214360-44-8

Basic information

• Product Name: 4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE
• Synonyms: 4-Cyanophenylboronic acid neopentyl ester
• CAS NO: 214360-44-8
• Molecular Formula: C₁₂H₁₄BNO₂
• Molecular Weight: 215.06
• Mol File: 214360-44-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 122 °C
• Boiling Point: 355.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE(214360-44-8)
• EPA Substance Registry System: 4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE(214360-44-8)

Safety Data

• Hazardous Substances Data: 214360-44-8(Hazardous Substances Data)

Usage

General Description

4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE is a chemical compound that contains a benzene ring with a nitrile group attached to it. The structure also includes a 1,3,2-dioxaborinane ring with two methyl groups attached to it. 4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE is commonly used as a building block in organic synthesis and pharmaceutical research. It has the potential to be used in the development of new drugs and agrochemicals due to its unique structural features. Additionally, it has been studied for its potential applications in material science and as a reagent in chemical reactions. Overall, 4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE has a wide range of potential uses in various fields of science and industry.

InChI:InChI=1S/C12H16BNO3/c1-12(2,8-15)9-17-13(16)11-5-3-10(7-14)4-6-11/h3-6,15-16H,8-9H2,1-2H3

Upstream product

• 77976-02-4 4-cyanobenzoyl fluoride 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 623-03-0 4-Cyanochlorobenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 57186-57-9 2-methoxy-5,5,-dimethy-1,3,2-dioxaborinane 
• 3058-39-7 4-iodobenzonitrile 
• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 138373-10-1 4-cyanophenyl mesylate 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 126747-14-6 4-cyanophenylboronic acid 

Downstream Products

• 619-65-8 4-cyanobenzoic Acid 
• 1449484-86-9 2-(4-cyanophenyl)-1-(pyridin-2-yl)piperidine 
• 140483-60-9 4'-(trifluoromethyl)-[1,1'-biphenyl]-4-carbonitrile 
• 1173294-93-3 4-(2-(pyridin-2-yl)benzoyl)benzonitrile 
• 55805-10-2 4-cyano-1-difluoromethylbenzene 
• 32111-34-5 4-(pyridine-2-yl)benzonitrile 
• 27634-88-4 4-cyclohexyl-1-cyanobenzene 
• 5565-36-6 1,4-bis-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzene 
• 38004-04-5 4-dodecylbenzonitrile 
• 1221233-18-6 4-(E-2-(hexyloxy)styryl)benzonitrile 
• 574755-28-5 (4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)trimethylsilane 
• 29240-33-3 4-(isopropyloxycarbonyl)benzonitrile 

Relevant articles and documents

Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis

This Article describes the development of a decarbonylative Pd-catalyzed aryl-fluoroalkyl bond-forming reaction that couples fluoroalkylcarboxylic acid-derived electrophiles [RFC(O)X] with aryl organometallics (Ar-M′). This reaction was optimized by interrogating the individual steps of the catalytic cycle (oxidative addition, carbonyl de-insertion, transmetalation, and reductive elimination) to identify a compatible pair of coupling partners and an appropriate Pd catalyst. These stoichiometric organometallic studies revealed several critical elements for reaction design. First, uncatalyzed background reactions between RFC(O)X and Ar-M′ can be avoided by using M′ = boronate ester. Second, carbonyl de-insertion and Ar-RF reductive elimination are the two slowest steps of the catalytic cycle when RF = CF3. Both steps are dramatically accelerated upon changing to RF = CHF2. Computational studies reveal that a favorable F2C-H - -X interaction contributes to accelerating carbonyl de-insertion in this system. Finally, transmetalation is slow with X = difluoroacetate but fast with X = F. Ultimately, these studies enabled the development of an (SPhos)Pd-catalyzed decarbonylative difluoromethylation of aryl neopentylglycol boronate esters with difluoroacetyl fluoride.

Ruthenium-Catalyzed Carbonylative Coupling of Anilines with Organoboranes by the Cleavage of Neutral Aryl C-N Bond

Herein, we report the first ruthenium-catalyzed Suzuki-type carbonylative reaction of electronically neutral anilines via C(aryl)-N bond cleavage. Without any ligand and base, diaryl ketones can be obtained in moderate to high yields by using Ru3/su

METHOD FOR PREPARING PHENYLBORONIC ACID NEOPENTYL GLYCOL ESTER

The present invention discloses a method for preparing a phenylboronic acid neopentyl glycol ester. A mixed nickel(II) complex with a formula of Ni[P(OR1)3][(R2NCH2CH2NR2)C]X2 is used as a catalyst. The method comprises: in the presence of potassium methoxide, efficiently catalyze a cross coupling reaction between a phenyl chloride and a bis(neopentyl glycolato)-diboron to prepare a phenylboronic acid neopentyl glycol ester. The invention provides the first embodiment of using a mixed nickel(II) complex with phosphonate ester and nitrogen heterocyclic carbene ancillary ligands to catalyze a cross coupling reaction.