4-Chloro-3-hydroxybenzoic acid

4-Chloro-3-hydroxybenzoic acid Property

Melting point:

219.5-220.5 °C

Boiling point:

345.4±27.0 °C(Predicted)

Density 

1.536±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO, Methanol

form 

Solid

pka

3.85±0.10(Predicted)

color 

Light Beige

InChI

InChI=1S/C7H5ClO3/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,9H,(H,10,11)

InChIKey

SCPUNJAMWFAYED-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

34113-69-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-chloro-3-hydroxy-(34113-69-4)

Safety

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2918199890

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Chloro-3-hydroxybenzoic acid Chemical Properties,Usage,Production

Uses

4-Chloro-3-hydroxy-Benzoic Acid acts as a potential inhibitor of influenza endonuclease used in the treatment of influenza. Also used in the synthesis of highly selective Tie-2 kinase inhibitors used in the treatment of tumors.

Synthesis

General procedure for the synthesis of 4-chloro-3-hydroxybenzoic acid from compound (CAS: 931409-94-8): boron tribromide (1 M in dichloromethane, 31 mL, 31.504 mmol) was slowly added dropwise to a solution of compound 38 (3.56 g, 15.752 mmol) in dichloromethane (30 mL) under ice bath cooling conditions. The reaction mixture was stirred at 0°C to room temperature for 18 hours. Upon completion of the reaction, the reaction was quenched with 0.88 aqueous ammonia solution and stirring was continued for 90 minutes at room temperature. Subsequently, the reaction mixture was acidified to pH 1 by dropwise addition of 2N aqueous hydrochloric acid solution and then extracted with ether (2 x 50 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 4-chloro-3-hydroxybenzoic acid as a light yellow solid in 90% yield (2.45 g). The product was characterized by 1H NMR (400 MHz, CD3OD): δ 7.36-7.38 (d, 1H), 7.44-7.47 (dd, 1H), 7.54-7.55 (d, 1H); LRMS APCI m/z 171 [M-H]-.

References

[1] Patent: WO2007/34325, 2007, A1. Location in patent: Page/Page column 53