223919-54-8

Basic information

• Product Name: 4-chloro-trans-beta-styrylboronic acid pinacol ester
• Synonyms: 4-chloro-trans-beta-styrylboronic acid pinacol ester;trans-2-(4-Chlorophenyl)vinylboronic acid pinacol ester;2-[(1E)-2-(4-Chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;-2-(4-Chlorostyryl);4-chloro-trans-beta-styrylboronic acid picol ester;(E)-2-(4-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 223919-54-8
• Molecular Formula: C₁₄H₁₈BClO₂
• Molecular Weight: 283
• Mol File: 223919-54-8.mol

Chemical Properties

• Melting Point: 88-92°C
• Boiling Point: 305.1±44.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-chloro-trans-beta-styrylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-trans-beta-styrylboronic acid pinacol ester(223919-54-8)
• EPA Substance Registry System: 4-chloro-trans-beta-styrylboronic acid pinacol ester(223919-54-8)

Safety Data

• WGK Germany: 1
• Hazardous Substances Data: 223919-54-8(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
4-chloro-trans-beta-styrylboronic acid pinacol ester is used as a research compound for its unique chemical properties and reactivity, contributing to the advancement of organic chemistry.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-chloro-trans-beta-styrylboronic acid pinacol ester is used as a key intermediate in the synthesis of various complex molecules, facilitating the development of new compounds and materials.

Upstream product

• 1073-67-2 4-vinylbenzyl chloride 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 154230-29-2 (E)-4-chlorostyrylboronic acid 
• 873-73-4 4-n-chlorophenylacetylene 
• 73183-34-3 bis(pinacol)diborane 
• 3240-10-6 (4-chlorophenyl)propiolic acid 
• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 
• 66482-29-9 1-[(E)-2-bromoethenyl]-4-chlorobenzene 
• 75927-49-0 pinacol vinylboronate 
• 26928-23-4 (E)-1-chloro-4-(2-fluorovinyl)benzene 
• 100-42-5 styrene 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 125951-04-4 (E)-diethyl (4-chlorostyryl)phosphonate 
• 154230-29-2 (E)-4-chlorostyrylboronic acid 
• 66482-29-9 1-[(E)-2-bromoethenyl]-4-chlorobenzene 
• 66482-30-2 (Z)-1-bromo-2-(4-chlorophenyl)ethylene 
• 168006-99-3 (E)-1-chloro-4-(2-iodovinyl)benzene 
• 1283152-85-1 (E)-2-[2-(4-chlorophenyl)ethenyl]benzaldehyde 

Relevant articles and documents

Selective hydroboration of alkynes via multisite synergistic catalysis by PCN-222(Cu)

Zirconium-based porphyrinic MOFs (PMOFs, MOF = metal-organic framework) have gained considerable attention in the field of electric/thermo/photo-catalysis as heterogeneous single-site catalysts; however, the study on multisite synergistic catalysis of PMO

Electrochemical Hydroboration of Alkynes

Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.

Cs4B4O3F10: First Fluorooxoborate with [BF4] Involving Heteroanionic Units and Extremely Low Melting Point

Herein, a new congruently melting mixed-anion compound Cs4B4O3F10 has been characterized as the first fluorooxoborate with [BF4] involving heteroanionic units. Compound Cs4B4O3F10 possesses two highly fluorinated anionic clusters and therefore its formula can be expressed as Cs3(B3O3F6) ? Cs(BF4). The influence of [BF4] units on micro-symmetry and structural evolution was discussed based on the parent compound. More importantly, Cs4B4O3F10 shows the lowest melting point among all the available borates and thus sets a new record for such system. This work is of great significance to enrich and tailor the structure of borates using perfluorinated [BF4] units.

Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions

The hydroboration of alkynes is crucial due to the wide applications in organic synthesis, while such reaction is often completed with low turnover frequency (TOF) value and long reaction time. Therefore, it is very important and necessary that the hydrob

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a

Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies

Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.

Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates

A copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The products are valuable synthetic intermediates by transformation of the boronate group. This methodology can be applied to the synthesis of novel trifluoromethylated analogues of trans-2-arylcyclopropylamines, which are prevalent motifs in biologically active compounds.

Tuning Polarity of Cu-O Bond in Heterogeneous Cu Catalyst to Promote Additive-free Hydroboration of Alkynes

Precise control of structural parameters to optimize the performance of heterogeneous catalysts remains a challenging issue. A direct route is to adjust the nature of chemical bonds around active centers, but this has not yet been achieved because of the

Solvent- and metal-free hydroboration of alkynes under microwave irradiation

Boronic esters are versatile building blocks extensively used in organic chemistry and essential to a variety of coupling reactions. In this work, the hydroboration reactions of alkynes were performed without metal catalysts using concomitant microwave ir

Catalyst-free and solvent-free hydroboration of alkynes

The hydroboration of alkynes with pinacolborane (HBpin) under catalyst- and solvent-free conditions was demonstrated. Various alkynes were smoothly converted into alkenyl boronate esters in good to excellent yields at 110 °C. The gram-scale hydroboration