484-73-1

Basic information

• Product Name: pyrocoll
• Synonyms: pyrocoll;4H,8H-3a,7a-Diaza-s-indacene-4,8-dione;5H,10H-Dipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione
• CAS NO: 484-73-1
• Molecular Formula: C₁₀H₆N₂O₂
• Molecular Weight: 186.17
• Mol File: 484-73-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 268°C
• Boiling Point: 320.64°C (rough estimate)
• Appearance: /
• Density: 1.3025 (rough estimate)
• Refractive Index: 1.5800 (estimate)
• CAS DataBase Reference: pyrocoll(CAS DataBase Reference)
• NIST Chemistry Reference: pyrocoll(484-73-1)
• EPA Substance Registry System: pyrocoll(484-73-1)

Safety Data

• Hazardous Substances Data: 484-73-1(Hazardous Substances Data)

Usage

Uses

Pyrocoll is a small secondary metabolite formed by the dimerisation of pyrrole-2-carboxylic acid and produced by many Streptomyces species. Pyrocoll is an important dereplication standard in discovery, displaying a highly distinctive UV spectrum. The biological activity of pyrocoll has received little attention.

Upstream product

• 4277-64-9 ethyl 1H-pyrrole-1-carboxylate 
• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 61985-23-7 methyl 1-imidazolecarboxylate 
• 634-97-9 pyrrole-2-carboxyl acid 

Downstream Products

• 634-97-9 pyrrole-2-carboxyl acid 

Relevant articles and documents

Flash flow pyrolysis: Mimicking flash vacuum pyrolysis in a high-temperature/high-pressure liquid-phase microreactor environment

Flash vacuum pyrolysis (FVP) is a gas-phase continuous-flow technique where a substrate is sublimed through a hot quartz tube under high vacuum at temperatures of 400-1100 °C. Thermal activation occurs mainly by molecule-wall collisions with contact times in the region of milliseconds. As a preparative method, FVP is used mainly to induce intramolecular high-temperature transformations leading to products that cannot easily be obtained by other methods. It is demonstrated herein that liquid-phase high-temperature/high- pressure (high-T/p) microreactor conditions (160-350 °C, 90-180 bar) employing near- or supercritical fluids as reaction media can mimic the results obtained using preparative gas-phase FVP protocols. The high-T/p liquid-phase "flash flow pyrolysis" (FFP) technique was applied to the thermolysis of Meldrum's acid derivatives, pyrrole-2,3-diones, and pyrrole-2-carboxylic esters, producing the expected target heterocycles in high yields with residence times between 10 s and 10 min. The exact control over flow rate (and thus residence time) using the liquid-phase FFP method allows a tuning of reaction selectivities not easily achievable using FVP. Since the solution-phase FFP method does not require the substrate to be volatile any more -a major limitation in classical FVP-the transformations become readily scalable, allowing higher productivities and space-time yields compared with gas-phase protocols. Differential scanning calorimetry measurements and extensive DFT calculations provided essential information on pyrolysis energy barriers and the involved reaction mechanisms. A correlation between computed activation energies and experimental gas-phase FVP (molecule-wall collisions) and liquid-phase FFP (molecule-molecule collisions) pyrolysis temperatures was derived.