126726-62-3

Basic information

• Product Name: Isopropenylboronic acid pinacol ester
• Synonyms: 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Isopropenylboronic acid pinacol ester;2-(1-Methylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Isopropenyl boronic acid pinacol ester;4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-(1-methylethenyl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane;2-Isopropenyl-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(Isopropenylboronic acid pinacol ester)
• CAS NO: 126726-62-3
• Molecular Formula: C₉H₁₇BO₂
• Molecular Weight: 168.04
• Product Categories: Alkyl;Organoborons;Alkenyl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents
• Mol File: 126726-62-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 157-161 °C
• Boiling Point: 47-49 °C (9 mbar)
• Flash Point: 42 °C
• Appearance: Clear, colorless to brown/Liquid
• Density: 0.894
• Vapor Pressure: 3.552mmHg at 25°C
• Refractive Index: 1.4320
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Isopropenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropenylboronic acid pinacol ester(126726-62-3)
• EPA Substance Registry System: Isopropenylboronic acid pinacol ester(126726-62-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38-43
• Safety Statements: 16-26-36/37
• RIDADR: UN 1993
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 126726-62-3(Hazardous Substances Data)

Usage

Description

Isopropenylboronic acid pinacol ester is a versatile ester reagent with a wide range of applications in organic synthesis and chemical reactions. It is known for its ability to participate in palladium-catalyzed Suzuki-Miyaura cross-coupling processes, inverse-electron-demand Diels-Alder reactions, Simmons-Smith cyclopropanation reactions, polyene cyclization, stereoselective aldol reactions, Grubbs cross-metathesis reactions, intramolecular Suzuki-Miyaura reactions, stereoselective cross-metathesis, dipolar cycloaddition, iodosulfonylation, asymmetric conjugate addition, and intramolecular hydroacylation. Additionally, it serves as an intermediate in the synthesis of various cyclic and acyclic organic compounds and can be used for highly diastereoand enantioselective allylboration of aldehydes.

Uses

Used in Organic Synthesis:
Isopropenylboronic acid pinacol ester is used as an intermediate for the synthesis of a variety of cyclic and acyclic organic compounds, providing a foundation for the creation of complex molecular structures.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
In the field of organic chemistry, Isopropenylboronic acid pinacol ester is used as a reagent for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds and the synthesis of biaryl compounds.
Used in Inverse-Electron-Demand Diels-Alder Reaction:
Isopropenylboronic acid pinacol ester is utilized as a reagent in inverse-electron-demand Diels-Alder reactions, allowing for the construction of six-membered rings and the synthesis of various complex organic molecules.
Used in Simmons-Smith Cyclopropanation Reaction:
This ester reagent is used in Simmons-Smith cyclopropanation reactions, which are crucial for the formation of cyclopropane rings in organic molecules.
Used in Polyene Cyclization:
Isopropenylboronic acid pinacol ester is employed as a reagent in polyene cyclization reactions, contributing to the synthesis of cyclic polyene compounds.
Used in Stereoselective Aldol Reactions:
As a reagent in stereoselective aldol reactions, Isopropenylboronic acid pinacol ester helps in the formation of carbon-carbon bonds with controlled stereochemistry, which is essential for the synthesis of enantiomerically pure compounds.
Used in Grubbs Cross-Metathesis Reaction:
This ester reagent is used in Grubbs cross-metathesis reactions, facilitating the exchange of olefinic bonds between molecules and enabling the synthesis of new compounds with unique structures.
Used in Intramolecular Suzuki-Miyaura Reaction:
Isopropenylboronic acid pinacol ester is used as a reagent in intramolecular Suzuki-Miyaura reactions, allowing for the formation of cyclic compounds through the coupling of molecular fragments.
Used in Stereoselective Cross-Metathesis:
This ester reagent is employed in stereoselective cross-metathesis reactions, enabling the synthesis of compounds with specific stereochemistry.
Used in Dipolar Cycloaddition:
Isopropenylboronic acid pinacol ester is used as a reagent in dipolar cycloaddition reactions, contributing to the formation of five-membered heterocyclic compounds.
Used in Iodosulfonylation:
This ester reagent is utilized in iodosulfonylation reactions, which are important for the introduction of sulfonyl groups into organic molecules.
Used in Asymmetric Conjugate Addition and Intramolecular Hydroacylation:
Isopropenylboronic acid pinacol ester is used as a reagent in asymmetric conjugate addition and intramolecular hydroacylation reactions, allowing for the synthesis of enantiomerically pure compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
Isopropenylboronic acid pinacol ester is used as a reagent in the preparation of various therapeutic kinase and enzymatic inhibitors, playing a crucial role in the development of new drugs for the treatment of various diseases.

