5-Bromo-3-chloro-2-hydroxybenzaldehyde

Name: 5-Bromo-3-chloro-2-hydroxybenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 19652-33-6
Cat. No. CS-0037097
Purity≥98%
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+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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5-Bromo-3-chloro-2-hydroxybenzaldehyde|CS-0037097

Structure of 19652-33-6

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General Information

CAS No. 19652-33-6
Cat. No. CS-0037097
Purity ≥98%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrClO₂
Molecular Weight 235.46
Synonym(s) 5-Bromo-3-chlorosalicylaldehyde
SMILES C1=C(C=C(C(=C1C=O)O)Cl)Br

Description

5-Bromo-3-chloro-2-hydroxybenzaldehyde features a unique combination of bromo, chloro, and hydroxy substituents on a benzaldehyde scaffold, enabling selective functionalization in complex synthetic sequences. The electron-deficient aromatic ring enhances reactivity in coupling processes, while the phenolic hydroxyl group provides a handle for derivatization. This compound exhibits bench-stable behavior under standard conditions and integrates efficiently into multi-step syntheses targeting bioactive molecules and advanced materials.

Application

5-Bromo-3-chloro-2-hydroxybenzaldehyde serves as a versatile building block for heterocyclic synthesis, enabling efficient access to substituted benzimidazoles, quinolines, and other medicinally relevant scaffolds. The ortho-hydroxy aldehyde functionality facilitates intramolecular cyclization, while the bromo and chloro substituents provide orthogonal handles for palladium-catalyzed cross-coupling reactions. Its bench-stable crystalline form allows for straightforward handling and purification, making it well-suited for iterative synthetic campaigns in medicinal chemistry and process development.

Synthesis

Route1
- In-stock
  
  1761-61-1
- ~80%
- In-stock
  
  19652-33-6
References
- G. D. Searle and Co. Patent: US6100423 A1, 2000 ;
Route2
- 100-97-0
- In-stock
  
  3964-56-5
- ~35%
- In-stock
  
  19652-33-6
References
- Silvestri, Maximilian A.; Nagarajan, Muthukaman; De Clercq, Erik; Pannecouque, Christophe; Cushman, Mark Journal of Medicinal Chemistry, 2004 , vol. 47, # 12 p. 3149 - 3162
Route3
- 67-66-3
- In-stock
  
  3964-56-5
- ~%
- In-stock
  
  19652-33-6
References
- Chandrasekhar, Srivari; Chandrashekar, Gudise Tetrahedron Asymmetry, 2005 , vol. 16, # 13 p. 2209 - 2214

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05
Signal Word : Danger	UN#: 1759
Class : 8	Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 37.3
LogP 2.6206
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Aldehyde

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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5-Bromo-3-chloro-2-hydroxybenzaldehyde

CAS No. 19652-33-6

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