2,5-Di-tert-butyl-1,4-benzoquinone

Chemical Properties

Yellow to golden crystalline powder

Uses

2,5-Di-tert-butyl-1,4-benzoquinone (DTBBQ) is an 2,5-disubstituted quinone. It is an antibacterial compound. It has been isolated from marine Streptomyces sp. VITVSK1. Pressure dependance on the intramolecular and intermolecular migration rates of Na⁺ and K⁺ in a 2,5-di-tert-butyl-1,4-benzoquinone ion pair have been evaluated by using a high-pressure EPR technique.

Definition

ChEBI: 2,5-di-tert-Butyl-1,4-benzoquinone is a member of p-quinones and a member of benzoquinones.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4545, 1981 DOI: 10.1021/jo00335a045
Synthetic Communications, 10, p. 615, 1980 DOI: 10.1080/00397918008063598
Tetrahedron Letters, 35, p. 5083, 1994 DOI: 10.1016/S0040-4039(00)73327-2

General Description

2,5-Di-tert-butyl-1,4-benzoquinone (DTBBQ) is an 2,5-disubstituted quinone. It is an antibacterial compound. It has been isolated from marine Streptomyces sp. VITVSK1. Pressure dependance on the intramolecular and intermolecular migration rates of Na⁺ and K⁺ in a 2,5-di-tert-butyl-1,4-benzoquinone ion pair have been evaluated by using a high-pressure EPR technique.

Flammability and Explosibility

Flammable

Synthesis

At 0 °C, 2,5-di-tert-butylhydroquinone (0.34 mmol) was dissolved in THF (1.0 mL) with Catalyst 2a (1.98 mg, 0.0034 mmol), and 30% aqueous H2O2 (50.0 mL, 0.44 mmol) was slowly added. The reaction mixture was stirred at 0 °C until the raw material was completely converted to 2,5-di-tert-butyl-1,4-benzoquinone. Upon completion of the reaction, the product was extracted with ether or dichloromethane, and the organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the target compound 2,5-di-tert-butyl-1,4-benzoquinone. It is worth noting that the resulting product usually has high purity and can meet the requirements for subsequent use without further purification by column chromatography.

References

[1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 1, p. 336 - 338
[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 7, p. 1445 - 1453
[3] Synthesis, 2012, vol. 44, # 8, p. 1183 - 1189
[4] Tetrahedron, 1987, vol. 43, # 17, p. 3963 - 3974
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2970 - 2973