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CS-W001157 4
Total: USD 88.00

Methyl 4-amino-3-chlorobenzoate

  • CAS No. 84228-44-4

  • Cat. No. CS-W016935
  • Purity≥98%
  • MDL No.MFCD01320686

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

Methyl 4-amino-3-chlorobenzoate|CS-W016935

Structure of 84228-44-4

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General Information

  • CAS No. 84228-44-4
  • Cat. No. CS-W016935
  • Purity ≥98%
  • MDL No. MFCD01320686
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈ClNO₂
  • Molecular Weight 185.61
  • Synonym(s) 4-Amino-3-chlorobenzoic Acid Methyl Ester
  • SMILES COC(=O)C1=CC(Cl)=C(N)C=C1

Description

Methyl 4-amino-3-chlorobenzoate features a para-amino group flanked by an ortho-chloro substituent on the aromatic ring, enabling selective coupling reactions in pharmaceutical synthesis. The ester functionality supports straightforward derivatization, while the electron-donating amino group enhances reactivity at the adjacent position. This compound serves as a key intermediate in the development of bioactive molecules requiring precise substitution patterns.

Application

Methyl 4-amino-3-chlorobenzoate serves as a versatile building block in medicinal chemistry, enabling direct access to substituted benzimidazoles and other heterocyclic scaffolds via cyclization reactions. The ortho-chloro group facilitates palladium-catalyzed coupling processes, while the methyl ester and primary amine functionalities allow for selective derivatization. Bench-stable and readily purified by recrystallization, it functions efficiently in multi-step syntheses requiring orthogonal functional group handling.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      4-Amino-3-chlorobenzoic acid|CS-W020673
      2486-71-7
    • ~99%
    • In-stock
      Methyl 4-amino-3-chlorobenzoate|CS-W016935
      84228-44-4

    References

    • Chen, Li; Feng, Lichun; Huang, Mengwei; Liu, Yongfu; Wu, Guolong; Wu, Jim Zhen; Zhou, Mingwei Patent: US2011/257151 A1, 2011 ; Location in patent: Page/Page column 75 ;
  • Route2

    References

    • Zanka, Atsuhiko; Kubota, Ariyoshi Synlett, 1999 , # 12 p. 1984 - 1986
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 42, # 25 p. 5277 - 5283

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   52.32
  • LogP   1.7088
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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