1-Bromo-4-methoxynaphthalene

Name: 1-Bromo-4-methoxynaphthalene
Brand: ChemScene
Availability: InStock
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CAS No. 5467-58-3
Cat. No. CS-0041681
Purity≥98%
MDL No.MFCD00155144

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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+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 5467-58-3

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General Information

CAS No. 5467-58-3
Cat. No. CS-0041681
Purity ≥98%
MDL No. MFCD00155144
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₉BrO
Molecular Weight 237.09
Synonym(s) 4-Bromo-1-naphthyl Methyl Ether
SMILES COC1=CC=C(Br)C2=C1C=CC=C2

Description

1-Bromo-4-methoxynaphthalene features a bromine atom at the 1-position and a methoxy group at the 4-position of the naphthalene core. This substitution pattern enhances regioselectivity in palladium-catalyzed cross-coupling reactions. The compound exhibits excellent bench stability and solubility in common organic solvents, enabling efficient integration into synthetic sequences for pharmaceutical intermediates and functional materials.

Application

1-Bromo-4-methoxynaphthalene serves as a versatile building block in cross-coupling reactions, enabling efficient construction of biaryl and functionalized naphthalene scaffolds. The bromine atom facilitates palladium-catalyzed coupling with boronic acids, esters, and organozinc reagents under standard conditions. The methoxy group provides electronic modulation and enhances solubility, while the compound exhibits good bench stability and is readily purified by flash chromatography or recrystallization.

Synthesis

Route1
- In-stock
  
  2216-69-5
- ~99%
- In-stock
  
  5467-58-3
References
- Krishna Mohan; Narender; Srinivasu; Kulkarni; Raghavan Synthetic Communications, 2004 , vol. 34, # 12 p. 2143 - 2152
Route2
- In-stock
  
  571-57-3
- 77-78-1
- ~78%
- In-stock
  
  5467-58-3
References
- Georghiou, Paris E.; Ashram, Muhammad; Li, Zhaopeng; Chaulk, Steven G. Journal of Organic Chemistry, 1995 , vol. 60, # 22 p. 7284 - 7289
Route3
- In-stock
  
  571-57-3
- 74-88-4
- ~89%
- In-stock
  
  5467-58-3
References
- Worth, Anna C.; Needham, Catherine E.; Franklin, Donald B.; Lampkins, Andrew J. Synthetic Communications, 2012 , vol. 42, # 18 p. 2694 - 2706

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 9.23
LogP 3.6109
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Material Science Material Building Blocks Liquid Crystal (LC) Building Blocks Bromobenzenes

Key Words

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1-Bromo-4-methoxynaphthalene

CAS No. 5467-58-3

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