264144-59-4

Basic information

• Product Name: CIS-STILBENEBORONIC ACID PINACOL ESTER
• Synonyms: CIS-STILBENEBORONIC ACID PINACOL ESTER;cis-(1,2-Diphenylethenyl)boronic acid pinacol cyclic ester;cis-Stilbeneboronic acid pinacol cyclic ester
• CAS NO: 264144-59-4
• Molecular Formula: C₂₀H₂₃BO₂
• Molecular Weight: 306.21
• EINECS: -0
• Mol File: 264144-59-4.mol
• Article Data: 57

Chemical Properties

• Melting Point: 92-94°C
• Boiling Point: 369.5°Cat760mmHg
• Flash Point: 177.3°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 2.52E-05mmHg at 25°C
• Refractive Index: 1.554
• BRN: 9269561
• CAS DataBase Reference: CIS-STILBENEBORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-STILBENEBORONIC ACID PINACOL ESTER(264144-59-4)
• EPA Substance Registry System: CIS-STILBENEBORONIC ACID PINACOL ESTER(264144-59-4)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 24/25-36/37
• Hazardous Substances Data: 264144-59-4(Hazardous Substances Data)

Usage

General Description

CIS-STILBENEBORONIC ACID PINACOL ESTER is a compound used in organic synthesis as a building block for various chemicals and materials. It is derived from cis-stilbeneboronic acid, a boronic acid derivative, and pinacol, a diol. The ester group in the molecule makes it suitable for cross-coupling reactions to form carbon-carbon bonds, which are important in the synthesis of pharmaceuticals, agrochemicals, and materials. The compound is known for its stability and effectiveness in catalyzing reactions, making it a valuable tool in organic chemistry research and manufacturing processes. Additionally, it has potential applications in the development of new materials and drug discovery due to its versatile reactivity and structural properties.

InChI:InChI=1/C20H23BO2/c1-19(2)20(3,4)23-21(22-19)18(17-13-9-6-10-14-17)15-16-11-7-5-8-12-16/h5-15H,1-4H3/b18-15+

Upstream product

• 501-65-5 diphenyl acetylene 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 
• 7732-18-5 water 
• 588-59-0 stilbene 
• 108-86-1 bromobenzene 
• 451-40-1 phenyl benzyl ketone 
• 19816-85-4 N'-(1,2-diphenylethylidene)-4-methylbenzenesulfonohydrazide 
• 645-49-8 cis-stilben 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 645-49-8 cis-stilben 
• 451-40-1 phenyl benzyl ketone 
• 1020073-95-3 (E)-4-(1,2-diphenylvinyl)benzonitrile 
• 119379-68-9 (E)-1,1'-(1-Iodo-1,2-ethenediyl)bisbenzene 
• 134-81-6 benzil 
• 1414852-68-8 2-benzoyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione 
• 602-15-3 9,10-diphenylphenanthrene 

Relevant articles and documents

Palladium-Catalyzed [3 + 2] Annulation of Alkynes with Concomitant Aromatic Ring Expansion: A Concise Approach to (Pseudo)azulenes

The construction of (pseudo)azulenes represents an appealing yet challenging task in organic synthetic chemistry. Herein, we disclose a palladium-catalyzed [3 + 2] annulation technique of alkynes with concomitant aromatic ring expansion driven by a diboron reagent and iodide, affording a concise approach to azulenes (7-fused-5 bicycle) and pseudoazulenes (6-fused-5 bicycle). Compared with the documented synthetic strategies, the route to (pseudo)azulenes developed herein is applicable for both homo- and cross-annulation processes and exhibits a broad substrate scope. It is worth noting that this transformation is not only suitable for the ring expansion of the phenyl moiety to afford azulenes but also applicable to the ring expansion of the electron-rich five-membered heterocycles to deliver pseudoazulenes. Experimental and computational investigations on the mechanism support the formal trans-palladium-boration across the alkyne, cis-addition of the alkyne, dearomative spiroannulation, and aromatic ring expansion process.

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.

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

The rapid cis-trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at -50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial drug compound, (E)- and (Z)-tamoxifen with high regioselectivity and productivity.