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Methyl diethylphosphonoacetate

CAS No.
1067-74-9
Chemical Name:
Methyl diethylphosphonoacetate
Synonyms
POME;APAZ-027;NSC 147757;LABOTEST-BB LT00452673;Mirogabalin Impurity 59;DIETHYLMETHYLPHOSPHONOACETATE;Methyl 2-(diethoxyphosphoryl);METHYL DIETHYLPHOSPHONOACETATE;MethylDiethylphosphonoacetate>Diethyl methyl phosphonylacetate
CBNumber:
CB9468917
Molecular Formula:
C7H15O5P
Molecular Weight:
210.16
MDL Number:
MFCD00009081
MOL File:
1067-74-9.mol
Last updated:2025-07-24 18:13:40

Methyl diethylphosphonoacetate Properties

Boiling point 127-131 °C9 mm Hg(lit.)
Density 1.145 g/mL at 25 °C(lit.)
refractive index n20/D 1.433(lit.)
Flash point >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Miscible with tetrahydrofuran.
form Liquid
color Clear colorless to faint yellow
BRN 1782397
InChI InChI=1S/C7H15O5P/c1-4-11-13(9,12-5-2)6-7(8)10-3/h4-6H2,1-3H3
InChIKey CTSAXXHOGZNKJR-UHFFFAOYSA-N
SMILES C(OC)(=O)CP(OCC)(OCC)=O
CAS DataBase Reference 1067-74-9(CAS DataBase Reference)
NIST Chemistry Reference Acetic acid, phosphono-, p,p-diethyl c-methyl ester(1067-74-9)
UNSPSC Code 12352108
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
10
HS Code  29310095
NFPA 704
1
2 0

Methyl diethylphosphonoacetate price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 158763 Methyl diethylphosphonoacetate 97% 1067-74-9 10g $59.99 2025-07-31 Buy
Sigma-Aldrich 158763 Methyl diethylphosphonoacetate 97% 1067-74-9 50g $175 2025-07-31 Buy
TCI Chemical D2873 Methyl Diethylphosphonoacetate >96.0%(GC) 1067-74-9 5g $20 2025-07-31 Buy
TCI Chemical D2873 Methyl Diethylphosphonoacetate >96.0%(GC) 1067-74-9 25g $47 2025-07-31 Buy
Usbiological 283239 Methyl diethylphosphonoacetate 1067-74-9 3.51g $297 2021-12-16 Buy
Product number Packaging Price Buy
158763 10g $59.99 Buy
158763 50g $175 Buy
D2873 5g $20 Buy
D2873 25g $47 Buy
283239 3.51g $297 Buy

Methyl diethylphosphonoacetate Chemical Properties,Uses,Production

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

Methyl diethylphosphonoacetate is used as a reagent in the preparation of allylic fluorides compounds and in regioselective Diels-Alder reactions. It also serves as a reactant in the preparation of substituted thiophenes and furans, which finds application in type 2 diabetes treatment. Further, it acts as a precursor in the synthesis of pyridone alkaloids and immunosuppressive cyclopentanediol derivatives. In addition to this, it is utilized in the modification of botulinum neurotoxin serotype A protease inhibitors.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Ethanol

