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

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

Uses

Used in Organic Synthesis:
4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE is used as a building block in organic synthesis for its ability to contribute to the formation of complex molecular structures.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE is utilized as a key intermediate in the development of new drugs, owing to its potential to enhance the properties of medicinal compounds.
Used in Agrochemical Development:
4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE is employed in the creation of new agrochemicals, potentially improving the effectiveness of pesticides and other agricultural products.
Used in Material Science:
In the field of material science, 4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE is studied for its potential to contribute to the development of novel materials with unique properties.
Used as a Chemical Reaction Reagent:
4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE serves as a reagent in various chemical reactions, facilitating specific transformations and processes in chemical research and production.

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

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

Downstream Products

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

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.

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

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

P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate

The direct reductive N-arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N-methylanilines from various stable isotopologues of nitromethane (i.e., CD3NO2, CH315NO2, and 13CH3NO2), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.

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.

Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides

This Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine nickel(aryl)(fluoride) intermediate. These investigations revealed that diboron reagents undergo transmetalation with this Ni(aryl)(fluoride) intermediate at rates significantly faster than their aryl boronate ester congeners. Furthermore, the reactivity of both boron reagents toward transmetalation is enhanced with increasing electrophilicity of the boron center. These mechanistic insights were leveraged to develop a catalytic decarbonylative borylation of acid fluorides that proved applicable to a variety of (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can be generated in situ directly from carboxylic acids. Furthermore, the mechanistic studies directed the identification of various air-stable Ni pre-catalysts for this transformation.

Method for preparing aryl boronate at room temperature

The invention discloses a method for preparing aryl boronate represented by a formula I at a room temperature. The method comprises: carrying out a reaction on a diboron compound represented by a formula II and an aryl halide in an organic solvent for 0.5-8 h at a room temperature under the actions of an alkali, a chloro(2-dicyclohexylphosphino-2',4',6'-tri-isopropyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium (II) catalyst and a 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl ligand, and carrying out post-treatment to obtain the corresponding aryl boronate. According to the present invention, the method has characteristics of mild reaction conditions, simple operation, wide application range, good compatibility with various functional groups on aryl, high efficiency and economy, can achieve high yield of aryl borate under normal pressure and normal pressure conditions, and is suitable for large-scale preparation of aryl borate. The formulas I and II are defined in the specification, wherein R' represents any one selected from phenyl with substituent, pyridyl, thienyl, indyl, pyrazolyl and naphthyl.

The drastic effect of cobalt and chromium catalysts in the borylation of arylzinc reagents

A new synthetic approach to arylboronic esters from arylzinc reagents with boryl electrophiles MeOB(OR)2 has been developed. Furthermore, this protocol could be applied to the cyclization/borylation of alkynylaryl iodides to afford cyclized vinylboronic esters.

Method for preparing arylboronic acid neopentyl glycol ester

The invention discloses a method for preparing arylboronic acid neopentyl glycol ester.The method includes the steps that a mixed-type nickel (II) complex with Ni(P(OR1)3)((R2NCH2CH2NR2)C)X2 as the chemical formula serves as a catalyst, and a cross coupling reaction of phenyl chlorine substitutes and bis(neopentyl glycolato) diboron is efficiently catalyzed in potassium methoxide to prepare the arylboronic acid neopentyl glycol ester.The method is the first case that the mixed-type nickel (II) complex catalyzes the cross coupling reaction with phosphite ester and n-heterocyclic carbine as auxiliary ligands.

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions

A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.