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CS-W001157 4
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2-Bromo-3-chloroaniline

  • CAS No. 96558-73-5

  • Cat. No. CS-W018623
  • Purity≥97%
  • MDL No.MFCD10699543

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

2-Bromo-3-chloroaniline|CS-W018623

Structure of 96558-73-5

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General Information

  • CAS No. 96558-73-5
  • Cat. No. CS-W018623
  • Purity ≥97%
  • MDL No. MFCD10699543
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrClN
  • Molecular Weight 206.47
  • Synonym(s) benzenamine, 2-bromo-3-chloro-
  • SMILES BrC1=C(N)C=CC=C1Cl

Description

2-Bromo-3-chloroaniline features a dual halogen substitution pattern on the aromatic ring, enabling selective coupling reactions in pharmaceutical synthesis. The ortho-bromo and meta-chloro arrangement imparts enhanced reactivity in palladium-catalyzed cross-couplings while maintaining stability under standard bench conditions. This configuration facilitates efficient integration into complex heterocyclic scaffolds.

Application

2-Bromo-3-chloroaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient construction of substituted heterocycles via palladium-catalyzed cross-coupling reactions. Its dual halogen functionality supports sequential functionalization, while the amino group offers direct derivatization potential. The compound exhibits good bench stability and is readily purified by recrystallization, facilitating integration into multi-step synthetic sequences.

Synthesis

  • Route1
    • tert-Butyl (2-bromo-3-chlorophenyl)carbamate|CS-0612925
      1463053-89-5
    • ~74%
    • In-stock
      2-Bromo-3-chloroaniline|CS-W018623
      96558-73-5

    References

    • TAKEDA PHARMACEUTICAL COMPANY LIMITED; LAWSON, John David; SABAT, Mark; SMITH, Christopher; WANG, Haixia; CHEN, Young K.; KANOUNI, Toufike Patent: WO2013/148603 A1, 2013 ; Location in patent: Paragraph 0185-0186 ;
  • Route2

    References

    • Tuccinardi, Tiziano; Bertini, Simone; Martinelli, Adriano; Minutolo, Filippo; Ortore, Gabriella; Placanica, Giorgio; Prota, Giovanni; Rapposelli, Simona; Carlson, Kathryn E.; Katzenellenbogen, John A.; Macchia, Marco Journal of Medicinal Chemistry, 2006 , vol. 49, # 16 p. 5001 - 5012
  • Route3

    References

    • US2007/112012 A1, ; Page/Page column 27 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06,GHS08,GHS09
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302-H311-H373-H411
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

  • TPSA   26.02
  • LogP   2.6847
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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