Sources

https://www.sigmaaldrich.com/catalog/product/aldrich/663212?lang=en®ion=US https://www.trc-canada.com/product-detail/?I821825

InChI:InChI=1/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 14559-87-6 isopropenylboronic acid 
• 557-93-7 2-bromoprop-1-ene 
• 73183-34-3 bis(pinacol)diborane 
• 67-64-1 acetone 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 28049-80-1 bis(diisopropylamino)chloroborane 

Downstream Products

• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 1011531-55-7 methyl 4-tert-butyl-3-(prop-1-en-2-yl)benzoate 
• 170648-20-1 (ClC₆H₄C₃H₂(CH₃)NO)B(OC(CH₃)2C(CH₃)2O) 
• 1067191-60-9 N-[4-(cyano-dimethyl-methyl)-3-isopropenyl-phenyl]-3,4-dimethoxy-benzamide 
• 1071497-55-6 8-fluoro-2-isopropenyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol 
• 1071497-60-3 8-chloro-2-isopropenyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol 
• 1093064-04-0 C₃₄H₂₆N₄O₂ 
• 1140897-36-4 3-(1-(4-chlorophenyl)cyclopropyl)-8-(prop-1-en-2-yl)-[1,2,4]triazolo[4,3-a]pyridine trifluoroacetate 
• 1178884-57-5 methyl 2-methyl-4-(prop-1-en-2-yl)benzoate 
• 1186637-51-3 3-chloro-5-(prop-1-en-2-yl)picolinonitrile 
• 1204819-45-3 [(R)-4-(3-isopropenyl-5-trifluoromethyl-benzene-sulfonyl-amino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester 
• 1304004-58-7 methyl 3-isopropenyl-5-(5-methylpyridin-2-yl)benzoate 
• 1150263-45-8 methyl 3-(5-chloropyridin-2-yl)-5-isopropenylbenzoate 
• 1224887-95-9 2-(2-chloro-5-isopropenyl-pyridin-4-ylamino)-N-methyl-benzamide 

Relevant articles and documents

Synthesis method of isopropenyl boronic acid pinacol ester

The invention discloses a synthesis method of isopropenyl boronic acid pinacol ester. The synthesis method comprises the following steps: generating a gem-diboronation product from acetone and biborate under the action of a copper carbene reagent, then carrying out elimination reaction in the presence of p-toluenesulfonic acid, and finally, subjecting the product and pinacol to a one-pot-process reaction to obtain the isopropenyl boronic acid pinacol ester. The method is simple to operate, the boronation reaction is directly carried out under the action of a metal copper catalyst, the use of 2-bromopropylene in a traditional process is avoided, and a new synthesis path is provided for the synthesis of the isopropenyl boronic acid pinacol ester.

Method for synthetizing isopropenyl boric acid ester

The invention discloses a method for synthetizing isopropenyl boric acid ester. Acetone is used as a raw material and subjected to a reaction with hydrazine hydrate to generate hydrazone, then, isopropenyl halogen is generated at the existence of NXS and organic base and then subjected to a one-pot reaction with metallic lithium and bi(disopropylamine) boron halide, diol and a polymerization inhibitor are added for a backflow reaction to obtain isopropenyl boronic acid ester, and the yield is 65-69%,. The method is easy and convenient to implement, purification is convenient, the yield is high, no ultralow temperature reaction is needed, and the method is suitable for industrial enlarged production.

Oxygen-promoted palladium(II) catalysis: Facile C(sp2)-C(sp 2) bond formation via cross-coupling of alkenylboronic compounds and olefins

(Chemical Equation Presented) Oxygen-promoted Pd(II) catalysis facilitated the synthesis of conjugated dienes by cross-coupling of alkenylboronic compounds and various olefins including highly substituted alkenes and cyclohexenone. Under mild conditions, these versatile reactions were efficient and highly stereoselective.