| Identification | Back Directory | [Name]
Phosphonic acid, (carbamoylmethyl)-, diethyl ester | [CAS]
5464-68-6 | [Synonyms]
(Diethoxyphosphinyl)acetamide
2-diethoxyphosphorylacetamide
2-diethoxyphosphorylethanamide
Diethyl carbamoylmethylphosphonate
Diethyl aminocarbonylmethylphosphonate
Diethyl carbamyl methyl phosphonic acid
Diethyl [(2-amino-2-oxo)ethyl]phosphonate
Carbamoylmethyl-phosphonic acid diethyl ester
Diethyl((2-amino-2-oxo)ethyl)phosphonate, 95 %
(2-Amino-2-oxoethyl)phosphonic acid diethyl ester
Phosphonic acid, (carbamoylmethyl)-, diethyl ester
Phosphonic acid, P-(2-amino-2-oxoethyl)-, diethyl ester
Diethyl carbamoylmethylphosphonate 2-diethoxyphosphorylacetamide | [Molecular Formula]
C6H14NO4P | [MDL Number]
MFCD00014805 | [MOL File]
5464-68-6.mol | [Molecular Weight]
195.15 |
| Chemical Properties | Back Directory | [Melting point ]
78-80 °C | [Boiling point ]
338.9±25.0 °C(Predicted) | [density ]
1.180±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder | [pka]
15.46±0.40(Predicted) | [Appearance]
Off-white to light yellow Solid | [BRN ]
1777584 | [InChI]
1S/C6H14NO4P/c1-3-10-12(9,11-4-2)5-6(7)8/h3-5H2,1-2H3,(H2,7,8) | [InChIKey]
QPVCUQOSWAXEOQ-UHFFFAOYSA-N | [SMILES]
CCOP(=O)(CC(N)=O)OCC |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H319 | [Precautionary statements ]
P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
36 | [Safety Statements ]
26 | [WGK Germany ]
3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [reaction suitability]
reaction type: C-C Bond Formation | [Synthesis]
General procedure for the synthesis of diethyl carbamoylmethylphosphonate from chloroacetamide and triethyl phosphite: 2-chloroacetamide (5.01 g, 53.6 mmol) and triethyl phosphite (9.19 mL, 53.6 mmol) were dissolved in o-xylene (14 mL), and heated and refluxed for 3.5 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure to give a dark brown tarry residue. The residue was dissolved in dichloromethane and filtered through a short silica gel column. The filtrate was concentrated and the resulting solid was recrystallized with ethyl acetate/pentane mixed solvent to afford diethyl carbamoylmethylphosphonate (3.42 g, 33% yield) as light brown crystals. The structure of the product was analyzed by 1H NMR (200 MHz, DMSO-d6) δ 7.35 (br s, 1H), 7.02 (br s, 1H), 4.02 (dq, 4H, J = 7.1 Hz, JPH = 1.1 Hz), 2.80 (d, 2H, JPH = 21.4 Hz), 1.23 (t, 6H, J = 7.0 Hz); 13C NMR (50 MHz, DMSO-d6) δ 166.0 (d, 2JCP = 5.1 Hz), 61.5 (d, 2JCP = 6.0 Hz), 34.5 (d, 1JCP = 131.6 Hz), 16.2 (d, 3JCP = 6.0 Hz); 31P NMR (81 MHz, DMSO-d6) δ 23.8 confirmed. Mass spectrometry results: ESIMS m/z 218 [M + Na]+; high resolution mass spectrometry (HRMS) calculated value C6H14NO4P [M]+ 195.0655, measured value 195.0653. | [References]
[1] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9140 - 9151
[2] Patent: WO2015/39173, 2015, A1. Location in patent: Page/Page column 12; 13
[3] Journal of Organic Chemistry, 1959, vol. 24, p. 434
[4] Journal of Organic Chemistry, 1958, vol. 23, p. 1883,1885
[5] Pesticide Science, 1994, vol. 40, # 1, p. 57 - 62 |
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