571571
Potassium 3-thiophenetrifluoroborate
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About This Item
Empirical Formula (Hill Notation):
C4H3BF3KS
CAS Number:
Molecular Weight:
190.04
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Form:
solid
InChI
1S/C4H3BF3S.K/c6-5(7,8)4-1-2-9-3-4;/h1-3H;/q-1;+1
SMILES string
[K+].F[B-](F)(F)c1ccsc1
InChI key
ULOOPHJJEPUNNH-UHFFFAOYSA-N
form
solid
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.
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines
Davies GHM, et al.
The Journal of Organic Chemistry, 82(10), 5380-5390 (2017)
Efficient synthesis of 6-(hetero) arylthieno [3, 2-b] pyridines by Suzuki-Miyaura coupling. Evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle
Queiroz M-J, et al.
European Journal of Medicinal Chemistry, 45(12), 5628-5634 (2010)
Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by Palladium Complexes of Hydroxynaphthalene-2-Oxazolines
Barbeiro CS, et at.
ChemistrySelect, 2(26), 8173-8177 (2017)
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