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Names | |||
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Preferred IUPAC name Acetamide [1] | |||
Systematic IUPAC name Ethanamide | |||
Other names Acetic acid amide Acetylamine | |||
Identifiers | |||
3D model (JSmol) | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.000.430 | ||
EC Number |
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KEGG | |||
PubChem CID | |||
RTECS number |
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UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
C2H5NO | |||
Molar mass | 59.068 g·mol−1 | ||
Appearance | colorless, hygroscopic solid | ||
Odor | odorless mouse-like with impurities | ||
Density | 1.159 g cm−3 | ||
Melting point | 79 to 81 °C (174 to 178 °F; 352 to 354 K) | ||
Boiling point | 221.2 °C (430.2 °F; 494.3 K) (decomposes) | ||
2000 g L−1 [2] | |||
Solubility | ethanol 500 g L−1 [2] pyridine 166.67 g L−1 [2] soluble in chloroform, glycerol, benzene [2] | ||
log P | −1.26 | ||
Vapor pressure | 1.3 Pa | ||
Acidity (pKa) | 15.1 (25 °C, H2O) [3] | ||
−0.577 × 10−6 cm3 g−1 | |||
Refractive index (nD) | 1.4274 | ||
Viscosity | 2.052 cP (91 °C) | ||
Structure | |||
trigonal | |||
Thermochemistry [4] | |||
Heat capacity (C) | 91.3 J·mol−1·K−1 | ||
Std molar entropy (S⦵298) | 115.0 J·mol−1·K−1 | ||
Std enthalpy of formation (ΔfH⦵298) | −317.0 kJ·mol−1 | ||
Hazards | |||
GHS labelling: | |||
![]() | |||
Warning | |||
H351 | |||
P201, P202, P281, P308+P313, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 126 °C (259 °F; 399 K) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 7000 mg kg−1 (rat, oral) | ||
Safety data sheet (SDS) | External MSDS | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. [5] The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Acetamide is also a naturally occurring mineral [6] with the IMA symbol: Ace. [7]
Acetamide can be produced in the laboratory from ammonium acetate by dehydration: [9]
Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination. [10]
It can also be made from anhydrous acetic acid, acetonitrile and very well dried hydrogen chloride gas, using an ice bath, alongside more valuable reagent acetyl chloride. Yield is typically low (up to 35%), and the acetamide made this way is generated as a salt with HCl.
In a similar fashion to some laboratory methods, acetamide is produced by dehydrating ammonium acetate or via the hydration of acetonitrile, a byproduct of the production of acrylonitrile: [5]
Acetamide is used as a plasticizer and an industrial solvent. [5] Molten acetamide is good solvent with a broad range of applicability. Notably, its dielectric constant is higher than most organic solvents, allowing it to dissolve inorganic compounds with solubilities closely analogous to that of water. [11] Acetamide has uses in electrochemistry and the organic synthesis of pharmaceuticals, pesticides, and antioxidants for plastics. [12] It is a precursor to thioacetamide. [13]
Acetamide has been detected near the center of the Milky Way galaxy. [14] This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins. This finding lends support to the theory that organic molecules that can lead to life (as we know it on Earth) can form in space.
On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67/P 's surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, four of which – acetamide, acetone, methyl isocyanate, and propionaldehyde [15] [16] [17] – were seen for the first time on a comet.
In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name. [18] [19]
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, as in asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid with the hydroxyl group replaced by an amine group ; or, equivalently, an acyl (alkanoyl) group joined to an amine group.
In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.
In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". 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.
The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was first developed by Johannes Nicolaus Brønsted and Thomas Martin Lowry independently in 1923. The basic concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory generalises the Arrhenius theory.
In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.
Acetylacetone is an organic compound with the chemical formula CH3−C(=O)−CH2−C(=O)−CH3. It is classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3−C(=O)−CH=C(−OH)−CH3. The mixture is a colorless liquid. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. Acetylacetone is a building block for the synthesis of many coordination complexes as well as heterocyclic compounds.
An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride.Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").
Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.
Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a colorless liquid. It is widely used as a chemical intermediate in the production of a wide variety of compounds.
Ammonium acetate, also known as spirit of Mindererus in aqueous solution, is a chemical compound with the formula NH4CH3CO2. It is a white, hygroscopic solid and can be derived from the reaction of ammonia and acetic acid. It is available commercially.
An inorganic nonaqueous solvent is a solvent other than water, that is not an organic compound. These solvents are used in chemical research and industry for reactions that cannot occur in aqueous solutions or require a special environment. Inorganic nonaqueous solvents can be classified into two groups, protic solvents and aprotic solvents. Early studies on inorganic nonaqueous solvents evaluated ammonia, hydrogen fluoride, sulfuric acid, as well as more specialized solvents, hydrazine, and selenium oxychloride.
Thioacetamide is an organosulfur compound with the formula C2H5NS. This white crystalline solid is soluble in water and serves as a source of sulfide ions in the synthesis of organic and inorganic compounds. It is a prototypical thioamide.
Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents.
In chemistry, aminolysis (/am·i·nol·y·sis/) is any chemical reaction in which a molecule is lysed by reacting with ammonia or an amine. The case where the reaction involves ammonia may be more specifically referred to as ammonolysis.
Thioacetic acid is an organosulfur compound with the molecular formula CH3C(O)SH. It is a thioic acid: the sulfur analogue of acetic acid, as implied by the thio- prefix. It is a yellow liquid with a strong thiol-like odor. It is used in organic synthesis for the introduction of thiol groups in molecules.
In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations.
Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a pungent and fruity odour. It is produced on a large scale industrially.
Acetamidine hydrochloride is an organic compound with the formula CH3C(NH)NH2·HCl, used in the synthesis of many nitrogen-bearing compounds. It is the hydrochloride of acetamidine, one of the simplest amidines.
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