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CS-W001157 4
Total: USD 88.00

4-Bromo-2-methyl-6-nitroaniline

  • CAS No. 77811-44-0

  • Cat. No. CS-M1979
  • Purity≥98%
  • MDL No.MFCD00052919

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

4-Bromo-2-methyl-6-nitroaniline|CS-M1979

Structure of 77811-44-0

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General Information

  • CAS No. 77811-44-0
  • Cat. No. CS-M1979
  • Purity ≥98%
  • MDL No. MFCD00052919
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇BrN₂O₂
  • Molecular Weight 231.05
  • Synonym(s) 4-Bromo-6-nitro-o-toluidine; 4-Bromo-2-methyl-6-nitroaniline
  • SMILES NC1=C([N+]([O-])=O)C=C(Br)C=C1C

Description

4-Bromo-2-methyl-6-nitroaniline features a bromine atom at the para position relative to the amino group, paired with a methyl substituent and a strongly electron-withdrawing nitro group. This combination imparts enhanced reactivity in cross-coupling processes and facilitates selective functionalization. The molecule exhibits robust stability under standard bench conditions and integrates readily into advanced synthetic sequences for pharmaceutical intermediates and specialty dyes.

Application

4-Bromo-2-methyl-6-nitroaniline serves as a versatile building block for pharmaceutical and agrochemical synthesis, enabling efficient construction of substituted heterocycles via palladium-catalyzed coupling reactions. Its ortho-directing nitro group and bromine handle facilitate sequential functionalization, while the methyl substituent enhances metabolic stability in downstream scaffolds. The compound exhibits good bench stability and is amenable to standard purification techniques, making it well-suited for iterative synthetic workflows in medicinal chemistry.

Synthesis

  • Route1

    References

    • LONZA LTD; BUeCHNER, Thomas; DRESSEL, Martina; HANSELMANN, Paul; KAISER, Rafael; KLEGRAF, Ellen; ZARAGOZA DOeRWALD, Florencio; DING, Zunliang; WONG, Heilam Patent: WO2010/81670 A2, 2010 ; Location in patent: Page/Page column 24 ;
  • Route2

    References

    • Kyowa Hakko Kirin Co., Ltd. Patent: EP2327690 A1, 2011 ; Location in patent: Page/Page column 84 ;
  • Route3

    References

    • Justus Liebigs Annalen der Chemie, , vol. 192, p. 210

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   2.24792
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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