Isopropenylboronic acid pinacol ester
Isopropenylboronic acid pinacol ester (CAS: 126726-62-3, C9H17BO2, MW: 168.04) is a valuable organoboron compound. This reagent is primarily utilised in palladium-catalyzed cross-coupling reactions, notably the Suzuki-Miyaura coupling. Its applications extend to various cycloaddition and cyclisation reactions, making it a versatile building block in organic synthesis, particularly for preparing complex molecules and potential therapeutic agents.
- IUPAC
- 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane,4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane,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
- Synonyms
- 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane4,4,5,5-tetramethyl-2-(1-methylethenyl)-1,3,2-dioxaborolane
Suzuki-Miyaura Cross-Coupling
This compound serves as a key reagent in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, facilitating the formation of carbon-carbon bonds for complex molecule synthesis.
Cycloaddition Reactions
It is employed in inverse-electron-demand Diels-Alder reactions and dipolar cycloadditions, enabling the construction of cyclic structures.
Stereoselective Synthesis
The reagent is instrumental in stereoselective aldol reactions, Simmons-Smith cyclopropanation, and Grubbs cross-metathesis reactions, crucial for controlling molecular stereochemistry.
Preparation of Bioactive Molecules
It finds application in the synthesis of diverse therapeutic agents, including kinase and enzymatic inhibitors, highlighting its importance in medicinal chemistry.
| Molecular weight | 168.04 |
|---|---|
| Empirical formula | C9H17BO2 |
| Assay | 95% |
| Boiling point | 47-49 °C/9 mbar |
| Density | 0.894 g/mL at 25 °C |
| Refractive index | n20/D 1.4320 |
| Storage temperature | 2-8°C |
| Contains / stabiliser | phenothiazine as stabilizer |
| Application | Reagent used for• Palladium-catalyzed Suzuki-Miyaura cross-coupling processes1 • Inverse-electron-demand Diels-Alder reaction2• Simmons-Smith Cyclopropanation Reaction3 • Polyene cyclization4 • Stereoselective aldol reactions5 • Grubbs cross-metathesis reaction5 • Intramolecular Suzuki-Miyaura reaction5 • Stereoselective cross-metathesis6 • Dipolar cycloaddition7• Iodosulfonylation8 • Asymmetric conjugate addition and intramolecular hydroacylation9 Reagent used in preparation of various therapeutic kinase and enzymatic inhibitors10 9 |
Hazard statements
- H226Flammable liquid and vapour
- H315Causes skin irritation
- H317May cause an allergic skin reaction
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P280Wear protective gloves, clothing and eye/face protection
- P305IF IN EYES
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 42 °C / 107.6 °F |
| Transport (UN / ADR) | UN 1993C 3 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 10-36/37/38-43 |
| Safety statements (S) | 26-36/37 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Isopropenylboronic acid pinacol ester used for?
+
Isopropenylboronic acid pinacol ester is used as a reagent in various organic synthesis reactions, including palladium-catalyzed Suzuki-Miyaura cross-coupling, inverse-electron-demand Diels-Alder reactions, and stereoselective aldol reactions. It is also utilised in the preparation of therapeutic kinase and enzymatic inhibitors.
What is the CAS number and formula for Isopropenylboronic acid pinacol ester?
+
The CAS number is 126726-62-3, and the empirical formula is C9H17BO2.
What grade and purity does Tech Serve Solutions supply?
+
Tech Serve Solutions supplies Isopropenylboronic acid pinacol ester with an assay of 95%. This product is intended for research and laboratory use and is not represented as USP, BP, or EP grade.
How should Isopropenylboronic acid pinacol ester be handled safely?
+
This compound is flammable and can cause skin, eye, and respiratory irritation. Handle with appropriate personal protective equipment, including eyeshields, gloves, and a suitable respirator, in a well-ventilated area. Refer to the safety data sheet for detailed handling and storage information.
How is Isopropenylboronic acid pinacol ester shipped?
+
Isopropenylboronic acid pinacol ester is shipped as a UN 1993, Class 3, Packing Group III substance, conforming to transport regulations.
How can I request a quote or sample?
+
To request a quote or sample, please contact our sales team through the website or by phone, providing the product name and CAS number.
▶ Related products
1-(2-Fluorobenzyl)piperazine
C11H15FN2
Chemical Synthesis
1-(2-Fluorophenyl)biguanide hydrochloride
Chemical Synthesis
1-(2-Fluorophenyl)cyclopropanecarboxylic acid
C10H9FO2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine
C10H13FN2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine monohydrochloride
C10H13FN2 · HCl
Chemical Synthesis
1-(2-Furoyl)-1H-benzotriazole
C11H7N3O2
Chemical Synthesis
1-(2-Furoyl)piperazine
C9H12N2O2
Chemical Synthesis
1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione
Chemical Synthesis
▶ Explore more
3-Methyl-1,5-di-p-tolyl-1,4-pentazadiene
Chemical Synthesis
3-Methyl-1,5-pentanediol
Chemical Synthesis
3-Methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine
C11H13N3
Chemical Synthesis
3-Methyl-1-(3′-sulfoamidophenyl)-5-pyrazolone
C10H11N3O3S
Chemical Synthesis