2,6-DIMETHOXY-1,4-BENZOQUINONE

2,6-DIMETHOXY-1,4-BENZOQUINONE Basic information
Product Name:2,6-DIMETHOXY-1,4-BENZOQUINONE
Synonyms:2,6-DIMETHOXY-1,4-BENZOQUINONE;2,6-DIMETHOXY-P-QUINONE;2,6-DIMETHOXY-P-BENZOQUINONE;2,6-DIMETHOXYBENZOQUINONE;2,6-DIMETHOXY-PARA-BENZOQUINONE;2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy-;2,6-Dimethoxybenzo-1,4-quinone;2,6-dimethoxy-p-benzoquinon
CAS:530-55-2
MF:C8H8O4
MW:168.15
EINECS:208-484-7
Product Categories:Anthraquinones, Hydroquinones and Quinones;Benzoquinones
Mol File:530-55-2.mol
2,6-DIMETHOXY-1,4-BENZOQUINONE Structure
2,6-DIMETHOXY-1,4-BENZOQUINONE Chemical Properties
Melting point 253-257 °C (dec.) (lit.)
Boiling point 257.07°C (rough estimate)
density 1.3037 (rough estimate)
refractive index 1.5090 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility DMSO: soluble(lit.)
form Crystalline Powder
color Yellow
Merck 14,3225
BRN 2048182
Stability:Stable. Combustible. Incompatible with oxidizing agents.
CAS DataBase Reference530-55-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS DK4750000
HS Code 29146990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
2,6-DIMETHOXY-1,4-BENZOQUINONE Usage And Synthesis
Description2,6-DimethoXY-1A-benzoquinone is an allergen in more than 50 different plants and wood species, e.g., mahogany, macore~, sipo, wenge, oak, beech, elms, and poplar. With acamelin, it is one of the allergens of Acacia melanoxylon. Sensitization can occur in woodworkers such as carpenters, joiners and sawyers.
Chemical Propertiesyellow powder
Uses2,6-Dimethoxy-1,4-benzoquinone may be used in the synthesis of 2-aryl-3,5-dimethoxy-1,4-benzoquinone derivatives.
Synthesis Reference(s)Chemistry Letters, 16, p. 771, 1987
The Journal of Organic Chemistry, 45, p. 1596, 1980 DOI: 10.1021/jo01297a010
General Description2,6-Dimethoxy-1,4-benzoquinone (DBQ, 2,6-DMBQ, DMOBQ) is a 1,4-benzoquinone derivative. It is a wood allergen, has been reported to cause various skin and mucosal symptoms on exposure to wood dusts. It is formed as a product due to the activity of bacterial Azospirillum lipoferum laccase on phenolic compounds of the syringic type. DBQ is one of the components isolated from the rhizome of Gynura japonica with a potential to show anti-platelet aggregation activity in vitro. It is an anticancer agent, whose kinetics of cyclic redox transformation induced by ascorbate (AscH-) has been studied using the Clark electrode and ESR techniques. Its electrochemical reduction in acetonitrile has been studied.
Contact allergens2,6-Dimethoxy-1,4-benzoquinone is an allergen in more than 50 different plants and wood species, e.g., mahog- any, macore, sipo, wenge, oak, beech, elms, and poplar. With acamelin, it is one of the allergens of Acacia mel- anoxylon. Sensitization can occur in woodworkers such as carpenters, joiners, and sawyers.
Purification MethodsCrystallise the quinone from H2O or acetic acid. It sublimes at 175-180o/1mm. It has UV with max at 287 and 377nm (CHCl3). [Beilstein 8 H 385, 8 I 683, 8 II 433, 8 III 3354, 8 IV 2710,]
2,6-DIMETHOXY-1,4-BENZOQUINONE Preparation Products And Raw materials
Preparation ProductsScutellarein 4',7- dimethyl ether-->COERULIGNONE-->NSC49647
5-Chloro-6-[(6-cyclohexylhexyl)thio]-2,3-dimethoxy-1,4-benzoquinone METHOXYBENZOQUINONE 2,3-dimethoxy-p-benzoquinone ,2,3-DIMETHOXY-1,4-BENZOQUINONE 3,5-Dimethoxy-1,2-benzoquinone 2,5-Bis(1-aziridinyl)-3,6-dimethoxy-1,4-benzoquinone 1-METHOXY-1,4-CYCLOHEXADIENE 2-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienyl]-3-methyl-5,6-dimethoxy-1,4-benzoquinone 4-METHOXY-3-BUTEN-2-ONE UBIQUINONE –O (2,3-DIMETHOXY-5 METHYL BENZOQUINONE 3,6-dichloro-2,5-dimethoxy-4-benzoquinone,2,5-Dichloro-3,6-dimethoxy-p-benzoquinone,2,5-Dichloro-3,6-dimethoxy-1,4-benzoquinone 3,4-Dimethoxy-1,2-benzoquinone 2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexenyl]-3-methyl-5,6-dimethoxy-1,4-benzoquinone 2,5-Bis(4-hydroxyphenyl)-3,6-dimethoxy-1,4-benzoquinone 2-(3-Pyridinylmethyl)-3-methyl-5,6-dimethoxy-p-benzoquinone 1,3-Dihydroxyacetone 1,3-DIMETHOXYACETONE 2,5-dimethoxy-4-benzoquinon 4,5-DIMETHOXY-1,2-BENZOQUINONE,4,5-DIMETHOXY-O-BENZOQUINONE

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