3,5-Dichloro-4-hydroxybenzoic acid Chemical Properties

Melting point:

264-266 °C (lit.)

Boiling point:

297.29°C (rough estimate)

Density 

1.5281 (rough estimate)

refractive index 

1.4845 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.83±0.10(Predicted)

color 

White to Off-White

BRN 

2616297

InChI

InChI=1S/C7H4Cl2O3/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,10H,(H,11,12)

InChIKey

AULKDLUOQCUNOK-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3336-41-2(CAS DataBase Reference)

NIST Chemistry Reference

3,5-Dichloro-4-hydroxybenzoic acid(3336-41-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

DG7502000

HS Code 

29182900

MSDS

• Language:English Provider:3,5-Dichloro-4-hydroxybenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,5-Dichloro-4-hydroxybenzoic acid Usage And Synthesis

Chemical Properties

White to light yellow crystal powder

Uses

3,5-Dichloro-4-hydroxybenzoic Acid can be used as cyclin dependent kinase inhibitors to treat cell proliferative disorders, such as, cancer.

Definition

ChEBI: 3,5-dichloro-4-hydroxybenzoic acid is a derivative of p-salicylic acid with chloro- substituents at C-3 and C-5 of the benzene ring. It is a monohydroxybenzoic acid and a dichlorobenzene. It is functionally related to a benzoic acid and a 4-hydroxybenzoic acid. It is a conjugate acid of a 3,5-dichloro-4-hydroxybenzoate.

Synthesis

The general procedure for the synthesis of 3,5-dichloro-4-hydroxybenzoic acid from 4-hydroxybenzoic acid was as follows: 10 mL of 33% hydrogen peroxide solution was slowly added to a suspension of 10 mL hydrochloric acid and 20 mL water containing 3.5 g (0.025 mol) of 4-hydroxybenzoic acid. Upon completion of the reaction, the resulting white precipitate was collected by filtration, washed well with hot water and purified by recrystallization from ethanol. Finally, 3.19 g of white crystalline product was obtained in 63.5% yield with a melting point of 265 °C. The 1H NMR spectral data of the product was as follows (ppm): 7.84 (s, 2H, H2,6). Elemental analysis results: measured values (%) C 40.64, H 1.87, Cl 34.34; calculated values (%) C 40.58, H 1.93, Cl 34.30 (molecular formula: C7H4Cl2O2).

References

[1] Organic Process Research and Development, 1999, vol. 3, # 1, p. 10 - 16
[2] Russian Journal of General Chemistry, 2015, vol. 85, # 3, p. 577 - 583
[3] Zh. Obshch. Khim., 2015, vol. 85, # 3, p. 413 - 419,7
[4] Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1167,1168
[5] Chem. Zentralbl., 1950, vol. 121, p. 1063

3,5-Dichloro-4-hydroxybenzoic acid(3336-41-2)Related Product Information

• Butylparaben
• 3-CHLORO-4-HYDROXYBENZOIC ACID
• 2-Chloro-4-hydroxybenzoic acid
• 4-Hydroxybenzhydrazide
• 3-Hydroxybenzoic acid
• 4-Hydroxybenzoic acid
• Methyl 3,5-dihydroxybenzoate
• 2'-Hydroxy-3-phenylpropiophenone
• Benzylparaben
• 3,5-Dihydroxybenzoic acid
• Salicylic acid
• Isopropylparaben
• Methylparaben
• 2,5-Dihydroxybenzoic acid
• 3,5-Dichlorobenzoic acid
• 3,5-DICHLORO-4-HYDROXYBENZOIC ACID METHYL ESTER
• 3,5-DICHLORO-4-HYDROXYBENZOIC ACID ETHYL ESTER
• 3,5-DICHLORO-2-HYDROXYBENZOIC ACID