dimethyl (2-oxoheptyl)phosphonate

• ChemBase ID: 74985
• Molecular Formular: C9H19O4P
• Molecular Mass: 222.218521
• Monoisotopic Mass: 222.10209572
• SMILES: P(=O)(OC)(OC)CC(=O)CCCCC
• Canonical SMILES: CCCCCC(=O)CP(=O)(OC)OC
• InChI: InChI=1S/C9H19O4P/c1-4-5-6-7-9(10)8-14(11,12-2)13-3/h4-8H2,1-3H3
• InChIKey: LQZCYXCHWNQBKX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl (2-oxoheptyl)phosphonate
• IUPAC Traditional name: dimethyl 2-oxoheptylphosphonate
• Synonyms: (2-Oxoheptyl)phosphonic acid dimethyl ester; Dimethyl (hexanoylmethyl)phosphonate; Dimethyl 2-oxoheptylphosphonate; 1-(Dimethoxyphosphoryl)-2-oxoheptane; Dimethyl (2-oxohept-1-yl)phosphonate 98%; (2-氧代庚基)膦酸二甲酯

Database IDs

• CAS Number: 36969-89-8
• EC Number: 253-293-4
• MDL Number: MFCD00009514
• Beilstein Number: 1946305
• PubChem SID: 162039903; 24849710
• PubChem CID: 580181

CALCULATED PROPERTIES

• Acid pKa: 15.192658
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.8255051
• LogD (pH = 7.4): 1.8255051
• Log P: 1.8255051
• Molar Refractivity: 54.5796 cm^3
• Polarizability: 22.115818 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 109 °C/0.4 mmHg(lit.); 109°C/0.4mm
• Flash Point: 110 °C; 110°C; 230 °F
• Density: 1.07 g/mL at 25 °C(lit.); 1.070
• Refractive Index: 1.4440; n20/D 1.444(lit.)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: 85%
• Grade: technical grade
• Linear Formula: CH3(CH2)4COCH2P(O)(OCH3)2

DETAILS

Sigma Aldrich - 157937

Application
A key intermediate in prostaglandin synthesis.
Reactant for:
• Beirut reaction for the preparation of phosphonylated quinoxaline dioxides1
• Preparation of pyrrolomorphinan derivatives as κ opioid agonists via cyclocondensation, Vilsmeier-Haack formylation, Horner-Wadsworth-Emmons reaction, and Kocienski-modified Julia olefination from naltrexone methyl ether2
• Synthesis of C-glycosides amphiphiles via solvent-free Horner-Wadsworth-Emmons reaction with unprotected sugars3
• Preparation of specific inhibitors of endocannabinoid biosynthesis4
Packaging
1 g in glass bottle