Information about Acetonitrile
| Acetonitrile | |
|---|---|
) | |
| IUPAC name | Ethanenitrile |
| Other names | Methyl cyanide |
| Identifiers | |
| CAS number | |
| RTECS number | AL7700000 |
| SMILES | CC#N |
| InChI | InChI=1/C2H3N/c1-2-3/h1H3 |
| Properties | |
| Molecular formula | CH3CN |
| Molar mass | 41.05 g/mol |
| Appearance | colorless liquid |
| Density | 0.786 g/mL liquid |
| Melting point | -45 °C |
| Boiling point | 82 °C |
| Solubility in water | miscible |
| Solubility | organic solvents |
| Acidity (pKa) | 25 |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Flammable, harmful |
| NFPA 704 |
|
| R-phrases | R11, R20/21/22, R36 |
| S-phrases | (S1/2), S16, S36/37 |
| Flash point | 2 °C |
| Related Compounds | |
| Related nitriles | propionitrile, butyronitrile |
| Related compounds | acetic acid, acetamide, ethylamine |
| Supplementary data page | |
| Structure and properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) | |
)
Industrial applications
Acetonitrile is used as a solvent but also as an intermediate in the production of many chemicals ranging from pesticides to perfumes. Production trends for acetonitrile generally follow those of acrylonitrile. The four main producers of acetonitrile in the United States are: INEOS, DuPont, J.T. Baker Chemical, and Sterling Chemicals. In 1992, 32.3 million pounds (14,700 t) of acetonitrile were produced in the U.S.Laboratory uses
Acetonitrile is commonly the solvent of choice for testing an unknown chemical reaction. It is polar with a convenient liquid range. It dissolves a wide range of compounds without complications due to the fact that it contains no acidic protons. Acetone has similar properties but is more acidic and more reactive toward bases and nucleophiles. (Note: the pKa given applies to the conjugate acid of acetonitrile, not the molecule itself.)In inorganic chemistry, acetonitrile is widely employed as a displaceable ligand where it is abbreviated MeCN. A good example is the use of PdCl2(MeCN)2 prepared by refluxing polymeric palladium chloride in acetonitrile.
It is a popular solvent in cyclic voltammetry because of its relatively high dielectric constant. MeCN is a two-carbon building block in organic synthesis.[1] Acetonitrile is also commonly used in column chromatography and the more modern high performance liquid chromatography where it serves as a mobile phase in the separation of molecules.
Safety
Acetonitrile is toxic and flammable. It is metabolized into hydrogen cyanide and thiocyanate.External links
- WebBook page for C2H3N
- International Chemical Safety Card 0088
- National Pollutant Inventory - Acetonitrile fact sheet
- NIOSH Pocket Guide to Chemical Hazards
References
1. ^ DiBiase, S. A.; Beadle, J. R.; Gokel, G. W.. "Synthesis of α,β-Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile". Org. Synth.; Coll. Vol. 7: 108.
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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smiles
File extension:
Type of format: chemical file format
The simplified molecular input line entry specification or SMILES
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File extension:
.smiType of format: chemical file format
The simplified molecular input line entry specification or SMILES
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The IUPAC International Chemical Identifier (InChI) is a textual identifier for chemical substances, designed to provide a human-readable standard way to encode molecular information and to facilitate the search for such information in databases and on the web.
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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In physics, density is mass m per unit volume V—how heavy something is compared to its size. A small, heavy object, such as a rock or a lump of lead, is denser than a lighter object of the same size or a larger object of the same weight, such as pieces of
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Water is a common chemical substance that is essential to all known forms of life.[1] In typical usage, water refers only to its liquid form or state, but the substance also has a solid state, ice, and a gaseous state, water vapor.
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. According to the Brønsted-Lowry theory of acids and bases an acid is only recognised by its reaction with a base.
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material safety data sheet (MSDS) is a form containing data regarding the properties of a particular substance. An important component of product stewardship and workplace safety, it is intended to provide workers and emergency personnel with procedures for handling or
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Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety.
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NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. It defines the colloquial "fire diamond" used by emergency personnel to quickly and easily identify the risks posed by nearby hazardous materials.
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R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations.
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S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The list was consolidated and republished in Directive 2001/59/EC , where translations into other EU languages may be found.
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The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture in air. At this temperature the vapor may cease to burn when the source of ignition is removed.
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A nitrile is any organic compound which has a -C≡N functional group. The -C≡N functional group is called a nitrile group. In the -CN group, the carbon atom and the nitrogen atom are triple bonded together.
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Propionitrile, or ethyl cyanide, is a low-molecular weight nitrile with the molecular formula C2H5CN. It is a clear liquid with an etherial, sweet odor.
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Butyronitrile, or propyl cyanide, is a low molecular weight nitrile with the molecular formula C3H7CN. It is a clear liquid that is miscible with ethanol, diethyl ether and dimethylformamide.
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Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. Its structural formula is represented as CH3COOH.
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Acetamide (or acetic acid amide or ethanamide), CH3CONH2, the amide of acetic acid, is a white crystalline solid in pure form. It is produced by dehydrating ammonium acetate.
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Ethylamine is a chemical compound with the formula CH3CH2NH2. It has a strong ammonia-like odor. It is miscible with virtually all solvents and is considered to be a weak base, as is typical for amines.
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P in mm Hg 1 10 40 100 400 760
T in °C –47.0(s) –16.3 7.7 27.0 62.5 81.8
Table data obtained from CRC Handbook of Chemistry and Physics, 44th ed. The "(s)" notation indicates temperature of solid/vapor equilibrium.
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T in °C –47.0(s) –16.3 7.7 27.0 62.5 81.8
Table data obtained from CRC Handbook of Chemistry and Physics, 44th ed. The "(s)" notation indicates temperature of solid/vapor equilibrium.
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The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. For example, typical glass has a refractive index of 1.
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The relative static permittivity (or static relative permittivity) of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux.
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Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry (UV/ VIS) involves the spectroscopy of photons and spectrophotometry. It uses light in the visible and adjacent near ultraviolet (UV) and near infrared (NIR) ranges.
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Infrared spectroscopy (IR spectroscopy) is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. It covers a range of techniques, the most common being a form of absorption spectroscopy.
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