Allylboronic acid pinacol ester
Allylboronic acid pinacol ester (CAS 72824-04-5), with the linear formula ((CH3)4C2O2)BCH2CH=CH2 and a molecular weight of 168.04, is a versatile organoboronate reagent. It is primarily employed in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, and various other transformations including olefin metathesis, radical additions, and stereoselective reactions. This compound serves as a key building block in the synthesis of complex organic molecules.
- IUPAC
- 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane,4,4,5,5-tetramethyl-2-(2-propen-1-yl)-1,3,2-dioxaborolane,4,4,5,5-tetramethyl-2-(2-propenyl)-1,3,2-dioxaborolane,Allyl pinacol boronate,Pinacol allylboronate,Pinacolyl 2-propenylboronate
- Synonyms
- 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane4,4,5,5-tetramethyl-2-(2-propen-1-yl)-1,3,2-dioxaborolane4,4,5,5-tetramethyl-2-(2-propenyl)-1,3,2-dioxaborolaneAllyl pinacol boronatePinacol allylboronatePinacolyl 2-propenylboronate
Suzuki-Miyaura Cross-Coupling
This reagent is extensively used in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, facilitating the formation of new carbon-carbon bonds. It enables the synthesis of diverse biaryl compounds and substituted alkenes.
Olefin Metathesis
Allylboronic acid pinacol ester participates in olefin metathesis reactions, a powerful tool for constructing carbon-carbon double bonds. It is also utilized in the preparation of catalysts for selective olefin metathesis.
Radical Addition Reactions
The compound is employed in intermolecular radical addition reactions, contributing to the formation of functionalized organic structures. These reactions are valuable in synthetic organic chemistry for building molecular complexity.
Chiral Synthesis
It is used in asymmetric allylboration of aldehydes, catalyzed by chiral phosphoric acids, enabling the stereoselective synthesis of chiral alcohols. This application is crucial in the preparation of enantiomerically enriched compounds.
Preparation of BACE1 Inhibitors
This boronate ester is a precursor in the synthesis of cyclic sulfone hydroxyethylamines, which are investigated as BACE1 inhibitors for potential therapeutic applications in reducing Amyloid β-Peptides.
| Molecular weight | 168.04 |
|---|---|
| Linear formula | ((CH3)4C2O2)BCH2CH=CH2 |
| Assay | 97% |
| Boiling point | 50-53 °C/5 mmHg(lit.) |
| Density | 0.896 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.4268(lit.) |
| Storage temperature | 2-8°C |
| Application | Reagent used for• Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis1 • Intermolecular radical additions2 • Allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids3 • Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes4 • Nucleic acid-templated energy transfer leading to a photorelease reaction5 • Stereoselective indium-catalyzed Hosomi-Sakurai reactions6 Reagent used in Preparation of• Cyclic sulfone hydroxyethylamines as BACE1 inhibitors for reduction of Amyloid β-Peptides7 • Transmetalation of carbene Ru iodide with Ag carboxylates to give C-H-activated Ru carbene complexes as catalysts for Z-selective olefin metathesis8 |
Hazard statements
- H226Flammable liquid and vapour
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- 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 | 46 °C / 114.8 °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 |
| Safety statements (S) | 26-36 |
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 Allylboronic acid pinacol ester used for?
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Allylboronic acid pinacol ester is used as a reagent in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, olefin metathesis, intermolecular radical additions, asymmetric allylboration, and in the preparation of BACE1 inhibitors and specific ruthenium carbene catalysts.
What is the CAS number and formula for Allylboronic acid pinacol ester?
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The CAS number is 72824-04-5 and the linear formula is ((CH3)4C2O2)BCH2CH=CH2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Allylboronic acid pinacol ester with an assay of 97%. This product is a technical/research grade material and is not represented as USP, BP, or EP grade.
What are the safety considerations for handling Allylboronic acid pinacol ester?
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Allylboronic acid pinacol ester is a flammable liquid and vapour (H226) and can cause skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). Appropriate personal protective equipment, including eyeshields, gloves, and suitable respiratory protection, should be used. Handle in a well-ventilated area, away from ignition sources.
How is Allylboronic acid pinacol ester shipped and exported?
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Allylboronic acid pinacol ester is shipped and exported according to relevant transportation regulations, including UN 1993 classification for flammable liquids.
How can I request a sample or quote for Allylboronic acid pinacol ester?
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To request a sample or quote, please contact our sales team through the website or by phone. Please specify the product name and CAS number (72824-04-5) in your request.
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