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CS-W001157 4
Total: USD 88.00

5-Amino-3-methylisothiazole-4-carbonitrile

  • CAS No. 41808-35-9

  • Cat. No. CS-0005575
  • Purity≥98%
  • MDL No.MFCD03422694

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

5-Amino-3-methylisothiazole-4-carbonitrile|CS-0005575

Structure of 41808-35-9

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General Information

  • CAS No. 41808-35-9
  • Cat. No. CS-0005575
  • Purity ≥98%
  • MDL No. MFCD03422694
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅N₃S
  • Molecular Weight 139.18
  • Synonym(s) 5-Amino-3-methyl-isothiazole-4-carbonitrile
  • SMILES N#CC1=C(N)SN=C1C

Description

5-Amino-3-methylisothiazole-4-carbonitrile features a fused heterocyclic core bearing a nucleophilic amino group and an electron-deficient carbonitrile, enabling selective conjugation in synthetic pathways. The methyl substituent enhances solubility and metabolic stability, while the isothiazole scaffold imparts robust reactivity under mild conditions. This compound serves as a key intermediate in bioactive molecule development.

Application

5-Amino-3-methylisothiazole-4-carbonitrile serves as a versatile heterocyclic building block for medicinal chemistry and agrochemical synthesis. Its amino and nitrile groups enable diverse functionalization, while the isothiazole core offers metabolic stability and favorable electronic properties. The molecule exhibits good bench stability and facilitates coupling reactions under mild conditions, making it suitable for modular library construction and scale-up applications.

Synthesis

  • Route1
    • (Z)-3-amino-2-cyanobut-2-enethioamide|CS-0664994
      41808-30-4
    • ~50%
    • In-stock
      5-Amino-3-methylisothiazole-4-carbonitrile|CS-0005575
      41808-35-9

    References

    • INTERMUNE, INC.; BUCKMAN, Brad, O.; NICHOLAS, John, B.; EMAYAN, Kumaraswamy; SEIWERT, Scott, D. Patent: WO2013/25733 A1, 2013 ; Location in patent: Paragraph 0436 ;
  • Route2
    • (E)-3-Amino-2-cyanobut-2-enethioamide|CS-0771539
      758721-53-8
    • ~81%
    • In-stock
      5-Amino-3-methylisothiazole-4-carbonitrile|CS-0005575
      41808-35-9

    References

    • Theoclitou, Maria-Elena; Aquila, Brian; Block, Michael H.; Brassil, Patrick J.; Castriotta, Lillian; Code, Erin; Collins, Michael P.; Davies, Audrey M.; Deegan, Tracy; Ezhuthachan, Jayachandran; Filla, Sandra; Freed, Ellen; Hu, Haiqing; Huszar, Dennis; Jayaraman, Muthusamy; Lawson, Deborah; Lewis, Paula M; Nadella, Murali V. P.; Oza, Vibha; Padmanilayam, Maniyan; Pontz, Timothy; Ronco, Lucienne; Russell, Daniel; Whitston, David; Zheng, Xiaolan Journal of Medicinal Chemistry, 2011 , vol. 54, # 19 p. 6734 - 6750
  • Route3

    References

    • INTERMUNE, INC.; BUCKMAN, Brad, O.; NICHOLAS, John, B.; EMAYAN, Kumaraswamy; SEIWERT, Scott, D. Patent: WO2013/25733 A1, 2013 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301+H311+H331
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   62.7
  • LogP   0.9054
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   0

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