Description

4-(Bromomethyl)phenylboronic acid (CAS No. 68162-47-0) is a high-purity boronic acid derivative with the molecular formula C₇H₈BBrO₂. This compound features a reactive bromomethyl group adjacent to a boronic acid moiety, making it a versatile building block in organic synthesis and cross-coupling reactions. Ideal for Suzuki-Miyaura coupling, it facilitates the formation of carbon-carbon bonds in pharmaceutical intermediates, agrochemicals, and advanced materials. The product is supplied as a white to off-white crystalline powder with ≥95% purity (HPLC), ensuring consistent performance in sensitive applications. Store in a cool, dry place under inert conditions to maintain stability. Suitable for researchers and industrial scientists seeking reliable boronic acid reagents.

Properties

• CAS Number: 68162-47-0
• Complexity: 113
• IUPAC Name: [4-(bromomethyl)phenyl]boronic acid
• InChI: InChI=1S/C7H8BBrO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H,5H2
• InChI Key: PDNOURKEZJZJNZ-UHFFFAOYSA-N
• Exact Mass: 213.98007
• Molecular Formula: C7H8BBrO2
• Molecular Weight: 214.85
• SMILES: B(C1=CC=C(C=C1)CBr)(O)O
• Topological: 40.5
• Monoisotopic Mass: 213.98007
• Synonyms: 68162-47-0, 4-(Bromomethyl)phenylboronic acid, DTXSID20370818, DTXCID90321852, 627-358-6, 4-bromomethylphenylboronic acid, (4-(Bromomethyl)phenyl)boronic acid, [4-(bromomethyl)phenyl]boronic Acid, 4-(bromomethyl)benzeneboronic acid, MFCD01318113, 4-Bromomethylbenzeneboronic acid, (4-bromomethylphenyl)boronic acid, 4-Boronobenzyl bromide, Boronic acid, [4-(bromomethyl)phenyl]-, 4-(Bromomethyl)phenylboronic acid(contains varying amounts of Anhydride), SCHEMBL40256, P-BORONOBENZYL BROMIDE, 4-bromomethylphenyl boronic acid, p-Bromomethylbenzene Boronic Acid, PDNOURKEZJZJNZ-UHFFFAOYSA-N, (4-(Bromomethyl)phenyl)boronicacid, SBB070792, AKOS015836208, AB08630, AC-9222, CS-W000960, PS-9528, ALPHA-BROMO-P-TOLUENEBORONIC ACID, SY014690, DB-025185, EN300-150254, Z1269236418

Application

4-(Bromomethyl)phenylboronic acid is widely used in palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura couplings, to synthesize biaryl compounds for drug discovery. It serves as a key intermediate in the preparation of PET imaging agents and boron-containing therapeutics. The bromomethyl group also enables further functionalization via nucleophilic substitution, expanding its utility in material science and polymer chemistry.

Safety and Hazards

GHS Hazard Statements

• H302 (89.1%): Harmful if swallowed [Warning Acute toxicity, oral]
• H314 (10.9%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H315 (89.1%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (89.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (89.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (89.1%)
• Skin Corr. 1C (10.9%)
• Skin Irrit. 2 (89.1%)
• Eye Irrit. 2 (89.1%)
• STOT SE 3 (89.1%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.