DiMethyl 1H-pyrrole-2,4-dicarboxylate

DiMethyl 1H-pyrrole-2,4-dicarboxylate Property

Melting point:

125-126 °C(Solv: methanol (67-56-1))

Boiling point:

355.0±22.0 °C(Predicted)

Density 

1.276±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

13.58±0.50(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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.

DiMethyl 1H-pyrrole-2,4-dicarboxylate Chemical Properties,Usage,Production

Synthesis

Step A: To a solution of dioxane (200 mL) containing cuprous oxide (832 mg, 5.9 mmol) and 1,10-phenanthroline (2.14 g, 11.89 mmol) was added sequentially methyl propargylate (10 g, 118.9 mmol) and methyl isocyanoacetate (8.95 g, 98.6 mmol) under nitrogen protection. The reaction mixture was heated with stirring at 100 °C for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth pad to remove the solid catalyst. The filtrate was concentrated under reduced pressure to remove the solvent and the resulting crude product was purified by silica gel column chromatography using a solvent mixture of ethyl acetate-hexane as eluent. The target fraction was collected and concentrated to give dimethyl 1H-pyrrole-2,4-dicarboxylate (8.6 g, 48% yield) as a white solid. The product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 300 MHz, DMSO-d6): δ 12.55 (s, 1H), 7.60 (s, 1H), 7.10 (s, 1H), 3.92 (s, 3H), 3.90 (s, 3H); liquid chromatography-mass spectrometry (LC-MS, ESI) showed the molecular ion peak m/z 184 ([M+H] +).

References

[1] Patent: WO2010/2472, 2010, A1. Location in patent: Page/Page column 118-119