Dimethyl hydroxymethylphosphonate

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CAS:24630-67-9
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Dimethyl hydroxymethylphosphonate Basic information
Product Name:Dimethyl hydroxymethylphosphonate
Synonyms:Dimethyl hydroxymethylphosphonate;Hydroxymethylphosphonic acid dimethyl ester;Phosphonic acid, P-(hydroxymethyl)-, dimethyl ester
CAS:24630-67-9
MF:C3H9O4P
MW:140.07
EINECS:
Product Categories:
Mol File:24630-67-9.mol
Dimethyl hydroxymethylphosphonate Structure
Dimethyl hydroxymethylphosphonate Chemical Properties
Boiling point 209℃
density 1.245
Fp 80℃
storage temp. Inert atmosphere,Room Temperature
pka12.73±0.10(Predicted)
AppearanceColorless to light yellow Liquid
InChIInChI=1S/C3H9O4P/c1-6-8(5,3-4)7-2/h4H,3H2,1-2H3
InChIKeyOIERWUPLBOKSRB-UHFFFAOYSA-N
SMILESP(CO)(=O)(OC)OC
CAS DataBase Reference24630-67-9(CAS DataBase Reference)
Safety Information
MSDS Information
Dimethyl hydroxymethylphosphonate Usage And Synthesis
Synthesis
Formaldehyde

50-00-0

Dimethyl phosphite

868-85-9

Dimethyl hydroxymethylphosphonate

24630-67-9

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 Preparation Products And Raw materials
Raw materialsFormaldehyde-->Dimethyl phosphite
Tag: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