Description

2,3,4,5,6-Pentafluorobenzeneboronic acid (CAS No. 1582-24-7) is a highly fluorinated boronic acid derivative with the molecular formula C₆H₂BF₅O₂. This compound, also known as (2,3,4,5,6-pentafluorophenyl)boronic acid, is a valuable reagent in organic synthesis and materials science due to its electron-deficient aromatic ring and reactive boronic acid group. The pentafluorophenyl moiety enhances its stability and reactivity, making it ideal for Suzuki-Miyaura cross-coupling reactions, a cornerstone in the construction of complex biaryl structures. With a purity of ≥95%, this product is rigorously tested by HPLC and NMR to ensure consistent quality for research and industrial applications. It is supplied as a white to off-white crystalline powder, soluble in common organic solvents such as THF, DMF, and DMSO. Store under inert conditions at 2-8°C to maintain stability.

Properties

• CAS Number: 1582-24-7
• Complexity: 191
• IUPAC Name: (2,3,4,5,6-pentafluorophenyl)boronic acid
• InChI: InChI=1S/C6H2BF5O2/c8-2-1(7(13)14)3(9)5(11)6(12)4(2)10/h13-14H
• InChI Key: VASOMTXTRMYSKD-UHFFFAOYSA-N
• Exact Mass: 212.0068003
• Molecular Formula: C6H2BF5O2
• Molecular Weight: 211.88
• SMILES: B(C1=C(C(=C(C(=C1F)F)F)F)F)(O)O
• Topological: 40.5
• Monoisotopic Mass: 212.0068003
• Synonyms: 2,3,4,5,6-PENTAFLUOROBENZENEBORONIC ACID, 627-867-3, 1582-24-7, Pentafluorophenylboronic acid, Perfluorophenylboronic acid, 2,3,4,5,6-PENTAFLUOROPHENYLBORONIC ACID, Pentafluorobenzeneboronic acid, (2,3,4,5,6-pentafluorophenyl)boronic Acid, (pentafluorophenyl)boronic acid, MFCD01074663, BORONIC ACID, B-(2,3,4,5,6-PENTAFLUOROPHENYL)-, BORONIC ACID, (PENTAFLUOROPHENYL)-, Pentafluorophenylboronicacid, C6H2BF5O2, Pentafluoroboronic acid, SCHEMBL125669, DTXSID00379743, BBL101329, SBB094561, STL555125, AKOS005175091, AB08108, CS-W013176, FP32234, GS-6218, SY029868, DB-010289, P1904, Pentafluorophenylboronic acid (contains varying amounts of Anhydride)

Application

2,3,4,5,6-Pentafluorobenzeneboronic acid is widely used in palladium-catalyzed cross-coupling reactions, particularly Suzuki-Miyaura couplings, to synthesize fluorinated biaryl compounds for pharmaceuticals and agrochemicals. Its electron-deficient aromatic ring facilitates reactions with aryl halides, enabling the creation of complex molecular architectures. This compound is also employed in the development of fluorescent probes and organic electronic materials due to its unique electronic properties. Researchers utilize it in the preparation of boron-containing polymers and covalent organic frameworks (COFs).

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.8%): 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 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (97.8%)

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