diethyl (bromodifluoromethyl)phosphonate

• ChemBase ID: 10595
• Molecular Formular: C5H10BrF2O3P
• Molecular Mass: 267.0056674
• Monoisotopic Mass: 265.95189925
• SMILES: O=P(OCC)(C(Br)(F)F)OCC
• Canonical SMILES: CCOP(=O)(C(Br)(F)F)OCC
• InChI: InChI=1S/C5H10BrF2O3P/c1-3-10-12(9,11-4-2)5(6,7)8/h3-4H2,1-2H3
• InChIKey: QRADKVYIJIAENZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (bromodifluoromethyl)phosphonate
• IUPAC Traditional name: diethyl bromodifluoromethylphosphonate
• Synonyms: Bromodifluoromethyl diethyl phosphonate; Diethyl bromodifluoromethanephosphonate; Diethyl (bromodifluoromethyl)phosphonate; Bromodifluoromethyl diethylphosphonate 97%; (Bromodifluoromethyl)phosphonic acid diethyl ester; Diethyl (bromodifluoromethyl)phosphonate; 二氟甲基膦酸二乙酯; 溴氟甲基膦酸二乙酯

Database IDs

• CAS Number: 65094-22-6
• MDL Number: MFCD00069118
• Beilstein Number: 1944045
• PubChem SID: 160973902; 24865745
• PubChem CID: 144101

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.7351935
• LogD (pH = 7.4): 2.7351935
• Log P: 2.7351935
• Molar Refractivity: 43.7335 cm^3
• Polarizability: 17.617662 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 40-41 °C/0.05 mmHg(lit.); 97-98°C/19mm; 99-102°C/16mm; 99-102°C/16mm
• Flash Point: >110°C(230°F); >113 °C; >235.4 °F
• Density: 1.503; 1.503 g/mL at 25 °C(lit.)
• Refractive Index: 1.4160; 1.4890; n20/D 1.417(lit.)
• Hydrophobicity(logP): 1.515

Safety Information

• Storage Warning: Irritant; IRRITANT, IRRITANT-HARMFUL
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 23-26-37-60
• TSCA Listed: false; 否
• 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

Product Information

• Purity: 95%; 96%; 97%; 98%
• Linear Formula: BrCF2P(O)(OC2H5)2

DETAILS

Sigma Aldrich - 411361

Packaging
5 g in glass bottle
Application
Reactant for:
• Preparation of phosphopeptide mimetic prodrugs targeted to Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat3)1
• Synthesis of Mycobacterium tuberculosis protein tyrosine phosphatase inhibitory difluoromethylphosphonic acid derivatives via multi step synthesis with Suzuki coupling and resolution as key steps2
• P-C bond cleavage on basic hydrolysis3
• Preparation of a prodrug for intracellular delivery of protein tyrosine phosphatase 1B (PTP1B) inhibitor (nonhydrolyzable difluoromethylphosphonate moiety)4