4024-72-0

Basic information

• Product Name: 2-diazoquinone
• Synonyms: 2-diazoquinone
• CAS NO: 4024-72-0
• Molecular Formula: C₆H₄N₂O
• Molecular Weight: 120.10876
• Mol File: 4024-72-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-diazoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-diazoquinone(4024-72-0)
• EPA Substance Registry System: 2-diazoquinone(4024-72-0)

Safety Data

• Hazardous Substances Data: 4024-72-0(Hazardous Substances Data)

Usage

General Description

2-diazoquinone is a diazo compound, which is an organic compound containing two linked nitrogen atoms. This particular chemical is a diazo derivative of quinone, which is a class of organic compounds with a cyclohexadienedione structure. 2-diazoquinone is a yellow to orange solid that is used in organic synthesis as a reagent for the preparation of diazo compounds. It is known for its ability to undergo diazo coupling reactions, which makes it an important building block in the synthesis of various organic compounds and pharmaceuticals. Additionally, 2-diazoquinone is a potentially hazardous compound and should be handled with caution due to its inherent instability and reactivity.

InChI:InChI=1/C6H4N2O2/c7-8-5-3-4(9)1-2-6(5)10/h1-2H,3H2

Upstream product

• 19183-06-3 2-hydroxyphenyldiazonium chloride 
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Downstream Products

• 273-59-6 aza-benzoxazole 
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• 45467-78-5 cyclohexene oxide 

Relevant articles and documents

Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters

A transition-metal-free C(sp2)?C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.

An efficient procedure for the synthesis of crystalline aryldiazonium trifluoroacetates - Synthetic applications

We have developed a very mild procedure for the synthesis of crystalline aryldiazonium trifluoroacetate salts in high yields under anhydrous conditions. Over thirty mono- or polyfunctional aniline derivatives have been diazotized by this method, including water- and acid-sensitive substrates. The o- and p-hydroxyaryldiazonium salts, derived from the corresponding anilines, could be deprotonated by treatment with K2CO3 to yield pure diazoquinones. NMR and UV/Vis spectra have been recorded for all the synthesized salts; the data are in good agreement with the rather limited published data and constitute a first extensive report of 13C-NMR chemical shifts in diazonium salts. An excellent linear relationship emerged between Brown's substituent constants S+(p) and the 13C(ipso) chemical shifts. The diazonium salts obtained proved to be much more soluble in organic solvents than their tetrafluoroborate counterparts. They were tested in Pd-mediated coupling reactions of various carbon-carbon double bonds, and were found to give good yields within short reaction times under very mild conditions. We believe that diazonium trifluoroacetates represent a very attractive alternative to diazonium tetrafluoroborates.

1,2,3-Benzoxadiazol - Nachweis in Argon-Matrix und in Loesung

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