87189-16-0

Basic information

• Product Name: POTASSIUM BROMODIFLUOROACETATE
• Synonyms: POTASSIUM BROMODIFLUOROACETATE;Potassium2-bromo-2,2-difluoroacetate;Potassium bromo(difluoro)acetate 97+%
• CAS NO: 87189-16-0
• Molecular Formula: C₂BrF₂O₂*K
• Molecular Weight: 213.02
• Mol File: 87189-16-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: POTASSIUM BROMODIFLUOROACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: POTASSIUM BROMODIFLUOROACETATE(87189-16-0)
• EPA Substance Registry System: POTASSIUM BROMODIFLUOROACETATE(87189-16-0)

Safety Data

• Hazardous Substances Data: 87189-16-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C2HBrF2O2.K/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1

Upstream product

• 667-27-6 Ethyl bromodifluoroacetate 

Downstream Products

• 260352-79-2 2,2-difluorocyclopropanecarboxylic acid butyl ester 
• 10349-38-9 p-methoxyphenylisonitrile 
• 28321-09-7 1-chloro-4-(2,2-difluorovinyl)benzene 
• 74670-68-1 1-(2,2-difluorovinyl)-4-(trifluoromethyl)benzene 
• 405-42-5 2',2'-difluorostyrene 
• 38936-00-4 4-cyano-β,β-difluorostyrene 
• 345226-22-4 1-bromo-2-chloro-4-(difluoromethoxy)benzene 
• 90605-29-1 1-(2,2-difluorovinyl)-3-(trifluoromethyl)benzene 

Relevant articles and documents

Visible-Light-Promoted Synthesis of α-CF2H-Substituted Ketones by Radical Difluoromethylation of Enol Acetates

An efficient and novel visible-light-promoted radical difluoromethylation of enol acetates for the synthesis of α-CF2H-substituted ketones has been described. Upon irradiation under blue LED with catalytic amounts of fac-Ir(ppy)3, this photocatalytic procedure employs difluoromethyltriphenylphosphonium bromide as a radical precursor. Various α-CF2H-substituted ketones are successfully created via designed systems based on the SET process. The methodology has also provided an operationally simple process with broad functional group compatibility.

Visible-Light-Induced Radical Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Quinazolinones

A mild and efficient visible-light-induced radical difluoromethylation/cyclization of unactivated alkenes toward the synthesis of substituted quinazolinones with easily accessible difluoromethyltriphenylphosphonium bromide has been developed. The transformation has the advantages of wide functional group compatibility, a broad substrate scope, and operational simplicity. The benign protocol offers a facile access to pharmaceutically valuable difluoromethylated polycyclic quinazolinones.

Nickel-Catalyzed Cross-Electrophile Coupling of the Difluoromethyl Group for Fluorinated Cyclopropane Synthesis

Herein, we report a new strategy for fluorinated cyclopropane synthesis. Photocatalytic olefin difluoromethylation is coupled with a nickel-catalyzed intramolecular cross-electrophile coupling (XEC) reaction between a difluoromethyl moiety and a benzylic ether. To the best of our knowledge, this is the first example of a XEC reaction employing a difluoromethyl group as an electrophile. A plausible mechanism is highlighted, and DFT calculations are included to support the observed stereochemical outcome.

18F-Trifluoromethanesulfinate Enables Direct C-H 18F-Trifluoromethylation of Native Aromatic Residues in Peptides

18F labeling strategies for unmodified peptides with [18F]fluoride require 18F-labeled prosthetics for bioconjugation more often with cysteine thiols or lysine amines. Here we explore selective radical chemistry to target aromatic residues applying C-H 18F-trifluoromethylation. We report a one-step route to [18F]CF3SO2NH4 from [18F]fluoride and its application to direct [18F]CF3 incorporation at tryptophan or tyrosine residues using unmodified peptides as complex as recombinant human insulin. The fully automated radiosynthesis of octreotide[Trp(2-CF218F)] enables in vivo positron emission tomography imaging.

