ChemicalBook Product Catalog Chemical Reagents Organic reagents aliphatic ketones 2,5-Di-tert-butyl-1,4-benzoquinone

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

Product Name2,5-Di-tert-butyl-1,4-benzoquinone
CAS2460-77-7
MFC14H20O2
MW220.31
EINECS219-552-0
MOL File2460-77-7.mol

Chemical Properties

Melting point	152-154 °C (lit.)
Boiling point	321.25°C (rough estimate)
Density	1.0106 (rough estimate)
vapor pressure	0.241Pa at 20℃
refractive index	1.4970 (estimate)
storage temp.	Sealed in dry,Room Temperature
form	powder to crystal
color	White to Yellow to Orange
Water Solubility	18.716mg/L at 25℃
BRN	2047945
InChI	1S/C14H20O2/c1-13(2,3)9-7-12(16)10(8-11(9)15)14(4,5)6/h7-8H,1-6H3
InChIKey	ZZYASVWWDLJXIM-UHFFFAOYSA-N
SMILES	CC(C)(C)C1=CC(=O)C(=CC1=O)C(C)(C)C
LogP	5.2 at 25℃
CAS DataBase Reference	2460-77-7(CAS DataBase Reference)
EPA Substance Registry System	2,5-Cyclohexadiene-1,4-dione, 2,5-bis(1,1-dimethylethyl)- (2460-77-7)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
RTECS	GU5140000
TSCA	TSCA listed
HS Code	29146990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Hazardous Substances Data	2460-77-7(Hazardous Substances Data)

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

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

Flammability and Explosibility

Flammable

Synthesis

88-58-4

2460-77-7

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

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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