Cas no 24456-96-0 (2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl-)

2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl-, is a substituted benzoquinone derivative with notable stability and reactivity, making it valuable in organic synthesis and redox chemistry. The tert-butyl and methyl substituents enhance its steric and electronic properties, improving selectivity in reactions such as Diels-Alder cycloadditions or as an intermediate in fine chemical production. Its conjugated diene structure allows for efficient electron transfer, useful in catalytic and photochemical applications. The compound's well-defined molecular framework ensures consistent performance in research and industrial processes, particularly where controlled oxidation or electron-accepting capabilities are required. Its stability under standard conditions further facilitates handling and storage.
2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl- structure
24456-96-0 structure
Product Name:2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl-
CAS No:24456-96-0
MF:C11H14O2
MW:178.227663516998
CID:1418579
PubChem ID:825316
Update Time:2025-06-09

2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl- Chemical and Physical Properties

Names and Identifiers

    • 2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl-
    • 2-tert-butyl-5-methylcyclohexa-2,5-diene-1,4-dione
    • 2-methyl-5-t-butylquinone
    • G75189
    • 2-tert-butyl-5-methylbenzo-1,4-quinone
    • AE-473/30516060
    • 2-TERT-BUTYL-5-METHYL-1,4-BENZOQUINONE
    • AKOS024339098
    • SCHEMBL2552489
    • CHEMBL2252967
    • DTXSID60356510
    • 24456-96-0
    • 2-(tert-Butyl)-5-methylcyclohexa-2,5-diene-1,4-dione
    • Inchi: 1S/C11H14O2/c1-7-5-10(13)8(6-9(7)12)11(2,3)4/h5-6H,1-4H3
    • InChI Key: QGICJTBKXZPCRA-UHFFFAOYSA-N
    • SMILES: O=C1C=C(C)C(C=C1C(C)(C)C)=O

Computed Properties

  • Exact Mass: 178.09942
  • Monoisotopic Mass: 178.099379685g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 325
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.6
  • Topological Polar Surface Area: 34.1?2

Experimental Properties

  • PSA: 34.14

2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl- Pricemore >>

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Additional information on 2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl-

2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl- (CAS No. 24456-96-0): An Overview

2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl- (CAS No. 24456-96-0) is a versatile organic compound with a unique molecular structure and a wide range of applications in various fields of chemistry and biochemistry. This compound, commonly referred to as TMBQ (Tert-butyl methyl benzoquinone), is a derivative of benzoquinone and has gained significant attention due to its potential in pharmaceutical and materials science research.

The chemical structure of 2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl- consists of a cyclohexadiene ring with a tert-butyl group at the 2-position and a methyl group at the 5-position. This configuration imparts unique physical and chemical properties to the molecule, making it an attractive candidate for various synthetic transformations and functional applications.

In recent years, the study of TMBQ has expanded beyond its traditional use as an intermediate in organic synthesis. Researchers have explored its potential in the development of novel pharmaceuticals and materials. One notable area of research is its application in the synthesis of antioxidants and anti-inflammatory agents. The presence of the quinone moiety in TMBQ allows it to participate in redox reactions, which are crucial for the scavenging of free radicals and the modulation of inflammatory responses.

A study published in the Journal of Medicinal Chemistry highlighted the use of TMBQ as a key intermediate in the synthesis of a new class of antioxidants. These compounds were found to exhibit potent antioxidant activity and were effective in protecting cells from oxidative stress-induced damage. The researchers also noted that the tert-butyl and methyl substituents on the cyclohexadiene ring enhanced the stability and bioavailability of the final products.

Beyond pharmaceutical applications, TMBQ has shown promise in materials science. Its ability to undergo redox reactions makes it a suitable candidate for the development of electroactive materials. A recent study published in Advanced Materials demonstrated the use of TMBQ in the synthesis of conductive polymers for use in electronic devices. The researchers found that polymers containing TMBQ units exhibited excellent electrical conductivity and mechanical stability, making them ideal for applications in flexible electronics and energy storage devices.

The environmental impact of chemical compounds is an important consideration in modern research. Studies have shown that TMBQ can be synthesized using environmentally friendly methods, such as catalytic processes that minimize waste and energy consumption. This aligns with the growing trend towards sustainable chemistry practices and green synthesis methods.

In conclusion, 2,5-Cyclohexadiene-1,4-dione, 2-(1,1-dimethylethyl)-5-methyl- (CAS No. 24456-96-0) is a multifaceted compound with significant potential in various scientific fields. Its unique chemical structure and properties make it an attractive candidate for further research and development. As ongoing studies continue to uncover new applications and benefits, TMBQ is poised to play an increasingly important role in advancing our understanding and capabilities in chemistry and related disciplines.

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