PYRROLE-2-CARBONITRILE

Base Information

• Chemical Name: PYRROLE-2-CARBONITRILE
• CAS No.: 4513-94-4
• Molecular Formula: C5H4N2
• Molecular Weight: 92.1002
• Hs Code.: 29339900
• European Community (EC) Number: 627-592-9
• NSC Number: 106054
• UNII: 6D25BMC1PP
• DSSTox Substance ID: DTXSID30196400
• Nikkaji Number: J305.636H
• Wikidata: Q27264530
• Mol file: 4513-94-4.mol

Synonyms:Pyrrole-2-carbonitrile(6CI,7CI,8CI);2-Cyanopyrrole;NSC 106054;

Chemical Property of PYRROLE-2-CARBONITRILE

Chemical Property:

• Appearance/Colour: clear yellow to orange liquid
• Vapor Pressure: 0.0195mmHg at 25°C
• Melting Point: 92℃
• Refractive Index: 1.5475-1.5505
• Boiling Point: 252.3 °C at 760 mmHg
• PKA: 14.18±0.50(Predicted)
• Flash Point: 97.6 °C
• PSA: 39.58000
• Density: 1.16 g/cm³
• LogP: 0.88638
• Storage Temp.: Room temperature.
• Sensitive.: Air & Light Sensitive
• Solubility.: Miscible with benzene, dichloromethane, tertrahydrofuran, dimeth
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 92.037448136
• Heavy Atom Count: 7
• Complexity: 99.9

Purity/Quality:

99% ^*data from raw suppliers

Pyrrole-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-41-37/38
• Safety Statements: 36/37-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC(=C1)C#N
• Uses: Pyrrole-2-carbonitrile is a reagent that is used to prepare heteroaryl-azabicycloheptane which is a new class of triple re-uptake inhibitors.

Technology Process of PYRROLE-2-CARBONITRILE

There total 8 articles about PYRROLE-2-CARBONITRILE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

1H-pyrrole-2-carbaldehyde oxime (32597-34-5) + acetylene (74-86-2,25067-58-7) → 2-pyrrole aldehyde (1003-29-8,254729-95-8) + 1H-pyrrole-2-carbonitrile (4513-94-4) + 1-vinyl-1H-pyrrole-2-carbaldehyde (60576-11-6)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 70 ℃; for 0.166667h; under 15201 - 16721.1 Torr;

DOI:10.1016/j.tetlet.2008.10.104

Reference yield: 13.0%

2-pyrrole aldehyde (1003-29-8,254729-95-8) → 1H-pyrrole-2-carbonitrile (4513-94-4) + N-amino-1H-pyrrole-2-carbonitrile (159326-66-6)

Guidance literature:

With potassium hydroxide; hydroxylamine-O-sulfonic acid; In water; at 20 ℃; for 2.5h;

DOI:10.21577/0103-5053.20210037

Reference yield:

homophthalic anhydride (703-59-3) + 1H-pyrrole-2-carbaldehyde oxime (32597-34-5) → 1H-pyrrole-2-carbonitrile (4513-94-4) + Homophthalic acid (89-51-0)

Guidance literature:

at 110 ℃; for 24h;

DOI:10.1002/chem.201704389

upstream raw materials:

1-methyl-1H-imidazole

chloroform

2-pyrrole aldehyde

1-methyl-1H-pyrazole

Downstream raw materials:

1-(2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl)pyrrole-2-carbonitrile

S-2-phenylbutyraldehyde

(S)-2-methylbutanal

(R)-3,3-Dimethyl-2-phenyl-1-butanol

Refernces

• 1、 Amarante, Giovanni W.,Pereira, Vinicius R. D.,da Silva, Adilson D.,dos Santos, Juliana A.. "Klein's Remdesivir-nucleobase synthesis revisited: Chemoselective cyanation of pyrrol-2-carboxaldehyde". . p. 1391 - 1395. Retrieved 2021/06/14.
• 2、 Wentrup, Curt,Reisinger, Ales,Kvaskoff, David. "4-Pyridylnitrene and 2-pyrazinylcarbene". . p. 754 - 760. Retrieved 2013/06/27.