1,2-Dimethoxybenzene

Last updated
1,2-Dimethoxybenzene
Veratrole.svg
1,2-Dimethoxybenzene-3D-balls.png
Names
Preferred IUPAC name
1,2-Dimethoxybenzene [1]
Other names
Veratrole
o-Dimethoxybenzene
Pyrocatechol dimethyl ether
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.860 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-045-3
PubChem CID
UNII
  • InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3 Yes check.svgY
    Key: ABDKAPXRBAPSQN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
    Key: ABDKAPXRBAPSQN-UHFFFAOYAD
  • COc1ccccc1OC
Properties
C8H10O2
Molar mass 138.166 g·mol−1
Density 1.084 g/cm3 [2]
Melting point 22–23 °C (72–73 °F; 295–296 K) [2]
Boiling point 206–207 °C (403–405 °F; 479–480 K) [2]
-87.39·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302
P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
2
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Occurrence

1,2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase. [3] 1,2-Dimethoxybenzene is an insect attractant. [3] Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species. [3]

Uses

1,2-Dimethoxybenzene is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution. [4]

An example of the use of veratrole is in the synthesis of Domipizone. [5]

Veratrole can easily be brominated with NBS to give 4-bromoveratrole. [6]

Related Research Articles

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Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.

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

Pyrrolysine is an α-amino acid that is used in the biosynthesis of proteins in some methanogenic archaea and bacteria; it is not present in humans. It contains an α-amino group, a carboxylic acid group. Its pyrroline side-chain is similar to that of lysine in being basic and positively charged at neutral pH.

Methylation, in the chemical sciences, is the addition of a methyl group on a substrate, or the substitution of an atom by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These terms are commonly used in chemistry, biochemistry, soil science, and biology.

<span class="mw-page-title-main">Steroid</span> Polycyclic organic compound having sterane as a core structure

A steroid is a biologically active polycyclic organic compound with four fused rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene.

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

Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring in foods, beverages, and pharmaceuticals.

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">Methoxy group</span> Chemical group (–OCH3)

In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula R−O−CH3.

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">Chalcone</span> Chemical compound

Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. They are widely known bioactive substances, fluorescent materials, and chemical intermediates.

<span class="mw-page-title-main">Catechol</span> Organic compound (C6H4(OH)2); benzene with two adjacent –OH groups

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

Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.

Organoselenium chemistry is the science exploring the properties and reactivity of organoselenium compounds, chemical compounds containing carbon-to-selenium chemical bonds. Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected. Organoselenium compounds are found at trace levels in ambient waters, soils and sediments.

1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula C6H4O2. It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and ethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many derivatives which are known.

Guaiacol is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing a methoxy functional group. Guaiacol appears as a viscous colorless oil, although aged or impure samples are often yellowish. It occurs widely in nature and is a common product of the pyrolysis of wood.

<span class="mw-page-title-main">Dakin oxidation</span> Organic redox reaction that converts hydroxyphenyl aldehydes or ketones into benzenediols

The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H2O2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H2O2 is reduced.

<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:

<i>beta</i>-Sitosterol Chemical compound

β-sitosterol (beta-sitosterol) is one of several phytosterols with chemical structures similar to that of cholesterol. It is a white, waxy powder with a characteristic odor, and is one of the components of the food additive E499. Phytosterols are hydrophobic and soluble in alcohols.

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

Tropolone is an organic compound with the chemical formula C7H5(OH)O. It is a pale yellow solid that is soluble in organic solvents. The compound has been of interest to research chemists because of its unusual electronic structure and its role as a ligand precursor. Although not usually prepared from tropone, it can be viewed as its derivative with a hydroxyl group in the 2-position.

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

1,2-Dioxolane is a chemical compound with formula C3H6O2, consisting of a ring of three carbon atoms and two oxygen atoms in adjacent positions. Its condensed structural formula is [–(CH
2
)3–O–O–]
.

References

  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 702. doi:10.1039/9781849733069-00648. ISBN   978-0-85404-182-4.
  2. 1 2 3 Merck Index, 11th Edition, 9857
  3. 1 2 3 Gupta, Alok K; Akhtar, Tariq A; Widmer, Alex; Pichersky, Eran; Schiestl, Florian P (2012). "Identification of white campion (Silene latifolia) guaiacol O-methyltransferase involved in the biosynthesis of veratrole, a key volatile for pollinator attraction". BMC Plant Biology. 12: 158. doi: 10.1186/1471-2229-12-158 . PMC   3492160 . PMID   22937972.
  4. Janssen, D. E.; Wilson, C. V. (1963). "4-Iodoveratrole". Organic Syntheses .; Collective Volume, vol. 4, p. 547
  5. EP 0129791,Zoller, Gerhard; Beyerle, Rudi& Just, Melittaet al.,"Tetrahydropyridazinone derivatives, process for their preparation and their use",published 985-01-02, assigned to Cassella AG
  6. Bannard, R. A. B.; Latremouille, G. (1953). "4-BROMOVERATROLE". Canadian Journal of Chemistry. 31 (4): 469. doi: 10.1139/v53-062 . ISSN   0008-4042.