dimethyl methylphosphonate

• ChemBase ID: 74984
• Molecular Formular: C3H9O3P
• Molecular Mass: 124.075521
• Monoisotopic Mass: 124.02893078
• SMILES: P(=O)(OC)(OC)C
• Canonical SMILES: COP(=O)(OC)C
• InChI: InChI=1S/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3
• InChIKey: VONWDASPFIQPDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl methylphosphonate
• IUPAC Traditional name: dimethyl methylphosphonate
• Synonyms: Dimethyl methylphosphonate; Dimethoxymethyl phosphine oxide; Fyrol DMMP; Methanephosphonic acid dimethyl ester; NSC 62240; Reoflam DMMP; Dimethyl methylphosphonate; DMMP; Methylphosphonic acid dimethyl ester; DIMETHYLMETHYLPHOSPHONATE; 甲基膦酸二甲酯; 甲基磷酸二甲酯

Database IDs

• CAS Number: 756-79-6
• EC Number: 212-052-3
• MDL Number: MFCD00008349
• Beilstein Number: 878263
• Merck Index: 143391
• PubChem SID: 162039902; 24893515; 24883205
• PubChem CID: 12958
• Chemspider ID: 12418
• Wikipedia Title: Dimethyl_methylphosphonate

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.11216304
• LogD (pH = 7.4): -0.11216304
• Log P: -0.11216304
• Molar Refractivity: 26.1426 cm^3
• Polarizability: 11.052001 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: colorless liquid
• Melting Point: -50°C
• Boiling Point: 180-181°C; 181 °C(lit.); 181°C
• Flash Point: 156.2 °F; 68°C; 68°C(154°F); 69 °C
• Density: 1.145 g/ml; 1.145 g/mL at 25 °C(lit.); 1.16
• Refractive Index: 1.413; 1.4130; n20/D 1.413; n20/D 1.413(lit.)
• Vapor Pressure: <0.1 mmHg ( 20 °C)

Safety Information

• Storage Warning: Harmful/Carcinogenic/Mutagenic/Teratogenic/Irritant
• RTECS: SZ9120000
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• German water hazard class: 2; 3
• Risk Statements: 46-36; 46-36-52/53; R:36/37/38
• Safety Statements: 53-26-45; 53-45-61; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H332; H340-H319-H227-H402-H412
• GHS Precautionary statements: P210-P280-P281-P305+P351+P338-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (GC); 97%
• Grade: purum
• Linear Formula: CH3P(O)(OCH3)2

DETAILS

MP Biomedicals - 05204081

NOT FOR EXPORT

Sigma Aldrich - D169102

Packaging
100, 500 g in poly bottle
5 g in glass bottle
Application
Reagent used in the conversion of esters to ketophosphonates.1,2,3
Used to test SXFA-coated SAW chemical sensors for organophosphorous compound detectionUsed as a chemical agent simulant for testing of protective performance of PSS membranes and functionalized sorbent membranesReactant for photocatalytic oxidationAdditive for synthesis of:
• Flame retardant high phosphorous containing unsaturated polyester resin
• UV-cured epoxy acrylate / microencapsulated phase change material

Sigma Aldrich - 64258

Other Notes
Convenient Wittig-Horner reagent7,8
Application
Used to test SXFA-coated SAW chemical sensors for organophosphorous compound detection1Used as a chemical agent simulant for testing of protective performance of PSS membranes2 and functionalized sorbent membranes3Reactant for photocatalytic oxidation4Additive for synthesis of:
• Flame retardant high phosphorous containing unsaturated polyester resin5
• UV-cured epoxy acrylate / microencapsulated phase change material6

REFERENCES

• See also Diethyl methylphosphonate, A14772 and Appendix 1.
• The lithio-derivative reacts with esters to give ?-ketophosphonates, useful precursors of ɑ?-unsaturated ketones by Horner-Wadsworth-Emmons olefination: J. Am. Chem. Soc., 88, 5654 (1966). An intramolecular version leads to cyclopentenones: Synth. Commun., 5, 1 (1975); Tetrahedron Lett., 22, 257 (1981). Dimethyl glutarate gives the 3-(phosphonatomethyl)cyclohexenone, olefination of which affords the corresponding 3-alkenylcycloalkenone. Dimethyl succinate also gives this reaction, but in lower yield; higher diesters give acyclic products: J. Org. Chem., 59, 1943 (1994):