Description

2-[3-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 214360-74-4) is a high-purity boronic ester derivative with the molecular formula C₁₃H₁₈BBrO₂. This compound features a reactive bromomethyl group adjacent to a phenyl-dioxaborolane moiety, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions and other organoboron chemistry applications. Its stable dioxaborolane ring ensures excellent shelf-life and handling properties under inert conditions. Ideal for pharmaceutical research, materials science, and agrochemical synthesis, this reagent is supplied with comprehensive analytical data (NMR, HPLC) to guarantee quality and consistency. Store under inert gas at -20°C to prevent degradation.

Properties

• CAS Number: 214360-74-4
• Complexity: 265
• IUPAC Name: 2-[3-(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)11-7-5-6-10(8-11)9-15/h5-8H,9H2,1-4H3
• InChI Key: WUIYGXGXVOHAFW-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=C2)CBr
• Topological: 18.5
• Monoisotopic Mass: 296.05832
• Synonyms: 214360-74-4, 2-(3-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-[3-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, DTXSID80378335, DTXCID80329362, 687-016-7, (3-Bromomethylphenyl)boronic acid pinacol ester, 3-Bromomethylphenylboronic acid, pinacol ester, 3-(Bromomethyl)phenylboronic acid pinacol ester, 1,3,2-DIOXABOROLANE, 2-[3-(BROMOMETHYL)PHENYL]-4,4,5,5-TETRAMETHYL-, MFCD02183481, 3-(Bromomethyl)phenylboronic acid, pinacol ester, 3-(bromomethyl)phenylboronic pinacol ester, 2-(3-(bromomethyl)phenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane, 3-bromomethylphenyl boronic acid pinacol ester, SCHEMBL3039403, (3-(BROMOMETHYL)PHENYL)BORONIC ACID PINACOL ESTER, WUIYGXGXVOHAFW-UHFFFAOYSA-N, BCP26753, AKOS015842129, AB11493, AS-2405, CS-W009968, SY103719, EN300-94270, D71321, 3-(Bromomethyl)benzeneboronic acid, pinacol ester, 3-Bromomethylphenylboronic acid pinacol ester, 95%, Z1268451788, 2-(3-Bromomethylphenyl)-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 for the synthesis of biaryl structures in drug discovery. It also serves as a precursor for functionalized boronates in materials science, enabling the development of OLEDs and organic semiconductors. Researchers utilize its bromomethyl group for further derivatization in peptide coupling or polymer chemistry.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Precautionary Statements

• P264, P270, P301+P317, P330, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)

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