Selenophene is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

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 an unsaturated compound containing a five-member

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 ...

with four

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms and one

selenium Selenium is a chemical element; it has symbol (chemistry), symbol Se and atomic number 34. It has various physical appearances, including a brick-red powder, a vitreous black solid, and a grey metallic-looking form. It seldom occurs in this elem ...

atom. It is a selenium analog of

furan Furan is a Heterocyclic compound, heterocyclic organic compound, consisting of a five-membered aromatic Ring (chemistry), ring with four carbon Atom, atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as f ...

and

thiophene Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reacti ...

. A colorless liquid, it is one of the more common selenium heterocycles.

Nomenclature

Atoms in selenophene are numbered sequentially around the ring, starting with the selenium atom as number 1 following normal

systematic nomenclature Chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC). IUPAC ...

rules. Oxidized forms include selenophene 1,1-dioxide. Related ring structures include those with only one double bond ( 2-selenolene and 3-selenolene) and the fully saturated structure selenolane.

Production

Mazza and Solazzo reported the first confirmed synthesis in 1927. By treating selenium with

acetylene Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...

and at about 300 °C yields up to 15% selenophene were obtained. Benzoselenophene (analogue of

benzothiophene Benzothiophene is an aromatic organic compound with a molecular formula C8H6S and an odor similar to naphthalene (mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite tar. Benzothiophene has no househol ...

) was also produced. Substituted selenophenes can be made using a Fiesselman procedure in which a β-chloro-aldehyde reacts with

sodium selenide Sodium selenide is an inorganic compound of sodium and selenium with the chemical formula Na2Se. Preparation This colourless solid is prepared by the reaction of selenium with a solution of sodium in liquid ammonia at −40 °C.Brauer, G. ed. ( ...

, and then

ethyl bromoacetate Ethyl bromoacetate is the chemical compound with the formula . It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid. It is a lachrymator and has a fruity, pungent odor. It is also a highly toxic alkylating agen ...

Properties

The selenophene molecule is flat. Being aromatic, it undergoes

electrophilic substitution Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a functional group in a compound, which is typically, but not always, aromatic. Aromatic substitution reactions are characteristic of aromatic compounds ...

reactions. As for thiophene, electrophiles tend to attack at the carbon positions next to the chalcogen. Such reactions are slower than that of furan, but faster than

References

{{Reflist Selenium(−II) compounds Heterocyclic compounds with 1 ring Selenium heterocycles