64-17-5

Acetic acid, 2-[bis[(trimethylsilyl)oxy]phosphinyl]-, methyl ester

67605-34-9

Methyl diethylphosphonoacetate

1067-74-9

TMSBr (90 μL, 0.691 mmol) was added to a solution of anhydrous CH2Cl2 (0.55 mL) of trimethyl phosphonoacetate (2; 50.3 mg, 0.276 mmol) at room temperature. After the reaction mixture was stirred under argon protection at room temperature for 5 h, the solvent was removed by vacuum evaporation to afford methyl 2-[bis[(trimethylmethylsilyl)oxy]phosphono}acetate (4), which was used for the next reaction without further purification. Subsequently, Ph3P (181 mg, 0.691 mmol) and I2 (175 mg, 0.691 mmol) were added to an anhydrous CHCl3 (1.8 mL) solution of 4 under argon protection. The reaction mixture was stirred at room temperature for 15 minutes and then imidazole (188 mg, 2.76 mmol) was added. Stirring was continued at room temperature for 15 minutes, then the reaction mixture was heated to 50°C and held for 30 minutes. Next, 2,2,2-trifluoroethanol (79 μl, 1.10 mmol) was added and the reaction mixture was stirred at 60°C for 5 hours. Upon completion of the reaction, the reaction mixture was filtered and the filtrate was evaporated under vacuum to give the crude product 1. The crude product was purified by column chromatography [silica gel PSQ 60B: n-hexane-EtOAc (2:1)] to give the final product methyl diethylphosphonoacetate (1; 82.3 mg, 94%) as a colorless oil.

References

[1] Synlett, 2018, vol. 29, # 11, p. 1461 - 1464

96-34-4
122-52-1
1067-74-9
Synthesis of Methyl diethylphosphonoacetate from Methyl chloroacetate and Triethyl phosphite
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View Lastest Price from Methyl diethylphosphonoacetate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Methyl diethylphosphonoacetate pictures 2025-08-08 Methyl diethylphosphonoacetate
1067-74-9
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mujin Biotechnology Co.,Ltd
Methyl diethylphosphonoacetate pictures 2025-06-27 Methyl diethylphosphonoacetate
1067-74-9
US $0.00 / KG 1KG 99% 500000kg Hebei Chuanghai Biotechnology Co., Ltd
Methyl diethylphosphonoacetate pictures 2025-06-20 Methyl diethylphosphonoacetate
1067-74-9
US $20.00-1.00 / kg 1kg 0.99 20 tons Hebei Yanxi Chemical Co., Ltd.
Diethyl methoxycarbonylmethanephosphonate for synthesis Acetic acid, (diethoxyphosphinyl)-, methyl ester Diethyl carbomethoxymethylphosphonate Methyl (diethoxyphosphoryl)acetate APAZ-027 METHYL P,P-DIETHYLPHOSPHONOACETATE METHYL DIETHYLPHOSPHONOACETATE LABOTEST-BB LT00452673 DIETHYLPHOSPHONOACETIC ACID METHYL ESTER DIETHYL METHOXYCARBONYLMETHANEPHOSPHONATE DIETHYLMETHYLPHOSPHONOACETATE diethyl methoxycarbonylmethyl phosphonate phosphonoacetic acid diethyl methyl ester Diethyl(methoxycarbonyl)methylphosphonate, 98 % Methyl diethylphosphonoacetate, Methyl (diethoxyphosphoryl)acetate Diethyl methoxycarbonylmethyl phosphonate~Phosphonoacetic acid diethyl methyl ester POME (Diethoxyphosphinyl)acetic acid methyl 2-(Diethoxyphosphinyl)acetic acid methyl ester Diethoxyphosphinylacetic acid methyl ester Methyl diethylphosphonoacetate,98% Methyl diethylphosphonoacetate, 98% 10GR Methyl 2-(diethoxyphosphoryl)acetate Methyl diethylphosphonoacetate 97% Methyl diethylphosphonoacetate, 95+% Methyl 2-(diethoxyphosphoryl) (Methoxycarbonylmethyl) diethoxyphosphine oxide NSC 147757 Acetic acid,2-(diethoxyphosphinyl)-, methyl ester 3-methoxycarbonylpentan-3-ylphosphonic acid MethylDiethylphosphonoacetate> Diethyl methyl phosphonylacetate Methylphosphonoyl acetate diethyl ester Mirogabalin Impurity 59 1067-74-9 C2H5O2POCH2CO2CH3 C-C Bond Formation Wittig & Horner-Emmons Reaction Horner-Emmons Reaction Olefination Synthetic Reagents Horner-Wadsworth-Emmons Reagents Horner-Emmons Reaction Synthetic Organic Chemistry Wittig & Horner-Emmons Reaction