2940-63-8

Basic information

• Product Name: 3-TERT-BUTYL-5-METHOXY-1,2-QUINONE
• Synonyms: 2-dione,3-(1,1-dimethylethyl)-5-methoxy-5-cyclohexadiene-1;3-(1,1-dimethylethyl)-5-methoxy-3,5-cyclohexadiene-1,2-dione;3-tert-butylanisole-4,5-quinone;3-T-butyl-5-methoxy-O-benzoquinone;3-tert-butyl-5-methoxy-o-benzoquinone;3-tert-Butyl-5-methoxy-3,5-cyclohexadiene-1,2-dione;3-tert-butyl-5-methoxy-cyclohexa-3,5-diene-1,2-dione;3-tert-butyl-5-methoxycyclohexa-3,5-diene-1,2-dione
• CAS NO: 2940-63-8
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• Product Categories: Anthraquinones, Hydroquinones and Quinones
• Mol File: 2940-63-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 297.1 °C at 760 mmHg
• Flash Point: 128.5 °C
• Appearance: /
• Density: 1.08 g/cm³
• Vapor Pressure: 0.00138mmHg at 25°C
• Refractive Index: 1.495
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-TERT-BUTYL-5-METHOXY-1,2-QUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-TERT-BUTYL-5-METHOXY-1,2-QUINONE(2940-63-8)
• EPA Substance Registry System: 3-TERT-BUTYL-5-METHOXY-1,2-QUINONE(2940-63-8)

Safety Data

• Hazardous Substances Data: 2940-63-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14O3/c1-11(2,3)8-5-7(14-4)6-9(12)10(8)13/h5-6H,1-4H3

Upstream product

• 80284-15-7 3-tert-butyl-5-methoxy-pyrocatechol 
• 121-00-6 3-tert-Butyl-4-hydroxyanisole 
• 4857-76-5 2,3,5-triacetoxy-tert-butylbenzene 

Downstream Products

• 80284-15-7 3-tert-butyl-5-methoxy-pyrocatechol 
• 1947-08-6 1,2,5-Trimethoxy-3-t-butylbenzol 
• 2493-29-0 4,5-diacetoxy-3-tert-butylanisole 

Relevant articles and documents

IBS-catalyzed regioselective oxidation of phenols to 1,2-quinones with oxone

We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone as a co-oxidant under mild conditions. The reaction rate of IBS-catalyzed oxidation under nonaqueous conditions was further accelerated in the presence of an inorganic base such as potassium carbonate (K2CO3), a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate (nBu4NHSO4), and a dehydrating agent such as anhydrous sodium sulfate (Na2SO4).

Evaluation of the cytotoxic potential of catechols and quinones structurally related to butylated hydroxyanisole

The cytotoxicity of 2- and 3-butylated hydroxyanisole (BHA) and 18 related aromatic compounds has been determined employing cultured P388 and KB cells. The phenolic compounds, 3-BHA and 2-BHA, had moderately low cytotoxic activity. Their corresponding catechols had ED50 values that were much lower than those of the parent compounds. This substantial increase in the cytotoxic activity is attributed to the presence of the catechol group, which is known to undergo one-electron oxidation readily to give the corresponding semiquinone radical. Other related catechols had similar cytotoxic activity. In general, derivatization of the catechol functionality resulted in a decrease of the cytotoxic potential of the compounds. Monoacetylation or monomethylation of the catechols gave products that were less potent cytotoxic agents than the parent compounds. Further loss of activity was observed when both hydroxy groups of the catechol function were blocked. Substitution of a methoxy group in place of a hydrogen atom in these compounds resulted in a significant increase of cytotoxicity, whereas the replacement of a methoxy group with a methyl group reduced the cytotoxicity. The catechols and quinones derived from 2-BHA were more active when compared with those derived from 3-BHA. The t-butyl group adjacent to the catechol or quinone moiety in the 3-BHA derivatives appeared to exert a significant steric effect toward the cytotoxic potential of these compounds. These results suggest the potential use of o-quinones and catechols as cytotoxic and antitumor agents.