1,4-Dimethoxybenzene

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1,4-Dimethoxybenzene
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance White crystals
Odor sweet, nut-like
Density 1.035 g/cm3[1]
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Solubility very soluble in ether, benzene
soluble in acetone
log P 2.03
Template:Longitem −86.65·10−6 cm3/mol
Viscosity 1.04 cP at 65 °C
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Template:Longitem 1,2-Dimethoxybenzene; 1,3-Dimethoxybenzene

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1,4-Dimethoxybenzene is an organic compound with the formula C6H4(OCH3)2. It is one of three isomers of dimethoxybenzene. It is a white solid with an intensely sweet floral odor. It is produced by several plant species.[2]

Occurrence

It occurs naturally in willow (Salix), tea, hyacinth, zucchini (Cucurbita pepo).[2] It appears to attract bees as it has a powerful response in their antenna.[3] In a study in mice, Iranian scientists identified 1,4-dimethoxybenzene as the major psychoactive chemical in musk willow (Salix aegyptiaca) by its ability to cause somnolescence and depressed activity.[4]

Preparation

It is produced by the methylation of hydroquinone using dimethylsulfate and an alkali.

Uses

1,4-Dimethoxybenzene is mainly used in perfumes and soaps.[2]

It is an intermediate in synthesis of organic compounds, including pharmaceuticals such as methoxamine and butaxamine.Script error: No such module "Unsubst".

Niche uses

It can be used as a developer in black and white film, and as a base in synthesizing catecholamines and phenethylamines.

References

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  1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and HealthScript error: No such module "TemplatePar". Script error: No such module "TemplatePar".
  2. a b c Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe and Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, 2003, Wiley-VCH. Script error: No such module "CS1 identifiers".
  3. Andreas Juergens, Ulrike Glueck, Gregor Aas and Stefan Doetterl "Diel fragrance pattern correlates with olfactory preferences of diurnal and nocturnal flower visitors in Salix caprea (Salicaceae)" in Botanical journal of the Linnean Society, 2014. Script error: No such module "CS1 identifiers".
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