2-Hydroxy-3,5-dimethylbenzaldehyde

Name: 2-Hydroxy-3,5-dimethylbenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 24623-61-8
Cat. No. CS-0038647
Purity≥97%
MDL No.None

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2-Hydroxy-3,5-dimethylbenzaldehyde|CS-0038647

Structure of 24623-61-8

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General Information

CAS No. 24623-61-8
Cat. No. CS-0038647
Purity ≥97%
MDL No. None
Storage Store at room temperature, keep dry and cool
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₀O₂
Molecular Weight 150.17
Synonym(s) UKRORGSYN-BB BBV-182329
SMILES CC1=CC(=C(C(=C1)C)O)C=O

Description

This ortho-hydroxy aldehyde features a sterically hindered aromatic core with two methyl groups flanking the aldehyde and hydroxyl functionalities. The adjacent hydroxyl group enables intramolecular hydrogen bonding, enhancing stability and directing electrophilic substitution regioselectively. This structural motif supports applications in asymmetric synthesis, ligand design, and functional material development under standard bench conditions.

Application

2-Hydroxy-3,5-dimethylbenzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted phenolic scaffolds and heterocyclic systems. Its ortho-hydroxyl and aldehyde functionalities offer complementary reactivity for condensation, cyclization, and coupling reactions, while the methyl groups enhance stability and modulate electronic properties. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for use in medicinal chemistry campaigns and process-scale synthesis.

Synthesis

Route1
- 50-00-0
- 105-67-9
- ~89%
- In-stock
  
  24623-61-8
References
- Knight, Paul D.; O'Shaughnessy, Paul N.; Munslow, Ian J.; Kimberley, Brian S.; Scott, Peter Journal of Organometallic Chemistry, 2003 , vol. 683, # 1 p. 103 - 113
Route2
- 105-67-9
- ~80%
- In-stock
  
  24623-61-8
References
- Adir et Compagnie Patent: US5391569 A1, 1995 ;
Route3
- 925-90-6
- 105-67-9
- ~56%
- In-stock
  
  24623-61-8
References
- PHARMACIA CORPRATION Patent: WO2004/60376 A1, 2004 ; Location in patent: Page/Page column 165-166 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H319
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 37.3
LogP 1.82154
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Hydroxy-3,5-dimethylbenzaldehyde

CAS No. 24623-61-8

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