4688-76-0

Basic information

• Product Name: 2-BIPHENYLBORONIC ACID
• Synonyms: 2-Biphenylboronic Acid (contains varying aMounts of Anhydride);2-Biphenylboronic Acid 2-Boronobiphenyl, 2-Phenylbenzeneboronic acid;Boronic acid, B-[1,1'-biphenyl]-2-yl-;2-Biphenylboronic acid (2-Phenylphenyl)boranediol;2-Biphenylboronic acid, >=98%;TIMTEC-BB SBB005895;BIPHENYL-2-BORONIC ACID
• CAS NO: 4688-76-0
• Molecular Formula: C₁₂H₁₁BO₂
• Molecular Weight: 198.03
• EINECS: -0
• Product Categories: blocks;BoronicAcids;Boronic Acids & Esters;Boronic acid;Boronic Acids & Esters;Ring Systems;Aryl;Boronic Acids;Boronic Acids and Derivatives
• Mol File: 4688-76-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: 167-172 °C(lit.)
• Boiling Point: 404 °C at 760 mmHg
• Flash Point: 198.1 °C
• Appearance: White to yellow/Powder or Low Melting Solid
• Density: 1.18
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 8.50±0.58(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 3031806
• CAS DataBase Reference: 2-BIPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BIPHENYLBORONIC ACID(4688-76-0)
• EPA Substance Registry System: 2-BIPHENYLBORONIC ACID(4688-76-0)

Safety Data

• Hazard Codes: C,Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-60-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4688-76-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-BIPHENYLBORONIC ACID is used as a reactant in Suzuki-Miyaura cross-coupling reactions with arylhalides, dibromovinyl precursors, alkenyl tosylates and mesylates, and quinoline carboxylates. This versatile reagent enables the formation of carbon-carbon bonds, which are crucial for constructing complex organic molecules and pharmaceutical compounds.
Used in Organic Synthesis:
2-BIPHENYLBORONIC ACID is used as a reactant for intramolecular Friedel-Crafts alkylation, which is essential for the synthesis of chiral tetralins. This reaction allows for the formation of cyclic structures with specific stereochemistry, which are valuable in the development of enantioselective catalysts and chiral pharmaceuticals.
Used in Hydroxylation Reactions:
2-BIPHENYLBORONIC ACID is used as a reactant for hydroxylation to phenols. This reaction is important for the synthesis of phenolic compounds, which have a wide range of applications in the chemical, pharmaceutical, and materials industries.
Used in Oxidative Coupling Reactions:
2-BIPHENYLBORONIC ACID is used as a reactant in oxidative coupling with alkynes, leading to the formation of various organic compounds with potential applications in materials science, pharmaceuticals, and agrochemicals. This reaction provides a convenient method for the synthesis of conjugated systems and other complex molecular structures.

Upstream product

• 67-56-1 methanol 
• 55124-35-1 diisopropylamine borane 
• 2052-07-5 2-Bromobiphenyl 
• 121-43-7 Trimethyl borate 
• 7732-18-5 water 
• 5419-55-6 Triisopropyl borate 
• 2113-51-1 2-iodobiphenyl 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 71-43-2 benzene 
• 13675-18-8 tetrahydroxydiboron 
• 90-41-5 2-phenylaniline 
• 583-55-1 1-Bromo-2-iodobenzene 
• 98-80-6 phenylboronic acid 
• 1449074-55-8 C₁₉H₁₅BN₂O 

Downstream Products

• 1196466-85-9 3-(biphenyl-2-yl)-3H-isobenzofuran-1-one 
• 1196467-01-2 6,7-dimethoxy-3-(biphenyl-2-yl)-3H-isobenzofuran-1-one 
• 250339-07-2 2-tert-butyl-9,10-bis(2-biphenyl)anthracene 
• 1492022-69-1 [Ru(η5-Cp)(η5-4-(2-biphenyl)indene)] 
• 1478097-98-1 C₂₅H₂₁N₂O₇P 
• 1454654-40-0 (5-biphenyl-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-(4-morpholin-4-yl-phenyl)-amine 
• 1454654-42-2 5-biphenyl-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine 
• 1442663-93-5 C₂₂H₁₉NO₂ 
• 1416332-85-8 (S)-ethyl 2-(2’-phenyl-biphenyl-4-yloxy)-3-phenylpropanoate 
• 1427642-41-8 4′′′-methoxy-1,1′:2′,1′′:4′′,1′′′-quaterphenyl 
• 1415582-00-1 C₃₈H₃₀O₂ 
• 1415581-85-9 C₃₈H₃₀O₂ 
• 1415581-79-1 C₂₆H₂₂O₂ 
• 1415581-92-8 C₃₂H₂₆O₂ 

