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.

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
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). N verify (what is YN ?) Infobox references

Occurrence

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

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.

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.