238088-31-8

Basic information

• Product Name: 2-Cyanoethylboronic acid, pinacol ester
• Synonyms: 2-Cyanoethylboronic acid, pinacol ester;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)propanenitrile
• CAS NO: 238088-31-8
• Molecular Formula: C9H16BNO2
• Molecular Weight: 181.03984
• Mol File: 238088-31-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 241.0±23.0 °C(Predicted)
• Appearance: /
• Density: 0.96±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Cyanoethylboronic acid, pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyanoethylboronic acid, pinacol ester(238088-31-8)
• EPA Substance Registry System: 2-Cyanoethylboronic acid, pinacol ester(238088-31-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• TSCA: No
• Hazardous Substances Data: 238088-31-8(Hazardous Substances Data)

Usage

General Description

2-Cyanoethylboronic acid, pinacol ester is a type of organic chemical compound often used in laboratory settings, particularly in the field of synthetic chemistry. It is commonly utilized in various reaction types including Suzuki-Miyaura cross-coupling reactions. 2-Cyanoethylboronic acid, pinacol ester is characterized by its boronic ester functional group bonded to a cyanoethyl group, which gives it unique reactivity patterns. It is generally used as a precursor or intermediate in the synthesis of more complex chemical structures. Furthermore, this compound needs to be handled with care as it may pose potential hazards, such as being irritative to the eyes, skin, and respiratory system.

Upstream product

• 107-13-1 acrylonitrile 
• 73183-34-3 bis(pinacol)diborane 
• 70557-99-2 2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 75-05-8 acetonitrile 
• 2417-90-5 bromopropionitrile 
• 166330-03-6 pinacol (bromomethyl)boronate 

Relevant articles and documents

Stereoselective Access to Alkylidenecyclobutanes through γ-Selective Cross-Coupling Strategies

Alkylidenecyclobutanes (ACBs) containing all-carbon quaternary stereocenters were simply and efficiently synthesized by combining boron-homologation and γ-selective cross-coupling strategies. This unique sequence led to excellent regio- and diastereoselec

Structure and reactivity of a preactivated sp2-sp3 diboron reagent: Catalytic regioselective boration of α,β-unsaturated conjugated compounds

A novel sp2-sp3 diboron reagent has been developed for the copper-catalyzed β-boration of α,β-unsaturated conjugated compounds. The reaction proceeds under mild conditions with various substrates, i.e., α,β-unsaturated esters, ketones, nitriles, ynones, amides, and aldehydes, in the absence of additives such as phosphine and sodium tert-butoxide to provide β-borylhomoenolates in good to excellent yields. The presence of an sp3-hybridized boron center, unambigously confirmed by X-ray crystallography, sufficiently activates the unsymmetrical pinacolato diisopropanolaminato diboron (PDIPA diboron, 2) to transfer the sp2-hybridized boron moiety chemoselectively. These observations suggest that the activation of one of the boron atoms is an essential step in the Cu-catalyzed β-boration catalytic cycle.

Sp2 - Sp3 hybridized mixed diboron: Synthesis, characterization, and copper-catalyzed β-boration of α,β- unsaturated conjugated compounds

A novel sp2 - sp3 hybridized mixed diboron and its reactivity on the copper-catalyzed β-boration of α,β-unsaturated conjugated compounds to afford the corresponding β-borated compounds is reported. The presence of sp3-hybr