ethyl 2-(diethoxyphosphoryl)acetate

• ChemBase ID: 74926
• Molecular Formular: C8H17O5P
• Molecular Mass: 224.191341
• Monoisotopic Mass: 224.08136027
• SMILES: P(=O)(OCC)(CC(=O)OCC)OCC
• Canonical SMILES: CCOC(=O)CP(=O)(OCC)OCC
• InChI: InChI=1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3
• InChIKey: GGUBFICZYGKNTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(diethoxyphosphoryl)acetate
• IUPAC Traditional name: triethyl phosphonoacetate
• Synonyms: Triethyl phosphonoacetate; Ethyl (diethoxyphosphoryl)acetate; Diethyl (ethoxycarbonylmethyl)phosphonate; (Diethoxyphosphinyl)acetic acid ethyl ester; NSC 13898; NSC 16128; Diethyl ethoxycarbonylmethylphosphonate; Triethyl carboxymethylphosphonate; Triethyl phosphonoacetate; 2-(Diethoxyphosphinyl)acetic Acid Ethyl Ester; Carbethoxymethyldiethyl Phosphonate; Phosphonoacetic acid triethyl ester; Ethyl 2-(diethoxyphosphoryl)acetate; Diethyl ethoxycarbonylmethyl-phosphonate; TRIETHYL PHOSPHONOACETATE; 乙氧基羰酰甲基膦酸二乙酯; 羧甲基膦酸三乙酯; 膦酰基乙酸三乙酯; 膦酰乙酸三乙酯

Database IDs

• CAS Number: 867-13-0
• EC Number: 212-757-6
• MDL Number: MFCD00009177
• Beilstein Number: 1343714
• PubChem SID: 162039844; 24900348; 24887466
• PubChem CID: 13345
• Wikipedia Title: Triethyl_phosphonoacetate

CALCULATED PROPERTIES

• Acid pKa: 17.777735
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.6265928
• LogD (pH = 7.4): 0.6265928
• Log P: 0.6265928
• Molar Refractivity: 51.6135 cm^3
• Polarizability: 21.043863 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Colorless, Clear liquid
• Melting Point: -24°C; -24°C
• Boiling Point: 142-145 °C at 9 mmHg; 142-145 °C/9 mmHg(lit.); 260-262°C; 260-262°C
• Flash Point: 105 °C; 105°C; 165°C(329°F); 221 °F
• Density: 1.125; 1.13; 1.13 g/mL at 25 °C(lit.)
• Refractive Index: 1.431; 1.4310; n20/D 1.431(lit.); n20/D 1.432

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Irritant
• RTECS: AG9800000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3082
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36/38; 51/53
• Safety Statements: 23-26-37; 61
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 3082 9/PG 3

Product Information

• Purity: >95%; ≥97.0% (GC); 95+%; 98%; 98+%
• Grade: purum
• Linear Formula: (C2H5O)2P(O)CH2CO2C2H5

DETAILS

MP Biomedicals - 02157016

Purity: >95%

Sigma Aldrich - T61301

Application
Horner-Emmons-Wadsworth reagent recently used in the synthesis of chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.7
Reactant involved in:
• Horner-Wadsworth-Emmons reactions1,2
• Intramolecular Heck-type cyclization and isomerizations3
• Tsuji-Trost type reactions4
• Intramolecular aryne-ene reactions5
• Synthesis of aldehydes6
Packaging
100 g in poly bottle
25 g in glass bottle

Sigma Aldrich - 79525

Other Notes
A Horner-Wittig reagent, review7,8; Improved procedure for the C2 homologation of esters to α,β-unsaturated esters9; Synthesis of α-(hydroxymethyl)acrylate10
Application
Reactant involved in:
• Horner-Wadsworth-Emmons reactions1,2
• Intramolecular Heck-type cyclization and isomerizations3
• Tsuji-Trost type reactions4
• Intramolecular aryne-ene reactions5
• Synthesis of aldehydes6

Toronto Research Chemicals - T777000

Reagent used for Horner-Emmons modification.

REFERENCES

• Hediger, M., et al.: Bioorg. Med. Chem., 12, 4995 (2004)
• Kim, J., et al.: Nat., 452, 239 (2004)
• Base-catalyzed aldol, Cannizzaro and saponification reactions can be minimized, by the use of, e.g.: K₂CO₃: Synthesis, 300 (1983); Tetrahedron Lett., 26, 53 (1985); F^-: Tetrahedron Lett., 21, 2161 (1980); N-ethyldiisopropylamine + LiCl: Tetrahedron Lett., 25, 2183 (1984); Et₃N + Li halides: J. Org. Chem., 50, 2624 (1985).
• Reaction with aqueous formaldehyde does not lead to the "expected" Wadsworth-Emmons product, but to ethyl ɑ-(hydroxymethyl)acrylate, a precursor of the synthetically useful ethyl ɑ-bromomethylacrylate, by condensation with the initially-formed "aldol" product: Org. Synth. Coll., 8, 265 (1993).
• Wadsworth-Emmons (Horner) reaction with aldehydes and ketones gives acrylic esters. See, e.g.: Org. Synth. Coll., 5, 509, 547 (1973), and Appendix 1.