phenylarsonic acid

propan-1-ol (71-23-8) + methylphosphonic acid (993-13-5) → methylphosphonic acid dipropyl ester (6410-56-6)

Conditions	Yield
With p-TsOH-Celite at 20℃;	90%
Stage #1: methylphosphonic acid With 1H-imidazole; iodine In dichloromethane at 45 - 50℃; for 0.5h; Gareg-Samuelsson reaction; Stage #2: propan-1-ol In dichloromethane at 45 - 50℃; for 0.75h; Gareg-Samuelsson reaction;	90%
With tetrachlorosilane at 0℃;	80%

Upstream product

• 676-97-1 methylphosphonic acid dichloroanhydride 
• 2404-73-1 dibutyl methylphosphonate 
• 105-39-5 chloroacetic acid ethyl ester 
• 60705-72-8 bis(4-t-butylphenyl) methylphosphonate 
• 676-96-0 Trimethylphosphine oxide 
• 64-17-5 ethanol 
• 101-02-0 triphenyl phosphite 
• 74-88-4 methyl iodide 
• 1445-75-6 diisopropyl methanephosphonate 
• 2565-58-4 chloromethylphosphonic acid 
• 142-73-4 iminodiacetic acid 
• 67-56-1 methanol 
• 12185-10-3 phosphorous 
• 96-64-0 soman 

Downstream Products

• 53072-87-0 1,5,9,13-Tetrahexyl-3,7,11,15,18,21-hexamethyl-2,4,6,8,10,12,14,16,17,19,20,22-dodecaoxa-3,7,11,15,18,21-hexaphospha-1,5,9,13-tetrasila-tricyclo[11.3.3.3^5,9]docosane 3,7,11,15,18,21-hexaoxide 
• 18848-68-5 Methylphosphonsaeure-bis-(methyl-diphenyl-silylester) 
• 18985-47-2 Methylphosphonsaeure-bis-(aethyl-diphenyl-silylester) 
• 18825-67-7 methylphosphonic acid bis(triphenylsilyl) ester 
• 4460-96-2 1,3,5-Trimethyl-3,5-diphenyl-cyclo-1-phosphonoxy-disiloxan 
• 4335-84-6 1,3,5,7-Tetramethyl-3,5-diphenyl-cyclo-1,3-diphosphonoxy-disiloxan 
• 4335-83-5 1,3,5,7-Tetramethyl-3,5,7-triphenyl-cyclo-1-phosphonoxy-trisiloxan 
• 4296-42-8 1,3,5,7,9-Pentamethyl-3,5,7,9-tetraphenyl-cyclo-1-phosphonoxy-tetrasiloxan 
• 1511-67-7 methylphosphonofluoridic acid 
• 676-97-1 methylphosphonic acid dichloroanhydride 
• 182688-60-4 Methyl-phosphonic acid mono-[(2R,3S,5R)-3-hydroxy-5-(6-oxo-2-phenylacetylamino-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester 
• 182688-59-1 Methyl-phosphonic acid mono-[(2R,3S,5R)-3-hydroxy-5-(2-oxo-4-phenylacetylamino-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester 
• 182688-61-5 Methyl-phosphonic acid mono-[(2R,3S,5R)-3-hydroxy-5-(6-phenylacetylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester 
• 1932-60-1 methylphosphonic acid monocyclohexyl ester 

Relevant articles and documents

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A Peanut-Like Sb-Embedded Polyoxoniobate Cage for Hydrolytic Decomposition of Chemical Warfare Agent

A Sb-embedded polyoxoniobate has been originally synthesized under hydrothermal conditions. Particularly, the peanut-like [Sb2Nb24O72]18? cluster cage in 1 with C2h symmetry is composed of two 9-nuclear {SbNb9O33} motifs and one {Nb6O24} crown-shaped ring. The compound 1 present the novel structure of Sb-substituted sandwich-type polyoxoniobate with antimoniobate cluster cage. Decomposition catalytic studies indicate that compound 1 exhibits good hydrolytic activity and stability on the degradation of nerve agent simulant dimethylphosphonate (DMMP).

Mass Spectrometric Identification of Methylphosphonic Acid: The Hydrolysis Product of Isopropyl Methylphosphonofluoridate and Pinacolyl Methylphosphonofluoridate

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Synthesis of the Tripeptides Tyr-Thr-Lys Phosphorylated with Isopropyl Methyl- and (Deuteromethyl)phosphonochloridates as Reference Standards for the Analysis of Biomedical Samples

A procedure for the phosphorylation of the tripeptide Tyr-Thr-Lys with isopropyl methyl- or (deuteromethyl)phosphonochloridate is developed. The phosphorylated tripeptides are intended for use as reference standards in the analysis of blood samples of people suspected to have been exposed to acetylcholinesterase inhibitors. Conditions of hromatographic separation and purification of the synthesized compounds are determined and optimized, which ensures the preparation of high-purity phosphorylated tripeptides.

Investigating the breakdown of the nerve agent simulant methyl paraoxon and chemical warfare agents GB and VX using nitrogen containing bases

A range of nitrogen containing bases was tested for the hydrolysis of a nerve agent simulant, methyl paraoxon (MP), and the chemical warfare agents, GB and VX. The product distribution was found to be highly dependant on the basicity of the base and the quantity of water used for the hydrolysis. This study is important in the design of decontamination technology, which often involve mimics of CWAs.