Lot numbers can be found on the outside label of a product:
3-Ethynyl-1,1'-biphenyl
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CAS No. 58650-11-6
- Cat. No. CS-0169599
- Purity≥98%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 58650-11-6
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General Information
- CAS No. 58650-11-6
- Cat. No. CS-0169599
- Purity ≥98%
- MDL No. None
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₄H₁₀
- Molecular Weight 178.23
- Synonym(s) 1-Ethynyl-3-phenylbenzene
- SMILES C#CC1=CC=CC(C2=CC=CC=C2)=C1
Description
3-Ethynyl-1,1'-biphenyl features a terminal alkyne group flanked by two aromatic rings, enabling efficient copper-catalyzed coupling reactions. This rigid, electron-rich scaffold integrates readily into conjugated systems, offering enhanced stability and predictable reactivity in synthetic workflows.
Application
3-Ethynyl-1,1'-biphenyl serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to conjugated biaryl architectures. Its terminal alkyne functionality facilitates reliable Sonogashira and Glaser-type couplings, while the biphenyl core provides structural rigidity and π-conjugation. The compound exhibits excellent bench stability and is readily purified by standard chromatographic methods, making it well-suited for iterative synthetic sequences in medicinal chemistry and materials science applications.
Synthesis
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Route1
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918540-87-1 - ~92%
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In-stock
58650-11-6
References
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Wyeth Patent: US2007/4730 A1, 2007 ; Location in patent: Page/Page column 11 ; US 20070004730 A1
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Route2
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In-stock
![[1,1'-Biphenyl]-3-carbaldehyde|CS-0128849](https://file.chemscene.com/productPIC/CS-0128849.gif)
1204-60-0 -
21047-57-4 - ~99%
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In-stock
58650-11-6
References
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Chen, Po C.; Wharton, Rebekah E.; Patel, Pratiq A.; Oyelere, Adegboyega K. Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 23 p. 7288 - 7300 Title/Abstract Full Text View citing articles Show Details Chen, Po C.; Patil, Vishal; Guerrant, William; Green, Patience; Oyelere, Adegboyega K. Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 9 p. 4839 - 4853
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Route3
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In-stock
1204-60-0
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90965-06-3
- ~71%
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In-stock
58650-11-6
References
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Fabre, Benjamin; Filipiak, Kamila; Zapico, Jose Maria; Diaz, Natalia; Carbajo, Rodrigo J.; Schott, Anne K.; Martinez-Alcazar, Maria Paz; Suarez, Dimas; Pineda-Lucena, Antonio; Ramos, Ana; De Pascual-Teresa, Beatriz Organic and Biomolecular Chemistry, 2013 , vol. 11, # 38 p. 6623 - 6641
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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 : H315-H319-H335
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Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 0
- LogP 3.3349
- H_Acceptors 0
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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