201852-49-5

Basic information

• Product Name: POTASSIUM BETA-STYRYLTRIFLUOROBORATE
• Synonyms: POTASSIUM BETA-STYRYLTRIFLUOROBORATE;POTASSIUM TRANS-STYRYLTRIFLUOROBORATE;beta-Styryltrifluoroboric acid potassium salt;Potassium b-styryltrifluoroborate;á-styryltrifluoroboric acid potassium salt;potassium á-styryltrifluoroborate;POTASSIUM SS-STYRYLTRIFLUOROBORATE;Potassium ~-styryltrifluoroborate
• CAS NO: 201852-49-5
• Molecular Formula: C₈H₇BF₃*K
• Molecular Weight: 210.05
• EINECS: -0
• Product Categories: Alkenyl;Boronic Acids and Derivatives;Trifluoroborate Salts;organoboron
• Mol File: 201852-49-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: >300°C
• Appearance: /
• Water Solubility: Soluble in water.
• BRN: 7782992
• CAS DataBase Reference: POTASSIUM BETA-STYRYLTRIFLUOROBORATE(CAS DataBase Reference)
• NIST Chemistry Reference: POTASSIUM BETA-STYRYLTRIFLUOROBORATE(201852-49-5)
• EPA Substance Registry System: POTASSIUM BETA-STYRYLTRIFLUOROBORATE(201852-49-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 201852-49-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 201852-49-5 differently. You can refer to the following data:
1. Potassium trans-beta-styryltrifluoroborate is used as a reactant for Suzuki-Miyaura cross-coupling, in enantioselective total synthesis of naseseazines A and B via regioselective Friedel-Crafts based arylative dimerization, in metal-free chlorodeboronation reactions, in preparation of aryl ketones via Lewis acid-catalyzed nucleophilic substitution and in preparation of Weinreb amides by palladium-catalyzed cross-coupling reactions.
2. Reactant for:Suzuki-Miyaura cross-couplingEnantioselective total synthesis of naseseazines A and B via regioselective Friedel-Crafts based arylative dimerizationMetal-free chlorodeboronation reactionsPreparation of aryl ketones via Lewis acid-catalyzed nucleophilic substitutionPreparation of Weinreb amides by palladium-catalyzed cross-coupling reactions

InChI:InChI=1/C8H7BF3.K/c10-9(11,12)7-6-8-4-2-1-3-5-8;/h1-7H;/q-1;+1/b7-6+;

Upstream product

• 536-74-3 phenylacetylene 
• 4363-35-3 Dihydroxy-styryl-boran 
• 1279123-63-5 potassium hydrogenfluoride 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 100-42-5 styrene 

Downstream Products

• 55666-17-6 (1E)-1,4-pentadienylbenzene 
• 21502-38-5 (1E,4E)-1-phenyl-1,4-hexadiene 
• 13041-70-8 (E)-4-bromostilbene 
• 17697-66-4 (E)-(5-methylhexa-1,4-dien-1-yl)benzene 
• 2840-87-1 (E)-1-styrylnaphthalene 
• 1001388-37-9 (R,E)-3-methyl-5-phenylpent-4-enal 
• 131545-72-7 1-p-Bromphenyl-4-phenyl-1,3-butadien 
• 886-65-7 1,4-diphenyl-1,3-butadiene 
• 27331-24-4 1-(4Methylphenyl)-4-Phenylbuta-1,3-diene 
• 54948-51-5 1,4-di-(4'-methylphenyl)-buta-1,3-diene 
• 36065-27-7 N-α-phenylethylacetamide 
• 1238357-70-4 2,2-diethoxy-trans-N-styryl-acetamide 
• 705-89-5 (E)-3,3,3-trifluoro-1-phenylpropene 
• 1526980-34-6 (S,E)-N-(1-(3,4-dichlorophenyl)-3-phenylallyl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Facile synthesis of iodonium salts by reaction of organotrifluoroborates with p-iodotoluene difluoride

A simple and easy method for the synthesis of various iodonium salts was developed, and involves the reaction of potassium organotrifluoroborates with p-iodotoluene difluoride under mild conditions. The one-pot synthesis of a (Z)-(2-fluoroalkenyl)iodonium

Stereoselective Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides

The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or

Reaction rate differences between organotrifluoroborates and boronic acids in BINOL-catalyzed conjugate addition to enones

Enantioselective organocatalysis has been successfully employed in combination with trifluoroborate reagents for novel organic transformations over the last decade. However, no experimental rate studies of these reactions have been reported. Herein we report Hammett plot analysis of the organocatalyzed enantioselective conjugate addition of alkenyl, aryl, and heteroaryl trifluoroborate salts to chalcone derivatives with substitution at both the β-aryl and keto-aryl positions. The rate trend for keto-aryl substitution diverges from that of boronic acid nucleophiles in that the keto-aryl substituent for trifluoroborate salts does not measurably impact reaction rate in a manner consistent with charge stabilization. In addition, variable temperature NMR in combination with quantitative thin-layer chromatography (TLC) analysis suggests that the reaction is impacted by the low solubility of the trifluoroborate salts, so particle size and stirring speed affect reaction rates.

H2-Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst

The first example of an efficient and direct dehydrogenative boration of alkenes for vinyl boronate ester synthesis was achieved using a zirconium catalyst. Our methodology avoids using precious transition metals, additional hydrogen acceptors, high temperatures, and long reaction times, which were required to overcome the reducing ability of borane, to give alkyl boronate esters. Detailed mechanistic studies revealed a reversible reaction pathway and further suggested applying the zirconium complex as a “shuttle catalyst” for transfer boration, which thus sidesteps the use of relatively sensitive borane.