p-Diazoquinone

Base Information

• Chemical Name: p-Diazoquinone
• CAS No.: 932-97-8
• Molecular Formula: C₆H₄N₂O
• Molecular Weight: 120.111
• DSSTox Substance ID: DTXSID00918611
• Nikkaji Number: J455.967C,J101.080H
• Wikidata: Q82890792
• ChEMBL ID: CHEMBL303169
• Mol file: 932-97-8.mol

Synonyms:4-diazoquinone;p-diazoquinone

Chemical Property of p-Diazoquinone

Chemical Property:

• Melting Point: 86 - 87 °C (diethyl ether)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 54.46000
• Density: g/cm³
• LogP: 0.88136
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 120.032362755
• Heavy Atom Count: 9
• Complexity: 129

Purity/Quality:

99% ^*data from raw suppliers

4-DIAZO-2,5-CYCLOHEXADIEN-1-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of p-Diazoquinone

There total 16 articles about p-Diazoquinone 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-Ethoxyphenol

4'-methyl-biphenyl-4-ol

2'-methyl-[1,1'-biphenyl]-4-ol

4-Phenylphenol

Refernces

Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides

10.1021/acs.orglett.7b00869

The study presents a highly enantioselective and broadly applicable method for spirocyclopropanation reactions of para-quinone methides using Cinchona alkaloid-based chiral ammonium ylides. The primary objective was to develop a straightforward protocol for synthesizing the chiral spiro[2.5]octa-4,7-dien-6-one skeleton, a structural motif prevalent in biologically active molecules. Key chemicals included para-quinone methides as acceptors for cyclopropanation reactions, quinone diazides, and ammonium ylides, particularly those derived from Cinchona alkaloids. These chemicals served to facilitate the formation of chiral spirocyclopropanes, which are valuable intermediates in the synthesis of complex pharmaceutical targets and possess pharmacological properties. The study optimized reaction conditions and identified the best-suited chiral amine leaving group, leading to high yields and excellent stereoselectivities in the synthesis of chiral spiro[2.5]octa-4,7-dien-6-ones.