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

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 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1668604
ChemSpider	21105878 Y
ECHA InfoCard	100.005.248
EC Number	205-771-9
PubChem CID	9016
RTECS number	CZ6650000
UNII	24WC6T6X0G Y
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[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]
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)[1]
Autoignition temperature	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). N verify (what is YN ?) 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.^{[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.