Description

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Bromide (CAS No. 377780-72-8) is a high-purity boronic ester derivative with the molecular formula C₁₃H₁₈BBrO₂. This compound features a reactive benzyl bromide group adjacent to a pinacol boronate ester, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions and other palladium-catalyzed transformations. Its stability under anhydrous conditions and compatibility with various organic solvents ensure reliable performance in synthetic applications. Ideal for pharmaceutical research, materials science, and agrochemical development, this reagent is rigorously tested to meet the highest standards of purity and consistency. Each batch is characterized by ¹H NMR, ¹³C NMR, and HPLC to guarantee superior quality for demanding research needs.

Properties

• CAS Number: 377780-72-8
• Complexity: 265
• IUPAC Name: 2-[2-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C13H18BBrO2/c1-12(2)13(3,4)17-14(16-12)11-8-6-5-7-10(11)9-15/h5-8H,9H2,1-4H3
• InChI Key: ROIXSNLOYHDYBP-UHFFFAOYSA-N
• Exact Mass: 296.05832
• Molecular Formula: C13H18BBrO2
• Molecular Weight: 297.00
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2CBr
• Topological: 18.5
• Monoisotopic Mass: 296.05832
• Synonyms: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Bromide, 687-067-5, 377780-72-8, 2-(2-(BROMOMETHYL)PHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE, 2-BROMOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, 2-[2-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-Bromomethylphenylboronic acid pinacol ester, (2-BROMOMETHYLPHENYL)BORONIC ACID, PINACOL ESTER, MFCD01632210, 2-(BROMOMETHYL)BENZENEBORONIC ACID PINACOL ESTER, 2-(Bromomethyl)phenylboronic Acid Pinacol Ester, 2-(Bromomethyl)benzeneboronic acid, pinacol ester, SCHEMBL2586990, (2-(BROMOMETHYL)PHENYL)BORONIC ACID PINACOL ESTER, DTXSID60397089, ROIXSNLOYHDYBP-UHFFFAOYSA-N, AKOS015960316, AB09488, AS-2478, CS-W013977, SY047736, 2-(bromomethyl)phenylboronic pinacol ester, 2-Bromoethylphenylboronic acid pinacol ester, DB-010355, T3393, 2-Bromomethylphenyl boronic acid pinacol ester, EN300-155798, 2-Bromomethylphenylboronic acid pinacol ester, 95%, 2-[2-(bromomethyl)-phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Application

This compound is widely used as a key intermediate in Suzuki-Miyaura cross-coupling reactions to form biaryl structures, essential in drug discovery and materials science. Its benzyl bromide moiety allows for further functionalization, enabling the synthesis of complex organic molecules. Researchers also employ it in the development of boron-containing polymers and advanced catalytic systems. The pinacol boronate group enhances stability while maintaining reactivity for selective transformations.

Safety and Hazards

GHS Hazard Statements

• H315 (97.6%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (97.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (95.2%): 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 (97.6%)
• Eye Irrit. 2 (97.6%)
• STOT SE 3 (95.2%)

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