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CS-W001157 4
Total: USD 88.00

3-Bromophenylacetylene

  • CAS No. 766-81-4

  • Cat. No. CS-W018828
  • Purity≥96%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

3-Bromophenylacetylene|CS-W018828

Structure of 766-81-4

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General Information

  • CAS No. 766-81-4
  • Cat. No. CS-W018828
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅Br
  • Molecular Weight 181.03
  • Synonym(s) 3'-Bromophenyl acetylene
  • SMILES C#CC1=CC=CC(Br)=C1

Description

3-Bromophenylacetylene is a bench-stable, moisture-tolerant alkyne reagent featuring a para-brominated aromatic ring that enables efficient copper-catalyzed coupling reactions. This electron-deficient acetylene integrates readily into complex molecular architectures, offering high functional group compatibility and predictable regioselectivity in Sonogashira and related transformations.

Application

3-Bromophenylacetylene serves as a valuable building block in transition-metal-catalyzed coupling reactions, enabling efficient access to substituted biaryls and conjugated systems. Its bromine substituent provides high reactivity in palladium-catalyzed cross-couplings, while the terminal alkyne functionality supports Sonogashira and Glaser-type homocoupling protocols. The compound exhibits excellent bench stability and is compatible with a wide range of functional groups, facilitating straightforward purification and integration into multi-step synthetic sequences.

Synthesis

  • Route1

    References

    • Malamas, Michael S.; Barnes, Keith; Johnson, Matthew; Hui, Yu; Zhou, Ping; Turner, Jim; Hu, Yun; Wagner, Erik; Fan, Kristi; Chopra, Rajiv; Olland, Andrea; Bard, Jonathan; Pangalos, Menelas; Reinhart, Peter; Robichaud, Albert J. Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 2 p. 630 - 639
  • Route2
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      1-Bromo-3-iodobenzene|CS-W008957
      591-18-4
    • null|null
      1066-54-2
    • ~%
    • In-stock
      3-Bromophenylacetylene|CS-W018828
      766-81-4

    References

    • US2008/51395 A1, ; Page/Page column 131 ; US 20080051395 A1
  • Route3
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      3-Bromobenzaldehyde|CS-W009197
      3132-99-8
    • null|null
      90965-06-3
    • ~81%
    • In-stock
      3-Bromophenylacetylene|CS-W018828
      766-81-4

    References

    • Kallander, Lara S.; Lu, Qing; Chen, Wenfang; Tomaszek, Thaddeus; Yang, Guang; Tew, David; Meek, Thomas D.; Hofmann, Glenn A.; Schulz-Pritchard, Christina K.; Smith, Ward W.; Janson, Cheryl A.; Ryan, M. Dominic; Zhang, Gui-Feng; Johanson, Kyung O.; Kirkpatrick, Robert B.; Ho, Thau F.; Fisher, Paul W.; Mattern, Michael R.; Johnson, Randall K.; Hansbury, Michael J.; Winkler, James D.; Ward, Keith W.; Veber, Daniel F.; Thompson, Scott K. Journal of Medicinal Chemistry, 2005 , vol. 48, # 18 p. 5644 - 5647

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS07,GHS09
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H226-H315-H411
Precautionary Statements : P210-P273-P280

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.4304
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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