4-BROMO-1-PHENYL-1H-PYRAZOLE Chemical Properties

Melting point:

78-79 °C

Boiling point:

296.2±13.0 °C(Predicted)

Density 

1.50±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

-1.34±0.10(Predicted)

color 

Brown

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933199090

4-BROMO-1-PHENYL-1H-PYRAZOLE Usage And Synthesis

Uses

4-Bromo-1-phenylpyrazole is used to prepare canagliflozin aryl C-glucoside with thiophene ring as sodium-dependent glucose co-transporter 2 (SGLT2) inhibitor for treatment of type 2 diabetes mellitus.

Synthesis

Example 29A Synthesis of 4-bromo-1-phenyl-1H-pyrazole: 1-phenylpyrazole (Aldrich, 1 g, 6.94 mmol) was dissolved in 10 mL of acetic acid, followed by the addition of 1.1 g of bromine (Fisher, 6.94 mmol) to a 10 mL solution of acetic acid. The reaction mixture was transferred to a pressure tube and the reaction was heated at 100 °C for 8 hours. After the reaction was completed, it was cooled to room temperature and the reaction solution was slowly poured into a 500 mL beaker containing ice and water and saturated aqueous NaHCO3 solution was added dropwise until the acetic acid was completely neutralized. The organic layer was separated by adding 50 mL of ethyl acetate (EtOAc) for extraction. The aqueous layer was then extracted with 2 x 15 mL of ethyl acetate, the organic phases were combined and dried with anhydrous Na2SO4. The organic phase was concentrated under reduced pressure to obtain the crude product. Purification by fast column chromatography (silica gel, 5:0 to 5:5 gradient elution of hexane-ethyl acetate) afforded 1.5 g of the target compound 4-bromo-1-phenyl-1H-pyrazole (6.72 mmol, 97% yield). Mass spectrum (DCI/NH3) m/z 223,225 (M+H)+.

References

[1] Chemistry - A European Journal, 2015, vol. 21, # 34, p. 11976 - 11979
[2] Patent: US2005/65178, 2005, A1. Location in patent: Page/Page column 31
[3] Patent: US2005/101602, 2005, A1. Location in patent: Page/Page column 68
[4] RSC Advances, 2016, vol. 6, # 93, p. 90031 - 90034
[5] Tetrahedron Letters, 2007, vol. 48, # 26, p. 4595 - 4599

4-BROMO-1-PHENYL-1H-PYRAZOLE(15115-52-3)Related Product Information

• 4-BROMO-1-PHENYL-1H-PYRAZOLE
• 4-BROMO-5-METHYL-1-PHENYL-1H-PYRAZOLE
• 5-Amino-4-bromo-3-phenyl-1H-pyrazole,5-Amino-4-bromo-3-phenyl-1H-pyrazole 95+%,3-Amino-4-bromo-5-phenyl-1H-pyrazole, 96%
• 1-[4-(BROMOMETHYL)PHENYL]-1H-PYRAZOLE
• 4-BROMO-3,5-DIMETHYL-1-PHENYL-1H-PYRAZOLE
• 3,4,5-TRIBROMO-1-(4-NITROPHENYL)-1H-PYRAZOLE
• 4-BROMO-3-PHENYL-1H-PYRAZOLE
• 4-BROMO-5-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE
• N-ALLYL-4-BROMO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-5-CARBOXAMIDE
• 2-([4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)ANILINO]METHYLIDENE)MALONONITRILE
• 4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)ANILINE
• N-(2-FLUOROBENZOYL)-N'-[4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)PHENYL]UREA
• DIETHYL 2-([4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)ANILINO]METHYLIDENE)MALONATE
• N-(4-CHLOROPHENYL)-N'-[4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)PHENYL]UREA
• N-(2,6-DICHLOROBENZOYL)-N'-[4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)PHENYL]UREA
• N1-[4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)PHENYL]-4-CHLOROBENZAMIDE
• N1-[4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)PHENYL]-4-CHLOROBENZENE-1-SULFONAMIDE
• N,N-DIMETHYL-N'-[4-(3,4,5-TRIBROMO-1H-PYRAZOL-1-YL)PHENYL]IMINOFORMAMIDE