dimethyl (2-oxopropyl)phosphonate

• ChemBase ID: 74987
• Molecular Formular: C5H11O4P
• Molecular Mass: 166.112201
• Monoisotopic Mass: 166.03949546
• SMILES: P(=O)(OC)(CC(=O)C)OC
• Canonical SMILES: COP(=O)(CC(=O)C)OC
• InChI: InChI=1S/C5H11O4P/c1-5(6)4-10(7,8-2)9-3/h4H2,1-3H3
• InChIKey: UOWIYNWMROWVDG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl (2-oxopropyl)phosphonate
• IUPAC Traditional name: dimethyl 2-oxopropylphosphonate
• Synonyms: Dimethyl (acetylmethyl)phosphonate; (Dimethoxyphosphoryl)acetone; Dimethyl (2-oxoprop-1-yl)phosphonate 97+%; Dimethyl acetonylphosphonate; Dimethyl 2-oxopropylphosphonate; dimethyl (2-oxopropyl)phosphonate; DIMETHYL (2-OXOPROPYL)-PHOSPHONATE; Acetylmethylphosphonic acid dimethyl ester; Dimethyl acetylmethylphosphonate; 丙酮基磷酸二甲酯; 2-氧代丙基膦酸二甲酯; 丙酮基膦酸二甲酯

Database IDs

• CAS Number: 4202-14-6
• EC Number: 224-110-5
• MDL Number: MFCD00008769
• Beilstein Number: 1766218
• PubChem SID: 162039905; 24886902; 24850888
• PubChem CID: 77872

CALCULATED PROPERTIES

• Acid pKa: 15.5211315
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.08418241
• LogD (pH = 7.4): -0.08418242
• Log P: -0.08418241
• Molar Refractivity: 36.1497 cm^3
• Polarizability: 14.842041 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 121-123°C/11mm; 76-79 °C/3 mmHg(lit.); 76-79°C @ 3 mm Hg; 76-79°C/3mm
• Flash Point: 199.4 °F; 93 °C; 93.3°C; 93°C(199°F)
• Density: 1.202; 1.202 g/ml; 1.202 g/mL at 25 °C(lit.)
• Refractive Index: 1.439; 1.4390; n20/D 1.439(lit.)
• Hydrophobicity(logP): -0.84

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (GC); 95%; 95+%; 97%; 98%
• Grade: technical
• Linear Formula: CH3COCH2P(O)(OCH3)2

DETAILS

MP Biomedicals - 02157834

Purity: 95%

Sigma Aldrich - 180696

Application
Reagent used together with tosyl azide in a one-pot alkynylation of aldehydes.1,2
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 75948

Other Notes
Wittig-Horner reagent used for the acetonylenation of aldehydes; best conditions for a high E/Z ratio (DBU, LiCl in CH3CN)1,2,3; Synthesis of β-keto phosphonates by γ-alkylation of dianion4

REFERENCES

• For use of ?-ketophosphonates in an annulation sequence for building a cyclohexadienone ring onto a cyclic ketone, see: Synthesis, 855 (1982):
  
• Successive treatment with NaH and n-BuLi gives the dianion which can be alkylated or acylated on the terminal position: see. e.g.: Synth. Commun., 22, 219 (1992); J. Chem. Soc., Perkin 1, 2259 (1998).
• Horner-Wadsworth-Emmons precursor of ɑ?-unsaturated ketones.