2-Bromo-6-methoxyaniline

Name: 2-Bromo-6-methoxyaniline
Brand: ChemScene
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CAS No. 5473-01-8
Cat. No. CS-0033843
Purity≥98%
MDL No.MFCD08741448

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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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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Structure of 5473-01-8

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General Information

CAS No. 5473-01-8
Cat. No. CS-0033843
Purity ≥98%
MDL No. MFCD08741448
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₈BrNO
Molecular Weight 202.05
Synonym(s) 2-BroMo-6-Methoxy-phenylaMine
SMILES NC1=C(OC)C=CC=C1Br

Description

2-Bromo-6-methoxyaniline features a bromine substituent at the ortho position relative to the amino group and a methoxy group at the para position, creating a uniquely activated aromatic scaffold. This electron-rich framework facilitates efficient coupling reactions in cross-coupling and Ullmann-type transformations. The compound exhibits excellent bench stability and solubility in common organic solvents, enabling straightforward integration into synthetic workflows for pharmaceutical intermediates and functional materials.

Application

2-Bromo-6-methoxyaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted anilines via Pd-catalyzed cross-coupling reactions. Its bromo group facilitates reliable C–C bond formation under standard Suzuki, Stille, or Negishi conditions, while the methoxy substituent provides moderate electron donation and enhanced solubility. The compound exhibits good bench stability and is readily purified by recrystallization, supporting scalable synthesis workflows.

Synthesis

Route1
- 90-04-0
- ~74%
- In-stock
  
  5473-01-8
References
- Merck and Co., Inc. Patent: US6291511 B1, 2001 ;
Route2
- 90-04-0
- ~0%
- 1141892-43-4
- In-stock
  
  59557-91-4
- In-stock
  
  5473-01-8
References
- Zysman-Colman, Eli; Arias, Karla; Siegel, Jay S. Canadian Journal of Chemistry, 2009 , vol. 87, # 2 p. 440 - 447
Route3
- 7726-95-6
- 90-04-0
- 64-19-7
- ~%
- In-stock
  
  5473-01-8
References
- Gazzetta Chimica Italiana, , vol. 62, p. 51,54

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H317-H411
Precautionary Statements : P261-P264-P270-P272-P273-P280-P302+P352-P363-P391-P501

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Computational Chemistry Data

TPSA 35.25
LogP 2.0399
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2-Bromo-6-methoxyaniline

CAS No. 5473-01-8

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