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3-(4-chlorobutyl)-1H-indole-5-carbonitrile

  • CAS No. 143612-79-7

  • Cat. No. CS-M1251
  • Molecule weight232.71
  • Purity≥95%
  • MDL No.MFCD09833261

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

3-(4-chlorobutyl)-1H-indole-5-carbonitrile|CS-M1251

Structure of 143612-79-7

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General Information

  • CAS No. 143612-79-7
  • Cat. No. CS-M1251
  • Purity ≥95%
  • MDL No. MFCD09833261
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₃ClN₂
  • Molecular Weight 232.71
  • Synonym(s) Vilazodone Intermediate 8; 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile
  • SMILES ClCCCCC1=CNC2=CC=C(C#N)C=C21

Description

3-(4-chlorobutyl)-1H-indole-5-carbonitrile features a reactive chloroalkyl tether appended to the indole core, enabling site-specific conjugation in bioconjugation and medicinal chemistry. The para-cyano group enhances electronic withdrawal, while the aliphatic chain offers flexible spacing. This compound serves as a modular building block for targeted probe development and functional material synthesis under standard conditions.

Application

3-(4-Chlorobutyl)-1H-indole-5-carbonitrile serves as a versatile building block for indole-based heterocycles, enabling efficient functionalization via nucleophilic substitution. The pendant chloroalkyl chain facilitates facile conjugation with amines, thiols, and other nucleophiles, while the nitrile group provides compatibility with standard transformations including hydrolysis or reductive amination. Its bench-stable nature and straightforward purification make it well-suited for medicinal chemistry campaigns and API intermediate synthesis.

Synthesis

  • Route1

    References

    • SYMED LABS LIMITED; MOHAN RAO, Dodda; JITHENDER, Aadepu Patent: WO2014/6637 A2, 2014 ; Location in patent: Page/Page column 41; 42 ;
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      1527470-83-2
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    • In-stock
      3-(4-chlorobutyl)-1H-indole-5-carbonitrile|CS-M1251
      143612-79-7

    References

    • WO2014/5134 A2, ; Paragraph 0065 ;
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 47, # 19 p. 4684 - 4692

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   39.58
  • LogP   3.60108
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   4

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