(E)-1-(4-Cyanophenyl)-2-diazonioethen-1-olate

Base Information

• Chemical Name: (E)-1-(4-Cyanophenyl)-2-diazonioethen-1-olate
• CAS No.: 3490-50-4
• Molecular Formula: C9H5 N3 O
• Molecular Weight: 171.158
• NSC Number: 254955
• DSSTox Substance ID: DTXSID40714715
• Nikkaji Number: J513.732B
• Mol file: 3490-50-4.mol

Synonyms:3490-50-4;4'-Cyano-alpha-diazoacetophenone;DTXSID40714715;4-(2-Diazo-acetyl)-benzonitrile;NSC254955;NSC-254955;(E)-1-(4-Cyanophenyl)-2-diazonioethen-1-olate

Chemical Property of (E)-1-(4-Cyanophenyl)-2-diazonioethen-1-olate

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 171.043261791
• Heavy Atom Count: 13
• Complexity: 287

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)C(=O)C=[N+]=[N-]

Technology Process of (E)-1-(4-Cyanophenyl)-2-diazonioethen-1-olate

There total 4 articles about (E)-1-(4-Cyanophenyl)-2-diazonioethen-1-olate 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: 83.0%

1,3-bis(4'-cyanophenyl)-1,3-propanedione → 2-diazo-1-(4-cyanophenyl)ethanone (3490-50-4)

Guidance literature:

With 4-toluenesulfonyl azide; methylamine; In ethanol; water; at 20 ℃; for 0.166667h;

DOI:10.1021/acs.joc.7b01187

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 4-cyanobenzoyl chlorIde (6068-72-0) → 2-diazo-1-(4-cyanophenyl)ethanone (3490-50-4)

Guidance literature:

Reference yield:

4-Cyanophenacyl bromide (20099-89-2) → 2-diazo-1-(4-cyanophenyl)ethanone (3490-50-4)

Guidance literature:

Multistep reaction; (i) N₂H₄, EtOH, (ii) MnO₂, CHCl₃;

upstream raw materials:

diazomethane

4-cyanobenzoyl chlorIde

4-Cyanophenacyl bromide

Downstream raw materials:

4-cyanophenylketene

4-chloroacetyl-benzoic acid

4-(chloroacetyl)benzoic acid chloride

N--L-phenylalanylpyrrolidine

Refernces

• 1、 Zhang, Jianlan,Chen, Wenwen,Huang, Dayun,Zeng, Xiaobao,Wang, Xinyan,Hu, Yuefei. "Tandem Synthesis of α-Diazoketones from 1,3-Diketones". . p. 9171 - 9174. Retrieved 2017/09/11.
• 2、 Goebel, Richard J.,Currie, Bruce L.,Bowers, Cyril Y.. "Potential Thyroliberin Affinity Labels. 1. Chloroacetyl-Substituted Phenylalanylpyrrolidines". . p. 366 - 370. Retrieved 2007/10/02.