FLUORINATION METHOD

The invention relates to a process for producing a compound comprising the anion [CF218FSO2]-, which process comprises treating a difluorocarbene source with (i) a source of 18F- and (ii) a source of SO2. The invention relates to a compound which comprises that anion. The invention also relates to the use of the compound comprising the anion [CF218FSO2]- to produce a compound comprising an 18F-trifluoromethyl functionalised aromatic group. Compounds comprising an 18F-trifluoromethyl functionalised aromatic group are also the subject of the present invention.

Divergent Reactivity of Stannane and Silane in the Trifluoromethylation of PdII: Cyclic Transition State versus Difluorocarbene Release

The transmetalation is a key elementary step in cross-coupling reactions. Yet, the precise nature of its mechanism and transition state geometry are frequently elusive. This report discloses our study of the transmetalation of [PdII]-F complexes with the silane- and stannane-based trifluoromethylation agents, R3SiCF3 and R3SnCF3. A divergent reactivity was uncovered, with the stannane showing selective R-group transfer, and the silane selective CF3-group transfer. Using a combined experimental and computational approach, we uncovered a hitherto unrecognized transmetalation mechanism with the widely employed R3SiCF3 reagent, explaining its unique activity in metal-catalyzed trifluoromethylations. While the stannane reacts via a cyclic, 4-membered transition state, the silane undergoes a fundamentally different pathway and releases a difluorocarbene in the transmetalation event. Molecular dynamics studies clearly reinforced the liberation of a free CF2 carbene, which reacts with [PdII]-F to ultimately generate [PdII]-CF3.

Radical Difluoromethylation of Thiols with (Difluoromethyl)triphenylphosphonium Bromide

A method for facile difluoromethylation of various thiols using (difluoromethyl)triphenylphosphonium bromide under mild reaction conditions is presented. The transformation proceeds in the absence of any transition metal using a bench-stable and readily accessible phosphonium salt. Deuterium labeling experiments and cyclic voltammetry measurements reveal that the difluoromethylation occurs via a SRN1-type mechanism. Substrate scope is broad, and various functional groups are tolerated (OH, NH2, amide, ester).

Access to Difluoromethylated Arenes by Pd-Catalyzed Reaction of Arylboronic Acids with Bromodifluoroacetate

An unprecedented example of Pd-catalyzed difluoromethylation of aryl boronic acids with bromodifluoroacetate is described. The reaction proceeds under mild reaction conditions with hydroquinone and Fe(acac)3 as additives. Preliminary mechanistic studies reveal that a difluorocarbene pathway is involved in the reaction, which is unusual compared to the most traditional approaches. This reaction has advantages of high efficiency and excellent functional group compatibility, even toward bromide and hydroxy group, thus providing a useful protocol for drug discovery and development.

Wittig gem-difluoroolefination of aldehydes with difluoromethyltriphenylphosphonium bromide

Wittig reaction of aldehydes with difluoromethyltriphenylphosphonium bromide leading to gem-difluoroolefins in moderate yields is described. The reaction displays a good substrate scope including aryl, heteroaryl and α,β-unsaturated aldehydes. Difluoromethyltriphenylphosphonium bromide could be easily prepared and stored for a long time under air atmosphere. The salt exhibits high thermal stability demonstrated by thermogravimetric analysis. Its structure was confirmed by NMR spectroscopy and single crystal X-ray analysis.

Synthesis and decarboxylative Wittig reaction of difluoromethylene phosphobetaine

A key intermediate, difluoromethylene phosphobetaine, in the Wittig reaction of ClCF2CO2Na-Ph3P with aldehydes was synthesized and characterized, which confirmed the reaction mechanism. The decarboxylation of this stable intermediate was a convenient approach for Wittig difluroolefination. Its reactivity could be adjusted by the modification of the substituent on the phosphorus.