1590389-14-2

Basic information

• Product Name: potassium trifluoro(4-fluorobenzoyl)borate
• Synonyms: potassium trifluoro(4-fluorobenzoyl)borate
• CAS NO: 1590389-14-2
• Molecular Weight: 230.011
• Mol File: 1590389-14-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: potassium trifluoro(4-fluorobenzoyl)borate(CAS DataBase Reference)
• NIST Chemistry Reference: potassium trifluoro(4-fluorobenzoyl)borate(1590389-14-2)
• EPA Substance Registry System: potassium trifluoro(4-fluorobenzoyl)borate(1590389-14-2)

Safety Data

• Hazardous Substances Data: 1590389-14-2(Hazardous Substances Data)

Usage

Uses

Potassium Acyltrifluroborates (KAT′s) are bench, air, and moisture stable reagents for rapid, chemoselective amide bond formations with hydroxylamines. These amide bond forming reactions proceed under aqueous conditions, without the need for coupling reagents or protecting groups. This product was introduced in collaboration with the Bode Research Group.

General Description

Potassium 4-fluorobenzoyltrifluoroborate belongs to the potassium acyltrifluoroborate (KAT) group. It can be synthesized from 1-(methoxy(4-fluorophenyl)methyl)-1H-benzotriazole.

Upstream product

• 460-00-4 1-Bromo-4-fluorobenzene 
• 7789-23-3 potassium fluoride 
• 7732-18-5 water 
• 459-57-4 4-fluorobenzaldehyde 
• 1590361-26-4 1-(methoxy(4-fluorophenyl)methyl)-1H-benzotriazole 

Downstream Products

• 33799-96-1 N-(2-phenylethyl)-4-fluorobenzamide 
• 551908-65-7 4-fluoro-N-(3-phenylpropyl)-benzamide 
• 1590361-34-4 (E)-2-((4-(dimethylamino)phenyl)diazenyl)-N-(3-(4-(phenethylcarbamoyl)phenoxy)propyl)benzamide 
• 1590361-28-6 C₂₅H₃₁N₃O₃S 
• 307524-52-3 4-fluoro-N-(4-methoxyphenethyl)benzamide 

Relevant articles and documents

Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs): Via trifluoroborate-iminiums (TIMs)

We report the facile formation of trifluoroborate-iminiums (TIMs) from potassium acyltrifluoroborates (KATs) and the transformation of TIMs to α-aminotrifluoroborates by reduction or Grignard additions. Conditions for the hydrolysis of α-aminotrifluoroborates to α-aminoboronic acids, which are important biologically active compounds, were established. This new methodology allows access to sterically demanding α-aminoboronic acids that are not easily prepared with currently available methods. This work also introduces TIMs, that can be easily prepared and handled, as a new category of functional groups that serve as precursors to valuable organic compounds.

Concise Synthesis of Potassium Acyltrifluoroborates from Aldehydes through Copper(I)-Catalyzed Borylation/Oxidation

Potassium acyltrifluoroborates (KATs) were prepared through copper(I)-catalyzed borylation of aldehydes and subsequent oxidation. This synthetic route is characterized by the wide range of aldehydes accessible, favorable step economy, mild reaction conditions, and tolerance of various functional groups, and it enables the facile generation of a range of KATs, for example, bearing halide, sulfide, acetal, or ester moieties. Moreover, this method was applied to the three-step synthesis of various α-amino acid analogues that bear a KAT moiety on the C-terminus by using naturally occurring amino acids as the starting material.

Rapid ligations with equimolar reactants in water with the potassium acyltrifluoroborate (KAT) amide formation

The identification of fast, chemoselective bond-forming reactions is one of the major contemporary challenges in chemistry. We show that chemoselective amide-forming ligations of potassium acyltrifluoroborates (KATs) and O-carbamoylhydroxylamines proceed in the presence of all unprotected functional groups with a second-order rate constant of 20 M-1 s-1. PEG chains, lipids, biotin, and dyes were introduced onto an unprotected 31-mer peptide (a GLP-1 analogue) with equimolar ratios of reactants within minutes at 1 mM and within 1 h at 100 μM, even with Mw 20 000 PEG. This conjugation reaction provides a new approach to the synthesis of molecules such as protein-protein and protein-polymer conjugates.