Names | |
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IUPAC name Isocyanomethane | |
Other names
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Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.008.917 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C2H3N | |
Molar mass | 41.053 g·mol−1 |
Appearance | Colorless liquid |
Density | 0.69 g/mL |
Melting point | −45 °C (−49 °F; 228 K) |
Boiling point | 59 to 60 °C (138 to 140 °F; 332 to 333 K) |
Miscible | |
Hazards | |
GHS labelling: | |
Warning | |
H302, H312, H332, H373 | |
P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P314, P322, P330, P363, P501 | |
NFPA 704 (fire diamond) | |
Related compounds | |
Related compounds | acetic acid, acetamide, ethylamine, Acetonitrile |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Methyl isocyanide or isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is isomeric and isoelectronic to methyl cyanide (acetonitrile), but its reactivity is very different. In contrast to the faintly sweet, ethereal odor of acetonitrile, the smell of methyl isocyanide, like that of other simple volatile isocyanides, is distinctly penetrating and vile. Methyl isocyanide is mainly used for making 5-membered heterocyclic rings. The C-N distance in methyl isocyanide is very short, 1.158 Å as is characteristic of isocyanides. [1]
Methyl isocyanide was first prepared by A. Gautier by reaction of silver cyanide with methyl iodide. [2] [3] The common method for preparing methyl isocyanides is the dehydration of N-methylformamide. [4] Many metal cyanides react with methylating agents to give complexes of methyl isocyanide. [5] This kind of reactivity has been invoked as being relevant to the origin of life. [6]
Methyl isocyanide is useful for the preparation of diverse heterocycles. It is often used to prepare transition metal isocyanide complexes. [7]
Methyl isocyanide is very endothermic (ΔfH⦵(g) = +150.2 kJ/mol, 3.66 kJ/g) and can isomerize explosively to acetonitrile. [8] A sample exploded when heated in a sealed ampoule, and during redistillation at 59 °C/1 bar, a drop of liquid fell back into the dry boiler flask and exploded violently. The explosive decomposition of methyl isocyanide has been studied in detail. [9]
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 sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.
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.
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. Its molecular structure 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.
In organic chemistry, a carbanion is an anion in which carbon is negatively charged. But the IUPAC confuses valence with coordination number, which are two different things, so IUPAC incorrectly considers that the carbon in carbanion is trivalent.
In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.
An isocyanide is an organic compound with the functional group –N+≡C−. It is the isomer of the related nitrile (–C≡N), hence the prefix is isocyano. The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds.
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds.
Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:
Triphenyl phosphite is the organophosphorus compound with the formula P(OC6H5)3. It is a colourless viscous liquid.
tert-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. tert-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the chemical reagent with formula C6Cl2(CN)2O2. This oxidant is useful for the dehydrogenation of alcohols, phenols, and steroid ketones. DDQ decomposes in water, but is stable in aqueous mineral acid.
Organogold chemistry is the study of compounds containing gold–carbon bonds. They are studied in academic research, but have not received widespread use otherwise. The dominant oxidation states for organogold compounds are I with coordination number 2 and a linear molecular geometry and III with CN = 4 and a square planar molecular geometry.
Methyl azide is an organic compound with the formula CH3N3. It is a white solid and it is the simplest organic azide.
Calcium perchlorate is classified as a metal perchlorate salt with the molecular formula Ca(ClO4)2. It is an inorganic compound that is a yellow-white crystalline solid in appearance. As a strong oxidizing agent, it reacts with reducing agents when heated to generate heat and products that may be gaseous. Calcium perchlorate has been categorized as having explosive reactivity. Ca(ClO4)2 is a common chemical on the soil of planet Mars, counting for almost 1% of the Martian dust, by weight.
Trichloroacetonitrile is an organic compound with the formula CCl3CN. It is a colourless liquid, although commercial samples often are brownish. It is used commercially as a precursor to the fungicide etridiazole. It is prepared by dehydration of trichloroacetamide. As a bifunctional compound, trichloroacetonitrile can react at both the trichloromethyl and the nitrile group. The electron-withdrawing effect of the trichloromethyl group activates the nitrile group for nucleophilic additions. The high reactivity makes trichloroacetonitrile a versatile reagent, but also causes its susceptibility towards hydrolysis.
In organic chemistry, methenium is a cation with the formula CH+
3. It can be viewed as a methylene radical with an added proton, or as a methyl radical with one electron removed. It is a carbocation and an enium ion, making it the simplest of the carbenium ions.
Transition metal nitrile complexes are coordination compounds containing nitrile ligands. Because nitriles are weakly basic, the nitrile ligands in these complexes are often labile.
Transition metal isocyanide complexes are coordination compounds containing isocyanide ligands. Because isocyanides are relatively basic, but also good pi-acceptors, a wide range of complexes are known. Some isocyanide complexes are used in medical imaging.
A Fischer carbene is a type of transition metal carbene complex, which is an organometallic compound containing a divalent organic ligand. In a Fischer carbene, the carbene ligand is a σ-donor π-acceptor ligand. Because π-backdonation from the metal centre is generally weak, the carbene carbon is electrophilic.
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