955-02-2

Basic information

• Product Name: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-
• CAS NO: 955-02-2
• Molecular Formula: C14H20N2O
• Molecular Weight: 232.326
• Mol File: 955-02-2.mol

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-(955-02-2)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-(955-02-2)

Safety Data

• Hazardous Substances Data: 955-02-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)is used as a reagent for the formation of carbon-carbon bonds through a reaction known as the [2+2] cycloaddition. This process is crucial in creating complex organic molecules and contributes to the development of new chemical compounds.
Used in Photolabile Protecting Groups:
In organic chemistry, 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)serves as a photolabile protecting group. This means that it can be selectively removed or activated using light, which is a valuable technique in controlling the reactivity of certain functional groups in a molecule. This application is particularly useful in the synthesis of sensitive compounds where traditional chemical methods may cause unwanted side reactions.
Safety Considerations:
Due to its diazo functional group, 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)can be hazardous and should be handled with caution in a laboratory setting. Proper safety measures, including the use of protective equipment and adherence to laboratory protocols, are essential when working with 2,5-Cyclohexadien-1-one, 4-diazo-2,6-bis(1,1-dimethylethyl)-.

Upstream product

• 94999-56-1 2,6-di-tert-butyl-1,4-benzoquinone 4-p-tosylhydrazone 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 950-58-3 2,6-di-tert-butyl-4-aminophenol 

Downstream Products

• 2455-14-3 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone 
• 128-38-1 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl 
• 5427-08-7 2,6-di-tert-butyl-4-cyclohexylphenol 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 19627-42-0 4-chloro-4-trichloromethyl-2,6-di-tert-butylcyclohexadienone 
• 82490-30-0 C₂₆H₃₀N₂O₃ 
• 2668-47-5 2,6-di(t-butyl)-4-phenylphenol 
• 107271-44-3 2,6-di-tert-butyl-4-(2,2,4,4-tetramethyl-3-thioxocyclobutylidene)cyclohexa-2,5-dienone 
• 107271-45-4 1,3-bis(3,5-di-tert-butyl-4-oxocyclohexa-1,5-dienylidene)-2,2,4,4-tetramethylcyclobutane 
• 107271-43-2 2,6-di-tert-butyl-4-(2,2,4,4-tetramethyl-3-oxocyclobutylidene)cyclohexa-2,5-dienone 
• 128-39-2 2,6-di-tert-butylphenol 
• 61613-02-3 4-allyloxy-2,6-di-t-butylphenol 
• 61613-01-2 5,7-Di-tert-butyl-1-hydroxymethyl-spiro[2.5]octa-4,7-dien-6-one 
• 106003-66-1 3-(4-hydroxy-3,5-di-tert-butylphenyl)-4-hydroxy-3-penten-2-one 

Relevant articles and documents

Chemoselective rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/propargyl sulfides

Here, we describe three types of rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/ propargyl sulfides. With Rh2(esp)2 as the catalyst, diazoquinones react with allyl/propargyl sulfides to form a sulfur ylide, which undergoes a chemoselective tautomerization/[2,3]-sigmatropic rearrangement reaction, a Doyle?Kirmse rearrangement/Cope rearrangement cascade reaction, or a Doyle?Kirmse rearrangement/elimination reaction, depending on the substituent of the sulfides. The protocol provides alkenyl and allenyl sulfides and multisubstituted phenols with moderate and high yields.

RhII-Catalyzed Intermolecular C?H Arylation of Aromatics with Diazo Quinones

We developed an efficient synthesis of biaryls by a dirhodium(II)-catalyzed aromatic C?H arylation with diazo quinones. The new biaryl synthesis can be performed under mild and neutral conditions and without directing group chelation assistance. The reaction tolerates various functionalities and is applicable to a broad range of aromatics. The regioselectivity of the C?H arylation was often high and predictable. The synthetic utility of the method was demonstrated by the late-stage modifications of a series of pharmaceuticals and functional materials as well as a short synthesis of a transthyretin amyloid inhibitor.

Quinone-type methanofullerene acceptors: Precursors for organic metals

We report details on the synthesis and electrochemistry of quinone-type methanofullerene derivatives in which, depending upon the substitution pattern on the cyclohexanedienone moiety, the reduction potential can be tuned, leading to novel fullerene deriv