2420-26-0

Basic information

• Product Name: 4-Chloro-2-hydroxybenzaldehyde
• Synonyms: 4-CHLORO-2-HYDROXY-BENZALDEHYDE;4-Chloro-2-hydroxy-benzaldehyde ,97%;4-chloro-2-hydoxybenzaldehyde;4-chloro-2-hydoxybenzaldehye;4-chlorosalicylaldehyde;2-hydroxy-4-chlorobenzaldehyde;4-Chlorosalicylaldehyde, 5-Chloro-2-formylphenol;4-Chloro-2-hydroxybenzaldehyde, 95+%
• CAS NO: 2420-26-0
• Molecular Formula: C₇H₅ClO₂
• Molecular Weight: 156.57
• EINECS: 1533716-785-6
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het
• Mol File: 2420-26-0.mol
• Article Data: 31

Chemical Properties

• Melting Point: 45.0 to 49.0 °C
• Boiling Point: 229.1 °C at 760 mmHg
• Flash Point: 92.4 °C
• Appearance: /
• Density: 1.404 g/cm³
• Vapor Pressure: 0.0468mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 7.21±0.10(Predicted)
• CAS DataBase Reference: 4-Chloro-2-hydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-hydroxybenzaldehyde(2420-26-0)
• EPA Substance Registry System: 4-Chloro-2-hydroxybenzaldehyde(2420-26-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 2420-26-0(Hazardous Substances Data)

Usage

Uses

4-Chloro-2-hydroxybenzaldehyde is an intermediate used to prepare benzodiazepine diones as Hdm2 antagonists. It is also used to synthesize hydroxy-dimethyl-oxo-cyclohexenyl-dimethyl-tetrahydro-xanthenone as oral neuropeptide Y5 receptor antagonist.

InChI:InChI=1/C7H5ClO2/c8-6-2-1-5(4-9)7(10)3-6/h1-4,10H

Upstream product

• 108-43-0 3-monochlorophenol 
• 76-03-9 trichloroacetic acid 
• 67-66-3 chloroform 
• 75-25-2 Bromoform 
• 7732-18-5 water 
• 5106-98-9 4-chlorosalicylic acid 
• 82944-19-2 7-chloro-2,2-dimethyl-benzo[1,3]dioxin-4-one 
• 50-00-0 formaldehyd 
• 106-43-4 para-chlorotoluene 
• 5306-98-9 5-chloro-2-methyl-phenol 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 88-33-5 5-chloro-2-formyl-benzenesulfonic acid 
• 90-02-8 salicylaldehyde 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 89130-16-5 N,N'-ethylenebis(2-hydroxy-5-chlorophenyleneimine) 
• 53581-86-5 4-chloro-2-methoxybenzaldehyde 
• 96126-91-9 4-chloro-2-hydroxy-α-isopropyl-benzylalcohol 
• 787633-69-6 2-(allyloxy)-4-chlorobenzaldehyde 
• 1068143-85-0 C₁₄H₁₂ClNO₂ 
• 74222-19-8 ethyl 6-chloro-1-benzofuran-2-carboxylate 
• 1187511-59-6 2-amino-N-benzyl-5-(4-bromobenzoyl)-4-(4-chloro-2-hydroxyphenyl)-1H-pyrrole-3-carboxamide 
• 1292288-46-0 N,N'-bis(4-chlorosalicylidene)-1,12-dodecanediamine 
• 1426547-46-7 5-chloro-2-formylphenyl trifluoromethanesulfonate 
• 1426547-37-6 5'-chloro-2'-(methoxymethyl)biphenyl-2,6-diol 
• 1426547-55-8 5-chloro-2',6'-bis(methoxymethoxy)biphenyl-2-carboxaldehyde 
• 1616385-27-3 C₂₄H₂₈Cl₂N₂O₂Pt 
• 1616385-23-9 C₂₄H₃₀Cl₂N₂O₂ 
• 1616385-24-0 C₂₅H₃₂Cl₂N₂O₂ 

Relevant articles and documents

Imine or Enamine? Insights and Predictive Guidelines from the Electronic Effect of Substituents in H-Bonded Salicylimines

Imine and enamine bonds decorate the skeleton of numerous reagents, catalysts, and organic materials. However, it is difficult to isolate at will a single tautomer, as dynamic equilibria occur easily, even in the solid state, and are sensitive to electronic and steric effect, including π-conjugation and H-bonding. Here, using as model Schiff bases generated from salicylaldehydes and TRIS in a set of linear free energy relationships (LFER), we disclose how the formation of either imines or enamines can be controlled and provide a comprehensive framework that captures the structural underpinning of this prediction. This work highlights the potentiality of tailor-made designs en route to compounds with desirable functionality.

Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines

Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones and sulfamate-derived cyclic imines has been developed, giving a series of imidazoline derivatives in moderate to excellent yields with good to excellent diastereoselectivities. A scale-up reaction worked well under mild reaction conditions. A possible mechanism was proposed on the basis of the results obtained.

Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines

A palladium-catalyzed enantioselective [4 + 2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines is described, affording the tetrahydroquinazolines bearing several functional rings in high yields (up to 99% yield) with good to excellent diastereoselectivities and excellent enantioselectivities (up to 96% ee). This reaction represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.