5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid Chemical Properties

Melting point:

283°C(lit.)

Boiling point:

374.9±42.0 °C(Predicted)

Density 

1.342±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

5.56±0.50(Predicted)

form 

Solid

color 

Beige

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C8H9NO3/c1-4-6(3-10)9-5(2)7(4)8(11)12/h3,9H,1-2H3,(H,11,12)

InChIKey

YCIHQDVIAISDPS-UHFFFAOYSA-N

SMILES

N1C(C=O)=C(C)C(C(O)=O)=C1C

CAS DataBase Reference

253870-02-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HS Code 

2933998090

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid Usage And Synthesis

Description

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid is an important organic intermediate to synthetize substituted pyrrole products.

Uses

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid is useful for the synthesis of 5-Bromo-7-azaindolin-2-one derivatives which possesses in vitro activity against selected cancer cell lines.

Uses

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid is a yellow crystalline substance, mainly used as pharmaceutical intermediates.

Application

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid can be used to prepare a drug carrier (cRGD-PEG-N＝CH-R6-Por (cPRP) triblock copolymer) for achieving highly efficient synergistic combined chemotherapy-photodynamic cancer therapy.

Synthesis

Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate (19.4 g, 100 mmol) was used as a raw material and dissolved in a solvent mixture of methanol (100 mL) and water (400 mL). A 5N KOH solution (200 mL) was slowly added under stirring conditions. The reaction mixture was heated to reflux and stirred continuously for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with 5N HCl solution to 3. Subsequently, the precipitate was collected by filtration and washed with distilled water. Finally, the resulting solid was dried under vacuum to afford the target product 2,4-dimethyl-5-formyl-1H-pyrrole-3-carboxylic acid (15.5 g, 94% yield) as a yellow-brown solid.

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 248 - 262
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 139 - 146
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3062 - 3065
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 14, p. 2782 - 2787
[5] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1116 - 1119

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid(253870-02-9)Related Product Information

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