Dimethyl methylphosphonate

Base Information

• Chemical Name: Dimethyl methylphosphonate
• CAS No.: 756-79-6
• Deprecated CAS: 351011-43-3,880251-70-7
• Molecular Formula: C3H9O3P
• Molecular Weight: 124.076
• European Community (EC) Number: 212-052-3
• NSC Number: 62240
• UN Number: 1993
• UNII: 20Z996230U
• DSSTox Substance ID: DTXSID0020494
• Nikkaji Number: J14.169K
• Wikipedia: Dimethyl_methylphosphonate
• Wikidata: Q417529
• ChEMBL ID: CHEMBL2924224
• Mol file: 756-79-6.mol

Synonyms:dimethyl methanephosphonate;dimethyl methylphosphonate;dimethylmethylphosphonate

Chemical Property of Dimethyl methylphosphonate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: <0.1 mm Hg ( 20 °C)
• Melting Point: <50°
• Refractive Index: n20/D 1.413(lit.)
• Boiling Point: 181 °C at 760 mmHg
• PKA: pKa (20°) in water: 2.37
• Flash Point: 68.9 °C
• PSA: 45.34000
• Density: 1.079 g/cm³
• LogP: 1.10210
• Water Solubility.: >=10 g/100 mL at 21 ºC
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 124.02893114
• Heavy Atom Count: 7
• Complexity: 82.2
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

O,O-Dimethyl Methylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xi
• Statements: 46-36-62
• Safety Statements: 53-26-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organophosphates, Other
• Canonical SMILES: COP(=O)(C)OC
• Uses: NMR probe for cell volume. Flame retardant. Simulant for nerve agents. 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 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.

Technology Process of Dimethyl methylphosphonate

There total 122 articles about Dimethyl methylphosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + phosphorous acid trimethyl ester (121-45-9) → dimethyl methane phosphonate (756-79-6)

Guidance literature:

1,1,1-tri(hydroxymethyl)propane; phosphorous acid trimethyl ester; at 80 - 120 ℃; for 4h;

With methyl p-toluene sulfonate; at 170 - 180 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield: 89.0%

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

Guidance literature:

With tetrachlorosilane; at 0 ℃;

DOI:10.1016/j.tetlet.2006.02.159

Reference yield: 74.0%

methanol (67-56-1) + methyl hydrogen methylphosphonate (1066-53-1) → dimethyl methane phosphonate (756-79-6)

Guidance literature:

With polymer supported sulfonated magnetic resin; In toluene; at 20 - 70 ℃; for 0.75h;

DOI:10.1016/j.tetlet.2014.10.086

upstream raw materials:

methylphosphonic acid dichloroanhydride

sodium methylate

triphenyl phosphite

methanol

Downstream raw materials:

methylphosphonic acid bis(trimethylsilyl) ester

dimethyl α-trimethylsilylmethylphosphonate

dibutyl methylphosphonate

methyl n-butyl methylphosphonate

Refernces

• 1、 Kibardin, A. M.,Gazizov, T. Kh.,Efremov, Yu. Ya.,Zinin, V. N.,Musin, R. Z.,Pudovik, A. N.. "REACTION OF TRIALKYL PHOSPHITES WITH 1,1,1-TRIFLUOROACETONE". . p. 656 - 660. Retrieved 1980.
• 2、 Belkin et al.. "". . . Retrieved 1976.
• 3、 Gay, Ian D.,McFarlan, A. J.,Morrow, B. A.. "Trimethyl Phosphite Adsorbed on Silica: An NMR and Infrared Study". . p. 1360 - 1368. Retrieved 1991.
• 4、 Monbaliu, Jean-Christophe M.,Toupy, Thomas. "Intensified Continuous Flow Michaelis-Arbuzov Rearrangement toward Alkyl Phosphonates". supporting information. p. 467 - 478. Retrieved 2022/02/25.
• 5、 -. "METHOD FOR PRODUCING ORGANOPHOSPHORUS COMPOUND". Paragraph 0045; 0079. . Retrieved 2020/05/02.