215951-86-3

Basic information

• Product Name: TRANS-2-CHLOROMETHYLVINYLBORONIC ACID
• Synonyms: (E)-(3-chloroprop-1-en-1-yl)boronic acid;(3-Chloroprop-1-en-1-yl)boronic acid
• CAS NO: 215951-86-3
• Molecular Formula: C₃H₆BClO₂
• Molecular Weight: 120.34
• Product Categories: blocks;BoronicAcids;Alkenyl;Boronic Acids;Boronic Acids and Derivatives
• Mol File: 215951-86-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 110-113 °C (dec.)(lit.)
• Boiling Point: 266.4°C at 760 mmHg
• Flash Point: 114.9°C
• Appearance: /
• Density: 1.203g/cm³
• Vapor Pressure: 0.00118mmHg at 25°C
• Refractive Index: 1.459
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 9.13±0.43(Predicted)
• CAS DataBase Reference: TRANS-2-CHLOROMETHYLVINYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2-CHLOROMETHYLVINYLBORONIC ACID(215951-86-3)
• EPA Substance Registry System: TRANS-2-CHLOROMETHYLVINYLBORONIC ACID(215951-86-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 215951-86-3(Hazardous Substances Data)

Usage

Description

TRANS-2-CHLOROMETHYLVINYLBORONIC ACID is an organic compound that features a vinyl group attached to a boronic acid moiety. It is characterized by its reactivity and stability, making it a versatile building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
TRANS-2-CHLOROMETHYLVINYLBORONIC ACID is used as a reactant for the Suzuki-Miyaura cross-coupling reaction, which is a widely employed method in the synthesis of various pharmaceutical compounds. This reaction allows for the formation of carbon-carbon bonds, enabling the creation of complex molecular structures with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, TRANS-2-CHLOROMETHYLVINYLBORONIC ACID serves as a valuable reactant for the Suzuki-Miyaura cross-coupling reaction. This reaction is crucial for the construction of a diverse range of organic molecules, including those with potential applications in materials science, agrochemistry, and other industries. The use of this boronic acid in cross-coupling reactions contributes to the development of novel compounds with desired properties and functionalities.

InChI:InChI=1/C3H6BClO2/c5-3-1-2-4(6)7/h1-2,6-7H,3H2/b2-1+

Synthetic route

2-propynyl chloride (624-65-7) + benzo[1,3,2]dioxaborole (274-07-7) → (3-chloroprop-1-en-1-yl)boronic acid (215951-86-3)

Conditions	Yield
With water hydroboration and hydroylsis;;
With H2O hydroboration and hydroylsis;;

2,3-dimethyl-2,3-butane diol (76-09-5) + (3-chloroprop-1-en-1-yl)boronic acid (215951-86-3) + L-cysteine ethyl ester hydrochloride (868-59-7) + trifluoroacetic acid (76-05-1) → C14H26BNO4S*C2HF3O2

Conditions	Yield
Stage #1: 2,3-dimethyl-2,3-butane diol; (3-chloroprop-1-en-1-yl)boronic acid; L-cysteine ethyl ester hydrochloride With caesium carbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: trifluoroacetic acid In acetonitrile	100%

(3-chloroprop-1-en-1-yl)boronic acid (215951-86-3) + α-phenylacrylanilide (64859-23-0) → (E)-6-chloro-N,2-diphenylhex-4-enamide

Conditions	Yield
With (μ2-Br)2Mn2(CO)8; ethanol; potassium carbonate In diethyl ether at 120℃; for 28h; Schlenk technique; chemoselective reaction;	64%

(3-chloroprop-1-en-1-yl)boronic acid (215951-86-3) + 3-chloro-1-methoxy-4-((1-methyl-1H-1,2,4-triazol-5-yl)methyl)isoquinolin-5-amine + 1-(4-Fluorophenyl)piperazine (2252-63-3) → 3-(3-(4-(4-fluorophenyl)piperazin-1-yl)prop-1-en-1-yl)-1-methoxy-4-((1-methyl-1H-1,2,4-triazol-5-yl)methyl)isoquinolin-5-amine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In dimethyl sulfoxide at 120℃; for 24.25h;	30%

Upstream product

• 624-65-7 2-propynyl chloride 
• 274-07-7 benzo[1,3,2]dioxaborole