2-Bromo-1-iodonaphthalene

Name: 2-Bromo-1-iodonaphthalene
Brand: ChemScene
Availability: InStock
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CAS No. 676267-05-3
Cat. No. CS-0569918
Purity≥97%
MDL No.None

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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 676267-05-3

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General Information

CAS No. 676267-05-3
Cat. No. CS-0569918
Purity ≥97%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₆BrI
Molecular Weight 332.96
Synonym(s) 2-bromo-1-iodo-naphthalene
SMILES C1=CC=C2C(=C1)C=CC(=C2I)Br

Description

2-Bromo-1-iodonaphthalene is a dual-halogenated naphthalene derivative featuring bromine at the 2-position and iodine at the 1-position. This regioselective substitution pattern enables precise cross-coupling applications in palladium-catalyzed reactions, where the iodine moiety serves as a highly reactive coupling handle. The molecule exhibits enhanced stability under standard handling conditions and integrates efficiently into complex molecular architectures during synthetic sequence design.

Application

2-Bromo-1-iodonaphthalene serves as a versatile biaryl building block in transition-metal-catalyzed cross-coupling reactions. The orthogonal halogen reactivity enables sequential functionalization, with the iodine moiety typically participating first in palladium-catalyzed couplings, followed by bromine activation. Its stability under standard handling conditions and compatibility with common coupling protocols make it a reliable choice for constructing complex naphthalene-based architectures in medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  771-14-2
- ~81%
- In-stock
  
  676267-05-3
References
- Jancarik, Andrej; Rybacek, Jiri; Cocq, Kevin; Chocholousova, Jana Vacek; Vacek, Jaroslav; Pohl, Radek; Bednarova, Lucie; Fiedler, Pavel; Cisarova, Ivana; Stara, Irena G.; Stary, Ivo Angewandte Chemie - International Edition, 2013 , vol. 52, # 38 p. 9970 - 9975 Angew. Chem., 2013 , vol. 125, # 38 p. 10154 - 10159,6
Route2
- 4185-62-0
- ~%
- In-stock
  
  676267-05-3
References
- Hodgson; Hathway Journal of the Chemical Society, 1944 , p. 538

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

TPSA 0
LogP 4.2069
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Key Words

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2-Bromo-1-iodonaphthalene

CAS No. 676267-05-3

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