Methyl 1H-pyrrole-3-carboxylate Property

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

Risk Statements 

36/37/38

Safety Statements 

26-37-60

WGK Germany 

3

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

Methyl 1H-pyrrole-3-carboxylate Chemical Properties,Usage,Production

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.