ChemicalBook > CAS DataBase List > Phosphonic acid, (carbamoylmethyl)-, diethyl ester

Phosphonic acid, (carbamoylmethyl)-, diethyl ester

Product Name
Phosphonic acid, (carbamoylmethyl)-, diethyl ester
CAS No.
5464-68-6
Chemical Name
Phosphonic acid, (carbamoylmethyl)-, diethyl ester
Synonyms
2-diethoxyphosphorylacetamide;(Diethoxyphosphinyl)acetamide;2-diethoxyphosphorylethanamide;Diethyl carbamoylmethylphosphonate;Diethyl aminocarbonylmethylphosphonate;Diethyl aminoformyl methyl phosphonate;Diethyl carbamyl methyl phosphonic acid;Diethyl [(2-amino-2-oxo)ethyl]phosphonate;Diethyl?P-(2-amino-2-oxoethyl)phosphonate;Carbamoylmethyl-phosphonic acid diethyl ester
CBNumber
CB61251744
Molecular Formula
C6H14NO4P
Formula Weight
195.15
MOL File
5464-68-6.mol
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Phosphonic acid, (carbamoylmethyl)-, diethyl ester Property

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
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Safety

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
26
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
744212
Product name
Diethyl carbamoylmethylphosphonate
Purity
95%
Packaging
1g
Price
$33.74
Updated
2025/07/31
Sigma-Aldrich
Product number
744212
Product name
Diethyl carbamoylmethylphosphonate
Purity
95%
Packaging
5g
Price
$138
Updated
2023/06/20
TRC
Product number
D474253
Product name
Diethyl(2-Amino-2-oxoethyl)phosphonate
Packaging
100mg
Price
$75
Updated
2021/12/16
AK Scientific
Product number
7920AB
Product name
Diethyl(2-amino-2-oxoethyl)phosphonate
Packaging
1g
Price
$94
Updated
2021/12/16
Biosynth Carbosynth
Product number
FD140038
Product name
Diethyl (2-amino-2-oxoethyl)phosphonate
Packaging
1g
Price
$108
Updated
2021/12/16
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Phosphonic acid, (carbamoylmethyl)-, diethyl ester Chemical Properties,Usage,Production

reaction suitability

reaction type: C-C Bond Formation

Synthesis

79-07-2

122-52-1

5464-68-6

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

Phosphonic acid, (carbamoylmethyl)-, diethyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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Phosphonic acid, (carbamoylmethyl)-, diethyl ester Suppliers

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5464-68-6, Phosphonic acid, (carbamoylmethyl)-, diethyl esterRelated Search:


  • Diethyl carbamoylmethylphosphonate
  • Diethyl carbamoylmethylphosphonate 2-diethoxyphosphorylacetamide
  • Carbamoylmethyl-phosphonic acid diethyl ester
  • Diethyl aminocarbonylmethylphosphonate
  • Phosphonic acid, (carbamoylmethyl)-, diethyl ester
  • Diethyl((2-amino-2-oxo)ethyl)phosphonate, 95 %
  • (2-Amino-2-oxoethyl)phosphonic acid diethyl ester
  • (Diethoxyphosphinyl)acetamide
  • 2-diethoxyphosphorylacetamide
  • 2-diethoxyphosphorylethanamide
  • Diethyl [(2-amino-2-oxo)ethyl]phosphonate
  • Phosphonic acid, P-(2-amino-2-oxoethyl)-, diethyl ester
  • Diethyl carbamyl methyl phosphonic acid
  • Diethyl aminoformyl methyl phosphonate
  • Diethyl?P-(2-amino-2-oxoethyl)phosphonate
  • 5464-68-6