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Malononitrile is an Evans p''K''a table
/ref> This allows it to be used in the
Malononitrile is a suitable starting material for the
WebBook page for C3H2N2
{{Authority control Alkanedinitriles
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
nitrile with the formula . It is a colorless or white solid. It can be prepared by dehydration
In physiology, dehydration is a lack of total body water, with an accompanying disruption of metabolic processes. It occurs when free water loss exceeds free water intake, usually due to exercise, disease, or high environmental temperature. Mil ...
of cyanoacetamide
2-Cyanoacetamide is an organic compound. It is an acetic amide with a nitrile functional group.
Uses
Cyanoacetamide is used in Fluorescence spectroscopy, spectrofluorimetric methods to determine the activity of Antihistamine#H1-antihistamines, an ...
.
Malononitrile is relatively acidic, with a p''K''a of 11 in water./ref> 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 tear gas commonly referred to as CS gas, which is used as a riot control agent ...
:
Malononitrile is a suitable starting material for the Gewald reaction
The Gewald reaction is an organic reaction involving the condensation of a ketone (or aldehyde when R2 = H) with a α-cyanoester in the presence of elemental sulfur and base to give a poly-substituted 2-amino-thiophene.
The reaction is named ...
, where the nitrile condenses with a ketone or aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
in the presence of elemental sulfur
Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...
and a base to produce a 2-aminothiophene
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 react ...
.
See also
*Malonic acid
Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid' ...
* Diethyl malonate
Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds su ...
References
External links
WebBook page for C3H2N2
{{Authority control Alkanedinitriles