5-Bromo-2-iodobenzaldehyde

Name: 5-Bromo-2-iodobenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 689291-89-2
Cat. No. CS-W019684
Molecule weight310.91
Purity≥96%
MDL No.MFCD07779026

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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 689291-89-2

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General Information

CAS No. 689291-89-2
Cat. No. CS-W019684
Purity ≥96%
MDL No. MFCD07779026
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrIO
Molecular Weight 310.91
Synonym(s) 2-Iodo-5-bromobenzaldehyde
SMILES O=CC1=CC(Br)=CC=C1I

Description

5-Bromo-2-iodobenzaldehyde features a dual halogen substitution pattern that enables efficient cross-coupling transformations. The electron-deficient aromatic ring pairs with a reactive aldehyde group, facilitating rapid functionalization in palladium-catalyzed reactions. This compound serves as a key intermediate for synthesizing complex pharmaceuticals and advanced materials under standard conditions.

Application

5-Bromo-2-iodobenzaldehyde serves as a versatile building block for transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The orthogonal reactivity of bromo and iodo groups facilitates sequential functionalization, while the aldehyde moiety supports derivatization via condensation or reduction. Bench-stable and compatible with standard Pd(0)-catalyzed protocols, it is well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  199786-58-8
- ~99%
- In-stock
  
  689291-89-2
References
- Zhou, Ningzhang; Wang, Li; Thompson, David W.; Zhao, Yuming Tetrahedron, 2011 , vol. 67, # 1 p. 125 - 143
Route2
- In-stock
  
  495414-06-7
- ~99%
- In-stock
  
  689291-89-2
References
- THE JOHNS HOPKINS UNIVERSITY; TOVAR, John Dayton; CARUSO, Jr., Anthony Patent: WO2011/127383 A2, 2011 ; Location in patent: Page/Page column 75 ;
Route3
- In-stock
  
  121554-10-7
- ~%
- In-stock
  
  689291-89-2
References
- US2009/156610 A1, ; Page/Page column 90 ;

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 17.07
LogP 2.8662
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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5-Bromo-2-iodobenzaldehyde

CAS No. 689291-89-2

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