2-CHLORO-5-HYDROXYBENZOIC ACID Chemical Properties

Melting point:

178-180°C

Boiling point:

364.5±27.0 °C(Predicted)

Density 

1.536±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.78±0.25(Predicted)

color 

White to Light yellow

CAS DataBase Reference

56961-30-9

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37

HazardClass 

IRRITANT

HS Code 

29182900

2-CHLORO-5-HYDROXYBENZOIC ACID Usage And Synthesis

Uses

2-Chloro-5-hydroxybenzoic Acid acts as a reagent for the synthesis, structure-activity relationship, and biological evaluation of a series of benzamides as potential multireceptor antipsychotics.

Synthesis

General procedure for the synthesis of 2-chloro-5-hydroxybenzoic acid from 5-amino-2-chlorobenzoic acid: aqueous sodium nitrite (90 mL, 0.5 M) was slowly added to a stirring suspension of 5-amino-2-chlorobenzoic acid (16) (5.01 g, 29.6 mmol) and sulfuric acid (6.00 mL, 0.167 mol) at 0 °C. During addition, the reaction temperature was maintained between 0 and 5 °C. After addition, stirring was continued in an ice bath for 1 hour. Subsequently, the reaction mixture was diluted with water (900 mL) and stirred under reflux conditions for 30 minutes. Upon completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate (3 x 500 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the light brown solid product 17 (4.97 g, 98% yield). The melting point of the product was 165-168 °C; IR (ZnSe) showed absorption peaks located at 3311, 2920, 2598, 1676, 1599, 1573, 1474, 1447, 1228, 826 cm-1 ; 1H NMR (300 MHz, MeOD) chemical shifts were δ 7.26 (1H, d, J = 8.7 Hz), 7.23 (1H, d, J = 3.0 Hz), 6.89 (1H, dd, J = 3.0 and 8.7 Hz) ppm, no 2xOH signal observed; 13C NMR (75 MHz, MeOD) chemical shifts were δ169.1, 157.4, 132.7, 132.8, 123.8, 120.7, 116.2 ppm; LRMS (-) ESI) showed m/z 171 ([M-H]-, 100%), 127 ([M-CO2H]-, 36%).

References

[1] Tetrahedron, 2018, vol. 74, # 12, p. 1207 - 1219
[2] Patent: WO2008/64432, 2008, A1. Location in patent: Page/Page column 58
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 13, p. 3720 - 3723
[4] Monatshefte fuer Chemie, 1921, vol. 42, p. 80
[5] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1924, vol. 54, p. 832

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