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CS-W001157 4
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2-Bromo-4-isopropylaniline

  • CAS No. 51605-97-1

  • Cat. No. CS-0154287
  • Purity≥96%
  • MDL No.MFCD00051585

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

2-Bromo-4-isopropylaniline|CS-0154287

Structure of 51605-97-1

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General Information

  • CAS No. 51605-97-1
  • Cat. No. CS-0154287
  • Purity ≥96%
  • MDL No. MFCD00051585
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₂BrN
  • Molecular Weight 214.10
  • Synonym(s) 2-bromo-4-propan-2-ylaniline
  • SMILES CC(C)C1=CC(=C(C=C1)N)Br

Description

2-Bromo-4-isopropylaniline features a bromine substituent at the ortho position relative to the aniline nitrogen, combined with a sterically hindered isopropyl group at the para position. This electronic and steric profile enhances stability and directs regioselective coupling in cross-coupling reactions. The molecule exhibits robust performance under standard bench conditions and serves as a key intermediate for pharmaceutical and agrochemical synthesis.

Application

2-Bromo-4-isopropylaniline serves as a versatile building block in medicinal chemistry, enabling direct incorporation of brominated arylamine motifs into pharmaceutical scaffolds. Its stability under standard reaction conditions and compatibility with palladium-catalyzed cross-coupling reactions facilitate efficient synthesis of biaryl derivatives. The isopropyl group provides steric bulk and modulates electronic properties, enhancing metabolic stability in target molecules.

Synthesis

  • Route1

    References

    • ALANTOS PHARMACEUTICALS HOLDING, INC. Patent: WO2008/63667 A1, 2008 ; Location in patent: Page/Page column 63 ; WO 2008/063667 A1
  • Route2
    • N-(2-bromo-4-isopropylphenyl)acetamide|CS-0514632
      68748-07-2
    • ~%
    • In-stock
      2-Bromo-4-isopropylaniline|CS-0154287
      51605-97-1

    References

    • Sterling; Bogert Journal of Organic Chemistry, 1939 , vol. 4, p. 20,26 Full Text Show Details Haworth; Barker Journal of the Chemical Society, 1939 , p. 1299,1301
  • Route3

    References

    • Sterling; Bogert Journal of Organic Chemistry, 1939 , vol. 4, p. 20,26 Full Text Show Details Haworth; Barker Journal of the Chemical Society, 1939 , p. 1299,1301

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2810
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302-H312-H315-H319-H331
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   26.02
  • LogP   3.1547
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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