635-93-8

Basic information

• Product Name: 5-Chlorosalicylaldehyde
• Synonyms: 2-HYDROXY-5-CHLOROBENZALDEHYDE;5-CHLOROSALICYLALDEHYDE;5-Chlorosalicylic aldehyde;5-CHLORO-2-HYDROXYBENZALDEHYDE;AKOS 90774;5-Chlorosalicyladehyde;5-Cl-salicylal;5-Chloro-2-Hydroxybenzaldehyde (5-Chlorosalicylaldehyde)
• CAS NO: 635-93-8
• Molecular Formula: C₇H₅ClO₂
• Molecular Weight: 156.57
• EINECS: 211-244-4
• Product Categories: FINE Chemical & INTERMEDIATES;Alcohols and Derivatives;Carbonyl Compounds;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Adehydes, Acetals & Ketones;Chlorine Compounds;Phenols;Aldehydes;C7;Carbonyl Compounds
• Mol File: 635-93-8.mol
• Article Data: 63

Chemical Properties

• Melting Point: 100-102 °C(lit.)
• Boiling Point: 217.69°C (rough estimate)
• Flash Point: 92.2 °C
• Appearance: White to very slightly yellow/Crystalline Powder
• Density: 1.2683 (rough estimate)
• Vapor Pressure: 0.0477mmHg at 25°C
• Refractive Index: 1.5812 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.73±0.18(Predicted)
• Sensitive: Air Sensitive
• BRN: 636632
• CAS DataBase Reference: 5-Chlorosalicylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chlorosalicylaldehyde(635-93-8)
• EPA Substance Registry System: 5-Chlorosalicylaldehyde(635-93-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-24/25-36/37/39
• RIDADR: UN2811/6.1/PG III
• WGK Germany: 3
• RTECS: VN5450000
• TSCA: Yes
• Hazardous Substances Data: 635-93-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 20, p. 609, 1990 DOI: 10.1080/00397919008244911Tetrahedron Letters, 15, p. 3463, 1974

Purification Methods

Steam distil it, then crystallise it from aqueous EtOH or *C6H6 (m 100o). It forms complexes with Cu2+ and Fe2+ . [Beilstein 8 H 53, 8 II 45, 8 III 181, 8 IV 224.]

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

Upstream product

• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 90-02-8 salicylaldehyde 
• 302-17-0 chloral hydrate 
• 106-48-9 4-chloro-phenol 
• 67-66-3 chloroform 
• 1121-74-0 potassium 4-chlorophenoxide 
• 76-03-9 trichloroacetic acid 
• 7791-25-5 sulfuryl dichloride 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 60-29-7 diethyl ether 
• 15454-33-8 chloromethanol 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 

Downstream Products

• 106473-92-1 4-chloro-2-[(3-morpholino-propylamino)-methyl]-phenol 
• 732-92-3 5-chlorosalicylaldehyde isonicotinoyl hydrazone 
• 92596-90-2 N-(5-chloro-2-hydroxybenzylidene)-4-hydroxyaniline 
• 53653-66-0 3-acetyl-6-chlorocoumarin 
• 132972-13-5 (E)-3-(5-chloro-2-hydroxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 79567-37-6 4-chloro-2-[(2,4-dichloro-phenylimino)-methyl]-phenol 
• 3542-65-2 6-chloro-3-(phenylcarbonyl)-2H-chromen-2-one 
• 36043-76-2 4-chloro-2-(p-tolylimino-methyl)-phenol 
• 96583-20-9 N-(5′-chlorosalicylidene)-4-chloroaniline 
• 115820-15-0 4-chloro-2-[(4-methoxy-phenylimino)-methyl]-phenol 
• 71937-06-9 4-[(5-chloro-2-hydroxybenzylidene)amino]benzoic acid 
• 53451-80-2 4-chloro-2-[(4-nitro-phenylimino)-methyl]-phenol 
• 10242-10-1 5-chlorobenzofuran-2-carboxylic acid 
• 15501-17-4 (E)-4-chloro-2-((phenylimino)methyl)phenol 

Relevant articles and documents

The X-ray structure of 5-chlorosalicylaldehyde

5-Chlorosalicylaldehyde [monoclinic, a = 3.800(2), b = 5.595(4), c = 15.174(11) ?, β = 93.221(17), space group P21] exhibits an unusual crystal structure with both intramolecular and intermolecular OH to CH=O hydrogen bonding, the latter leading to chains of molecules aligned along the b axis. A survey of previous substituted salicylaldehyde structures shows three main hydrogen bonding patterns: intramolecular only (14), intramolecular and intermolecular dimeric (5), and intramolecular and intermolecular polymeric (3).

Driving the Emission Towards Blue by Controlling the HOMO-LUMO Energy Gap in BF2-Functionalized 2-(Imidazo[1,5-a]pyridin-3-yl)phenols

Several boron compounds with 2-(imidazo[1,5-a]pyridin-3-yl)phenols, differentiated by the nature of the substituent (R) in the para position of the hydroxy group, have been synthesized and thoroughly characterized both in solution (1H, 13C, 11B, 19F NMR) and in the solid state (X-ray). All derivatives displayed attractive photophysical properties like very high Stokes shift, high fluorescence quantum yields and a good photostability in solution. Time-Dependent Density Functional Theory (TD-DFT) calculations allowed to define the main electronic transitions as intra ligand transitions (1ILT), which was corroborated by the Natural Transition Orbitals (NTOs) shapes. The HOMO-LUMO energy gap was correlated to the electronic properties of the substituent R on the phenolic ring, as quantified by its σp Hammett constant.

Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles

A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.