4-diazo-2,5-cyclohexadienone

Base Information

• Chemical Name: 4-diazo-2,5-cyclohexadienone
• CAS No.: 89713-14-4
• Molecular Formula: C₆H₄N₂O
• Molecular Weight: 120.111
• Mol file: 89713-14-4.mol

Synonyms:

Chemical Property of 4-diazo-2,5-cyclohexadienone

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-diazo-2,5-cyclohexadienone

There total 16 articles about 4-diazo-2,5-cyclohexadienone 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: 75.0%

4-nitrobenzenediazonium tetrafluoroborate (456-27-9) + 4-nitro-benzenediazohydroxide, sodium salt (32352-96-8) → C6H4N3O2(1+)*C6H4N2O + 4-diazo-2,5-cyclohexadienone (89713-14-4,932-97-8,6925-01-5)

Guidance literature:

In dimethyl sulfoxide; Product distribution; Mechanism;

Reference yield: 54.0%

4-amino-phenol (123-30-8) → 4-diazo-2,5-cyclohexadienone (89713-14-4,932-97-8,6925-01-5)

Guidance literature:

4-amino-phenol; With hydrogenchloride; In ethanol; water; at 0 ℃; for 0.166667h;

With sodium nitrite; In ethanol; water; at 0 ℃; for 2.16667h;

DOI:10.1021/acs.orglett.0c03493

Reference yield: 23.0%

4-hydroxyphenyldiazonium chloride (1073-71-8,50909-74-5) → 4-diazo-2,5-cyclohexadienone (89713-14-4,932-97-8,6925-01-5)

Guidance literature:

With silver(l) oxide; In ethanol; at 0 ℃; for 2h; in the dark;

DOI:10.1002/hlca.19810640215

upstream raw materials:

4-oxocyclohexa-2,5-dienylidene carbene

p-chlorobenzenediazonium tetrafluoroborate

4-nitrobenzenediazonium tetrafluoroborate

4-nitro-benzenediazohydroxide, sodium salt

Downstream raw materials:

4-(prop-2-enyl)phenol

Refernces

• 1、 Zhang, Shang-Shi,Jiang, Chun-Yong,Wu, Jia-Qiang,Liu, Xu-Ge,Li, Qingjiang,Huang, Zhi-Shu,Li, Ding,Wang, Honggen. "Cp?Rh(iii) and Cp?Ir(iii)-catalysed redox-neutral C-H arylation with quinone diazides: quick and facile synthesis of arylated phenols". supporting information. p. 10240 - 10243. Retrieved 2015/06/22.
• 2、 Colas, Christophe,Goeldner, Maurice. "An efficient procedure for the synthesis of crystalline aryldiazonium trifluoroacetates - Synthetic applications". . p. 1357 - 1366. Retrieved 2007/10/03.