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 used for palladium-catalyzed Suzuki-Miyaura cross-coupling processes, inverse-electron-demand Diels-Alder reaction, Simmons-Smith cyclopropanation reaction, polyene cyclization, stereoselective aldol reactions, Grubbs cross-metathesis reaction, intramolecular Suzuki-Miyaura reaction, Stereoselective cross-metathesis, dipolar cycloaddition, iodosulfonylation, asymmetric conjugate addition and intramolecular hydroacylation and preparation of various therapeutic kinase and enzymatic inhibitors1. It can be used as an intermediate in the synthesis of variety of cyclic and acyclic organic compounds. It is also shown that the α-Substituted Allyl/Croty of this compound can be used for highly Diastereoand Enantioselective allylboration of aldehydes2.

Sources

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

Uses

Different sources of media describe the Uses of 126726-62-3 differently. You can refer to the following data:
1. suzuki reaction
2. Isopropenylboronic Acid Pinacol Ester, can be used as an intermediate in the synthesis of variety of cyclic and acyclic organic compounds. It is also shown that the α-Substituted Allyl/Croty of this compound can be used for highly Diastereo- and Enantioselective allylboration of aldehydes.
3. Reagent used forPalladium-catalyzed Suzuki-Miyaura cross-coupling reactions Inverse-electron-demand Diels-Alder reaction Simmons-Smith Cyclopropanation Reaction Polyene cyclization Stereoselective aldol reactions Grubbs cross-metathesis reaction Intramolecular Suzuki-Miyaura reaction Stereoselective cross-metathesis Dipolar cycloadditionIodosulfonylation Asymmetric conjugate addition and intramolecular hydroacylation Reagent used in preparation of various therapeutic kinase and enzymatic inhibitors

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 
• 170648-20-1 (ClC₆H₄C₃H₂(CH₃)NO)B(OC(CH₃)2C(CH₃)2O) 
• 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 
• 1232688-65-1 1-isopropenyl-4,5-dimethoxy-2-nitro-benzene 
• 1239719-99-3 C₁₆H₁₃ClFN₃ 
• 1239720-07-0 C₁₆H₁₃ClFN₃ 
• 1239717-65-7 C₂₆H₂₁FN₄O 
• 1257231-24-5 2-acetoxy-7-benzyloxy-3-(prop-1-en-2-yl)naphthalene 
• 1326706-87-9 rac-2-(2-isopropenyl-phenyl)-2-(2,2,2-trifluoroacetylamino)acetic acid methyl ester 
• 1326706-82-4 rac-2-(2,2,2-trifluoroacetylamino)-3-(2-isopropenylphenyl)propionic acid methyl ester 

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.