3-Pyridinecarbonitrile,6-(2-propenyl)-(9CI)

Base Information

• Chemical Name: 3-Pyridinecarbonitrile,6-(2-propenyl)-(9CI)
• CAS No.: 219727-44-3
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.176
• Mol file: 219727-44-3.mol

Synonyms:3-Pyridinecarbonitrile,6-(2-propenyl)- (9CI); 6-Allylnicotinonitrile

Chemical Property of 3-Pyridinecarbonitrile,6-(2-propenyl)-(9CI)

Chemical Property:

• PSA: 36.68000
• LogP: 1.68178

Purity/Quality:

99%min ^*data from raw suppliers

6-Allylnicotinonitrile 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Pyridinecarbonitrile,6-(2-propenyl)-(9CI)

There total 5 articles about 3-Pyridinecarbonitrile,6-(2-propenyl)-(9CI) 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: 50.0%

allyl bromide (106-95-6) + 5-cyano-2-iodopyridine (289470-22-0) → 6-(prop-2-en-1-yl)pyridine-3-carbonitrile (219727-44-3)

Guidance literature:

5-cyano-2-iodopyridine; With isopropylmagnesium bromide; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

allyl bromide; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1021/jo000235t

Reference yield:

6-chloronicotinonitrile (33252-28-7) + allyltributylstanane (24850-33-7) → 6-(prop-2-en-1-yl)pyridine-3-carbonitrile (219727-44-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 90 ℃; for 3h;

Reference yield:

6-Chloro-3-pyridinecarboxylic acid (5326-23-8) → 6-(prop-2-en-1-yl)pyridine-3-carbonitrile (219727-44-3)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 0 - 25 °C

2: ammonia / water / 0.5 h / 0 °C

3: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 2 h / 0 °C

4: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 3 h / 90 °C

With bis-triphenylphosphine-palladium(II) chloride; 1,3,5-trichloro-2,4,6-triazine; oxalyl dichloride; ammonia; N,N-dimethyl-formamide; In dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

allyl bromide

5-cyano-2-iodopyridine

6-Chloro-3-pyridinecarboxylic acid

6-Chloronicotinoyl chloride

Downstream raw materials:

6-(2-hydroxyethyl)pyridine-3-carbonitrile

Refernces

• 1、 Abarbri, Mohamed,Thibonnet, Jerome,Berillon, Laurent,Dehmel, Florian,Rottlaender, Mario,Knochel, Paul. "Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange". . p. 4618 - 4634. Retrieved 2007/10/03.