214360-47-1

Basic information

• Product Name: 2-Cyanophenylboronic acid neopentyl ester
• Synonyms: AKOS BRN-0190;(2-CYANOPHENYL)BORONIC ACID 2,2-DIMETHYLPROPANEDIOL-1,3 CYCLIC ESTER;2-CYANOPHENYLBORONIC ACID, NEOPENTYL ESTER;2-(5,5-DiMethyl-1,3,2-dioxaborinan-2-yl)benzonitrile;2-Cyanophenylboronic acid neopentyl ester 2-Cyanophenylboronic acid 2,2-dimethylpropanediol-1,3-cyclic ester;2-(2-Cyanophenyl)-5,5-dimethyl-1,3,2-dioxaborinane (This product is only available in Japan.);2-Cyanophenylboronic acid, neopentyl ester ESTER
• CAS NO: 214360-47-1
• Molecular Formula: C₁₂H₁₄BNO₂
• Molecular Weight: 215.06
• Product Categories: Heterocyclic Compounds
• Mol File: 214360-47-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 368.1 °C at 760 mmHg
• Flash Point: 176.4 °C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 1.3E-05mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-Cyanophenylboronic acid neopentyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyanophenylboronic acid neopentyl ester(214360-47-1)
• EPA Substance Registry System: 2-Cyanophenylboronic acid neopentyl ester(214360-47-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• TSCA: No
• Hazardous Substances Data: 214360-47-1(Hazardous Substances Data)

Usage

General Description

2-Cyanophenylboronic acid neopentyl ester is a compound often used in organic synthesis and pharmaceutical research. It is an ester derivative of the parent compound 2-cyanophenylboronic acid, with the neopentyl group serving as a protecting group to increase its stability and reactivity. 2-Cyanophenylboronic acid neopentyl ester is commonly utilized in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds, and it has shown to be effective in the synthesis of a variety of biologically active molecules. Additionally, it is known for its ability to resist decomposition under acidic conditions, making it a versatile and valuable reagent in the laboratory.

InChI:InChI=1/C12H14BNO2/c1-12(2)8-15-13(16-9-12)11-6-4-3-5-10(11)7-14/h3-6H,8-9H2,1-2H3

Upstream product

• 100-47-0 benzonitrile 
• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 2042-37-7 o-cyanobromobenzene 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 

Downstream Products

• 135689-93-9 4-(2-Cyanophenyl)benzaldehyde 
• 26487-08-1 2-cyano-N,N-dimethylbenzamide 
• 1579952-89-8 2-(6-((E)-2-((1R,3aR,4aR,4'R,8aR,9S,9aS)-1-methyl-2',3-dioxodecahydro-1H-spiro[naphtho[2,3-c]furan-6,4'-oxazolidin]-9-yl)vinyl)pyridin-3-yl)benzonitrile 
• 1579953-07-3 2-(6-((E)-2-((1R,3aR,4aR,4'S,8aR,9S,9aS)-1-methyl-2',3-dioxodecahydro-1H-spiro[naphtho[2,3-c]furan-6,4'-oxazolidin]-9-yl)vinyl)pyridin-3-yl)benzonitrile 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 1400934-21-5 5-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-2-hydroxymethyl-1H-imidazole 
• 1400934-18-0 5-butyl-1-[[2'-(tert-butoxycarbonyl)biphenyl-4-yl]methyl]-2-hydroxymethyl-3-[(2-(trimethylsilyl)ethoxy)methyl]-1H-imidazolium bromide 
• 163294-74-4 5-butyl-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-imidazole-2-carboxylic acid 
• 160540-35-2 5-butyl-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-imidazole-2-carboxaldehyde 
• 155091-94-4 1-<<2'-<(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl>-5-butylimidazole-2-carboxaldehyde 
• 155091-75-1 5-butyl-2-hydroxymethyl-4-iodo-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-imidazole 
• 1400933-99-4 4-bromo-5-butyl-2-hydroxymethyl-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-imidazole 
• 1400933-97-2 5-butyl-4-chloro-2-hydroxymethyl-1-[[2'-(2H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-imidazole 
• 155091-97-7 5-butyl-2-hydroxymethyl-4-iodo-1-<<2'-<(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl>imidazole 

Relevant articles and documents

Preparation method of o-nitrile phenylboronic acid-1, 3-propylene glycol ester

The invention discloses a preparation method of o-nitrile phenylboronic acid-1, 3-propylene glycol ester, which belongs to the technical field of organic boric acid chemistry. The method comprises thefollowing steps of starting from o-bromobenzonitrile, carrying out a one-pot reaction with borate/n-butyllithium or metal lithium/boron halide amine, after the reaction is detected to be finished, carrying out acidolysis to obtain 2-nitrile phenylboronic acid, or directly filtering, distilling, adding 1, 3-propylene glycol to form ester, pulping, and purifying to obtain the o-nitrile phenylboronic acid-1, 3-propylene glycol ester. The key point of the process is that the reaction liquid is added into the acid water for quenching after the reaction is finished, so that the condition that the acid water is added into a reaction system to be subjected to an alkaline environment first and then to an acid environment is avoided, the yield is kept stable in different amplification stages, and the process has an industrial amplification prospect. And corresponding boric acid ester can be smoothly obtained by replacing propylene glycol with other glycols.

An efficient synthesis of sterically hindered arylboronic acids

Boronic acids are important intermediates and molecular recognition moieties in a wide variety of applications. In our research, we have found that the synthesis of ortho-substituted arylboronic acids is problematic with the commonly used bis(pinacolato)diboron in palladium-mediated borylation reactions. As a substitute, we have found that bis(neopentyl glycolato)diboron is a much more efficient borylation agent for the synthesis of sterically hindered ortho-substituted arylboronic acids.