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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:
65094-22-6
Molecular Weight:
267.01
MDL number:
MFCD00069118
UNSPSC Code:
12352108
PubChem Substance ID:
24865745
NACRES:
NA.22

Quality Level

100

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.)

functional group

bromo
fluoro
phosphonate

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

411361-5G:
411361-VAR:
411361-BULK:
411361-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT2458
MKCR1674
MKCS4307
MKCR8320
MKCP4707

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