Methyl 2-pyrrolecarboxylate Chemical Properties

Melting point:

74-78 °C(lit.)

Boiling point:

104-105 °C(Press: 9 Torr)

Density 

1.184±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Solid

pka

15.16±0.50(Predicted)

color 

Light Beige

Water Solubility 

Soluble in water.

InChI

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

InChIKey

VONGYFFEWFJHNP-UHFFFAOYSA-N

SMILES

N1C=CC=C1C(OC)=O

LogP

1.170

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

Methyl 2-pyrrolecarboxylate Usage And Synthesis

Description

Methyl 2-pyrrolecarboxylate is a crystalline or powder,It can be used as an organic reagent and can be obtained by the reaction of pyrrole with dimethyl carbonate.

Uses

Methyl 1H-Pyrrole-2-carboxylate is an intermediate used to prepare pyrrolyl aryl sulfones with activity against HIV-1. It is also used in the synthesis of diaryl pyrrolecarboxylates as combretastatin A-4/lamellarin T hybrids with anti-mitotic and cytotoxic activity.

Definition

ChEBI: Methyl 1H-pyrrole-2-carboxylate is a member of pyrroles.

Synthesis

50 mL of SOCl2 was slowly added dropwise to a solution of pyrrole-2-carboxylic acid (1) (16.65 g, 0.15 mol) dissolved in 10 mL of MeOH at 0 °C for a controlled time of 30 min. Subsequently, the reaction mixture was warmed up to 35 °C with continuous stirring for 24 hours. Upon completion of the reaction, the solvent was removed by vacuum evaporation, and the resulting residue was purified by column chromatography with the eluent being a mixed solvent of ethyl acetate/petroleum ether, which ultimately afforded Intermediate 2 as a white solid in 85% yield with a melting point of 72-73 °C.

References

[1] Canadian Journal of Chemistry, 2002, vol. 80, # 12, p. 1662 - 1667
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 7091 - 7100
[3] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 20, p. 2997 - 3003
[4] Patent: EP1386913, 2004, A1. Location in patent: Page 88
[5] Patent: EP986382, 2008, B1. Location in patent: Page/Page column 23

Methyl 2-pyrrolecarboxylate(1193-62-0)Related Product Information

• Pyrrole-2-carboxylic acid
• Ethyl pyrrole-2-carboxylate
• 3-HYDROXYINDOLE-2-CARBOXYLIC ACID METHYL ESTER
• ETHYL 5,6-DIMETHOXYINDOLE-2-CARBOXYLATE
• Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate
• Ethyl 5-Bromoindole-2-carboxylate
• ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE
• Ethyl 2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrolepropionate
• Diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate
• Ethyl 5-chloro-2-indolecarboxylate
• Ethyl 5-hydroxyindole-2-carboxylate
• ETHYL 4-ETHYL-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE
• Ethyl indole-2-carboxylate
• 3-ACETYL-2,4-DIMETHYL-5-CARBETHOXYPYRROLE
• ETHYL 5-METHYLINDOLE-2-CARBOXYLATE
• Methyl 1H-pyrrole-1-carboxylate 97%,METHYL 1H-PYRROLE-1-CARBOXYLATE
• 1H-Pyrrole-3-carboxylic acid, methyl ester (9CI)
• ETHYL 5-METHYL-1H-PYRROLE-2-CARBOXYLATE