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2-Bromo-5-(tert-butyl)aniline

  • CAS No. 58164-14-0

  • Cat. No. CS-0154918
  • Purity≥98%
  • MDL No.MFCD11846050

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

2-Bromo-5-(tert-butyl)aniline|CS-0154918

Structure of 58164-14-0

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General Information

  • CAS No. 58164-14-0
  • Cat. No. CS-0154918
  • Purity ≥98%
  • MDL No. MFCD11846050
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₄BrN
  • Molecular Weight 228.13
  • Synonym(s) 2-broMo-5-tert-butylaniline
  • SMILES CC(C)(C)C1=CC(=C(C=C1)Br)N

Description

2-Bromo-5-(tert-butyl)aniline features a sterically hindered tert-butyl group that enhances stability and modulates reactivity. This electron-rich arylamine integrates readily into coupling reactions, offering improved solubility and handling under standard conditions.

Application

2-Bromo-5-(tert-butyl)aniline serves as a valuable building block in medicinal chemistry and agrochemical synthesis, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The tert-butyl group provides steric protection and enhances metabolic stability, while the bromo substituent offers high reactivity in Suzuki, Stille, and Negishi couplings. Bench-stable and readily purified by column chromatography, it functions reliably in multi-step synthetic sequences requiring orthogonality and functional group tolerance.

Synthesis

  • Route1

    References

    • Cairns, Andrew G.; Senn, Hans Martin; Murphy, Michael P.; Hartley, Richard C. Chemistry - A European Journal, 2014 , vol. 20, # 13 p. 3742 - 3751
  • Route2

    References

    • Wegner, Hermann A.; Reisch, Helge; Rauch, Karsten; Demeter, Attila; Zachariasse, Klaas A.; De Meijere, Armin; Scott, Lawrence T. Journal of Organic Chemistry, 2006 , vol. 71, # 24 p. 9080 - 9087

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.02
  • LogP   3.3288
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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