Description

1,1′-Biphenyl-4-yl-boronic acid (CAS No. 5122-94-1) is a high-purity boronic acid derivative with the molecular formula C₁₂H₁₁BO₂. This compound, also known as (4-phenylphenyl)boronic acid, is a versatile building block in organic synthesis and pharmaceutical research. Its biphenyl scaffold and boronic acid functional group make it an essential reagent for Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex molecular architectures. The product is supplied as a white to off-white crystalline powder with ≥95% purity (HPLC), ensuring optimal performance in sensitive applications. Suitable for use in medicinal chemistry, material science, and catalysis, it is packaged under inert conditions to maintain stability and shelf life. Store in a cool, dry place away from moisture and light.

Properties

• CAS Number: 5122-94-1
• Complexity: 182
• IUPAC Name: (4-phenylphenyl)boronic acid
• InChI: InChI=1S/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15H
• InChI Key: XPEIJWZLPWNNOK-UHFFFAOYSA-N
• Exact Mass: 198.0852098
• Molecular Formula: C12H11BO2
• Molecular Weight: 198.03
• SMILES: B(C1=CC=C(C=C1)C2=CC=CC=C2)(O)O
• Topological: 40.5
• Monoisotopic Mass: 198.0852098
• Synonyms: 4-Biphenylboronic acid, 5122-94-1, [1,1′-biphenyl]-4-ylboronic acid, 1,1′-Biphenyl-4-yl-boronic acid, (1,1′-Biphenyl)-4-ylboronic acid, DTXSID90199230, DTXCID20121721, 675-084-0, biphenyl-4-boronic acid, (4-phenylphenyl)boronic acid, (1,1′-biphenyl-4-yl)boronic acid, Biphenylboronic acid, 1,1′-biphenyl-4-ylboronic acid, biphenyl-4-ylboronic acid, 4-phenylbenzeneboronic acid, MFCD00093311, boronic acid, [1,1′-biphenyl]-4-yl-, 4-Biphenylboronic acid(contains varying amounts of Anhydride), Boronic acid, (1,1′-biphenyl)-4-yl-, 4-phenylphenylboronic acid, (4-Phenylphenyl)Boranediol, 4-biphenyl boronic acid, Phenylboronic acid, 23, (4-biphenylyl)boronic acid, biphenyl-4-yl-boronic acid, 4-phenyl-phenylboronic acid, 4-phenylphenyl boronic acid, 4-(phenyl)phenylboronic acid, SCHEMBL129728, CHEMBL485742, SCHEMBL6676881, BDBM26132, 4-(dihydroxyboryl)-1,1′-biphenyl, BCP22752, 4-Biphenylboronic acid, >=95.0%, SBB092240, AKOS000277884, AB03333, AC-5005, BCP9000022, CS-W002364, FB62320, HY-W002364, NCGC00249525-01, NCGC00249525-02, AS-14566, BP-12155, SY031947, (1,1-BIPHENYL-4-YL)BORONIC ACID, [1,1-BIPHENYL]-4-YLBORONIC ACID, DB-010656, B2294, EN300-03905, Z119990214, 4-Biphenylboronic Acid, (contains varying amounts of Anhydride), InChI=1/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15

Application

1,1′-Biphenyl-4-yl-boronic acid is widely used as a key intermediate in Suzuki-Miyaura cross-coupling reactions for synthesizing biaryl compounds in pharmaceutical and agrochemical research. It serves as a precursor in the development of organic electronic materials, such as OLEDs and semiconductors, due to its conjugated biphenyl structure. Researchers also utilize it in the design of boronic acid-based sensors and probes for detecting biological molecules.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (90.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (90.9%)

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