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

• ChemBase ID: 141731
• Molecular Formular: C20H29BO2S2
• Molecular Mass: 376.38406
• Monoisotopic Mass: 376.17020257
• SMILES: B1(OC(C(O1)(C)C)(C)C)c1ccc(s1)c1ccc(s1)CCCCCC
• Canonical SMILES: CCCCCCc1ccc(s1)c1ccc(s1)B1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C20H29BO2S2/c1-6-7-8-9-10-15-11-12-16(24-15)17-13-14-18(25-17)21-22-19(2,3)20(4,5)23-21/h11-14H,6-10H2,1-5H3
• InChIKey: XTTRNSNHDCYSEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• IUPAC Traditional name: 2-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(5′-Hexyl-2,2′-bithien-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4,4,5,5-Tetramethyl-2-[5′-hexyl-2,2′-bithien-5-yl]-1,3,2-dioxaborolane; 5′-N-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester; 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5′-N-hexyl-2,2′-bithiophene; 5-Hexyl-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene; 5′-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester; 5-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)-5′-N-己基-2,2′-联噻吩; 5-己基-5′-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)-2,2′-联噻吩; 5′-N-己基-2,2′-联噻吩-5-硼酸频哪醇酯; 5′-己基-2,2′-联噻吩-5-硼酸频哪醇酯

Database IDs

• CAS Number: 579503-59-6
• MDL Number: MFCD05664380
• PubChem SID: 24882530; 162235965
• PubChem CID: 12153150

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.942
• LogD (pH = 7.4): 6.942
• Log P: 6.942
• Molar Refractivity: 101.7733 cm^3
• Polarizability: 43.26454 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 36-40 °C(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C20H29BO2S2

DETAILS

Sigma Aldrich - 632961

Packaging
1, 5 g in glass bottle
Application
Reagent use for
• Suzuki-Miyaura cross-coupling reactions and shape-shifting in contorted dibenzotetrathienocoronenes1
• Oligothiophene self-assembly induction into fibers with tunable shape and function2
• Stille coupling and p-conjugated packing structure and hole mobility of bithiophene-bithiazole copolymers with alkyl-thiophene side chains3 Reagent used in Preparation of
• Solution-processed ambipolar field-effect transistor4
• Light harvesting small molecules for use in solution-processed small molecule bulk heterojunction solar cell devices5
• Light-emitting diode (OLED) materials6
• Unsymmetric substituted benzothiadiazole-containing vinyl monomers for RAFT polymerization7
• Pd-catalyzed condensations and synthesis of isoindigo-based oligothiophenes for molecuar bulk heterojunction solar cells8
• Thiophene-benzothiadiazole based donor-acceptor-donor materials9