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2-Chloro-3-methylaniline

  • CAS No. 29027-17-6

  • Cat. No. CS-0131372
  • Purity≥98%
  • MDL No.MFCD11113332

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

2-Chloro-3-methylaniline|CS-0131372

Structure of 29027-17-6

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General Information

  • CAS No. 29027-17-6
  • Cat. No. CS-0131372
  • Purity ≥98%
  • MDL No. MFCD11113332
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈ClN
  • Molecular Weight 141.60
  • Synonym(s) 2-Chloro-m-toluidine
  • SMILES NC1=CC=CC(C)=C1Cl

Description

2-Chloro-3-methylaniline features a chlorinated aromatic ring with adjacent methyl and amino groups, enabling selective functionalization in pharmaceutical intermediates. This electron-rich scaffold integrates readily into complex heterocycles under standard coupling conditions, offering high reactivity without requiring extensive protection.

Application

2-Chloro-3-methylaniline serves as a versatile building block in medicinal chemistry, enabling direct incorporation of chlorinated and methylated aromatic motifs into target molecules. Its ortho-chloro substituent enhances reactivity in palladium-catalyzed cross-coupling reactions, while the aniline functionality facilitates derivatization via acylation, alkylation, or diazotization. The compound exhibits bench stability and is compatible with standard purification protocols, making it well-suited for scalable synthesis of heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1

    References

    • Teppema; Sebrell Journal of the American Chemical Society, 1927 , vol. 49, p. 1757
  • Route2

    References

    • Cohen; Dakin Journal of the Chemical Society, 1901 , vol. 79, p. 1128 Journal of the Chemical Society, 1902 , vol. 81, p. 1327,1347 Full Text Show Details Wynne; Greeves P.Ch.S., # 154
  • Route3
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      620-25-7
    • ~%
    • In-stock
      2-Chloro-3-methylaniline|CS-0131372
      29027-17-6

    References

    • Bamberger Chemische Berichte, 1902 , vol. 35, p. 3706

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

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Computational Chemistry Data

  • TPSA   26.02
  • LogP   2.23062
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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