Names | |
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IUPAC name Indane-1,2,3-trione | |
Other names Indanetrione | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
EC Number |
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PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C9H4O3 | |
Molar mass | 160.128 g·mol−1 |
Appearance | white powder |
Density | 1.482 g/cm3 |
Boiling point | 338.4 °C (641.1 °F; 611.5 K) |
Hazards | |
GHS labelling: [1] | |
Warning | |
H302, H315, H319, H335 | |
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Indane-1,2,3-trione is the organic compound with the formula C6H4(CO)3. The compound is the dehydrated derivative of C6H4(CO)2C(OH)2, known as ninhydrin, which is used to reveal fingerprints.
Indane-1,2,3-trione, which reacts readily with nucleophiles (including water). Whereas for most carbonyl compounds, a carbonyl form is more stable than a product of water addition (hydrate), ninhydrin forms a stable hydrate of the central carbon because of the destabilizing effect of the adjacent carbonyl groups.
To generate the ninhydrin chromophore (2-(1,3-dioxoindan-2-yl)iminoindane-1,3-dione), the amine must condense to give a Schiff base. The reaction of ninhydrin with secondary amines gives an iminium salt, which is also coloured, generally being yellow–orange.
A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
An ester is a chemical compound derived from an acid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.
In chemistry, a ketone is a functional group with the structure R2C=O, where R can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond). The simplest ketone is acetone (R = R' = methyl), with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.
A ketene is an organic compound of the form R′R″C=C=O, where R and R' are two arbitrary monovalent chemical groups. The name may also refer to the specific compound ethenone H2C=C=O, the simplest ketene.
In chemistry, an aldehyde is an organic compound containing a functional group with the structure −C(H)=O. The functional group itself is known as an aldehyde or formyl group. Aldehydes are common and play important roles in the technology and biological spheres.
Hydrazine is an inorganic compound with the chemical formula N2H4. It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour.
An acetal is a functional group with the connectivity R2C(OR')2). Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments not hydrogen. The two R' groups can be equivalent to each other (a "symmetric acetal") or not (a "mixed acetal"). Acetals are formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical stability and reactivity as compared to the analogous carbonyl compounds. The central carbon atom has four bonds to it, and is therefore saturated and has tetrahedral geometry.
Hydrazones are a class of organic compounds with the structure R
1R
2C=NNH
2. They are related to ketones and aldehydes by the replacement of the oxygen with the NNH
2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.
A dicarbonyl is a molecule containing two carbonyl (C=O) 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.
A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.
In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions differ from electrophilic additions in that the former reactions involve the group to which atoms are added accepting electron pairs, whereas the latter reactions involve the group donating electron pairs.
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.
Ninhydrin (2,2-dihydroxyindane-1,3-dione) is an organic compound with the formula C6H4(CO)2C(OH)2. It is used to detect ammonia and amines. Upon reaction with these amines, ninhydrin converts to deep blue or purple derivatives, the latter known as Ruhemann's purple. Ninhydrin is most commonly used to detect fingerprints, as the terminal amines of lysine residues in peptides and proteins sloughed off in fingerprints react with ninhydrin.
Cobalt(II) chloride is an inorganic compound of cobalt and chlorine, with the formula CoCl
2. The compound forms several hydrates CoCl
2•nH
2O, for n = 1, 2, 6, and 9. Claims of the formation of tri- and tetrahydrates have not been confirmed. The anhydrous form is a blue crystalline solid; the dihydrate is purple and the hexahydrate is pink. Commercial samples are usually the hexahydrate, which is one of the most commonly used cobalt compounds in the lab.
A tetrahedral intermediate is a reaction intermediate in which the bond arrangement around an initially double-bonded carbon atom has been transformed from trigonal to tetrahedral. Tetrahedral intermediates result from nucleophilic addition to a carbonyl group. The stability of tetrahedral intermediate depends on the ability of the groups attached to the new tetrahedral carbon atom to leave with the negative charge. Tetrahedral intermediates are very significant in organic syntheses and biological systems as a key intermediate in esterification, transesterification, ester hydrolysis, formation and hydrolysis of amides and peptides, hydride reductions, and other chemical reactions.
A geminal diol is any organic compound having two hydroxyl functional groups (-OH) bound to the same carbon atom. Geminal diols are a subclass of the diols, which in turn are a special class of alcohols. Most of the geminal diols are considered unstable.
Nucleophilic acyl substitution describe a class of substitution reactions involving nucleophiles and acyl compounds. In this type of reaction, a nucleophile – such as an alcohol, amine, or enolate – displaces the leaving group of an acyl derivative – such as an acid halide, anhydride, or ester. The resulting product is a carbonyl-containing compound in which the nucleophile has taken the place of the leaving group present in the original acyl derivative. Because acyl derivatives react with a wide variety of nucleophiles, and because the product can depend on the particular type of acyl derivative and nucleophile involved, nucleophilic acyl substitution reactions can be used to synthesize a variety of different products.
1,3-Indandione (sometimes simply indanedione) is an organic compound with the molecular formula C6H4(CO)2CH2. It is a β-diketone on an indane framework. It is a colorless or white solid although samples can appear yellowish or even green. It is a widely used building block
A triketone or trione is a molecule containing three ketone groups.
2,3,4-Pentanetrione (or IUPAC name pentane-2,3,4-trione, triketopentane or dimethyl triketone) is the simplest linear triketone, a ketone with three C=O groups. It is an organic molecule with formula CH3COCOCOCH3.