4-Bromo-2-hydroxybenzaldehyde

Name: 4-Bromo-2-hydroxybenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 22532-62-3
Cat. No. CS-W001114
Molecule weight201.02
Purity≥98%
MDL No.MFCD06252606

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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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4-Bromo-2-hydroxybenzaldehyde|CS-W001114

Structure of 22532-62-3

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General Information

CAS No. 22532-62-3
Cat. No. CS-W001114
Purity ≥98%
MDL No. MFCD06252606
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅BrO₂
Molecular Weight 201.02
Synonym(s) None
SMILES BrC1=CC(O)=C(C=O)C=C1

Description

4-Bromo-2-hydroxybenzaldehyde features a bromine substituent at the para position relative to the aldehyde, combined with a phenolic hydroxyl group ortho to the carbonyl. This arrangement imparts enhanced electron-withdrawing character and facilitates intramolecular hydrogen bonding, improving stability and directing electrophilic substitution reactions. The compound serves as a key intermediate in synthesizing bioactive heterocycles and functionalized aromatic scaffolds under standard conditions.

Application

4-Bromo-2-hydroxybenzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling direct access to substituted benzofurans and other heterocyclic scaffolds via electrophilic cyclization. The ortho-hydroxy aldehyde functionality facilitates efficient intramolecular reactions, while the bromine substituent provides a reliable handle for palladium-catalyzed cross-coupling transformations. Its bench-stable crystalline form and compatibility with standard purification methods make it well-suited for iterative synthesis workflows in medicinal chemistry and materials development.

Synthesis

Route1
- 50-00-0
- 591-20-8
- ~48%
- In-stock
  
  22532-62-3
References
- Angewandte Chemie - International Edition, , vol. 44, # 44 p. 7204 - 7208
Route2
- 67-66-3
- 591-20-8
- ~5%
- In-stock
  
  22532-62-3
- In-stock
  
  22532-61-2
- In-stock
  
  22532-60-1
References
- Journal of Medicinal Chemistry, , vol. 35, # 4 p. 734 - 740
Route3
- In-stock
  
  194163-05-8
- ~%
- In-stock
  
  22532-62-3
References
- Journal of Medicinal Chemistry, , vol. 40, # 18 p. 2843 - 2857

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H410
Precautionary Statements : P264-P270-P273-P330-P391-P501

Quality Control

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Computational Chemistry Data

TPSA 37.3
LogP 1.9672
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Building Blocks Functional Group Phenol

Building Blocks Functional Group Aldehyde

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Bromo-2-hydroxybenzaldehyde

CAS No. 22532-62-3

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