4-Pyrazoleboronic acid pinacol ester

CAS 269410-08-4(CH3)4C2O2BC3N2H3Chemical Synthesis

4-Pyrazoleboronic acid pinacol ester (CAS: 269410-08-4) is a chemical compound with a molecular weight of 194.04. This organometallic reagent, specifically a boronate ester, is crucial for various synthetic organic chemistry applications. It is primarily utilised in Suzuki-Miyaura cross-coupling reactions and ruthenium-catalyzed asymmetric hydrogenation, serving as a key building block in the synthesis of complex molecules, particularly those with privileged pyrazole scaffolds.

IUPAC: 4,4,5,5-Tetramethyl-2-(1H-pyrazol-2-yl)-1,3,2-dioxaborolane,4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane,4,4,5,5-Tetramethyl-2-(pyrazol-4-yl)-1,3,2-dioxaborolane,4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole,Pyrazol-4-ylboronic acid pinacol ester
Synonyms: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolePyrazol-4-ylboronic acid pinacol ester4,4,5,5-Tetramethyl-2-(1H-pyrazol-2-yl)-1,3,2-dioxaborolane4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane4,4,5,5-Tetramethyl-2-(pyrazol-4-yl)-1,3,2-dioxaborolane

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4-Pyrazoleboronic acid pinacol ester ((CH3)4C2O2BC3N2H3) — chemical structure, CAS 269410-08-4; Chemistry, fine chemical supplied by Tech Serve Solutions

Boronate EstersChemical SynthesisHeteroaryl Boronate EstersOrganometallic Reagents

01 /Applications

Suzuki-Miyaura Cross-Coupling Reactions

This pinacol ester serves as an effective coupling partner in Suzuki-Miyaura cross-coupling reactions, facilitating the formation of new carbon-carbon bonds. It is instrumental in constructing complex molecular architectures.

Ruthenium-Catalyzed Asymmetric Hydrogenation

The compound is employed as a reagent in ruthenium-catalyzed asymmetric hydrogenation processes. This application is significant for the stereoselective synthesis of chiral molecules.

Synthesis of Enzyme and Kinase Inhibitors

It is a valuable intermediate in the preparation of inhibitors targeting numerous critical therapeutic enzymes and kinases. These targets include VEGF, Aurora, Rho (ROCK), JAK2, and others, highlighting its importance in medicinal chemistry.

02 /Properties

Molecular weight	194.04
Linear formula	(CH3)4C2O2BC3N2H3
Assay	97%
Application	Reagent used for• Suzuki-Miyaura cross-couplings1 • Ruthenium-catalyzed asymmetric hydrogenation2 Reagent used in preparation of inhibitors of many highly significant therapeutic enzymes and kinases containing the privileged scaffold pyrazole, including• VEGF3 • Aurora3,4• Rho (ROCK)2• Janus Kinase 2 (JAK)5 • c-MET6 • ALK6 • S-nitrosoglutathione reductase7 • CDC78 • Acetyl-CoA carboxylase9 • Prosurvival Bcl-2 protein10 • Viral RNA-Dependent RNA polymerase11 • Long Chain Fatty Acid Elongase 612• PI313 • AKT14 • Chk115 •
Melting point	142-146 °C(lit.)

03 /Safety & handling

GHS hazard pictogram: Harmful / irritant (GHS07) — Harmful / irritant

Warning

Hazard statements

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	dust mask type N95 (US), Eyeshields, Gloves
Water hazard class (WGK, DE)	3
Hazard codes (EU)	Xi
Risk statements (R)	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.

04 /Identifiers & registry

CAS number

269410-08-4

MDL number

MFCD03453063

PubChem substance

24874465

05 /Quality & supply

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.

06 /Frequently asked questions

What is 4-Pyrazoleboronic acid pinacol ester used for?

4-Pyrazoleboronic acid pinacol ester is used as a reagent in Suzuki-Miyaura cross-coupling reactions and ruthenium-catalyzed asymmetric hydrogenation. It is also a key intermediate in the synthesis of various enzyme and kinase inhibitors, including those targeting VEGF, Aurora, and JAK2.

What is the CAS number and formula for 4-Pyrazoleboronic acid pinacol ester?

The CAS number is 269410-08-4, and its linear formula is (CH3)4C2O2BC2N2H3.

What grade and purity does Tech Serve Solutions supply?

Tech Serve Solutions supplies 4-Pyrazoleboronic acid pinacol ester with an assay of 97%. We do not represent this product as USP, BP, EP, or any other pharmacopoeia grade.

How should 4-Pyrazoleboronic acid pinacol ester be handled safely?

This compound is a Warning substance (GHS07) and may cause skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). When handling, wear a dust mask type N95 (US), eyeshields, and gloves. Ensure adequate ventilation and avoid breathing dust.

Is 4-Pyrazoleboronic acid pinacol ester a controlled substance?

Based on the provided data, there is no indication that 4-Pyrazoleboronic acid pinacol ester is a controlled substance.

How is 4-Pyrazoleboronic acid pinacol ester packed, shipped, or exported?

Tech Serve Solutions exports fine chemicals globally. Specific packaging and shipping details for 4-Pyrazoleboronic acid pinacol ester comply with international regulations for hazardous materials.

How can I request a sample or quote for 4-Pyrazoleboronic acid pinacol ester?

To request a sample or a quote for 4-Pyrazoleboronic acid pinacol ester, please contact our sales department via the website or direct email, providing your specific requirements.