4-Chloro-2-hydroxybenzaldehyde Chemical Properties

Melting point:

45.0 to 49.0 °C

Boiling point:

229.1±20.0 °C(Predicted)

Density 

1.404±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Solid

pka

7.21±0.10(Predicted)

color 

Off-White to Pale Brown

InChI

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

InChIKey

QNZWAJZEJAOVPN-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(Cl)C=C1O

CAS DataBase Reference

2420-26-0

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2913000090

4-Chloro-2-hydroxybenzaldehyde Usage And Synthesis

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.

Synthesis

To a 1L three-necked round-bottomed flask was added 3-chlorophenol (33.6 g, 0.3 mol), anhydrous MgCl2 (85.7 g, 0.9 mmol), triethylamine (75.9 g, 0.75 mol) and anhydrous acetone (340 mL). The resulting solution was stirred at 25 °C for 30 min, followed by the addition of paraformaldehyde (45 g, 1.5 mol). The reaction mixture was heated to reflux for 5 h under nitrogen protection. When TLC monitoring showed complete consumption of the feedstock, the acetone was evaporated under reduced pressure. The residue was acidified to pH 3 with 10% hydrochloric acid solution and extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a brownish-red oil (18.1 g, 43.1% yield), which can be used directly in subsequent reactions without further purification (Byun et al., 2008; Uini and Lars, 1999).

References

[1] Applied Organometallic Chemistry, 2018, vol. 32, # 2,
[2] Drug Metabolism and Disposition, 2017, vol. 45, # 12, p. 1354 - 1363
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1530 - 1536
[4] Organic Letters, 2015, vol. 17, # 23, p. 5824 - 5827
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 30, p. 7268 - 7274

4-Chloro-2-hydroxybenzaldehyde(2420-26-0)Related Product Information

• 5-Chlorosalicylaldehyde
• Salicylaldehyde
• p-Anisaldehyde
• Benzaldehyde
• 4-Hydroxybenzaldehyde
• 2-Chloro-3-hydroxypyridine
• 3-Hydroxybenzaldehyde
• Difluorochloromethane
• 1-AMINO-2-CHLORO-4-HYDROXY-9,10-ANTHRACENEDIONE
• Buclosamide
• 4'-CHLORO-2'-HYDROXYACETOPHENONE
• Xipamide
• 2,4-DICHLORO-6-HYDROXYBENZALDEHYDE
• 4-Chloro-2-methoxybenzoic acid
• Alloclamide
• 4-Chlorosalicylic acid
• 7-chloro-4-oxo-4H-chromene-2-carboxylic acid
• 1-(4-CHLORO-2-HYDROXYPHENYL)PROPAN-1-ONE