Relevant articles and documents

Rh(III)-Catalyzed Annulation of 2-Biphenylboronic Acid with Diverse Activated Alkenes

Rhodium(III)-catalyzed annulation of 2-biphenylboronic acids with three classes of activated alkenes has been realized, leading to the synthesis of fused or bridged cyclic skeletons via transmetalation-initiated C-H activation. In the annulative coupling of 2-biphenylboronic acid with a CF3-substituted enone, the bulky cyclopentadienyl ligand (CptBu) in the catalyst proved effective to promote the reductive elimination process prior to protonolysis, affording the [4 + 2] annulated products instead of the simple 1,4-addition product. Seven-membered rings were obtained when disubstituted cyclopropenones were employed. Bridged cycles were isolated from the coupling of 2-biphenylboronic acid with benzoquinones as a result of 2-fold Michael additions. The substrate scopes were found to be broad with up to 99% yield under air-tolerant conditions.

Preparation method of triphenylene derivative

The invention relates to the field of organic chemistry, and in particular, relates to a preparation method of a triphenylene derivative. The invention provides the preparation method of the triphenylene derivative, wherein the method comprises the step: carrying out cyclization reaction on a compound represented by a formula 4 in the presence of acid, an initiator and an oxidant to provide a compound represented by a formula 5. According to the preparation method of the triphenylene derivative, provided by the invention, arylation reaction is carried out by using the acid and the oxidant, sothat side reactions generated in the reaction are few, the overall conversion rate of the reaction is high, and the raw materials are economical and practical; and in addition, the whole reaction route has high reaction yield and is convenient for industrial production and operation, and good industrialization prospects are realized.

Ag-Catalyzed Cyclization of Arylboronic Acids with Elemental Selenium for the Synthesis of Selenaheterocycles

A general method for the synthesis of five-membered and six-membered selenaheterocycles through Ag-catalyzed C?Se bond-forming reaction is reported. This reaction proceeds via intramolecular cyclization of arylboronic acids with selenium powder. Preliminary mechanism studies demonstrate that this transformation involves a selenium-centred radical intermediate. (Figure presented.).

Aryl boronic acid preparation method

The invention belongs to the technical field of fine chemical engineering, and relates to an aryl boronic acid preparation method. In the prior art, aryl boronic acid as a novel safe and environmentally-friendly arylation reagent is widely used in scientific research and production of various fine chemicals containing aryl structures in the fields of medicines, pesticides, advanced materials and the like; and the aryl boronic acid compound preparation method reported in the disclosed literature has problems of harsh reaction conditions and high cost. A purpose of the invention is to provide amethod, wherein an aryl boron compound is formed by carrying out a reaction on a Grignard reagent and trialkyl borate under mild conditions, the composition of the aryl boron compound is converted from the main component diaryl borate into the main component aryl borate, and the aryl borate is hydrolyzed to obtain aryl boric acid, so that the preparation cost of the acyl aryl boric acid compound can be remarkably reduced, and the method has good practical application prospect.

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.

Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide

A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.

Copper(II)-Mediated [11C]Cyanation of Arylboronic Acids and Arylstannanes

A copper-mediated method for the transformation of diverse arylboron compounds and arylstannanes to aryl-[11C]-nitriles is reported. This method is operationally simple, uses commercially available reagents, and is compatible with a wide variety of substituted aryl- and heteroaryl substrates. This method is applied to the automated synthesis of high specific activity [11C]perampanel in 10% nondecay-corrected radiochemical yield (RCY).

Rhodium-Catalyzed Oxidative Annulation of (2-Arylphenyl)boronic Acids with Alkynes: Selective Synthesis of Phenanthrene Derivatives

A rhodium-catalyzed annulative coupling of (2-arylphenyl)boronic acids with alkynes has been developed for the facile construction of phenanthrene frameworks. The reaction proceeded without external bases, and dioxygen worked as a terminal oxidant. Deuter

Photocyclodehydrofluorination

Mallory-type photocyclization involves a series of photoreactions of stilbenes, o-terphenyls and related derivatives, which undergo intramolecular cyclization via dihydrophenanthrene intermediates. In typical Mallory photocyclizations, oxidants are usually needed to produce the final phenanthrene-containing product. In the research described here, appropriately fluorinated stilbenes and o-terphenyls undergo ring closure and HF is eliminated. This photocyclodehydrofluorination (PCDHF) reaction is very useful to produce a wide range of selectively fluorinated polynuclear aromatic hydrocarbons that possess a phenanthrene (or heterocyclic analogue of phenanthrene) substructure. These fluorinated products are of great interest in various aspects of the materials science.

Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis

An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.