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CS-W001157 4
Total: USD 88.00

3,4-Diaminocyclobut-3-ene-1,2-dione

  • CAS No. 5231-89-0

  • Cat. No. CS-0046703
  • Purity≥97%
  • MDL No.None

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

3,4-Diaminocyclobut-3-ene-1,2-dione|CS-0046703

Structure of 5231-89-0

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General Information

  • CAS No. 5231-89-0
  • Cat. No. CS-0046703
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₄N₂O₂
  • Molecular Weight 112.09
  • Synonym(s) Squaramide
  • SMILES O=C1C(N)=C(N)C1=O

Description

3,4-Diaminocyclobut-3-ene-1,2-dione features a strained cyclobutenedione core with two amine substituents at adjacent positions, enabling direct integration into conjugated systems. This scaffold delivers enhanced electron-donating capacity and facilitates rapid cyclization under mild conditions, making it valuable for constructing heterocyclic architectures in synthetic organic chemistry.

Application

3,4-Diaminocyclobut-3-ene-1,2-dione serves as a versatile diaminocyclobutenedione scaffold for the synthesis of bioactive heterocycles and peptide mimetics. Its inherent stability and dual amine functionality enable efficient coupling reactions and facilitate incorporation into complex molecular architectures. The molecule functions as a key building block in medicinal chemistry campaigns targeting kinase inhibitors and cyclic peptide analogs, offering excellent functional group tolerance and straightforward purification via crystallization or chromatography.

Synthesis

  • Route1

    References

    • Fu, Nanyan; Allen, Annette D.; Kobayashi, Shinjiro; Tidwell, Thomas T.; Vukovic, Sinisa; Arumugam, Selvananthan; Popik, Vladimir V.; Mishima, Masaaki Journal of Organic Chemistry, 2007 , vol. 72, # 6 p. 1951 - 1956

Safety Information

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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   86.18
  • LogP   -1.553
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   0

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