2-Chloro-3-hydroxybenzaldehyde

Name: 2-Chloro-3-hydroxybenzaldehyde
Brand: ChemScene
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CAS No. 56962-10-8
Cat. No. CS-B0145
Purity≥96%
MDL No.MFCD06798118

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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 56962-10-8

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General Information

CAS No. 56962-10-8
Cat. No. CS-B0145
Purity ≥96%
MDL No. MFCD06798118
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅ClO₂
Molecular Weight 156.57
Synonym(s) 2-CHLORO-3-HYDROXYBENZALDEHYDE 97
SMILES O=CC1=CC=CC(O)=C1Cl

Description

2-Chloro-3-hydroxybenzaldehyde features a hydroxyl group ortho to the aldehyde, enabling intramolecular hydrogen bonding that enhances stability and influences reactivity. The electron-withdrawing chlorine substituent modulates electrophilicity at the carbonyl center, facilitating selective transformations in synthetic routes. This bifunctional scaffold integrates readily into complex molecular architectures under standard conditions.

Application

2-Chloro-3-hydroxybenzaldehyde serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles, quinoline derivatives, and other heterocyclic scaffolds. The ortho-chloro and phenolic hydroxyl groups provide complementary reactivity for electrophilic substitution, Suzuki coupling, and directed metalation. Its bench-stable nature and compatibility with common protecting group strategies facilitate streamlined synthetic sequences.

Synthesis

Route1
- 100-83-4
- ~55%
- In-stock
  
  56962-10-8
References
- NEUROCRINE BIOSCIENCES, INC. Patent: WO2005/7165 A1, 2005 ; Location in patent: Page 46 ; WO 2005/007165 A1
Route2
- 507-40-4
- 100-83-4
- ~%
- In-stock
  
  56962-10-8
References
- Journal of the American Chemical Society, , vol. 73, p. 702
Route3
- 100-83-4
- ~0%
- In-stock
  
  7310-94-3
- In-stock
  
  56962-12-0
- In-stock
  
  56962-10-8
References
- Bovonsombat, Pakorn; Ali, Rameez; Khan, Chiraphorn; Leykajarakul, Juthamard; Pla-On, Kawin; Aphimanchindakul, Suraj; Pungcharoenpong, Natchapon; Timsuea, Nisit; Arunrat, Anchalee; Punpongjareorn, Napat Tetrahedron, 2010 , vol. 66, # 34 p. 6928 - 6935

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS07,GHS09
Signal Word : Danger	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335-H410
Precautionary Statements : P261-P264-P270-P271-P273-P280-P302+P352-P304+P340-P330-P362+P364-P391-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 37.3
LogP 1.8581
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2-Chloro-3-hydroxybenzaldehyde

CAS No. 56962-10-8

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