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CS-W001157 4
Total: USD 88.00

1,3-Dichloro-5-ethynylbenzene

  • CAS No. 99254-90-7

  • Cat. No. CS-0046892
  • Purity≥96%
  • MDL No.None

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

1,3-Dichloro-5-ethynylbenzene|CS-0046892

Structure of 99254-90-7

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General Information

  • CAS No. 99254-90-7
  • Cat. No. CS-0046892
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄Cl₂
  • Molecular Weight 171.02
  • Synonym(s) 3,5-Dichlorophenylacetylene
  • SMILES C#CC1=CC(Cl)=CC(Cl)=C1

Description

1,3-Dichloro-5-ethynylbenzene features a rigid aromatic core with orthogonal functional handles: two chlorine atoms at the 1,3-positions enable selective cross-coupling, while the para-ethynyl group provides a reactive alkyne for copper-catalyzed click chemistry or Sonogashira coupling. This dual functionality supports modular assembly of complex architectures in synthetic organic and materials chemistry.

Application

1,3-Dichloro-5-ethynylbenzene serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed coupling reactions due to its orthogonal functional groups. The ethynyl moiety facilitates Sonogashira and Glaser-type couplings, while the dichloro substitution pattern supports further functionalization via cross-coupling or nucleophilic aromatic substitution. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for constructing complex aromatic scaffolds and conjugated systems in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • [2-(3,5-dichlorophenyl)ethynyl]trimethylsilane|CS-0236411
      351865-83-3
    • ~86%
    • In-stock
      1,3-Dichloro-5-ethynylbenzene|CS-0046892
      99254-90-7

    References

    • 3-Dimensional Pharmaceuticals, Inc. Patent: US2002/169200 A1, 2002 ;
  • Route2

    References

    • MERCK and CO., INC. Patent: WO2006/14618 A2, 2006 ; Location in patent: Page/Page column 35 ; WO 2006/014618 A2
  • Route3

    References

    • Musso, David L; Clarke, Morris J; Kelley, James L; Boswell, G Evan; Chen, Grace Organic and biomolecular chemistry, 2003 , vol. 1, # 3 p. 498 - 506

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.9747
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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