3-Methoxy-4-nitroaniline

Name: 3-Methoxy-4-nitroaniline
Brand: ChemScene
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CAS No. 16292-88-9
Cat. No. CS-M0192
Purity≥98%
MDL No.MFCD06661773

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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+
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General Information

CAS No. 16292-88-9
Cat. No. CS-M0192
Purity ≥98%
MDL No. MFCD06661773
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₈N₂O₃
Molecular Weight 168.15
Synonym(s) Benzenamine,3-methoxy-4-nitro
SMILES NC1=CC(OC)=C([N+]([O-])=O)C=C1

Description

3-Methoxy-4-nitroaniline features a para-substituted aromatic core with complementary electron-withdrawing and donor groups, enabling robust coupling in cross-coupling and condensation reactions. The methoxy group enhances solubility and stabilizes reaction intermediates, while the nitro functionality serves as a high-affinity handle for downstream functionalization. This compound integrates seamlessly into complex molecular architectures under standard conditions.

Application

3-Methoxy-4-nitroaniline serves as a versatile intermediate in the synthesis of functionalized aromatic scaffolds, enabling efficient access to substituted anilines and heterocycles via standard reduction, coupling, and cyclization protocols. Its methoxy and nitro groups provide orthogonal reactivity for sequential transformations, while its bench-stable crystalline form facilitates handling and purification in multi-step syntheses.

Synthesis

Route1
- 20628-19-7
- ~88%
- In-stock
  
  16292-88-9
References
- Leclerc; Marciniak; Decker; Schwartz Journal of Medicinal Chemistry, 1986 , vol. 29, # 12 p. 2433 - 2438
Route2
- 91-23-6
- ~37%
- In-stock
  
  16292-88-9
References
- Makosza, Mieczyslaw; Bialecki, Maciej Journal of Organic Chemistry, 1998 , vol. 63, # 15 p. 4878 - 4888
Route3
- 536-90-3
- ~54%
- In-stock
  
  16292-88-9
- 16133-49-6
References
- Iranpoor, Nasser; Firouzabadi, Habib; Nowrouzi, Najmeh; Firouzabadi, Dena Tetrahedron Letters, 2006 , vol. 47, # 38 p. 6879 - 6881

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 78.39
LogP 1.1856
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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3-Methoxy-4-nitroaniline

CAS No. 16292-88-9

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