Methyl 1H-pyrrole-3-carboxylate Chemical Properties

Melting point:

85-89 °C

Boiling point:

284℃

Density 

1.184

Flash point:

126℃

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

15.42±0.50(Predicted)

color 

Off-white to light yellow

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C6H7NO2/c1-9-6(8)5-2-3-7-4-5/h2-4,7H,1H3

InChIKey

WLBNVSIQCFHAQB-UHFFFAOYSA-N

SMILES

N1C=CC(C(OC)=O)=C1

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37-60

WGK Germany 

3

HS Code 

29339900

Storage Class

11 - Combustible Solids

Methyl 1H-pyrrole-3-carboxylate Usage And Synthesis

Uses

Methyl pyrrole-3-carboxylate is used as an organic chemical synthesis intermediate.

Application

A solution of methyl 1H-pyrrole-3-carboxylate (4.48 g, 35.8 mmol) in THF (70 mL) was cooled to -78 °C, N-bromosuccinimide (6.30 g, 35.4 mmol) was added, pyridine (five drops) was added, and the mixture was left standing in a freezer (-20 °C) for 3 days. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted using EtOAc. The extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-EtOAc = 9/1-1/1) to give Methyl 5-bromo-1H-pyrrole-3-carboxylate (3.59 g, 49percent) as a pale-yellow solid.

Synthesis

The general procedure for the synthesis of methyl 3-pyrrolecarboxylate from 3-pyrrolecarboxylic acid and methanol was as follows: 1H-pyrrole-3-carboxylic acid (4.3 g, 38.7 mmol) was dissolved in methanol (40 mL) and cooled to 0-5 °C. 6N hydrochloric acid (9 mL) was added slowly, keeping the temperature at 0-5 °C. The reaction mixture was stirred at room temperature for 5 minutes and subsequently heated to reflux and kept overnight. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove most of the solvent. The concentrate was cooled to 0 °C and saturated sodium bicarbonate solution was slowly added to adjust the pH to about 7. The mixture was extracted with ethyl acetate, the organic layers were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to give methyl 1H-pyrrole-3-carboxylate as a brown solid (4 g, 83% yield). The product was confirmed by 1HNMR (400 MHz, CDCl3): δ 8.56 (broad single peak, 1H), 7.43 (single peak, 1H), 6.75 (single peak, 1H), 6.65 (single peak, 1H), 3.92 (single peak, 3H).LC-MS analysis: calculated exact mass 125.05, measured value m/z 126.2 [M + H]+.

Research

Pyrrole and Methyl 1H-Pyrrole-3-Carboxylate could be used to prepare the Soft Actuators by Electrochemical Copolymerization. In specific, a counter electrode (Ti), a reference electrode (Ag/AgCl), and a working electrode (Ti) were immersed into methyl benzoate solutions of 0.25 M of pyrrole and methyl 1-H pyrrole-3-carboxylate with 100:0, 98:2, 95:5, 80:20 mol ratios and 0.2 M N, N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl) imide. The thickness of the prepared films was measured to be approximately 100 μm using a micrometer. The PPy actuator was used as the working electrode in the 1 M LiTFSI aqueous electrolyte solutions. The Py copolymer film, fabricated from pyrrole solution containing 2 and 5 mol% of methyl 1-H pyrrole-3-carboxylate, showed a reduced actuating strain of approximately 2%, but the creep strain was reduced to less than 1%[1].

References

[1] Yamasaki, Jun et al. “Soft Actuators Prepared by Electrochemical Copolymerization of Pyrrole and Methyl 1H-Pyrrole-3-Carboxylate.” 2013. 0.

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