Description

(3-Bromophenyl)boronic acid (CAS No. 89598-96-9) is a high-purity boronic acid derivative with the molecular formula C₆H₆BBrO₂. This organoboron compound is widely utilized in cross-coupling reactions, particularly in Suzuki-Miyaura coupling, due to its excellent reactivity and stability. The product is supplied as a white to off-white crystalline powder with a typical purity of ≥97%, ensuring optimal performance in synthetic applications. It is sensitive to moisture and should be stored under inert conditions to maintain integrity. Ideal for pharmaceutical, agrochemical, and materials science research, this reagent is rigorously tested via NMR, HPLC, and elemental analysis to guarantee consistency and reliability.

Properties

• CAS Number: 89598-96-9
• Complexity: 110
• IUPAC Name: (3-bromophenyl)boronic acid
• InChI: InChI=1S/C6H6BBrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H
• InChI Key: AFSSVCNPDKKSRR-UHFFFAOYSA-N
• Exact Mass: 199.96442
• Molecular Formula: C6H6BBrO2
• Molecular Weight: 200.83
• SMILES: B(C1=CC(=CC=C1)Br)(O)O
• Topological: 40.5
• Monoisotopic Mass: 199.96442
• Synonyms: (3-bromophenyl)boronic Acid, 677-281-7, 3-Bromophenylboronic acid, 89598-96-9, 3-Bromophenylboronicacid, 3-Bromobenzeneboronic Acid, 3-Bromophenyl boronic acid, MFCD00239386, CHEMBL278140, 3-?Bromophenylboronic Acid, Boronic acid, (3-bromophenyl)-, Boronic acid, B-(3-bromophenyl)-;3-Bromophenylboronic acid, 3-Bromophenylboronic, 3-borophenylboronic acid, 3-bromo-phenylboronic acid, (3-bromophenyl)boronicAcid, 3-bromo-benzeneboronic acid, 3-bromobenzene boronic acid, 3-bromo-phenyl boronic acid, SCHEMBL73569, 3-bromo benzene boronic acid, 3-bromo-benzene-boronic acid, (3-bromophenyl) boronic acid, AKOS BRN-0083, DTXSID90370209, AFSSVCNPDKKSRR-UHFFFAOYSA-N, BCP22684, BDBM50282571, RB2089, SBB092696, AKOS002678199, AB05452, AS-2312, CS-W004715, FB11555, HY-W004715, NCGC00249482-01, AC-24800, BP-11422, SY019959, DB-010545, B2890, EN300-107096, Z1269164934, Boronic acid,B-(3-romophenyl)-;3-Bromophenylboronic acid, 3-Bromophenylboronic Acid (contains varying amounts of Anhydride), InChI=1/C6H6BBrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10

Application

(3-Bromophenyl)boronic acid is a key intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of biaryl compounds for drug discovery and materials science. It is also used in the preparation of aryl halides and as a building block for functionalized polymers and ligands. Researchers leverage its reactivity in catalytic cycles for C-C bond formation under mild conditions.

Safety and Hazards

GHS Hazard Statements

• H302 (11.1%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (11.1%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (88.9%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (88.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (11.1%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (11.1%)
• Acute Tox. 4 (11.1%)
• Skin Irrit. 2 (88.9%)
• Eye Irrit. 2A (88.9%)
• Acute Tox. 4 (11.1%)
• STOT SE 3 (66.7%)

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