5′-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester - ≥97% , CAS No.579503-59-6

CAS: 579503-59-6 Cat. No.: H171077 Molecular Weight: 376.38 EC Number: 627-390-0

GRADE & PURITY ≥97%

Synonyms

4,4,5,5-TETRAMETHYL-2-[5'-HEXYL-2,2'-BITHIEN-5-YL]-1,3,2-DIOXABOROLANE | 5'-Hexyl-2,2'-bithiophene-5-boronic acid pinacol ester | 5-hexyl-2,2'-bithiophene-5'-boronic acid pinacol ester | 5-Hexyl-2,2-bithiophene-5-boronic acid pinacol ester | SCHEMBL119235

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

Product Application:

Reagent use for：
Suzuki-Miyaura cross-coupling reactions and shape-shifting in contorted dibenzotetrathienocoronenes;
Oligothiophene self-assembly induction into fibers with tunable shape and function;
Stille coupling and p-conjugated packing structure and hole mobility of bithiophene-bithiazole copolymers with alkyl-thiophene side chains.
Reagent used in Preparation of:
Solution-processed ambipolar field-effect transistor;
Light harvesting small molecules for use in solution-processed small molecule bulk heterojunction solar cell devices;
Light-emitting diode (OLED) materials;
Unsymmetric substituted benzothiadiazole-containing vinyl monomers for RAFT polymerization;
Pd-catalyzed condensations and synthesis of isoindigo-based oligothiophenes for molecuar bulk heterojunction solar cells;
Thiophene-benzothiadiazole based donor-acceptor-donor materials.

Specifications

Synonyms

4, 4, 5, 5-TETRAMETHYL-2-[5'-HEXYL-2, 2'-BITHIEN-5-YL]-1, 3, 2-DIOXABOROLANE | 5'-Hexyl-2, 2'-bithiophene-5-boronic acid pinacol ester | 5-hexyl-2, 2'-bithiophene-5'-boronic acid pinacol ester | 5-Hexyl-2, 2-bithiophene-5-boronic acid pinacol ester | SCHEMBL119235

Specifications & Purity

≥97%

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504766934
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504766934
• Canonical Smiles: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(S2)C3=CC=C(S3)CCCCCC
• IUPAC Name: 2-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChIKey: XTTRNSNHDCYSEL-UHFFFAOYSA-N
• 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
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(S2)C3=CC=C(S3)CCCCCC
• WGK Germany: 3
• Molecular Weight: 376.38
• Reaxy-Rn: 10468955
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10468955&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Bi- and oligothiophenes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Bi- and oligothiophenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Bi- and oligothiophenes
• Alternative Parents: 2,5-disubstituted thiophenes Heteroaromatic compounds Dioxaborolanes Boronic acid esters Oxacyclic compounds Organic metalloid salts Organooxygen compounds Organometalloid compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Bithiophene - 2,5-disubstituted thiophene - Heteroaromatic compound - Thiophene - 1,3,2-dioxaborolane - Boronic acid ester - Boronic acid derivative - Oxacycle - Organic metalloid salt - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organic metalloid moeity - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Melt Point(°C): 36-40 °C (lit.)
• Molecular Weight: 376.400 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 376.17 Da
• Monoisotopic Mass: 376.17 Da
• Topological Polar Surface Area: 74.900 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 427.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3