1,4-Dimethoxybenzene

1,4-Dimethoxybenzene
IUPAC name 1,4-Dimethoxybenzene
Other names Hydroquinone dimethyl ether; p-Methoxyanisole; 2-Benzimidazolinone; Dimethyl ether hydroquinone; USAF AN-9; Dimethylhydroquinone ether; Quinol dimethyl ether; p-Dimethoxybenzene
Identifiers
CAS number	150-78-7 Y
ChemSpider	8666 Y
UNII	24WC6T6X0G Y
RTECS number	CZ6650000
Jmol-3D images	Image 1
SMILES COc1ccc(OC)cc1
Properties
Molecular formula	C8H10O2
Molar mass	138.16 g mol−1
Appearance	White crystals
Density	1.053 g/cm3[1]
Melting point	53-57 °C, 326-330 K, 127-135 °F ([1])
Boiling point	213 °C, 486 K, 415 °F ([1])
Solubility in water	Slightly soluble
Viscosity	1.04 cP at 65 °C
Structure
Molecular shape	Planar
Hazards
EU classification	Irritant (Xi)
R-phrases	R36 R37 R38
S-phrases	S26 S37 S39
Flash point	125 °C (257 °F)
Autoignition temperature	795 °C (1,463 °F)[1]
Related compounds
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Infobox references

1,4-Dimethoxybenzene is the para form of dimethoxybenzene, a volatile aromatic ether with a sweet floral odor. It occurs naturally in willow (Salix) and zucchini (Cucurbita pepo). It appears to attract bees as it has a powerful response in their antenna.

Uses

Dimethoxybenzene is useful as an intermediate in synthesis of pharmaceuticals as well as other organic molecules. It is used in some paints and as a diazo dye. Cosmetically it is used on greasy skin, and with sulfur to treat acne, or as a dandruff treatment. Because of its floral odor, it is useful in perfumes and flavors. It can be used as a developer in black and white film, and as a base in synthesizing catecholamines and phenethylamines.

DMB was identified as the major psychoactive chemical in musk willow.^[2]

References

1. ^ ^{a b c d} 1,4-Dimethoxybenzene at Sigma-Aldrich
2. ^ Isaac Karimi, Hossein Hayatgheybi, Tayebeh shamspur, Adem Kamalak, Mehrdad Pooyanmehr, Yaser Marandi (2011). "Chemical composition and effect of an essential oil of Salix aegyptiaca L. (Musk willow) in hypercholesterolemic rabbit model". Brazilian Journal of Pharmacognosy 21 (3): 407–414.