Description

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 68716-49-4) is a high-purity boronic ester derivative widely used in organic synthesis and pharmaceutical research. With the molecular formula C₁₂H₁₆BBrO₂, this compound serves as a versatile intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds for advanced material and drug development. The pinacol boronate ester group enhances stability and reactivity, making it ideal for controlled functionalization of aromatic systems. Supplied as a white to off-white crystalline solid, it is rigorously tested for quality (≥95% purity by HPLC) and packaged under inert conditions to ensure long-term stability. Suitable for use in academic, industrial, and pharmaceutical laboratories.

Properties

• CAS Number: 68716-49-4
• Complexity: 244
• IUPAC Name: 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C12H16BBrO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,1-4H3
• InChI Key: AZCNDGAXOZWQPV-UHFFFAOYSA-N
• Exact Mass: 282.04267
• Molecular Formula: C12H16BBrO2
• Molecular Weight: 282.97
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)Br
• Topological: 18.5
• Monoisotopic Mass: 282.04267
• Synonyms: 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, DTXSID30444493, DTXCID70395314, 68716-49-4, 4-Bromophenylboronic acid pinacol ester, 4-Bromophenylboronic acid, pinacol ester, 1,3,2-Dioxaborolane, 2-(4-bromophenyl)-4,4,5,5-tetramethyl-, MFCD11110553, 2-(4-bromo-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, (4-BROMOPHENYL)BORONIC ACID PINACOL ESTER, SCHEMBL171682, SCHEMBL3142593, AZCNDGAXOZWQPV-UHFFFAOYSA-N, AKOS016004712, 4-Bromophenylboronic acid,pinacol ester, AS-2516, NCGC00662706-01, tetra-methylethylene p-bromophenylboronate, SY037980, B4771, CS-0036048, EN300-316477, Z2044796873, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene, 1-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene, 4-bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene, 2-(4-Bromophenyl)-4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolane

This compound is primarily employed in Suzuki-Miyaura cross-coupling reactions to synthesize biaryl structures, a key step in pharmaceutical and agrochemical manufacturing. It facilitates the introduction of bromophenyl groups into complex molecules under mild conditions. Researchers also utilize it in polymer chemistry and material science to modify aromatic frameworks. Compatible with Pd-catalyzed transformations, it is a staple in high-throughput screening libraries for drug discovery.

Safety and Hazards

GHS Hazard Statements

• H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (33.3%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (33.3%): 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 (66.7%)
• Skin Irrit. 2 (66.7%)
• Eye Irrit. 2A (66.7%)
• STOT SE 3 (66.7%)

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