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571571 Sigma-Aldrich

Potassium 3-thiophenetrifluoroborate

  • CAS Number 192863-37-9

  • Empirical Formula (Hill Notation) C4H3BF3KS

  • Molecular Weight 190.04

  •  MDL number MFCD03701626

  •  PubChem Substance ID 24874750

  •  NACRES NA.22

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Properties

Related Categories Boronic Acids and Derivatives, Chemical Synthesis, Heteroaryl Trifluoroborate Salts, Organometallic Reagents, Trifluoroborate Salts More...
Quality Level   100
SMILES string   [K+].F[B-](F)(F)c1ccsc1
InChI   1S/C4H3BF3S.K/c6-5(7,8)4-1-2-9-3-4;/h1-3H;/q-1;+1
InChI key   ULOOPHJJEPUNNH-UHFFFAOYSA-N

Description

General description

Potassium 3-thiophenetrifluoroborate is a nucleophilic boronated coupling reagent used to construct a C-C bond by reacting with aryl halides in the presence of a catalyst or under thermal conditions.

Application

Potassium 3-thiophenetrifluoroborate can be used as a reactant to prepare:
•  Methyl 3-amino-6-(thien-3-yl)thieno[3,2-b]pyridine-2-carboxylate by reacting with 6-bromothieno[3,2-b]pyridine.
•  Thiophene derivatives via Suzuki-Miyaura cross-coupling reaction with aryl halides using palladium complex as a catalyst.
•  2-(Thiophen-3-yl)-3,1,2-benzoxazaborininone and 2-(thiophen-3-yl)-1,3,2-benzoxazaborininone by treating with 2-aminobenzoic acid and 2-hydroxybenzamide, respectively.

Packaging

1 g in poly bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Chemfiles Volume 4 Article 2 - Potassium Trifluoroborates

Alkyl, aryl, and alkenyl trifluoroborate salts are compelling alternatives to boronic acids in Suzuki–Miyaura coupling and in rhodium catalyzed carbon-carbon bond forming reactions. These salts are a...
Chemfiles Volume 4 Article 2
Keywords: Catalysis, Cross couplings, Ligands

Related Content

Organotrifluoroborates in Chemical Synthesis

Potent Boronic Acid Surrogates In the vast array of catalytic carbon-carbon bond forming reactions, the Suzuki-Miyaura protocol has proven to be a particularly attractive method.  The organoborane nu...
Keywords: Addition reactions, Catalysis, Coupling reactions, Cross couplings, Halogenations, Suzuki-Miyaura coupling

Peer-Reviewed Papers
15

References

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