Lot numbers can be found on the outside label of a product:
2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No. 917985-54-7
- Cat. No. CS-0091653
- Purity≥95%
- MDL No.MFCD10567052
*For research and further manufacturing use only, not for direct human use.
Structure of 917985-54-7
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General Information
- CAS No. 917985-54-7
- Cat. No. CS-0091653
- Purity ≥95%
- MDL No. MFCD10567052
- Storage -20°C, sealed storage, away from moisture
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₆H₂₇BO₂S
- Molecular Weight 294.26
- Synonym(s) 5-Hexylthiopheneboronic acid pinacol ester
- SMILES CC1(C)C(C)(C)OB(C2=CC=C(CCCCCC)S2)O1
Description
This boronate ester features a hexylthiophene moiety enabling efficient coupling in Suzuki-Miyaura reactions. The tetramethyl-1,3,2-dioxaborolane scaffold imparts stability and ease of handling, while the alkylthiophene group enhances solubility and electronic tuning for conjugated polymer synthesis.
Application
2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The hexylthiophene moiety provides enhanced solubility and facilitates access to conjugated π-systems, while the tetramethyl-substituted dioxaborolane offers excellent air and moisture stability. It enables efficient construction of functionalized thiophene-based scaffolds in organic synthesis and materials chemistry with high yield and minimal purification challenges.
Synthesis
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Route1
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61676-62-8 -
In-stock
211737-28-9 - ~99%
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In-stock
917985-54-7
References
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UTI LIMITED PARTNERSHIP; BERLINGUETTE, Curtis; BOMBEN, Paolo Patent: WO2012/155247 A1, 2012 ; Location in patent: Page/Page column 76 ;
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Route2
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In-stock
18794-77-9 -
61676-62-8
- ~73%
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In-stock
917985-54-7
References
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Wu, Kuan-Lin; Li, Cheng-Hsuan; Chi, Yun; Clifford, John N.; Cabau, Lydia; Palomares, Emilio; Cheng, Yi-Ming; Pan, Hsiao-An; Chou, Pi-Tai Journal of the American Chemical Society, 2012 , vol. 134, # 17 p. 7488 - 7496
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Route3
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In-stock
18794-77-9
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25015-63-8
- ~98%
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In-stock
917985-54-7
References
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Gorodetsky, Alon A.; Chiu, Chien-Yang; Schiros, Theanne; Palma, Matteo; Cox, Marshall; Jia, Zhang; Sattler, Wesley; Kymissis, Ioannis; Steigerwald, Michael; Nuckolls, Colin Angewandte Chemie - International Edition, 2010 , vol. 49, # 43 p. 7909 - 7912
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 18.46
- LogP 4.1701
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 6
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Key Words
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