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Key Documents

411361

Sigma-Aldrich

Diethyl (bromodifluoromethyl)phosphonate

96%

Synonym(s):

(Bromodifluoromethyl)phosphonic acid diethyl ester

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About This Item

Linear Formula:
BrCF2P(O)(OC2H5)2
CAS Number:
Molecular Weight:
267.01
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.417 (lit.)

bp

40-41 °C/0.05 mmHg (lit.)

density

1.503 g/mL at 25 °C (lit.)

SMILES string

CCOP(=O)(OCC)C(F)(F)Br

InChI

1S/C5H10BrF2O3P/c1-3-10-12(9,11-4-2)5(6,7)8/h3-4H2,1-2H3

InChI key

QRADKVYIJIAENZ-UHFFFAOYSA-N

Application

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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