4-BROMOPYRROLE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

168-170°C

Boiling point:

393.0±27.0 °C(Predicted)

Density 

1.969±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder

pka

4.06±0.10(Predicted)

color 

light beige

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933998090

4-BROMOPYRROLE-2-CARBOXYLIC ACID Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-bromopyrrole-2-carboxylic acid from 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroacetophenone is as follows: a THF solution (5 mL) of 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroacetophenone (4.7 mmol) was prepared as described by Belanger et al. ( Tetrahedron Lett. 1979, 2505-2508). The solution was stirred at room temperature and 1 mL of a 10% aqueous NaOH (aq) solution was added and stirring was continued for 1 hour. Upon completion of the reaction, the solvent was removed under reduced pressure and the crude product was partitioned between water and ethyl acetate. Subsequently, the pH was adjusted to 5 with 10% aqueous HCl. The phases were separated and the aqueous layer was extracted again with ethyl acetate. The organic phases were combined and dried with magnesium sulfate. Evaporation of the solvent gave 4-bromo-1H-pyrrole-2-carboxylic acid as a solid, which could be used in the next reaction without further purification. Yield: 64%; LCMS (retention time): 2.74 min (Method B); MS (ES+) gave m/z: 191 and 193.

References

[1] Patent: WO2006/123257, 2006, A2. Location in patent: Page/Page column 63
[2] Patent: WO2007/107319, 2007, A1. Location in patent: Page/Page column 7-8

4-BROMOPYRROLE-2-CARBOXYLIC ACID(27746-02-7)Related Product Information

• 4-Bromopyrazole
• Pyrrole-2-carboxylic acid
• 4-Bromopyrazole-1-carboxylic acid tert-butyl ester
• Methyl 4-bromopyrrole-2-carboxylate
• 4-BROMOPYRROLE-2-CARBOXYLIC ACID
• METHYL 4-BROMO-1-METHYL-1H-PYRROLE-2-CARBOXYLATE
• METHYL 4,5-DIBROMO-1H-PYRROLE-2-CARBOXYLATE
• ETHYL 4-BROMO-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE
• 4-BROMO-1-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID
• 1-(tert-Butyl) 2-methyl 4-bromo-1H-pyrrole-1,2-dicarboxylate
• METHYL 4-BROMO-1-(PHENYLSULFONYL)-1H-PYRROLE-2-CARBOXYLATE
• 4,5-DIBROMO-1H-PYRROLE-2-CARBOXYLIC ACID
• 4-BROMO-PYRROLE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-ETHYL ESTER
• ETHYL 4-BROMO-1H-PYRROLE-2-CARBOXYLATE
• METHYL 4-BROMO-1-[(5-CHLORO-2-METHOXYPHENYL)SULFONYL]-1H-PYRROLE-2-CARBOXYLATE
• 4-bromo-5-(chlorosulfonyl)-1H-pyrrole-2-carboxylic acid
• SPECS AQ-776/42801554
• 4,5-DIBROMO-1-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID