1,4-Diamino-2,3-dihydroanthraquinone

Last updated
1,4-Diamino-2,3-dihydroanthraquinone
14Diamino23dihydroanthraquinone.svg
Names
Preferred IUPAC name
1,4-Diamino-2,3-dihydroanthracene-9,10-dione
Other names
Solvent violet 47
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.244 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-367-1
PubChem CID
UNII
  • InChI=1S/C14H12N2O2/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-4H,5-6,15-16H2 Yes check.svgY
    Key: SSGALQHXKMAJTL-UHFFFAOYSA-N Yes check.svgY
  • O=C2c1ccccc1C(=O)C=3C2=C(N)CCC=3N
Properties
C14H12N2O2
Molar mass 240.262 g·mol−1
AppearanceDark greenish to brownish powder
Density 1.4 g/cm3
Melting point 248 to 252 °C (478 to 486 °F; 521 to 525 K)
Boiling point 375.1 °C (707.2 °F; 648.2 K)
Soluble in hot nitrobenzene
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Mutagenic; emits NOx vapors when heated to decomposition.
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H317
P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P501
Flash point 180.7 °C (357.3 °F; 453.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,4-Diamino-2,3-dihydroanthraquinone is an anthraquinone dye used with Disperse Red 9 in colored smoke to introduce a violet color. It is also used in dyes and marine flares.

Synthesis

1,4-Diaminoanthraquinone is reacted with sodium dithionite to produce 1,4-diamino-2,3-dihydroanthraquinone. [1]

Related Research Articles

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">Dicarbonyl</span> Molecule containing two adjacent C=O groups

In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.

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<span class="mw-page-title-main">Juglone</span> Chemical produced by walnut trees

Juglone, also called 5-hydroxy-1,4-naphthalenedione (IUPAC) is a phenolic organic compound with the molecular formula C10H6O3. In the food industry, juglone is also known as C.I. Natural Brown 7 and C.I. 75500. It is insoluble in benzene but soluble in dioxane, from which it crystallizes as yellow needles. It is an isomer of lawsone, which is the active dye compound in the henna leaf.

Solvent Black 3 is an azo dye. It is a non-fluorescent, relatively thermostable lysochrome diazo dye used for staining of neutral triglycerides and lipids on frozen sections and some lipoproteins on paraffin sections. It has the appearance of a dark brown to black powder with maximum absorption at 596–605 nm and melting point 120–124 °C. It stains blue-black.

<span class="mw-page-title-main">Colored smoke</span> Type of smoke

Colored smoke is a kind of smoke created by an aerosol of small particles of a suitable pigment or dye.

<span class="mw-page-title-main">Disperse Red 11</span> Chemical compound

Disperse Red 11, or 1,4-diamino-2-methoxyanthraquinone, is a red disperse dye derived from anthraquinone. It is water insoluble.

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

Brown FK, also called Kipper Brown, Chocolate Brown FK, and C.I. Food Brown 1, is a brown mixture of six synthetic azo dyes, with addition of sodium chloride, and/or sodium sulfate. It is very soluble in water. When used as a food dye, its E number is E154.

In enzymology, a vitamin-K-epoxide reductase (warfarin-insensitive) is an enzyme that catalyzes the chemical reaction

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In chemistry, a diamino acid, also called a diamino carboxylic acid, is a molecule including a carboxylic acid and two amine functional groups. Diamino acids belong to the class of amino acids.

1-Naphthol, or α-naphthol, is a organic compound with the formula C10H7OH. It is a fluorescent white solid. 1-Naphthol differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol. Both isomers are soluble in simple organic solvents. They are precursors to a variety of useful compounds.

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

Chloranil is a quinone with the molecular formula C6Cl4O2. Also known as tetrachloro-1,4-benzoquinone, it is a yellow solid. Like the parent benzoquinone, chloranil is a planar molecule that functions as a mild oxidant.

A hydroxybenzoquinone is any of several organic compounds that can be viewed as derivatives of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).

The molecular formula C14H12N2O2 may refer to:

<span class="mw-page-title-main">2,5-Diaminotoluene</span> Chemical compound

2,5-Diaminotoluene is an organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. 2,5-Diaminotoluene is a colorless crystalline solid, although commercial samples are often colored owing to air oxidation. It is commonly used in hair coloring.

Disperse dye is a category of synthetic dye intended for polyester and related hydrophobic fibers. Disperse dyes are polar molecules containing anthraquinone or azo groups. It is estimated that 85% of disperse dyes are azos or anthraquinone dyes.

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

1,4-Naphthoquinone or para-naphthoquinone is a quinone derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it produces a reddish-brown color. Vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit. It is an isomer of 1,2-naphthoquinone.

<span class="mw-page-title-main">1,2,4,5-Tetrabromobenzene</span> Chemical compound

1,2,4,5-Tetrabromobenzene is an aryl bromide and a four-substituted bromobenzene with the formula C6H2Br4. It is one of three isomers of tetrabromobenzene. The compound is a white solid. 1,2,4,5-Tetrabromobenzene is an important metabolite of the flame retardant hexabromobenzene.

References

  1. Heyer, Thomas; Niclas, Hans-Joachim; Dietzel, Stephan (1989). "NMR-Untersuchungen zur Tautomerie bei Dihydroanthracendionen (NMR studies on tautomerism in dihydroanthracenediones)". Zeitschrift für Chemie (Journal of Chemistry). 29 (4): 139–140. doi:10.1002/zfch.19890290408 . Retrieved 11 May 2024.