Dimethyl hydroxymethylphosphonate Chemical Properties

Boiling point:

209℃

Density 

1.245

Flash point:

80℃

storage temp. 

Inert atmosphere,Room Temperature

pka

12.73±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C3H9O4P/c1-6-8(5,3-4)7-2/h4H,3H2,1-2H3

InChIKey

OIERWUPLBOKSRB-UHFFFAOYSA-N

SMILES

P(CO)(=O)(OC)OC

CAS DataBase Reference

24630-67-9(CAS DataBase Reference)

Dimethyl hydroxymethylphosphonate Usage And Synthesis

Synthesis

Under stirring conditions, dimethyl phosphite (10.0 mL, 109 mmol), triethylamine (1.5 mL, 10.9 mmol) and paraformaldehyde (3.26 g) were mixed. The mixture was heated in an oil bath (external temperature) at 100°C. After 2.5 hours of reaction, the mixture was cooled to room temperature and subsequently concentrated under vacuum. The residue was purified by fast column chromatography (eluent: ethyl acetate/methanol, 95:5, v/v) to afford dimethyl hydroxymethylphosphonate as a colorless oil (9.41 g, 62% yield). The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 4.32 (1H, br s), 3.95 (2H, d, J = 6 Hz), 3.83 (3H, s), 3.81 (3H, s); 31P{1H} NMR (400.1 MHz, CDCl3): δ 27.8; 13C NMR (100.6 MHz. CDCl3): δ 53.5, 56.0, 57.6.

References

[1] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 12, p. 2432 - 2443
[2] Chemistry - A European Journal, 2009, vol. 15, # 9, p. 2064 - 2070
[3] Patent: WO2006/20779, 2006, A2. Location in patent: Page/Page column 77
[4] Organic Letters, 2012, vol. 14, # 18, p. 4798 - 4801
[5] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 3, p. 315 - 322

Dimethyl hydroxymethylphosphonate(24630-67-9)Related Product Information

• Diethyl (hydroxymethyl)phosphonate
• DIMETHYL PHOSPHATE
• TRIMETHYL PHOSPHONOFORMATE
• butonate
• Trichlorfon
• Ethyl diethoxyphosphinylformate
• DIETHYL 1-HYDROXYBUTYLPHOSPHONATE
• Dimethyl phosphite
• 2-ETHOXY-TRIETHYLPHOSPHONOACETATE
• DIETHYL(DIETHOXYMETHYL)PHOSPHONATE
• DIPHENYL (2,4-DICHLOROPHENYL)(HYDROXY)METHYLPHOSPHONATE
• DIMETHYL (2,2,2-TRICHLORO-1-([(3-CHLOROANILINO)CARBONYL]OXY)ETHYL)PHOSPHONATE
• DIMETHYL (2,2,2-TRICHLORO-1-([(4-CHLOROANILINO)CARBONYL]OXY)ETHYL)PHOSPHONATE
• METHYL DIETHOXY PHOSPHINYL FORMATE
• DIMETHYL (1-([(BUTYLAMINO)CARBONYL]OXY)-2,2,2-TRICHLOROETHYL)PHOSPHONATE
• DIMETHYL [3-(4-BROMOPHENYL)-3-CHLORO-1-HYDROXYALLYL]PHOSPHONATE
• DIMETHYL [2,2,2-TRICHLORO-1-(([3-(TRIFLUOROMETHYL)ANILINO]CARBONYL)OXY)ETHYL]PHOSPHONATE
• DIPHENYL HYDROXY(4-PYRIDINYL)METHYLPHOSPHONATE