4-Hydroxythiobenzamide Chemical Properties

Melting point:

181-185℃

Boiling point:

320.4±44.0 °C(Predicted)

Density 

1.338±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.24±0.26(Predicted)

color 

Light Yellow

InChI

InChI=1S/C7H7NOS/c8-7(10)5-1-3-6(9)4-2-5/h1-4,9H,(H2,8,10)

InChIKey

VDTNKXSVUGXUOJ-UHFFFAOYSA-N

SMILES

C1(C(N)=S)=CC=C(O)C=C1

CAS DataBase Reference

25984-63-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

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

Safety Statements 

26-36/37/39-36/37

HS Code 

29242990

4-Hydroxythiobenzamide Usage And Synthesis

Uses

4-Hydroxythiobenzamide(25984-63-8) is used in the synthesis of PPARα agonists used in increasing HDLc levels. Also used in the synthesis of potent CDK5 inhibitors in the treatment of Alzheimer’s disease.

Description

4-Hydroxythiobenzamide is a key intermediate in febuxostat, a highly effective drug for treating gout. In addition, 4-hydroxythiobenzamide has been used to synthesize a variety of bioactive compounds, such as PPARγ agonists (used to increase high-density lipoprotein cholesterol levels) and potent CDK5 inhibitors (used in neurological disorders and cancer research).

Chemical Properties

4-Hydroxythiobenzamide has an appearance ranging from light orange to yellow to green, powder to crystalline, melting point 192 °C, soluble in methanol.

Uses

febuxostat intermediate

Uses

4-Hydroxythiobenzamide is used in the synthesis of PPARα agonists used in increasing HDLc levels. Also used in the synthesis of potent CDK5 inhibitors in the treatment of Alzheimer’s disease.

Synthesis

4-Hydroxythiobenzamide is an important intermediate of Febuxostat, a new anti-gout drug. A patent discloses a method for preparing p-hydroxythiobenzamide. Specifically, a certain amount of water, p-cyanophenol, sodium hydrosulfide, and secondary amine are mixed evenly. At a specific temperature, an organic weak acid is added dropwise. After the reaction is completed, the mixture is filtered, and the filter cake is dried to obtain 4-Hydroxythiobenzamide.

References

[1] Patent: US2005/75503, 2005, A1. Location in patent: Page/Page column 3
[2] Patent: US2012/78013, 2012, A1. Location in patent: Page/Page column 4
[3] Patent: CN106928108, 2017, A. Location in patent: Paragraph 0043; 0044; 0046; 0048; 0063; 0065; 0067; 0071
[4] Patent: WO2016/46836, 2016, A2. Location in patent: Page/Page column 3
[5] Synthetic Communications, 2000, vol. 30, # 6, p. 1083 - 1094

4-Hydroxythiobenzamide(25984-63-8)Related Product Information

• ethyl 2-(4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
• ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE
• ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
• Febuxostat
• 4-HYDROXYTHIOBENZAMIDE
• 4-METHOXYTHIOBENZAMIDE
• 2,3-DIHYDRO-1,4-BENZODIOXINE-6-CARBOTHIOAMIDE
• 6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-1-THIONE
• Tritiozine
• Vanitiolide
• 4-Ethoxybenzenecarbothioamide
• Benzamide
• THIOBENZAMIDE
• 4-[5-(TRIFLUOROMETHYL)PYRID-2-YLOXY]THIOBENZAMIDE
• 4-METHOXY-3-NITROBENZENE-1-CARBOTHIOAMIDE
• 2,3-DIHYDROBENZO[B]FURAN-5-CARBOTHIOAMIDE
• 1,3-BENZODIOXOLE-5-CARBOTHIOAMIDE
• 1-BENZYL-3-(TERT-BUTYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID