1,4-Dimethoxybenzene

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.[3]

1,4-Dimethoxybenzene
1,4-Dimethoxybenzene molecule
Names
Preferred IUPAC name
1,4-Dimethoxybenzene
Other names
Hydroquinone dimethyl ether; p-Methoxyanisole; Dimethyl ether hydroquinone; USAF AN-9; Dimethylhydroquinone ether; Quinol dimethyl ether; p-Dimethoxybenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.248
EC Number
  • 205-771-9
RTECS number
  • CZ6650000
UNII
  • InChI=1S/C8H10O2/c1-9-7-3-5-8(10-2)6-4-7/h3-6H,1-2H3
    Key: OHBQPCCCRFSCAX-UHFFFAOYSA-N
  • COc1ccc(OC)cc1
Properties
C8H10O2
Molar mass 138.166 g·mol−1
Appearance White crystals
Odor sweet, nut-like
Density 1.035 g/cm3[1]
Melting point 54 to 56 °C (129 to 133 °F; 327 to 329 K)[2]
Boiling point 212.6 °C (414.7 °F; 485.8 K)[2]
Slightly soluble
Solubility very soluble in ether, benzene
soluble in acetone
log P 2.03
-86.65·10−6 cm3/mol
Viscosity 1.04 cP at 65 °C
Structure
Planar
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 94 °C (201 °F; 367 K)[1]
795 °C (1,463 °F; 1,068 K)[2]
Explosive limits 1.2-56%
Related compounds
Related compounds
 1,2-Dimethoxybenzene; 1,3-Dimethoxybenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Occurrence

It occurs naturally in willow (Salix), tea, hyacinth, zucchini (Cucurbita pepo).[3] It appears to attract bees as it has a powerful response in their antenna.[4] 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.[5]

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.[3]

It is an intermediate in synthesis of organic compounds, including pharmaceuticals such as methoxamine and butaxamine.

Niche uses

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

References
  1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. at Sigma-Aldrich
  3. 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. doi:10.1002/14356007.a11_141
  4. 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. doi:10.1111/boj.12183
  5. 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. doi:10.1590/s0102-695x2011005000030.
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