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CS-W001157 4
Total: USD 88.00

2-Bromo-4-nitroaniline

  • CAS No. 13296-94-1

  • Cat. No. CS-W005164
  • Molecule weight217.02
  • Purity≥97%
  • MDL No.MFCD00025152

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

2-Bromo-4-nitroaniline|CS-W005164

Structure of 13296-94-1

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General Information

  • CAS No. 13296-94-1
  • Cat. No. CS-W005164
  • Purity ≥97%
  • MDL No. MFCD00025152
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂O₂
  • Molecular Weight 217.02
  • Synonym(s) 2-BROMO-4-NITRO-PHENYLAMINE
  • SMILES NC1=CC=C([N+]([O-])=O)C=C1Br

Description

2-Bromo-4-nitroaniline features a bromine substituent flanked by a nitro group and an amino moiety, enabling direct incorporation into cross-coupling and electrophilic substitution cascades. This electron-deficient aryl halide delivers high reactivity under standard conditions, supporting efficient construction of complex heterocycles and functionalized biaryls in synthetic workflows.

Application

2-Bromo-4-nitroaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct coupling reactions via its bromo group and subsequent functionalization through the nitro moiety. Its bench-stable nature and compatibility with palladium-catalyzed cross-coupling protocols facilitate efficient access to substituted biaryls and heterocyclic scaffolds. The molecule exhibits predictable reactivity in reduction, displacement, and cyclization processes, making it a practical choice for iterative synthesis workflows.

Synthesis

  • Route1
    • null|null
      100-01-6
    • ~99%
    • In-stock
      2-Bromo-4-nitroaniline|CS-W005164
      13296-94-1

    References

    • Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qin-Guo Synthesis, 2004 , # 17 p. 2809 - 2812
  • Route2
    • null|null
      615-36-1
    • ~44%
    • In-stock
      2-Bromo-6-nitroaniline|CS-W006849
      59255-95-7
    • In-stock
      2-Bromo-4-nitroaniline|CS-W005164
      13296-94-1

    References

    • Synthesis, , # 10 p. 761 - 763
  • Route3

    References

    • Lan, Tian; Yuan, Xian Xia; Yu, Jiang Hong; Jia, Chao; Wang, Yu Shi; Zhang, Hui Juan; Ma, Zi Feng; Ye, Wei Dong Chinese Chemical Letters, 2011 , vol. 22, # 3 p. 253 - 255

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

Quality Control

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Computational Chemistry Data

  • TPSA   69.16
  • LogP   1.9395
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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