3-Chloro-4-hydroxybenzaldehyde Chemical Properties

Melting point:

133-137 °C (lit.)

Boiling point:

150 °C / 14mmHg

Density 

1.2683 (rough estimate)

refractive index 

1.5812 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

6.30±0.18(Predicted)

color 

White to Light yellow to Light orange

Sensitive 

Air Sensitive

InChI

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

InChIKey

VGSOCYWCRMXQAB-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(O)C(Cl)=C1

CAS DataBase Reference

2420-16-8(CAS DataBase Reference)

NIST Chemistry Reference

3-Chloro-4-hydroxybenzaldehyde(2420-16-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-43-41-37/38-22-20/21/22

Safety Statements 

26-37/39-36/37/39-36-37

WGK Germany 

3

Hazard Note 

Irritant/Air Sensitive

HS Code 

29130000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Chloro-4-hydroxybenzaldehyde Usage And Synthesis

Chemical Properties

White solid

Synthesis

The general procedure for the synthesis of 3-chloro-4-hydroxybenzaldehyde from 4-hydroxybenzaldehyde was as follows: N-chlorosuccinimide (1.1 g, 8.18 mmol) was added to a solution of 4-hydroxybenzaldehyde (1.0 g, 8.18 mmol) dissolved in 10 ml of chloroform. The reaction mixture was heated and stirred at 50°C for 15 hours. After completion of the reaction, it was cooled to room temperature and concentrated under reduced pressure to remove the solvent. The residue was dissolved in 25 ml of ethyl acetate, washed sequentially with water and saturated saline, and the organic phase was dried with anhydrous sodium sulfate. After filtration, the crude product was obtained by concentration under reduced pressure. The crude product was purified by silica gel column chromatography using 12% ethyl acetate in hexane solution as eluent to give 1.1 g (86% yield) of 3-chloro-4-hydroxybenzaldehyde.1H-NMR (400 MHz, CDCl3) δ (ppm): 9.840 (s, 1H), 7.898-7.894 (d, 1H, J = 1.6 Hz), 7.749- 7.724 (dd, 1H, J = 8.4Hz), 7.164-7.143 (d, 1H, J = 8.4Hz), 6.288 (s, 1H).

References

[1] Tetrahedron Letters, 1994, vol. 35, # 28, p. 5043 - 5046
[2] Patent: WO2010/127212, 2010, A1. Location in patent: Page/Page column 35
[3] Patent: WO2010/127208, 2010, A1. Location in patent: Page/Page column 55
[4] Tetrahedron Asymmetry, 1997, vol. 8, # 24, p. 4003 - 4006
[5] Synthetic Communications, 2012, vol. 42, # 24, p. 3655 - 3663,9

3-Chloro-4-hydroxybenzaldehyde(2420-16-8)Related Product Information

• 3-Hydroxybenzaldehyde
• 3-CHLORO-4-HYDROXYBENZOIC ACID
• Protocatechuic acid
• Salicylaldehyde
• 4-Hydroxybenzaldehyde
• 2-Chloro-3-hydroxypyridine
• Benzaldehyde
• Difluorochloromethane
• Ethacrynic acid
• 5-CHLOROVANILLIC ACID
• METHYL 3,5-DICHLORO-4-HYDROXYBENZOATE
• METHYL 3-CHLORO-4-HYDROXYBENZOATE
• 3,5-Dichloro-4-hydroxybenzoic acid
• 3-CHLORO-4-METHOXYBENZALDEHYDE
• METHYL 3-CHLORO-4-METHOXYBENZOATE
• 3-CHLORO-4-METHOXYBENZOIC ACID
• ETHYL 3,5-DICHLORO-4-HYDROXYBENZOATE
• 5-Chlorosalicylaldehyde