871333-97-0

Basic information

• Product Name: 4,4-DIMETHYLCYCLOHEXA-1,5-DIENYLBORONIC ACID PINACOL ESTER
• Synonyms: 4,4-DiMethylcyclohexa-1,5-diene-1-boronic acid pinacol ester, 96%;2-(4,4-DiMethylcyclohexa-1,5-dien-1-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;(4,4-Dimethylcyclohexa-1,5-dien-1-yl)boronic acid, pinacol ester;4,4-DIMETHYLCYCLOHEXA-1,5-DIENYLBORONIC ACID PINACOL ESTER;4,4-Dimethylcyclohexa-1,5-dienylboronic acid pinacol ester 96%
• CAS NO: 871333-97-0
• Molecular Formula: C14H23BO2
• Molecular Weight: 234.14
• Product Categories: blocks;BoronicAcids
• Mol File: 871333-97-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 32-34
• Boiling Point: 257.2 °C at 760 mmHg
• Flash Point: 109.4 °C
• Appearance: /
• Density: 0.95 g/cm³
• Vapor Pressure: 0.0237mmHg at 25°C
• Refractive Index: 1.479
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 4,4-DIMETHYLCYCLOHEXA-1,5-DIENYLBORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-DIMETHYLCYCLOHEXA-1,5-DIENYLBORONIC ACID PINACOL ESTER(871333-97-0)
• EPA Substance Registry System: 4,4-DIMETHYLCYCLOHEXA-1,5-DIENYLBORONIC ACID PINACOL ESTER(871333-97-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 871333-97-0(Hazardous Substances Data)

Usage

General Description

4,4-Dimethylcyclohexa-1,5-dienylboronic acid pinacol ester is a chemical compound used in organic synthesis and medicinal chemistry. It is a boronic acid derivative with a pinacol ester group, which makes it a versatile reagent for cross-coupling reactions and the synthesis of complex organic molecules. 4,4-DIMETHYLCYCLOHEXA-1,5-DIENYLBORONIC ACID PINACOL ESTER is known for its ability to react with various electrophiles, such as alkyl halides and aryl halides, to form carbon-carbon bonds. It is also used as a building block in the preparation of pharmaceuticals and agrochemicals due to its ability to modulate biological activities and properties of target compounds. Overall, 4,4-Dimethylcyclohexa-1,5-dienylboronic acid pinacol ester is a valuable tool in the field of chemical synthesis and drug discovery.

InChI:InChI=1/C14H23BO2/c1-12(2)9-7-11(8-10-12)15-16-13(3,4)14(5,6)17-15/h7-9H,10H2,1-6H3

Upstream product

• 62461-14-7 N'-(4,4-dimethylcyclohex-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide 
• 73183-34-3 bis(pinacol)diborane 

Relevant articles and documents

Synthesis of Alkenylboronates from N-Tosylhydrazones through Palladium-Catalyzed Carbene Migratory Insertion

The palladium-catalyzed oxidative borylation reaction of N-tosylhydrazones has been developed. The reaction features mild conditions, broad substrate scope, and good functional group tolerance. It thus represents a highly efficient and practical method for the synthesis of di-, tri-, and tetrasubstituted alkenylboronates from readily available N-tosylhydrazones. One-pot Suzuki coupling and other transformations highlight the synthetic utility of the approach. DFT calculations have revealed that palladium-carbene formation and subsequent boryl migratory insertion are the key steps in the catalytic cycle. The high stereoselectivity observed in the formation of trisubstituted alkenylboronates has been explained by distortion-interaction analysis and NBO analysis.