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

Description

2-BIPHENYLBORONIC ACID is an organic compound that features a biphenyl group attached to a boronic acid moiety. It is known for its unique chemical properties, which make it a versatile building block in organic synthesis and a key component in various chemical reactions.

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.

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Downstream Products

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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.

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.).

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.