Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate Chemical Properties

Melting point:

122-123°C

Boiling point:

162°C/11mmHg(lit.)

Density 

1.1222 (rough estimate)

refractive index 

1.4680 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Soluble), Chloroform (Slightly), Methanol (Slightly)

pka

16.44±0.50(Predicted)

form 

Solid

color 

Red to Very Dark Red

λmax

258nm(EtOH)(lit.)

InChI

InChI=1S/C9H13NO2/c1-4-12-9(11)8-6(2)5-10-7(8)3/h5,10H,4H2,1-3H3

InChIKey

QWSFDUPEOPMXCV-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2199-51-1(CAS DataBase Reference)

NIST Chemistry Reference

2,4-Dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester(2199-51-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-45-22

Hazard Note 

Irritant

HS Code 

29337900

Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate Usage And Synthesis

Chemical Properties

White to light brown crystalline

Uses

2,4-Dimethyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester is used in the preparation of blue pyrrole dyes. 2,4-Dimethyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester is also used as an intermediate in the synthesis of receptor tyrosine kinase (RTK) inhibitors and their metabolites.

Uses

ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate is used in the preparation of blue pyrrole dyes. It is also used as an intermediate in the synt hesis of receptor tyrosine kinase (RTK) inhibitors and their metabolites.

Synthesis

Step (ii): Preparation of 2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester In a 10-liter four-necked round-bottomed flask equipped with a mechanical stirrer, thermometer casing, gas introduction tube, and air condenser, 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester (II) (1.5 kg, 5.6 mol) and isopropanol (4.5 L) were added and stirred at 25-30 °C. Concentrated hydrochloric acid (2.2 L) was added slowly through the addition funnel. After addition, the reaction mixture was warmed up to 45-50 °C and maintained at this temperature until complete cessation of gas release. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solution was cooled to 25-30 °C and quenched in an ice-water bath. The product was separated by filtration and dried at 50 °C. A dried product of 721.3 g was obtained with 77.3% yield and >96% HPLC purity.

References

[1] Synlett, 2010, # 17, p. 2561 - 2564
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3062 - 3065
[3] Journal of the American Chemical Society,
[4] Journal of the American Chemical Society, 2009, vol. 131, p. 8578 - 8586
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 139 - 146

Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate(2199-51-1)Related Product Information

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