2-(diethoxyphosphoryl)acetic acid

• ChemBase ID: 74944
• Molecular Formular: C6H13O5P
• Molecular Mass: 196.138181
• Monoisotopic Mass: 196.05006015
• SMILES: O=C(CP(=O)(OCC)OCC)O
• Canonical SMILES: CCOP(=O)(CC(=O)O)OCC
• InChI: InChI=1S/C6H13O5P/c1-3-10-12(9,11-4-2)5-6(7)8/h3-5H2,1-2H3,(H,7,8)
• InChIKey: DVQMPWOLBFKUMM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diethoxyphosphoryl)acetic acid
• IUPAC Traditional name: (diethoxyphosphoryl)acetic acid
• Synonyms: (Diethoxyphosphoryl)acetic acid; Diethylphosphonoacetic acid; Diethyl (hydroxycarbonylmethyl)phosphonate; (Diethoxyphosphinyl)acetic acid; Diethyl carboxymethylphosphonate; NSC 272281; Diethylphosphonoacetic acid; 2-(Diethoxyphosphoryl)acetic acid; DIETHYLPHOSPHONOACETIC ACID; 二乙基磷乙酸

Database IDs

• CAS Number: 3095-95-2
• MDL Number: MFCD00192032
• PubChem SID: 24856264; 162039862
• PubChem CID: 36704

CALCULATED PROPERTIES

• Acid pKa: 4.3356194
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.99808514
• LogD (pH = 7.4): -2.75822
• Log P: 0.1934423
• Molar Refractivity: 42.0958 cm^3
• Polarizability: 17.191698 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 150 °C/0.05 mmHg(lit.); 150°C/0.05mm
• Flash Point: >110 °C; >110°C; >230 °F
• Density: 1.220 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.445(lit.)

Safety Information

• Storage Warning: Harmful/Irritant
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 95%; 95+%; 97%
• Linear Formula: (C2H5O)2P(O)CH2CO2H

DETAILS

Sigma Aldrich - 268127

Packaging
25 mL in poly bottle
5 mL in glass bottle
Application
Acts as a nucleophile for nucleophilic addition reactions for synthesis of allene epoxides1Reactant for:
• Stereoselectivity studies of the Staudinger reaction2
• Enantioselective formation of diols via epoxidation and hydration reactions3
• Horner-Wadsworth-Emmons reactions4,5
• Remote chelation controlled Ireland-Claisen rearrangement6
• Ugi-Dieckmann reactions for synthesis of tetramic acid derivatives7
Used to make phosphonoester intermediates for intramolecular HEW reactions.