5123-05-7

Basic information

• Product Name: 1,3,2-Dioxaborinane, 2-[1,1'-biphenyl]-4-yl-5,5-dimethyl-
• Synonyms: B-<4-Biphenylyl>-<2,2-dimethyl-propan-1,3-diol-boronat>CTK1G5185;biphenyl-4-boronic acid neopentyl glycol ester
• CAS NO: 5123-05-7
• Molecular Formula: C17H19BO2
• Molecular Weight: 266.148
• Mol File: 5123-05-7.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborinane, 2-[1,1'-biphenyl]-4-yl-5,5-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborinane, 2-[1,1'-biphenyl]-4-yl-5,5-dimethyl-(5123-05-7)
• EPA Substance Registry System: 1,3,2-Dioxaborinane, 2-[1,1'-biphenyl]-4-yl-5,5-dimethyl-(5123-05-7)

Safety Data

• Hazardous Substances Data: 5123-05-7(Hazardous Substances Data)

Usage

Chemical class

Dioxaborinane derivative
It belongs to a class of organic compounds containing a dioxaborinane ring.

Structure

Consists of a dioxaborinane ring, a 1,1'-biphenyl group, and 5,5-dimethyl substitutions
The compound has a unique structure that contributes to its stability and reactivity.

Stability

Known for its stability
The compound is stable and can be used in various chemical reactions without decomposing easily.

Compatibility

Compatible with a wide range of functional groups
It can be used in reactions with various functional groups, making it a versatile reagent in organic chemistry.

Applications

Used in organic synthesis for the production of pharmaceuticals, agrochemicals, and materials
The compound serves as a building block for creating a variety of useful products.

Interest in development

Subject of interest in the development of new catalysts and materials
Its unique structure and properties make it a promising candidate for the development of novel catalysts and materials.

Reactivity

Valuable reagent in organic chemistry
Due to its stability and compatibility with various functional groups, it is a valuable reagent for use in organic chemistry.

Upstream product

• 5122-94-1 4-biphenylboronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 2714-87-6 [1,1′-biphenyl]-4-carbonyl fluoride 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 92-88-6 4,4'-Dihydroxybiphenyl 
• 16881-71-3 4'-methoxy-1,1'-biphenyl-4-ol 
• 613-37-6 4-methoxylbiphenyl 
• 91815-47-3 4,4″-sulfinyldi-1,1′-biphenyl 
• 2051-62-9 4'-biphenyl chloride 
• 17865-11-1 (4-(trimethylsilyl)phenyl)boronic acid 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 574755-28-5 (4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)trimethylsilane 
• 169963-54-6 4-(morpholino)biphenyl 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 

Downstream Products

• 92-92-2 biphenyl-4-carboxylic acid 
• 92-94-4 [1,1';4',1'']terphenyl 
• 720-75-2 methyl 4-phenylbenzoate 
• 177551-63-2 [1,1′-biphenyl]-4-yl(trifluoromethyl)sulfane 
• 68862-02-2 2-([1,1'-biphenyl]-4-yl)naphthalene 
• 1638192-41-2 4-(2,2-difluoro-1-phenylvinyl)-1,1'-biphenyl 
• 93324-66-4 2-(4-phenylphenyl)pyridine 
• 112321-79-6 2-([1,1'-biphenyl]-4-yl)-6-phenylpyridine 
• 1435463-74-3 2-([1,1'-biphenyl]-4-yl)-2-phenyl-1,3,2-oxazaborolidin-3-ium-2-uide 

Relevant articles and documents

Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex

We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-Type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.

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.

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.