4-bromo-2-methoxy-6-nitroaniline

Name: 4-bromo-2-methoxy-6-nitroaniline
Brand: ChemScene
Availability: InStock
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CAS No. 77333-45-0
Cat. No. CS-0210517
Molecule weight247.05
Purity≥97%
MDL No.MFCD18088522

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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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4-bromo-2-methoxy-6-nitroaniline|CS-0210517

Structure of 77333-45-0

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General Information

CAS No. 77333-45-0
Cat. No. CS-0210517
Purity ≥97%
MDL No. MFCD18088522
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₇BrN₂O₃
Molecular Weight 247.05
Synonym(s) 4-Bromo-2-methoxy-6-nitro-phenylamine
SMILES COC1=CC(=CC(=C1N)[N+](=O)[O-])Br

Description

4-Bromo-2-methoxy-6-nitroaniline features a nitro group at the para position relative to the amino functionality, enhancing electrophilic reactivity while the methoxy substituent provides electron-donating stabilization. This combination enables selective coupling in cross-coupling reactions and facilitates downstream functionalization in pharmaceutical intermediates and advanced materials synthesis under standard conditions.

Application

4-Bromo-2-methoxy-6-nitroaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct incorporation into complex heterocyclic scaffolds via Suzuki-Miyaura and Ullmann coupling reactions. The molecule exhibits robust bench stability, tolerates diverse functional groups, and facilitates efficient purification due to its crystalline nature. Its ortho-substituted arylamine framework supports sequential transformations, making it ideal for the construction of multi-functionalized aromatic systems in lead optimization campaigns.

Synthesis

Route1
- In-stock
  
  16554-45-3
- ~81%
- In-stock
  
  77333-45-0
References
- Qu, Junya; Rivero, Ralph; Sanchez, Robert; Tedesco, Rosanna Patent: US2012/88767 A1, 2012 ; Location in patent: Page/Page column 16; 22 ;
Route2
- In-stock
  
  603-85-0
- ~%
- In-stock
  
  77333-45-0
References
- Qu, Junya; Rivero, Ralph; Sanchez, Robert; Tedesco, Rosanna Patent: US2012/88767 A1, 2012 ;

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 78.39
LogP 1.9481
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-bromo-2-methoxy-6-nitroaniline

CAS No. 77333-45-0

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