Names | |||
---|---|---|---|
IUPAC name Malononitrile [1] | |||
Preferred IUPAC name Propanedinitrile [1] | |||
Other names Malonodinitrile, Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile [2] | |||
Identifiers | |||
3D model (JSmol) | |||
773697 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.003.368 | ||
EC Number |
| ||
1303 | |||
MeSH | dicyanmethane | ||
PubChem CID | |||
RTECS number |
| ||
UNII | |||
UN number | 2647 | ||
CompTox Dashboard (EPA) | |||
| |||
| |||
Properties | |||
C3H2N2 | |||
Molar mass | 66.063 g·mol−1 | ||
Appearance | Colourless or white solid [2] | ||
Density | 1.049 g cm−3 | ||
Melting point | 32 °C; 89 °F; 305 K | ||
Boiling point | 220.1 °C; 428.1 °F; 493.2 K | ||
13% (20 °C) [2] | |||
Thermochemistry | |||
Heat capacity (C) | 110.29 J K−1 mol−1 | ||
Std molar entropy (S⦵298) | 130.96 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) | 187.7 to 188.1 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | −1,654.0 to −1,654.4 kJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H301, H311, H331, H410 | |||
P261, P273, P280, P301+P310, P311 | |||
Flash point | 86 °C (187 °F; 359 K) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
| ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | none [2] | ||
REL (Recommended) | TWA 3 ppm (8 mg/m3) [2] | ||
IDLH (Immediate danger) | N.D. [2] | ||
Related compounds | |||
Related alkanenitriles | |||
Related compounds | DBNPA | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Malononitrile is an organic compound nitrile with the formula CH2(CN)2. 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.
It can be prepared by dehydration of cyanoacetamide. [3] This method is mainly practiced in China where environmental rules are lax. Most commonly malononitrile is produced by the gas-phase reaction of acetonitrile and cyanogen chloride: [4]
About 20,000,000 kg are produced annually (2007). Important outlets include the synthesis of thiamine, the drug triamterene and minoxidil, and the dyes disperse Yellow 90 and disperse Blue 354. [4]
Malononitrile is relatively acidic, with a pKa of 11 in water. [5] This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:
Malononitrile is a suitable starting material for the Gewald reaction, where the nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base to produce a 2-aminothiophene. [6]
Sodium cyanide is a poisonous compound with the formula NaCN. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base.
Acetonitrile, often abbreviated MeCN, is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.
Phenacyl chloride, also commonly known as chloroacetophenone, is a substituted acetophenone. It is a useful building block in organic chemistry. Apart from that, it has been historically used as a riot control agent, where it is designated CN. It should not be confused with cyanide, another agent used in chemical warfare, which has the chemical structure CN−.
Acrylonitrile is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N. It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses. Acrylonitrile was first synthesized by the French chemist Charles Moureu (1863–1929) in 1893.
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's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.
Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.
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.
Butyronitrile or butanenitrile or propyl cyanide, is a nitrile with the formula C3H7CN. This colorless liquid is miscible with most polar organic solvents.
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.
Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is a colorless waxy solid which melts at 58 °C.
Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.
Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents.
Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.
Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.
Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.
Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH2CN. It is the simplest cyanohydrin and it is derived from formaldehyde. It is a colourless liquid that dissolves in water and ether. Because glycolonitrile decomposes readily into formaldehyde and hydrogen cyanide, it is listed as an extremely hazardous substance. In January 2019, astronomers reported the detection of glycolonitrile, another possible building block of life among other such molecules, in outer space.
Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.
m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.