2-Chloro-4-hydroxybenzaldehyde Chemical Properties

Melting point:

145-147 °C (lit.)

Boiling point:

272.5±20.0 °C(Predicted)

Density 

1.404±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in organic solvents.

pka

6.81±0.18(Predicted)

form 

solid

Appearance

Off-white to light yellow Solid

Sensitive 

Air Sensitive

InChI

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

InChIKey

ZMOMCILMBYEGLD-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(O)C=C1Cl

CAS DataBase Reference

56962-11-9(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 2-chloro-4-hydroxy-(56962-11-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29124900

MSDS

• Language:English Provider:SigmaAldrich

2-Chloro-4-hydroxybenzaldehyde Usage And Synthesis

Uses

2-Chloro-4-hydroxybenzaldehyde, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Uses

2-Chloro-4-hydroxybenzaldehyde may be used in chemical synthesis.

General Description

N-Thioamide thiosemicarbazone derivatives of 2-chloro-4-hydroxy-benzaldehyde have been prepared. pK values for acid dissociation of 2-chloro-4-hydroxybenzaldehyde has been evaluated.

Synthesis

The general procedure for the synthesis of 2-chloro-4-hydroxybenzaldehyde from 3-chlorophenol (CAS 108-43-0) (49.2 g, 0.380 mol) and trichloromethane was as follows: first, 3-chlorophenol, calcium hydroxide (122.0 g) and sodium carbonate (139.4 g) were suspended in water (872 mL). Subsequently, trichloromethane (90.6 g, 0.760 mol) was slowly added over 80 min and the reaction mixture was refluxed for 3 h under vigorous stirring. After completion of the reaction, the mixture was cooled in an ice bath. Next, concentrated hydrochloric acid (385 mL) and trichloromethane (300 mL) were added for extraction and the aqueous layer was discarded. The organic layer was dried with anhydrous sodium sulfate (50 g) followed by evaporation of the solvent under vacuum. The residue was purified by silica gel column chromatography (silica gel 63-100 μm, 600 g, eluents sequentially carbon tetrachloride, chloroform, chloroform/ethyl acetate 93:7). Fractions containing the target product were collected, combined, and the solvents were evaporated and co-evaporated with dioxane to yield 2-chloro-4-hydroxybenzaldehyde (9.77 g, 0.062 mol, 16% yield) as a white powder.1H NMR (DMSO-d6) data were as follows: δ 11.06 (s, 1H, aldehydic hydrogens); 10.14 (s, 1H, hydroxyhydrogens); 7.75 ( d, 1H, J = 8.5 Hz, arylhydrogen); 6.92 (d, 1H, J = 2 Hz, arylhydrogen); 6.85 (dd, 1H, J1 = 8.5 Hz, J2 = 2 Hz, arylhydrogen).

References

[1] Patent: WO2006/136924, 2006, A1. Location in patent: Page/Page column 98
[2] Patent: WO2011/20615, 2011, A1. Location in patent: Page/Page column 45; 47; 48
[3] Patent: EP2289883, 2011, A1. Location in patent: Page/Page column 19
[4] Journal of Chemical & Engineering Data, 1983, vol. 28, # 1, p. 139 - 141
[5] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698

2-Chloro-4-hydroxybenzaldehyde(56962-11-9)Related Product Information

• 2-Chloro-4-hydroxybenzoic acid
• Salicylaldehyde
• 2-Nitrobenzaldehyde
• 3-Hydroxybenzaldehyde
• 4-Dimethylaminobenzaldehyde
• 3-Methoxybenzaldehyde
• Benzaldehyde
• p-Anisaldehyde
• 4-Hydroxybenzaldehyde
• 2-CHLORO-4-CYANOBENZOIC ACID
• Difluorochloromethane
• 2-CHLORO-3-HYDROXYBENZALDEHYDE 97
• 2-CHLORO-4-HYDROXYBENZALDEHYDE,3-Chloro-4-hydroxybenzaldehyde 98%,3-Chloro-4-hydroxybenzaldehyde, 99+%,3-CHLORO-4-HYDROXYBENZALDEHYDE
• 2,3-Dichloro-4-hydroxybenzaldehyde
• 4-TERT-BUTYL-5-CHLORO-2-HYDROXYBENZALDEHYDE
• 3,5-DICHLOROSALICYLALDEHYDE
• 4-Chloro-2-hydroxybenzaldehyde
• 2,6-DICHLORO-4-HYDROXYBENZALDEHYDE