Indolizine-1-carbonitrile

Base Information

• Chemical Name: Indolizine-1-carbonitrile
• CAS No.: 3352-05-4
• Molecular Formula: C9H6N2
• Molecular Weight: 142.16
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50396041
• Nikkaji Number: J1.212.296I
• Wikidata: Q82196505
• Mol file: 3352-05-4.mol

Synonyms:Indolizine-1-carbonitrile;3352-05-4;1-Indolizinecarbonitrile;cyanoindolizine;SCHEMBL343454;DTXSID50396041;IKMSBSJONUMYEI-UHFFFAOYSA-N;CS-0242049;EN300-243853

Chemical Property of Indolizine-1-carbonitrile

Chemical Property:

• PSA: 28.20000
• LogP: 1.81098
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 142.053098200
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

95% ^*data from raw suppliers

1-Indolizinecarbonitrile 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2C=C1)C#N
• General Description: 1-Indolizinecarbonitrile is a cyano-substituted indolizine derivative characterized by its electron-accepting properties, which influence both its spectroscopic and reactivity profiles. The presence of the cyano group at the 1-position contributes to increased λmax values in UV spectra and deeper coloration compared to unsubstituted indolizines. 1-Indolizinecarbonitrile is synthesized via the Chichibabin method, demonstrating the broader reactivity of indolizines with electron-withdrawing substituents. However, unlike acetyl-substituted analogs, it does not undergo base-catalyzed rearrangement to indoles without additional electronegative substituents.

Technology Process of Indolizine-1-carbonitrile

There total 13 articles about Indolizine-1-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: 89.0%

1-cyanoindolizine-3-carboxylic acid (394212-97-6) → indolizine-1-carbonitrile (3352-05-4)

Guidance literature:

In methoxybenzene; for 24h; Heating;

DOI:10.1002/1099-0690(200110)2001:19<3705::AID-EJOC3705>3.0.CO;2-L

Reference yield: 84.0%

1-(carboxymethyl)pyridinium chloride (6266-23-5) + acrylonitrile (107-13-1,25014-41-9) → indolizine-1-carbonitrile (3352-05-4)

Guidance literature:

With manganese(IV) oxide; triethylamine; In toluene; at 90 ℃; for 2h;

DOI:10.1055/s-2000-8195

Reference yield: 71.0%

2-bromoacrylonitrile (920-34-3) + 1-[(benzotriazol-1-yl)methyl]pyridinium chloride (111198-06-2) → indolizine-1-carbonitrile (3352-05-4)

Guidance literature:

With sodium hydroxide; In acetonitrile; for 16h; Heating;

DOI:10.1021/jo9906936

upstream raw materials:

2-bromoacrylonitrile

1-[(benzotriazol-1-yl)methyl]pyridinium chloride

1-(carboxymethyl)pyridinium chloride

acrylonitrile

Downstream raw materials:

methyl 4-(1-cyanoindolizine-3-yl) benzoate

4-(1-Cyanoindolizine-3-yl)-2-hydroxybenzoic acid

4-(1-cyanoindolizine-3-yl)benzoica acid

methyl 4-(1-cyanoindolizine-3-yl)-2-methoxymethoxybenzoate

Refernces

STRUCTURE AND AMBIPHILIC REACTIVITY OF INDOLIZINES. 2. 8(6)-ACETYL- AND CYANOINDOLIZINES

10.1007/BF00663856

The research focuses on the synthesis and reactivity of 8(6)-acetyl- and cyanoindolizines. The purpose is to explore the effects of substituents on the structure and reactivity of indolizines, particularly those substituted in the pyridine ring, as this area has received little attention. The researchers used the Chichibabin method to synthesize these compounds from 2-methyl-3(5)-acetyl and cyanopyridines and α-bromoketones. Key chemicals used include 2-methyl-3-cyanopyridine, bromoacetone, and sodium bicarbonate. The study concludes that electron-acceptor substituents in positions 6 and 8 of the indolizine nucleus deepen the color and increase the λmax values in UV spectra, with the 8-isomers being more deeply colored than the 6-isomers. Additionally, the researchers attempted base-catalyzed rearrangement of acetylindolizines to indoles but found that the presence of a nitro-group or a similarly electronegative substituent is necessary for successful recyclization.