Malononitrile 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 ...

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...

with the formula . It is a colorless or white solid, although aged samples appear yellow or even brown. It is a widely used building block in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

Preparation and reactions

It can be prepared by

dehydration In physiology, dehydration is a lack of total body water that disrupts metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of water. Mild deh ...

of cyanoacetamide. This method is mainly practiced in China where environmental rules are lax. Most commonly malononitrile is produced by the gas-phase reaction of

acetonitrile Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not class ...

and

cyanogen chloride Cyanogen chloride is an inorganic compound with the formula . This triatomic pseudohalogen is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compound cyanogen bromide, a room-temperature solid that is ...

: : About 20,000,000 kg are produced annually (2007). Important outlets include the synthesis of

thiamine Thiamine, also known as thiamin and vitamin B1, is a vitamin – an Nutrient#Micronutrients, essential micronutrient for humans and animals. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosp ...

, the drug

triamterene Triamterene (traded under names such as Dyrenium and Dytac) is a potassium-sparing diuretic often used in combination with thiazide diuretics for the treatment of high blood pressure or swelling. The combination with hydrochlorothiazide, is kno ...

and

minoxidil Minoxidil is a medication used for the treatment of high blood pressure and pattern hair loss. It is an antihypertensive and a vasodilator. It is available as a generic medication by prescription in oral administration, oral tablet (pharmacy), ...

, and the dyes disperse Yellow 90 and disperse Blue 354. Malononitrile is relatively acidic, with a p''K''_a of 11 in water. This allows it to be used in the

Knoevenagel condensation In organic chemistry, the Knoevenagel condensation () reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation. A Knoevenagel condensation is a nucleophilic addition o ...

, for example in the preparation of

CS gas The compound 2-chlorobenzalmalononitrile (also called ''o''-chlorobenzylidene malononitrile; chemical formula: C10H5ClN2), a cyanocarbon, is the defining component of the lachrymatory agent commonly referred to as CS gas, a tear gas which ...

Despite its relative obscurity, Malononitrile is very useful in several reactions, the prime example being a suitable starting reagent for the Gewald reaction, where the nitrile condenses with a

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 ( ...

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 ...

in the presence of elemental

sulfur Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms ...

and a base to produce a 2-amino

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 ...

Interstellar occurrence

Due to its permanent dipole moment (i.e., 3.735 ± 0.017 D), malononitrile was detected in spectral emissions coming from

interstellar cloud An interstellar cloud is an accumulation of gas, plasma, and cosmic dust in galaxies. Put differently, an interstellar cloud is a denser-than-average region of the interstellar medium, the matter and radiation that exists in the space between ...

TMC-1 through the

QUIJOTE , the full title being ''The Ingenious Gentleman Don Quixote of La Mancha'', is a Spanish novel by Miguel de Cervantes. Originally published in two parts in 1605 and 1615, the novel is considered a founding work of Western literature and is of ...

line survey conducted with the Yebes 40 m radio telescope.

References

External links

WebBook page for C3H2N2

{{Authority control Alkanedinitriles