937-37-1

Basic information

• Product Name: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethyl-
• CAS NO: 937-37-1
• Molecular Formula: C8H8N2O
• Molecular Weight: 148.164
• Mol File: 937-37-1.mol

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethyl-(937-37-1)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethyl-(937-37-1)

Safety Data

• Hazardous Substances Data: 937-37-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethylis used as a reagent in organic synthesis for the generation of free radicals. Its diazo group allows for the formation of radicals that can initiate various chemical reactions, making it a useful intermediate in the synthesis of complex organic molecules.
Used in Metal-Catalyzed Reactions:
In the field of catalysis, 2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethylis utilized in metal-catalyzed reactions. Its diazo group can coordinate with metal centers, facilitating the activation of substrates and promoting selective transformations. This property makes it a valuable component in the development of new catalytic processes.
Used in Pharmaceutical Industry:
2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethylis used as a building block in the synthesis of pharmaceutical compounds. Its unique reactivity and the ability to generate radicals can be harnessed to construct novel drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethylis employed as a precursor for the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and versatility enable the development of new active ingredients with improved efficacy and selectivity.
Used in Materials Science:
2,5-Cyclohexadien-1-one, 4-diazo-2,6-dimethylis also used in materials science for the synthesis of novel materials with unique properties. Its ability to generate radicals and participate in metal-catalyzed reactions can be utilized to create new polymers, coatings, and other materials with specific characteristics for various applications.

Upstream product

• 14033-85-3 4-Amino-3,5-dimethylphenol hydrochloride 
• 5344-97-8 3,5-dimethyl-4-nitrophenol 
• 79426-35-0 2,6-dimethyl-1,4-benzoquinone 4-p-tosylhydrazone 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 

Downstream Products

• 81355-77-3 Acetic acid 4-(4-acetoxy-3,5-dimethyl-phenyl)-2,5-diphenyl-furan-3-yl ester 
• 21543-86-2 1,2-Dibenzoyl-5,7-dimethyl-spiro[2.5]octa-4,7-dien-6-one 

Relevant articles and documents

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.

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

Direct Observation of the Cyclopropene-Vinylcarbene Rearrangement. Matrix Isolation of Bicyclohexa-3,5-dien-2-ones

4-Oxocyclohexa-2,5-dienylidenes 4b-g have been generated in argon matrices at 10 K by visible-light irradiation of the corresponding quinone diazides 5.Carbenes 4 have been characterized by IR and UV-vis spectroscopy and by their characteristic thermal reaction with molecular oxygen.On irradiation into the longest-wavelength absorption (420-700 nm), carbenes 4c-g rearrange to give the highly strained bicyclohexa-3,5-dien-2-ones 3c-g while 4b is photostable under the same conditions.The photochemical 4 -> 3 rearrangement is completely reversible: infrared irradiation or visible light irradiation (λ > 470 nm) of the cyclopropenes 3 lead back to triplet carbenes 4 quantitatively.In addition, several of the 1,3-bridged cyclopropenes 3 undergo a thermal rearrangement to give carbenes 4.This indicates that the highly strained cyclopropenes 3 are thermodynamically less stable than the corresponding carbenes 4 and kinetically only stabilized by a shallow energy barrier.Even under the conditions of matrix isolation at cryogenic temperatures, cyclopropenes 3 are metastable compounds.