ChemicalBook > CAS DataBase List > Isopropenylboronic acid pinacol ester

Isopropenylboronic acid pinacol ester

Description Sources

Product Name: Isopropenylboronic acid pinacol ester
CAS No.: 126726-62-3
Chemical Name: Isopropenylboronic acid pinacol ester
Synonyms: 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane;2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Isopropenylboronic acid picol ester;Isopropenylboronic acid pinacol este;Isopropenylboronic acid pinacol ester;2-Isopropenyl boronic acid pinacol ester;4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-;Isopropenylboronic acid pinacol ester, 98%min;4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,3-dioxaborolane
CBNumber: CB0972288
Molecular Formula: C9H17BO2
Formula Weight: 168.04
MOL File: 126726-62-3.mol

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Isopropenylboronic acid pinacol ester Property

Melting point:: 157-161 °C
Boiling point:: 47-49 °C/9 mbar
Density: 0.894 g/mL at 25 °C
refractive index: 1.4320
Flash point:: 42 °C
storage temp.: 2-8°C
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Liquid
color: Clear, colorless to brown
InChI: InChI=1S/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3
InChIKey: SVSUYEJKNSMKKW-UHFFFAOYSA-N
SMILES: O1C(C)(C)C(C)(C)OB1C(C)=C
CAS DataBase Reference: 126726-62-3

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Safety

Hazard Codes: Xi
Risk Statements: 10-36/37/38-43
Safety Statements: 16-26-36/37
RIDADR: UN 1993
WGK Germany: 3
TSCA: No
HazardClass: IRRITANT
PackingGroup: Ⅲ
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 663212
Product name: Isopropenylboronic acid pinacol ester
Purity: contains phenothiazine as stabilizer, 95%
Packaging: 5g
Price: $116
Updated: 2025/07/31

Sigma-Aldrich

Product number: 663212
Product name: Isopropenylboronic acid pinacol ester
Purity: contains phenothiazine as stabilizer, 95%
Packaging: 25g
Price: $347
Updated: 2025/07/31

TCI Chemical

Product number: I1038
Product name: 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Purity: min. 98.0 %
Packaging: 1G
Price: $34
Updated: 2025/07/31

TCI Chemical

Product number: I1038
Product name: 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Purity: min. 98.0 %
Packaging: 5G
Price: $102
Updated: 2025/07/31

TRC

Product number: I821825
Product name: Isopropenylboronic acid pinacol ester
Packaging: 25g
Price: $395
Updated: 2021/12/16

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Isopropenylboronic acid pinacol ester Chemical Properties,Usage,Production

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&region=US
https://www.trc-canada.com/product-detail/?I821825

Uses

suzuki reaction

Uses

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.

Uses

Reagent used for

Palladium-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 cycloaddition
Iodosulfonylation
Asymmetric conjugate addition and intramolecular hydroacylation

Reagent used in preparation of various therapeutic kinase and enzymatic inhibitors

Synthesis

76-09-5

557-93-7

28049-80-1

126726-62-3

General procedure for the synthesis of isopropenylboronic acid pinacol esters from pinacol, 2-bromopropene and compound (CAS:28049-80-1): 2-bromopropene (89.58 g, 0.741 mol) was dissolved in 750 mL of tetrahydrofuran, and slowly added dropwise from -10 °C to 0 °C with a mixture of bis(diisopropylamino)boron chloride (183 g, 0.74 mol) and lithium metal (10.4 g, 1.5 mol) mixture followed by 110 mL of tetrahydrofuran under strictly controlled reaction conditions. After the dropwise addition, the reaction was maintained at this temperature for 1 h. Then the temperature was raised to 25 °C and the reaction was continued for 5 h. The reaction was completed with the addition of pinacol. Upon completion of the reaction, pinacol (98.8 g), 2,6-di-tert-butyl-4-methylphenol (4.58 g) and 120 mL of tetrahydrofuran were added and the reaction mixture was heated to reflux. Purification by distillation under reduced pressure afforded 82.1 g of colorless transparent liquid isopropenylboronic acid pinacol ester in 66% yield and 99.7% GC purity. Finally, 2,6-di-tert-butyl-4-methylphenol (0.45 g) was added as a stabilizer for long-term storage.

References

[1] Patent: CN105503923, 2016, A. Location in patent: Paragraph 0018

Isopropenylboronic acid pinacol ester Preparation Products And Raw materials

Raw materials

Trimethyl borate Pinacol ISOPROPENYLMAGNESIUM BROMIDE

Preparation Products

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View Lastest Price from Isopropenylboronic acid pinacol ester manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

Product: isopropenylboronic acid pinacol ester 126726-62-3
Price: US $3.00-9.00/KG
Min. Order: 0.1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2025-07-02

Career Henan Chemical Co

Product: Isopropenylboronic acid pinacol ester 126726-62-3
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100KG
Release date: 2020-01-03

126726-62-3, Isopropenylboronic acid pinacol esterRelated Search:

Pinacol Methyl acrylate Dimethyl succinate N-Isopropylacrylamide POLY(N-ISOPROPYL ACRYLAMIDE) BUTYL OLEATE Olibanum oil Tris(trimethylsilyl)phosphate Triisopropyl borate Bis(pinacolato)diboron ISOPROPENYLMAGNESIUM BROMIDE Isopropenyloxytris(triMethylsilyl)silane 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ISOPROPYLHYDRAZINE HYDROCHLORIDE Isopropylboronic acid (-)-DIOP ETHYL 4-AMINO-5-IMIDAZOLECARBOXYLATE Ethyl isobutyrylacetate

2-(1-Methylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-Isopropenyl boronic acid pinacol ester

2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Isopropenylboronic 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)

2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(Prop-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1,3,2-Dioxaborolane,4,4,5,5-tetraMethyl-2-(1-Methylethenyl)-

Isopropenylboronic acid pinacol ester contains phenothiazine as stabilizer, 95%

Isopropenylboronic acid pinacol ester 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

lsopropen ylboronic acid pinacol ester (Single largest impurity under 0.5%)

4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-

Isopropenylboronic acid picol ester

IsoprIsopenylboronic acid pinacol ester, 97%, stabilized with 0.5% phenothiazine

Isopropenylboronic acid pinacol este

4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,3-dioxaborolane

2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 90%,

4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane,98% (stabilized with TBC)

Isopropenylboronic acid pinacol ester, 98%min

126726-62-3

Alkenyl Boronate Esters

Boronate Esters

Boronic Acids and Derivatives

Chemical Synthesis

Organometallic Reagents

Alkyl

Organoborons