Methyl 4-amino-2-nitrobenzoate

Name: Methyl 4-amino-2-nitrobenzoate
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CAS No. 84228-45-5
Cat. No. CS-0128687
Purity≥98%
MDL No.MFCD00228651

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Methyl 4-amino-2-nitrobenzoate|CS-0128687

Structure of 84228-45-5

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General Information

CAS No. 84228-45-5
Cat. No. CS-0128687
Purity ≥98%
MDL No. MFCD00228651
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈N₂O₄
Molecular Weight 196.16
Synonym(s) ST5437238
SMILES NC1=CC=C(C(OC)=O)C([N+]([O-])=O)=C1

Description

Methyl 4-amino-2-nitrobenzoate features a para-amino group flanked by an ortho-nitro substituent, enabling precise electronic tuning for synthetic applications. This bench-stable derivative integrates readily into multi-step routes requiring controlled electron density and serves as a key intermediate in pharmaceutical and dye synthesis workflows.

Application

Methyl 4-amino-2-nitrobenzoate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted anilines and heterocyclic scaffolds. Its complementary amino and nitro groups allow for sequential functionalization via selective reduction, coupling, or cyclization reactions. The methyl ester facilitates purification and stability during storage, while the ortho-nitro group enhances reactivity in electrophilic substitution processes. This compound functions reliably in multi-step synthesis workflows requiring controlled regiochemistry and bench-stable intermediates.

Synthesis

Route1
- In-stock
  
  610-36-6
- 74-88-4
- ~98%
- In-stock
  
  84228-45-5
References
- NISSAN CHEMICAL INDUSTRIES, LTD. Patent: WO2004/108683 A1, 2004 ; Location in patent: Page 561-562 ;
Route2
- 75-09-2
- In-stock
  
  610-36-6
- ~%
- In-stock
  
  84228-45-5
References
- Allergan Patent: US5663357 A1, 1997 ;
Route3
- 18959-17-6
- ~%
- In-stock
  
  84228-45-5
References
- Cohen; Mc Candlish Journal of the Chemical Society, 1905 , vol. 87, p. 1265

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 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 4-amino-2-nitrobenzoate

CAS No. 84228-45-5

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