Methyl 4-amino-2-chlorobenzoate

Name: Methyl 4-amino-2-chlorobenzoate
Brand: ChemScene
Availability: InStock
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CAS No. 46004-37-9
Cat. No. CS-W018864
Purity≥98%
MDL No.MFCD03840484

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Methyl 4-amino-2-chlorobenzoate|CS-W018864

Structure of 46004-37-9

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General Information

CAS No. 46004-37-9
Cat. No. CS-W018864
Purity ≥98%
MDL No. MFCD03840484
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈ClNO₂
Molecular Weight 185.61
Synonym(s) Methyl 2-chloro-4-aminobenzoate
SMILES NC1=CC(=C(C(=O)OC)C=C1)Cl

Description

Methyl 4-amino-2-chlorobenzoate is a key intermediate featuring a para-amino group flanked by an ortho-chloro substituent and an ester functionality. This electron-rich aromatic system enables efficient coupling reactions, particularly in pharmaceutical synthesis where the amino group serves as a nucleophilic handle. The molecule demonstrates good stability under standard bench conditions and solubility in common organic solvents, facilitating straightforward purification and integration into multi-step sequences.

Application

Methyl 4-amino-2-chlorobenzoate serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles, quinolines, and other heterocyclic scaffolds. The ortho-chloro and para-amino groups provide complementary reactivity for cross-coupling, cyclization, and derivatization under standard conditions. Its bench-stable nature and ease of purification facilitate integration into multi-step synthetic sequences.

Synthesis

Route1
- In-stock
  
  13324-11-3
- ~99%
- In-stock
  
  46004-37-9
References
- Frantz, Marie-Celine; Rodrigo, Jordi; Boudier, Laure; Durroux, Thierry; Mouillac, Bernard; Hibert, Marcel Journal of Medicinal Chemistry, 2010 , vol. 53, # 4 p. 1546 - 1562
Route2
- 67-56-1
- In-stock
  
  2457-76-3
- ~98%
- In-stock
  
  46004-37-9
References
- NOVARTIS AG; HEBACH, Christina; JOLY, Emilie; KALLEN, Joerg; TERNOIS, James Gilbert; TINTELNOT-BLOMLEY, Marina Patent: WO2013/8162 A1, 2013 ; Location in patent: Page/Page column 116 ;
Route3
- In-stock
  
  2457-76-3
- 77-78-1
- ~60%
- In-stock
  
  46004-37-9
References
- KIRIN BEER KABUSHIKI KAISHA Patent: EP1724268 A1, 2006 ; Location in patent: Page/Page column 86 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
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 52.32
LogP 1.7088
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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Methyl 4-amino-2-chlorobenzoate

CAS No. 46004-37-9

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