Indene is an

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

, polycyclic

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...

with

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

. It is composed of a

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

ring (The) Ring(s) may refer to: * Ring (jewellery), a round band, usually made of metal, worn as ornamental jewelry * To make a sound with a bell, and the sound made by a bell Arts, entertainment, and media Film and TV * ''The Ring'' (franchise), a ...

fused with a

cyclopentene Cyclopentene is a chemical compound with the formula . It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%. It is one of t ...

ring. This

flammable A combustible material is a material that can burn (i.e., sustain a flame) in air under certain conditions. A material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort ...

liquid is colorless although samples often are pale yellow. The principal industrial use of indene is in the production of indene/ coumarone thermoplastic resins. Substituted indenes and their closely related

indane Indane or indan is an organic compound with the formula C9H10. It is a colorless liquid hydrocarbon. It is a petrochemical, a bicyclic compound. It occurs at the level of about 0.1% in coal tar. It is usually produced by hydrogenation of inde ...

derivatives are important structural motifs found in many

natural products A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical s ...

and biologically active molecules, such as

sulindac Sulindac is a nonsteroidal anti-inflammatory drug (NSAID) of the arylalkanoic acid class that is marketed as Clinoril. Imbaral (not to be confused with mebaral) is another name for this drug. Its name is derived from sul(finyl)+ ind(ene)+ ac(eti ...

Isolation

Indene occurs naturally in

coal-tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoriasi ...

fractions A fraction (from , "broken") represents a part of a whole or, more generally, any number of equal parts. When spoken in everyday English, a fraction describes how many parts of a certain size there are, for example, one-half, eight-fifths, thre ...

boiling around 175–185 °C. It can be obtained by heating this fraction with

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

to precipitate solid "sodio-indene". This step exploits indene's weak acidity evidenced by its

deprotonation Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.ed ...

by sodium to give the indenyl derivative. The sodio-indene is converted back to indene by steam

distillation Distillation, also classical distillation, is the process of separating the component substances of a liquid mixture of two or more chemically discrete substances; the separation process is realized by way of the selective boiling of the mixt ...

Reactivity

Indene readily polymerises. Oxidation of indene with acid dichromate yields homophthalic acid (''o''-carboxylphenylacetic acid). It condenses with diethyl

oxalate Oxalate (systematic IUPAC name: ethanedioate) is an anion with the chemical formula . This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (), and several esters such as ...

in the presence of

sodium ethoxide Sodium ethoxide, also referred to as sodium ethanolate, is the Ionic compound, ionic, organic compound with the formula , , or NaOEt (Et = ethyl group, ethyl). It is a white solid, although impure samples appear yellow or brown. It dissolves in p ...

to form indene–oxalic ester, and with

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

s or

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

s in the presence of

alkali In chemistry, an alkali (; from the Arabic word , ) is a basic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a soluble base has a pH greater than 7.0. The a ...

to form benzofulvenes, which are highly coloured. Treatment of indene with

organolithium In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...

reagents gives lithium indenyl compounds: : Indenyl is a

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

organometallic chemistry Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...

, giving rise to many transition metal indenyl complexes.

References

External links

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Isolation

Reactivity

See also

References

External links