5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole Chemical Properties

Melting point:

239-243 °C(lit.)

Boiling point:

303.5±52.0 °C(Predicted)

Density 

1.52±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

9.77±0.30(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C8H6F2N2OS/c9-7(10)13-4-1-2-5-6(3-4)12-8(14)11-5/h1-3,7H,(H2,11,12,14)

InChIKey

HJMVPNAZPFZXCP-UHFFFAOYSA-N

SMILES

C1(=S)NC2=CC=C(OC(F)F)C=C2N1

CAS DataBase Reference

97963-62-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

Pantoprazole EP Impurity C. Pantoprazole USP Related Compound C.

General Description

5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole may be used in the synthesis of pantoprazole, a drug for treating gastroesophageal reflux disease and gastrointestinal disorders.

Synthesis

In a four-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer, the alkaline solution was prepared: 6.6 g of sodium carbonate was dissolved in 20 g of tap water, stirred until completely dissolved, cooled slightly, and then 34.8 g of 4-(difluoromethoxy)benzene-1,2-diamine was added, stirring was continued for 20 minutes. The reaction mixture was heated to 30°C and 20 g of carbon disulfide was slowly added dropwise, controlling the dropwise temperature at 25-35°C. After the dropwise addition was completed, the temperature was raised to 30-40°C and the condensation reaction was maintained at this temperature for 6 hours. Subsequently, continue heating to 60-70°C and maintain this temperature for cyclization for 6 hours. After the reaction was completed, activated carbon was added for decolorization. The pH of the filtrate was adjusted to 5-6 with sulfuric acid, and after filtration, washing and drying, 33.2 g of 5-difluoromethoxy-2-mercapto-1H-benzimidazole was obtained in 95.4% yield (based on 4-(difluoromethoxy)benzene-1,2-diamine).

References

[1] Patent: CN103539746, 2016, B. Location in patent: Paragraph 0037; 0038
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4161 - 4167

5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole(97963-62-7)Related Product Information

• PANTOPRAZOLE SULPHONE SODIUM SALT
• (Trifluoromethoxy)benzene
• Benzimidazole
• 2-Mercaptobenzimidazole
• 4-(Trifluoromethoxy)aniline
• Phenformin
• 5-Difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]thio}-1H-benzimidazole
• 2-(Trifluoromethoxy)aniline
• tert-Butyl 4-(4-nitropyridin-3-yl)piperazine-1-carboxylate
• 5-Methyl-3,4-diphenylisoxazole
• 4-(5-methyl-4-phenylisoxazol-3-yl)benzenesulfonamide
• Parecoxib Impurity H
• Parecoxib Impurity 16
• Parecoxib Impurity 18
• Parecoxib Impurity 20
• Parecoxib Impurity 14
• Parecoxib Impurity 16
• Parecoxib Impurity 13