1,4-Dimethoxybenzene

1,4-Dimethoxybenzene
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
CAS Number	150-78-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1668604;
ChemSpider	21105878 ;
ECHA InfoCard	100.005.248
EC Number	205-771-9;
PubChem CID	9016;
RTECS number	CZ6650000;
UNII	24WC6T6X0G ;
CompTox Dashboard (EPA)	DTXSID0022014 ;
	InChI InChI=1S/C8H10O2/c1-9-7-3-5-8(10-2)6-4-7/h3-6H,1-2H3 Key: OHBQPCCCRFSCAX-UHFFFAOYSA-N;
	SMILES COc1ccc(OC)cc1;
Properties
Chemical formula	C8H10O2
Molar mass	138.166 g·mol−1
Appearance	White crystals
Odor	sweet, nut-like
Density	1.035 g/cm3
Melting point	54 to 56 °C (129 to 133 °F; 327 to 329 K)
Boiling point	212.6 °C (414.7 °F; 485.8 K)
Solubility in water	Slightly soluble
Solubility	very soluble in ether, benzene ; soluble in acetone
log P	2.03
Magnetic susceptibility (χ)	-86.65·10−6 cm3/mol
Viscosity	1.04 cP at 65 °C
Structure
Molecular shape	Planar
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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)
Autoignition; temperature	795 °C (1,463 °F; 1,068 K)
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). verify (what is ?) Infobox references

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]

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.^{[citation needed]}

Niche uses

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

References

^ ^a ^b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ ^a ^b ^c [1] at Sigma-Aldrich
^ ^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. doi:10.1002/14356007.a11_141
^ 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
^ 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.

[GESTIS-1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[Aldrich-2] [1] at Sigma-Aldrich

[Ullmann-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

[Juergens-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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