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

Description

POTASSIUM BETA-STYRYLTRIFLUOROBORATE is a chemical compound that serves as a versatile reactant in various organic synthesis processes. It is known for its ability to participate in a range of reactions, including Suzuki-Miyaura cross-coupling, enantioselective total synthesis, metal-free chlorodeboronation, and the preparation of aryl ketones and Weinreb amides.

Uses

Used in Organic Synthesis:
POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used as a reactant for various organic synthesis applications, including:
1. Suzuki-Miyaura Cross-Coupling:
POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used as a reactant in Suzuki-Miyaura cross-coupling reactions, which are widely employed for the formation of carbon-carbon bonds in organic synthesis.
2. Enantioselective Total Synthesis of Naseseazines A and B:
In the enantioselective total synthesis of naseseazines A and B, POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used for regioselective Friedel-Crafts based arylative dimerization, contributing to the formation of the desired chiral compounds.
3. Metal-Free Chlorodeboronation Reactions:
POTASSIUM BETA-STYRYLTRIFLUOROBORATE is utilized in metal-free chlorodeboronation reactions, which are important for the synthesis of various organic compounds without the need for metal catalysts.
4. Preparation of Aryl Ketones:
In the preparation of aryl ketones, POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used as a reactant in Lewis acid-catalyzed nucleophilic substitution reactions, enabling the formation of aryl ketones from aryl halides and metal enolates.
5. Preparation of Weinreb Amides:
POTASSIUM BETA-STYRYLTRIFLUOROBORATE is used in the preparation of Weinreb amides through palladium-catalyzed cross-coupling reactions, which are valuable intermediates in organic synthesis and have applications in the synthesis of various pharmaceuticals and agrochemicals.

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

Downstream Products

• 1152-30-3 (E)-ethyl 4-styrylbenzoate 
• 1694-19-5 E-1-(phenyl)-2-(4'-methoxyphenyl)ethene 
• 125972-78-3 trans-2-acetyl-5-(β-phenylvinyl)thiophene 
• 538-49-8 2-[(E)-2-phenylethenyl]pyridine 
• 26057-47-6 (E,E)-1,5-diphenyl-1,4-pentadiene 
• 4714-21-0 4-methylstilbene 
• 3112-03-6 4-acetylstilbene 
• 5808-05-9 (1Z,3E)-1,4-diphenylbuta-1,3-diene 
• 55666-17-6 (1E)-1,4-pentadienylbenzene 
• 2840-87-1 (E)-1-styrylnaphthalene 
• 109898-18-2 (E)-(4-methylpenta-1,4-dien-1-yl)benzene 
• 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 

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.