1,4-Dimethoxybenzene

Last updated
1,4-Dimethoxybenzene
P-Dimethoxybenzene.svg
1,4-Dimethoxybenzene-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-771-9
PubChem CID
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
AppearanceWhite 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:
GHS-pictogram-exclam.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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.

Related Research Articles

<span class="mw-page-title-main">Willow</span> Salix, genus of trees

Willows, also called sallows and osiers, of the genus Salix, comprise around 350 species of typically deciduous trees and shrubs, found primarily on moist soils in cold and temperate regions.

Perfume is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Perfumes can be defined as substances that emit and diffuse a pleasant and fragrant odor. They consist of manmade mixtures of aromatic chemicals and essential oils. The 1939 Nobel Laureate for Chemistry, Leopold Ružička stated in 1945 that "right from the earliest days of scientific chemistry up to the present time, perfumes have substantially contributed to the development of organic chemistry as regards methods, systematic classification, and theory."

<span class="mw-page-title-main">Musk</span> Class of aromatic substances used in perfumes

Musk is a class of aromatic substances commonly used as base notes in perfumery. They include glandular secretions from animals such as the musk deer, numerous plants emitting similar fragrances, and artificial substances with similar odors. Musk was a name originally given to a substance with a strong odor obtained from a gland of the musk deer. The substance has been used as a popular perfume fixative since ancient times and is one of the most expensive animal products in the world. The name originates from the Late Greek μόσχος 'moskhos', from Persian mushk and Sanskrit मुष्क muṣka derived from Proto-Indo-European noun múh₂s meaning "mouse". The deer gland was thought to resemble a scrotum. It is applied to various plants and animals of similar smell and has come to encompass a wide variety of aromatic substances with similar odors, despite their often differing chemical structures and molecular shapes.

Lactones are cyclic carboxylic esters are intramolecular esters derived from hydroxy carboxylic acids. They can be saturated or unsaturated. Some contain heteroatoms replacing one or more carbon atoms of the ring.

The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds", resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.

<span class="mw-page-title-main">Air freshener</span> Product used to mask odors

Air fresheners are products designed to reduce unwanted odors in indoor spaces, or to introduce pleasant fragrances, or both. They typically emit fragrance to mask odors, but may use other methods of action such as absorbing, bonding to, or chemically altering compounds in the air that produce smells, killing organisms that produce smells, or disrupting the sense of smell to reduce perception of unpleasant smells.

In organic chemistry, dihydroxybenzenes (benzenediols) are organic compounds in which two hydroxyl groups are substituted onto a benzene ring. These aromatic compounds are classed as phenols. There are three structural isomers: 1,2-dihydroxybenzene is commonly known as catechol, 1,3-dihydroxybenzene is commonly known as resorcinol, and 1,4-dihydroxybenzene is commonly known as hydroquinone.

<span class="mw-page-title-main">1,4-Dioxane</span> Chemical compound

1,4-Dioxane is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers are rarely encountered.

<span class="mw-page-title-main">Cyclopentanone</span> Chemical compound

Cyclopentanone is the organic compound with the formula (CH2)4CO. This cyclic ketone is a colorless volatile liquid.

<span class="mw-page-title-main">DABCO</span> Chemical compound

DABCO (1,4-diazabicyclo[2.2.2]octane), also known as triethylenediamine or TEDA, is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in polymerization and organic synthesis.

<span class="mw-page-title-main">1,4-Benzoquinone</span> Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

<span class="mw-page-title-main">Farnesol</span> Chemical compound

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions, it is a colorless liquid. It is hydrophobic, and thus insoluble in water, but miscible with oils.

<span class="mw-page-title-main">Dimethoxybenzene</span> Index of chemical compounds with the same name

In organic chemistry, dimethoxybenzene is an organic compound which is derived from benzene by substituting two methoxy groups. Dimethoxybenzene comes in three structural isomers:

<span class="mw-page-title-main">1,2-Dimethoxybenzene</span> Chemical compound

1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C6H4(OCH3)2. It is one of three isomers of dimethoxybenzene. It is a colorless liquid, with a pleasant odor and slight solubility in water. It is the dimethyl ether derived from pyrocatechol.

<span class="mw-page-title-main">1,4-Dihydropyridine</span> Chemical compound

1,4-Dihydropyridine (DHP) is an organic compound with the formula CH2(CH=CH)2NH. The parent compound is uncommon, but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are L-type calcium channel blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.

The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines by reductive amination in the presence of heat. The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the formamide variant, the temperature can be greater than 165 °C.

<span class="mw-page-title-main">Cyclohexenone</span> Chemical compound

Cyclohexenone is an organic compound which is a versatile intermediate used in the synthesis of a variety of chemical products such as pharmaceuticals and fragrances. It is colorless liquid, but commercial samples are often yellow.

Synthetic musks are a class of synthetic aroma compounds to emulate the scent of deer musk and other animal musks. Synthetic musks have a clean, smooth and sweet scent lacking the fecal notes of animal musks. They are used as flavorings and fixatives in cosmetics, detergents, perfumes and foods, supplying the base note of many perfume formulas. Most musk fragrance used in perfumery today is synthetic.

<span class="mw-page-title-main">Philip Kraft</span> German chemist (born 1969)

Philip Kraft is a German organic chemist. Since 1996 he has been employed by Givaudan, a leading Flavor and Fragrance company, where he designs captive odorants for use in perfumes. He has lectured at the University of Bern, the University of Zurich, and the ETH Zurich.

<span class="mw-page-title-main">1,3-Dimethoxybenzene</span> 1,3-Dimethoxybenzene is an organic compound. It is one of three isomers of dimethoxybenzene.

1,3-Dimethoxybenzene is an organic compound with the formula C6H4(OCH3)2. It is one of three isomers of dimethoxybenzene.

References

  1. 1 2 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 at Sigma-Aldrich
  3. 1 2 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 .