1,5-Dihydroxynaphthalene

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1,5-Dihydroxynaphthalene
Naphthalin-1,5-diol.svg
Names
Preferred IUPAC name
Naphthalene-1,5-diol
Other names
Azurol; 1,5-Naphthalenediol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.353 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H8O2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6,11-12H
    Key: BOKGTLAJQHTOKE-UHFFFAOYSA-N
  • InChI=1/C10H8O2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6,11-12H
    Key: BOKGTLAJQHTOKE-UHFFFAOYAJ
  • c1cc2c(cccc2O)c(c1)O
Properties
C10H8O2
Molar mass 160.172 g·mol−1
Appearancewhite solid
Melting point 259–261 °C (498–502 °F; 532–534 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,5-Dihydroxynaphthalene is an organic compound with the formula C10H6(OH)2. It is one of several isomers of dihydroxynaphthalene. A white solid, degraded samples often appear grey to light brown solid [1] that are soluble in polar organic solvents. It is a precursor to certain dyes.

Preparation and use

1,5-Dihydroxynaphthalene is prepared from naphthalene-1,5-disulfonic acid by hydrolysis with strong base followed by acidification.

It couples with various aryl diazonium salts to give diazo dyes. Oxidation with chromium trioxide gives juglone, a naturally occurring dye. [2]

In supramolecular chemistry, 1,5-dihydroxynaphthalene is a popular reagent. [3] [4]

Related Research Articles

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

Naphthalene is an organic compound with formula C
10
H
8
. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is best known as the main ingredient of traditional mothballs.

1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an organic compound with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.

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

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

<span class="mw-page-title-main">Sublimation (phase transition)</span> Transition of a substance directly from the solid to the gas state

Sublimation is the transition of a substance directly from the solid to the gas state, without passing through the liquid state. Sublimation is an endothermic process that occurs at temperatures and pressures below a substance's triple point in its phase diagram, which corresponds to the lowest pressure at which the substance can exist as a liquid. The reverse process of sublimation is deposition or desublimation, in which a substance passes directly from a gas to a solid phase. Sublimation has also been used as a generic term to describe a solid-to-gas transition (sublimation) followed by a gas-to-solid transition (deposition). While vaporization from liquid to gas occurs as evaporation from the surface if it occurs below the boiling point of the liquid, and as boiling with formation of bubbles in the interior of the liquid if it occurs at the boiling point, there is no such distinction for the solid-to-gas transition which always occurs as sublimation from the surface.

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

Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14
H
8
O
2
. Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.

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

Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.

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

Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is C16H10. This yellow solid is the smallest peri-fused PAH. Pyrene forms during incomplete combustion of organic compounds.

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

Decalin, a bicyclic organic compound, is an industrial solvent. A colorless liquid with an aromatic odor, it is used as a solvent for many resins or fuel additives.

1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

Pyrazolone is 5-membered heterocycle containing two adjacent nitrogen atoms. It can be viewed as a derivative of pyrazole possessing an additional carbonyl (C=O) group. Compounds containing this functional group are useful commercially in analgesics and dyes.

The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The reaction is widely used in the synthesis of dye precursors aminonaphthalenesulfonic acids.

<span class="mw-page-title-main">Armstrong's acid</span> Chemical compound

Armstrong's acid (naphthalene-1,5-disulfonic acid) is a fluorescent organic compound with the formula C10H6(SO3H)2. It is one of several isomers of naphthalenedisulfonic acid. It a colorless solid, typically obtained as the tetrahydrate. Like other sulfonic acids, it is a strong acid. It is named for British chemist Henry Edward Armstrong.

<span class="mw-page-title-main">2-Naphthol</span> Chemical compound

2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a widely used intermediate for the production of dyes and other compounds.

1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.

Naphthalenetetracarboxylic dianhydride (NTDA) is an organic compound related to naphthalene. The compound is a beige solid. NTDA is most commonly used as a precursor to naphthalenediimides (NDIs), a family of compounds with many uses.

<span class="mw-page-title-main">Naphthalene-1-sulfonic acid</span> Organic chemical compound

Naphthalene-1-sulfonic acid is an organic compound with the formula C10H7SO3H. A colorless, water-soluble solid, it is often available as the dihydrate C10H7SO3H.2H2O. It is one of two monosulfonic acids of naphthalene, the other being the more stable naphthalene-2-sulfonic acid. The compound is mainly used in the production of dyes.

<span class="mw-page-title-main">Naphthalene-2-sulfonic acid</span> Chemical compound

Naphthalene-2-sulfonic acid is an organic compound with the formula C10H7SO3H. A colorless, water-soluble solid, it is often available as the mono- and trihydrates C10H7SO3H.2H2O. It is one of two monosulfonic acids of naphthalene, the other being naphthalene-1-sulfonic acid. The compound is mainly used in the production of dyes via nitration en route to aminonaphthalenesulfonic acids. The compound is prepared by sulfonation of naphthalene with sulfuric acid, however under equilibrating conditions that allow the 1-sulfonic acid isomer to convert to the more stable 2-sulfonic acid.

<span class="mw-page-title-main">1,5-Diaminonaphthalene</span> Chemical compound

1,5-Diaminonaphthalene is an organic compound with the formula C10H6(NH2)2. It is one of several diaminonaphthalenes. It is a colorless solid that darkens in air due to oxidation.

<span class="mw-page-title-main">1-Nitronaphthalene</span> Chemical compound

1-Nitronaphthalene is an organic compound with the formula C10H7NO2. It is one of two isomers of nitronaphthalene. A pale yellow, sublimable solid, 1-nitronaphthalene is the main product of the direct nitration of naphthalene. It is an intermediate in the production of naphthylamine, a precursor to dyes.

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

Lithium naphthalene is an organic salt with the chemical formula Li+C
10
H
8
. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It is usually generated in situ. Lithium naphthalene crystallizes with ligands bound to Li+.

References

  1. European Commission. Directorate General for Health & Consumers (2010). Opinion on 1,5-Naphthalenediol : COLIPA n° A18 (PDF). Brussels: European Commission. doi:10.2772/27149. ISBN   978-92-79-12751-9. OCLC   1056423805.
  2. Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN   3527306730..
  3. Li, Qiaowei; Zhang, Wenyu; Miljanić, Ognjen Š.; Sue, Chi-Hau; Zhao, Yan-Li; Liu, Lihua; Knobler, Carolyn B.; Stoddart, J. Fraser; Yaghi, Omar M. (2009). "Docking in Metal-Organic Frameworks". Science. 325 (5942): 855–859. Bibcode:2009Sci...325..855L. doi:10.1126/science.1175441. hdl: 10220/6961 . PMID   19679809. S2CID   12410454.
  4. Mukhopadhyay, Pritam; Iwashita, Yuya; Shirakawa, Michihiro; Kawano, Shin-Ichiro; Fujita, Norifumi; Shinkai, Seiji (2006). "Spontaneous Colorimetric Sensing of the Positional Isomers of Dihydroxynaphthalene in a 1D Organogel Matrix". Angewandte Chemie International Edition. 45 (10): 1592–1595. doi:10.1002/anie.200503158. PMID   16470894.