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 Reference

530-55-2(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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,6-DIMETHOXY-1,4-BENZOQUINONE Usage And Synthesis

Description

2,6-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 Properties

yellow powder

Uses

2,6-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 Description

2,6-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 allergens

2,6-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 Methods

Crystallise 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(530-55-2)Related Product Information

• 2,5-dimethoxy-4-benzoquinon
• 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-Methyl-4,5-dimethoxy-p-benzoquinone
• 1,4-Benzoquinone
• 1,3-Dihydroxyacetone
• METHOXYBENZOQUINONE
• 2,6-DIMETHOXY-1,4-BENZOQUINONE
• 1-METHOXY-1,4-CYCLOHEXADIENE
• 4-METHOXY-3-BUTEN-2-ONE
• 2,3-dimethoxy-p-benzoquinone ,2,3-DIMETHOXY-1,4-BENZOQUINONE
• 4,5-DIMETHOXY-1,2-BENZOQUINONE,4,5-DIMETHOXY-O-BENZOQUINONE
• 1,3-DIMETHOXYACETONE
• 3,5-Dimethoxy-1,2-benzoquinone
• 2-(3-Pyridinylmethyl)-3-methyl-5,6-dimethoxy-p-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
• 2,5-Bis(4-hydroxyphenyl)-3,6-dimethoxy-1,4-benzoquinone
• 5-Chloro-6-[(6-cyclohexylhexyl)thio]-2,3-dimethoxy-1,4-benzoquinone