Description

Diethyl (2-amino-2-oxoethyl)phosphonate (CAS No. 5464-68-6) is a high-purity organophosphorus compound with the molecular formula C₆H₁₄NO₄P. This versatile reagent is widely utilized in organic synthesis, pharmaceutical research, and material science due to its unique phosphonate and amide functional groups. It serves as a key intermediate in the preparation of α-aminophosphonic acids, peptidomimetics, and bioactive molecules. The product is supplied as a white to off-white crystalline powder with ≥95% purity (HPLC), ensuring consistency for critical applications. Its stability under standard laboratory conditions makes it ideal for long-term storage. Suitable for use in coupling reactions, nucleophilic substitutions, and as a precursor for heterocyclic compounds, this chemical is a valuable asset for researchers developing novel therapeutics or agrochemicals.

Properties

• CAS Number: 5464-68-6
• Complexity: 184
• IUPAC Name: 2-diethoxyphosphorylacetamide
• InChI: InChI=1S/C6H14NO4P/c1-3-10-12(9,11-4-2)5-6(7)8/h3-5H2,1-2H3,(H2,7,8)
• InChI Key: QPVCUQOSWAXEOQ-UHFFFAOYSA-N
• Exact Mass: 195.06604493
• Molecular Formula: C6H14NO4P
• Molecular Weight: 195.15
• SMILES: CCOP(=O)(CC(=O)N)OCC
• Topological: 78.6
• Monoisotopic Mass: 195.06604493
• Synonyms: 5464-68-6, Diethyl (2-amino-2-oxoethyl)phosphonate, 2-diethoxyphosphorylacetamide, Diethyl carbamoylmethylphosphonate, Phosphonic acid, (carbamoylmethyl)-, diethyl ester, diethyl (carbamoylmethyl)phosphonate, Diethyl aminocarbonylmethylphosphonate, MFCD00014805, F0304-0021, diethyl(2-amino-2-oxoethyl)phosphonate, Phosphonic acid, (2-amino-2-oxoethyl)-, diethyl ester, Diethylphosphonoacetamid, Diethylphosphonoacetamide, diethylphosphono-acetamide, (diethoxyphosphoryl)acetamide, 2-(diethylphosphono)acetamide, SCHEMBL2857622, SCHEMBL2872034, DTXSID60280088, QPVCUQOSWAXEOQ-UHFFFAOYSA-N, SMSSF-0042776, NSC15422, NSC-15422, diethyl 2-amino-2-oxoethylphosphonate, AKOS003614392, GS-6295, Diethyl carbamoylmethylphosphonate, 95%, DA-34849, SY116312, CS-0129422, (Carbamoylmethyl)-Phosphonic Acid Diethyl Ester, EN300-155023, F11907

Diethyl (2-amino-2-oxoethyl)phosphonate is primarily employed as a building block in medicinal chemistry for synthesizing phosphonate-based protease inhibitors and antibacterial agents. It facilitates Horner-Wadsworth-Emmons reactions to form α,β-unsaturated carbonyl derivatives. Researchers also utilize it in metal-catalyzed cross-coupling reactions to construct C-P bonds. In material science, it contributes to flame-retardant polymer modifications. Its dual functionality allows simultaneous derivatization at both phosphonate and amide groups.

Safety and Hazards

GHS Hazard Statements

• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statements

• P264+P265, P280, P305+P351+P338, and P337+P317

Hazard Classes and Categories

• Eye Irrit. 2 (100%)

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