5′-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester
5′-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester (CAS: 579503-59-6) is an organoboron compound with a molecular weight of 376.38 g/mol. This thiophene derivative is primarily utilised as a reagent in organic synthesis, particularly for Suzuki-Miyaura and Stille cross-coupling reactions. Its applications extend to materials science, contributing to the development of organic electronic devices, light-harvesting molecules, and conjugated polymers.
- IUPAC
- 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
- Synonyms
- 2-(5′-Hexyl-2,2′-bithien-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane4,4,5,5-Tetramethyl-2-[5′-hexyl-2,2′-bithien-5-yl]-1,3,2-dioxaborolane5′-N-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5′-N-hexyl-2,2′-bithiophene5-Hexyl-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene
Suzuki-Miyaura Cross-Coupling Reactions
This boronate ester serves as a key reagent in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex organic molecules, including contorted dibenzotetrathienocoronenes.
Organic and Printed Electronics
It is employed in the preparation of materials for organic electronic devices, such as solution-processed ambipolar field-effect transistors and light-emitting diodes (OLEDs).
Materials Science
The compound facilitates the induction of oligothiophene self-assembly into fibres with controllable shape and function, and is used in synthesising novel polymers for various material applications.
Stille Coupling
Used in Stille coupling reactions to synthesise p-conjugated packing structures and improve the hole mobility of bithiophene-bithiazole copolymers.
| Molecular weight | 376.38 |
|---|---|
| Empirical formula | C20H29BO2S2 |
| Assay | 97% |
| 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 heterojunc |
| Melting point | 36-40 °C(lit.) |
Hazard statements
- H302Harmful if swallowed
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22 |
| Safety statements (S) | 36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is 5′-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester used for?
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5′-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester is used as a reagent in Suzuki-Miyaura and Stille cross-coupling reactions, and in the preparation of materials for organic electronics, such as field-effect transistors, OLEDs, and solar cells.
What are the CAS number and formula for this compound?
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The CAS number is 579503-59-6, and the empirical formula is C20H29BO2S2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this product at a minimum purity of 97%. We do not represent this product as USP, BP, or EP grade.
How should this chemical be handled and stored?
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This compound is classified as harmful if swallowed (H302). When handling, wear a dust mask type N95, eyeshields, and gloves. Store in a cool, dry place.
Is this chemical a controlled substance?
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Based on the provided data, this chemical is not listed as a controlled substance.
How are Tech Serve Solutions' chemicals packed, shipped, and exported?
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Tech Serve Solutions professionally packs, handles, and exports chemicals globally, adhering to all relevant regulations to ensure safe and timely delivery.
How can I request a quote or sample?
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Please contact our sales team via the website or by telephone to request a quote or a sample of 5′-Hexyl-2,2′-bithiophene-5-boronic acid pinacol ester.
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