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5-(2-Chloro-phenyl)-[1,3,4]thiadiazol-2-ylamine

  • CAS No. 828-81-9

  • Cat. No. CS-0070937
  • Purity≥97%
  • MDL No.None

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

5-(2-Chloro-phenyl)-[1,3,4]thiadiazol-2-ylamine|CS-0070937

Structure of 828-81-9

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General Information

  • CAS No. 828-81-9
  • Cat. No. CS-0070937
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆ClN₃S
  • Molecular Weight 211.67
  • Synonym(s) 5-(2-Chlorophenyl)-1,3,4-thiadiazol-2-amine
  • SMILES NC1=NN=C(C2=CC=CC=C2Cl)S1

Description

This thiadiazole derivative features a 2-chlorophenyl group linked to a [1,3,4]thiadiazol-2-ylamine scaffold, delivering enhanced electronic modulation and metabolic stability. The electron-deficient heterocycle enables efficient coupling in cross-coupling protocols, while the chloro substituent facilitates further functionalization via palladium-catalyzed transformations. Bench-stable and compatible with standard reaction conditions, this compound serves as a key building block for bioactive molecule synthesis.

Application

5-(2-Chlorophenyl)-[1,3,4]thiadiazol-2-ylamine serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles through standard coupling and functionalization protocols. Its ortho-chlorophenyl group enhances electrophilic reactivity and facilitates downstream derivatization via palladium-catalyzed cross-coupling. The thiadiazole scaffold provides metabolic stability and favorable pharmacokinetic properties, while the primary amine functionality allows for facile conjugation and salt formation. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step syntheses of targeted scaffolds.

Synthesis

  • Route1

    References

    • Padhy, Arun Kumar; Nag; Panda Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 8 p. 998 - 1001
  • Route2
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    • In-stock
      5-(2-Chloro-phenyl)-[1,3,4]thiadiazol-2-ylamine|CS-0070937
      828-81-9

    References

    • Giri; Nizamuddin; Srivastava Agricultural and Biological Chemistry, 1983 , vol. 47, # 1 p. 103 - 105
  • Route3

    References

    • Gupta, Monika Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 16 p. 4919 - 4923

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   51.8
  • LogP   2.4407
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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