2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

• ChemBase ID: 141524
• Molecular Formular: C16H27BO2S
• Molecular Mass: 294.26038
• Monoisotopic Mass: 294.1824815
• SMILES: B1(OC(C(O1)(C)C)(C)C)c1c(ccs1)CCCCCC
• Canonical SMILES: CCCCCCc1ccsc1B1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C16H27BO2S/c1-6-7-8-9-10-13-11-12-20-14(13)17-18-15(2,3)16(4,5)19-17/h11-12H,6-10H2,1-5H3
• InChIKey: XCXAUPBHQCCWCI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• IUPAC Traditional name: 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 3-Hexyl-2-thienylboronic acid; 2-(3-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 3-Hexylthiophene-2-boronic acid pinacol ester; 2-(3-己基-2-噻吩基)-4,4,5,5-四甲基-1,3,2-二氧杂硼烷; 3-己基噻吩-2-硼酸频哪醇酯

Database IDs

• CAS Number: 850881-09-3
• MDL Number: MFCD11045447
• PubChem SID: 162235758
• PubChem CID: 16663552

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.943
• LogD (pH = 7.4): 5.943
• Log P: 5.943
• Molar Refractivity: 80.025 cm^3
• Polarizability: 33.6297 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: >110 °C; >230 °F
• Density: 0.983 g/mL at 25 °C
• Refractive Index: n20/D 1.490-1.499

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C16H27BO2S

DETAILS

Sigma Aldrich - 697400

Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Suzuki-Miyaura cross-coupling reactions1
• p-type/n-type switching of ambipolar bithiazole-benzothiadiazole-based polymers in solar cells1
• Hierarchical self-assembly of semiconductor functionalized peptide a-helixes and optoelectronic properties2 Reagent used in Preparation of
• Photovoltaic materials, polymers, and thiophene-based compounds with photophysical, electrochemical, and fluorescent properties3,4,5
• Polymer solar cells for Low band gap poly(1,4-arylene-2,5-thienylene)s with benzothiadiazole units6
• Dithienothiophene-based dyes for dye-sensitized solar cells7