Description

4,4,5,5-Tetramethyl-2-(4-(pentafluoro-lambda6-sulfanyl)phenyl)-1,3,2-dioxaborolane (CAS: 1286278-34-9) is a high-purity boronic ester derivative featuring a pentafluorosulfanyl (SF₅) functional group. This compound, with the molecular formula C₁₂H₁₆BF₅O₂S, is a valuable building block for advanced organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. The SF₅ moiety imparts unique electronic and steric properties, making it ideal for pharmaceutical, agrochemical, and materials science research. Its stability under various conditions ensures reliable performance in complex synthetic pathways. Offered as a crystalline solid with ≥95% purity, this reagent is meticulously packaged under inert conditions to guarantee longevity and reactivity.

Properties

• CAS Number: 1286278-34-9
• Complexity: 412
• IUPAC Name: pentafluoro-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-lambda6-sulfane
• InChI: InChI=1S/C12H16BF5O2S/c1-11(2)12(3,4)20-13(19-11)9-5-7-10(8-6-9)21(14,15,16,17)18/h5-8H,1-4H3
• InChI Key: GSABJOBFIHVJIB-UHFFFAOYSA-N
• Exact Mass: 330.0884219
• Molecular Formula: C12H16BF5O2S
• Molecular Weight: 330.13
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)S(F)(F)(F)(F)F
• Topological: 19.5
• Monoisotopic Mass: 330.0884219
• Synonyms: 1286278-34-9, 4,4,5,5-tetramethyl-2-[4-(pentafluoro-lambda6-sulfanyl)phenyl]-1,3,2-dioxaborolane, 4,4,5,5-Tetramethyl-2-(4-(pentafluoro-lambda6-sulfanyl)phenyl)-1,3,2-dioxaborolane, 841-779-4, MFCD20489194, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenylsulfur pentafluoride, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)phenylpentafluorosulfur(VI), 4-(Pentafluorothio)benzeneboronic acid, pinacol ester, [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfur pentafluoride, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-PHENYLSULFUR PENTAFLUORID+, pentafluoro-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-lambda6-sulfane, 4,4,5,5-Tetramethyl-2-[4-(pentafluorosulfanyl)phenyl]-1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-(4-(pentafluorosulfanyl)phenyl)-1,3,2-dioxaborolane, SCHEMBL15104700, LBC27834, BBL103485, STL557295, AKOS025213309, AT34596, [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]sulfur pentafluoride, NCGC00662564-01, SY296349, CS-0236355, EN300-1704475, 4-(Pentafluorosulfanyl)phenylboronic Acid Pinacol Ester, Z2049757163, 4,4,5,5-TETRAMETHYL-2-(4-(PENTAFLUORO-L6-SULFANYL)PHENYL)-1,3,2-DIOXABOROLANE, 4,4,5,5-tetramethyl-2-[4-(pentafluoro-lambda~6~-sulfanyl)phenyl]-1,3,2-dioxaborolane

Application

This compound is widely used in organoboron chemistry as a key intermediate for Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of biaryl structures with SF₅ substituents. Its applications extend to medicinal chemistry, where the SF₅ group enhances metabolic stability and lipophilicity of drug candidates. Researchers also utilize it in material science to develop advanced polymers and liquid crystals with tailored electronic properties.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): 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, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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