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Methyl 1H-pyrrole-3-carboxylate

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Methyl 1H-pyrrole-3-carboxylate Basic information

Product Name:
Methyl 1H-pyrrole-3-carboxylate
Synonyms:
  • 1H-Pyrrole-3-carboxylic acid, methyl ester (9CI)
  • Methyl 1H-pyrrole-3-carboxylate
  • Methyl1H-pyrrole-3-carboxylat
  • Methyl 1H-pyrrole-3-carboxylate, 95+%
  • 1H-Pyrrole-3-carboxylic acid methyl ester
  • Methyl Pyrrole-3-carboxylate
  • 3-(Methoxycarbonyl)-1H-pyrrole
  • Methyl 3-pyrrolecarboxylate
CAS:
2703-17-5
MF:
C6H7NO2
MW:
125.13
Product Categories:
  • 6
  • Building Blocks
  • ACIDHALIDE
  • Heterocyclic Building Blocks
  • Pyrroles
Mol File:
2703-17-5.mol
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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
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
26-37-60
WGK Germany 
3
HS Code 
29339900
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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.

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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