Methyl 3-amino-5-nitrobenzoate

Name: Methyl 3-amino-5-nitrobenzoate
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CAS No. 23218-93-1
Cat. No. CS-W005262
Purity≥95%
MDL No.MFCD00461253

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Methyl 3-amino-5-nitrobenzoate|CS-W005262

Structure of 23218-93-1

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General Information

CAS No. 23218-93-1
Cat. No. CS-W005262
Purity ≥95%
MDL No. MFCD00461253
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈N₂O₄
Molecular Weight 196.16
Synonym(s) Benzoic acid, 3-aMino-5-nitro-, Methyl ester
SMILES COC(C1=CC(N)=CC([N+]([O-])=O)=C1)=O

Description

Methyl 3-amino-5-nitrobenzoate features a para-nitro group flanking an ortho-amino substituent on the aromatic ring, enabling dual reactivity in synthetic transformations. This electron-deficient scaffold integrates readily into pharmaceutical intermediates and functional materials, offering enhanced solubility and stability under standard conditions.

Application

Methyl 3-amino-5-nitrobenzoate serves as a versatile synthetic intermediate in medicinal chemistry, enabling direct functionalization at the amino and nitro positions. The ortho-directed reactivity facilitates electrophilic substitution and coupling reactions, while the ester group provides a handle for subsequent transformations. Bench-stable and readily purified by crystallization, it functions effectively in multi-step syntheses of heterocyclic scaffolds and API precursors.

Synthesis

Route1
- 67-56-1
- 618-84-8
- ~99%
- In-stock
  
  23218-93-1
References
- Mancuso, Lena; Juerjens, Gerrit; Hermane, Jekaterina; Harmrolfs, Kirsten; Eichner, Simone; Fohrer, Joerg; Collisi, Wera; Sasse, Florenz; Kirschning, Andreas Organic Letters, 2013 , vol. 15, # 17 p. 4442 - 4445
Route2
- 2702-58-1
- ~66%
- In-stock
  
  23218-93-1
References
- Terpko, Marc O.; Heck, Richard F. Journal of Organic Chemistry, 1980 , vol. 45, # 24 p. 4992 - 4993
Route3
- 99-33-2
- ~%
- In-stock
  
  23218-93-1
References
- Journal of Organic Chemistry, , vol. 45, # 24 p. 4992 - 4993

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 95.46
LogP 0.9636
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl 3-amino-5-nitrobenzoate

CAS No. 23218-93-1

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