Methyl 2-amino-4-chlorobenzoate

Name: Methyl 2-amino-4-chlorobenzoate
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CAS No. 5900-58-3
Cat. No. CS-W008083
Purity≥98%
MDL No.MFCD00017568

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Methyl 2-amino-4-chlorobenzoate|CS-W008083

Structure of 5900-58-3

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General Information

CAS No. 5900-58-3
Cat. No. CS-W008083
Purity ≥98%
MDL No. MFCD00017568
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 4-chloroanthranilate
SMILES O=C(OC)C1=CC=C(Cl)C=C1N

Description

Methyl 2-amino-4-chlorobenzoate features a para-chloro substituent and an ortho-amino group on the aromatic ring, enabling facile functionalization in synthetic sequences. This electron-rich scaffold integrates readily into pharmaceutical intermediates and agrochemical building blocks, offering enhanced solubility and stability under standard conditions.

Application

Methyl 2-amino-4-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-amino and para-chloro groups offer complementary reactivity for sequential functionalization, while the methyl ester facilitates downstream transformations. Bench-stable and readily purified by recrystallization, it functions reliably in standard coupling and cyclization protocols.

Synthesis

Route1
- 67-56-1
- 89-77-0
- ~91%
- In-stock
  
  5900-58-3
References
- Cai, Sui Xiong; Zhou, Zhang-Lin; Huang, Jin-Cheng; Whittemore, Edward R.; Egbuwoku, Zizi O.; Lue, Yixin; Hawkinson, Jon E.; Woodward, Richard M.; Weber, Eckard; Keana, John F. W. Journal of Medicinal Chemistry, 1996 , vol. 39, # 17 p. 3248 - 3255
Route2
- In-stock
  
  42087-80-9
- ~29%
- In-stock
  
  5900-58-3
References
- Markiewicz, John T.; Wiest, Olaf; Helquist, Paul Journal of Organic Chemistry, 2010 , vol. 75, # 14 p. 4887 - 4890
Route3
- 77-76-9
- 89-77-0
- ~64%
- In-stock
  
  5900-58-3
References
- Theeraladanon, Chumpol; Arisawa, Mitsuhiro; Nishida, Atsushi; Nakagawa, Masako Tetrahedron, 2004 , vol. 60, # 13 p. 3017 - 3035

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 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 2-amino-4-chlorobenzoate

CAS No. 5900-58-3

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