Diazene, bis(4-ethynylphenyl)-

Base Information

• Chemical Name: Diazene, bis(4-ethynylphenyl)-
• CAS No.: 92792-15-9
• Molecular Formula: C16H10N2
• Molecular Weight: 230.269
• DSSTox Substance ID: DTXSID00476468
• Nikkaji Number: J1.714.592D

Synonyms:92792-15-9;Diazene, bis(4-ethynylphenyl)-;1,2-bis(4-ethynylphenyl)diazene;BIS(4-ETHYNYLPHENYL)DIAZENE;4,4'-diethynylazobenzene;SCHEMBL137428;YSZC1528;DTXSID00476468;(E)-1,2-Bis(4-ethynylphenyl)diazene;(1E)-1,2-bis(4-ethynylphenyl)-diazene;CS-0170526;10.14272/UWRWLWRXCLCEAL-ISLYRVAYSA-N;10.14272/UWRWLWRXCLCEAL-ISLYRVAYSA-N.1;doi:10.14272/UWRWLWRXCLCEAL-ISLYRVAYSA-N;doi:10.14272/UWRWLWRXCLCEAL-ISLYRVAYSA-N.1;J-500155

Chemical Property of Diazene, bis(4-ethynylphenyl)-

Chemical Property:

• Boiling Point: 376.2±27.0 °C(Predicted)
• PSA: 24.72000
• Density: 0.95±0.1 g/cm3(Predicted)
• LogP: 4.06460
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 230.084398327
• Heavy Atom Count: 18
• Complexity: 338

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CC=C(C=C1)N=NC2=CC=C(C=C2)C#C

Technology Process of Diazene, bis(4-ethynylphenyl)-

There total 3 articles about Diazene, bis(4-ethynylphenyl)- 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: 88.0%

4-Ethynylaniline (14235-81-5) → 1,2-bis(4-ethynylphenyl)diazene (92792-15-9)

Guidance literature:

4-Ethynylaniline; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.0833333h;

With N-chloro-succinimide; In dichloromethane; at -78 ℃; for 0.166667h;

DOI:10.1021/acs.joc.7b01530

Reference yield:

(4-Nitrophenyl)acetylene (937-31-5) → 1,2-bis(4-ethynylphenyl)diazene (92792-15-9) + 4-ethylnitrobenzene (100-12-9,94234-68-1,34527-20-3) + 4-vinyl benzylamine (1520-21-4,25086-42-4) + 4-Ethynylaniline (14235-81-5) + 1,2-bis(4-ethynylphenyl)hydrazine + 4-aminoethylbenzene (589-16-2)

Guidance literature:

With sodium tetrahydroborate; In water; at 20 ℃;

DOI:10.1002/cctc.201700776

Reference yield:

bis-(4-iodo-phenyl)-diazene (1601-97-4,21650-53-3) → 1,2-bis(4-ethynylphenyl)diazene (92792-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(l) iodide; palladium diacetate; triphenylphosphine; diisopropylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique

1.2: Reflux; Inert atmosphere; Schlenk technique

2.1: potassium hydroxide / tetrahydrofuran; methanol; water / 2 h / 20 °C / Inert atmosphere; Schlenk technique

With copper(l) iodide; palladium diacetate; diisopropylamine; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; methanol; water;

DOI:10.1021/acs.inorgchem.6b01509

upstream raw materials:

bis-(4-iodo-phenyl)-diazene

4-Ethynylaniline

(4-Nitrophenyl)acetylene

Downstream raw materials:

[(Au(P(C₆H₅)3))2(CCC₆H₄N₂C₆H₄CC)]

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