Names | |
---|---|
IUPAC name Thioacetamide | |
Preferred IUPAC name Ethanethioamide [1] | |
Other names acetothioamide, TAA, thioacetimidic acid, TA, TAM | |
Identifiers | |
3D model (JSmol) | |
506006 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.493 |
EC Number |
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KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 3077 |
CompTox Dashboard (EPA) | |
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Properties | |
C2H5NS | |
Molar mass | 75.13 g/mol |
Appearance | colourless crystals |
Odor | slight mercaptan |
Density | 1.319 g/cm3 [2] |
Melting point | 115 °C (239 °F; 388 K) |
Boiling point | decomposes |
good | |
-42.45·10−6 cm3/mol | |
Structure | |
monoclinic | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Foul stench, carcinogenic |
GHS labelling: | |
Danger | |
H302, H315, H319, H350, H412 | |
P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P337+P313, P362, P405, P501 | |
Safety data sheet (SDS) | MSDS |
Related compounds | |
Related compounds | acetamide, dithioacetic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Thioacetamide is an organosulfur compound with the formula C2 H5 N S. 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.
Thioacetamide is known to induce acute or chronic liver disease (fibrosis and cirrhosis) in the experimental animal model. Its administration in rat induces hepatic encephalopathy, metabolic acidosis, increased levels of transaminases, abnormal coagulation, and centrilobular necrosis, which are the main features of the clinical chronic liver disease so thioacetamide can precisely replicate the initiation and progression of human liver disease in an experimental animal model. [3]
Thioacetamide is widely used in classical qualitative inorganic analysis as an in situ source for sulfide ions. Thus, treatment of aqueous solutions of many metal cations to a solution of thioacetamide affords the corresponding metal sulfide:
Related precipitations occur for sources of soft trivalent cations (As3+, Sb3+, Bi3+) and monovalent cations (Ag+, Cu+).
Thioacetamide is prepared by treating acetamide with phosphorus pentasulfide as shown in the following idealized reaction: [4]
The C2NH2S portion of the molecule is planar; the C-S, C-N, and C-C distances are 1.68, 1.31, and 1.50 Å, respectively. The short C-S and C-N distances indicate multiple bonding. [2]
Thioacetamide is carcinogen class 2B.
It is known to produce marked hepatotoxicity in exposed animals. Toxicity values are 301 mg/kg in rats (LD50, oral administration), 300 mg/kg in mice (LD50, intraperitoneal administration). [5] This is evidenced by enzymatic changes, which include elevation in the levels of serum alanine transaminase, aspartate transaminase and aspartic acid. [6]
In chemistry, azide is a linear, polyatomic anion with the formula N−3 and structure −N=N+=N−. It is the conjugate base of hydrazoic acid HN3. Organic azides are organic compounds with the formula RN3, containing the azide functional group. The dominant application of azides is as a propellant in air bags.
Sulfide (British English also sulphide) is an inorganic anion of sulfur with the chemical formula S2− or a compound containing one or more S2− ions. Solutions of sulfide salts are corrosive. Sulfide also refers to large families of inorganic and organic compounds, e.g. lead sulfide and dimethyl sulfide. Hydrogen sulfide (H2S) and bisulfide (SH−) are the conjugate acids of sulfide.
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. 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 with the IMA symbol: Ace.
Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula [Et4N]+, consisting of four ethyl groups attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salts of inorganic anions. It is used similarly to tetrabutylammonium, the difference being that its salts are less lipophilic, more easily crystallized and more toxic.
Fibrosis, also known as fibrotic scarring, is a pathological wound healing in which connective tissue replaces normal parenchymal tissue to the extent that it goes unchecked, leading to considerable tissue remodelling and the formation of permanent scar tissue.
Thiourea is an organosulfur compound with the formula SC(NH2)2 and the structure H2N−C(=S)−NH2. It is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom ; however, the properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the general structure R2N−C(=S)−NR2.
A thioamide is a functional group with the general structure R1−C(=S)−NR2R3, where R1, R2 and R3 are any groups. Analogous to amides, thioamides exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier.
Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.
Iproniazid is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity. The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France until its discontinuation in 2015.
Diallyl disulfide is an organosulfur compound derived from garlic and a few other genus Allium plants. Along with diallyl trisulfide and diallyl tetrasulfide, it is one of the principal components of the distilled oil of garlic. It is a yellowish liquid which is insoluble in water and has a strong garlic odour. It is produced during the decomposition of allicin, which is released upon crushing garlic and other plants of the family Alliaceae. Diallyl disulfide has many of the health benefits of garlic, but it is also an allergen causing garlic allergy. Highly diluted, it is used as a flavoring in food. It decomposes in the human body into other compounds such as allyl methyl sulfide.
Dimethyl phthalate (DMP) is an organic compound and phthalate ester. it is a colourless and oily liquid that is soluble in organic solvents, but which is only poorly soluble in water.
o-Toluidine (ortho-toluidine) is an organic compound with the chemical formula CH3C6H4NH2. It is the most important of the three isomeric toluidines. It is a colorless liquid although commercial samples are often yellowish. It is a precursor to the herbicides metolachlor and acetochlor.
Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungicides. In general these applications are declining in step with growing concerns about their impact on the environment and human health. The parent compounds are arsane and arsenic acid. Despite their toxicity, organoarsenic biomolecules are well known.
Chelates in animal feed is jargon for metalloorganic compounds added to animal feed. The compounds provide sources of various metals that improve the health or marketability of the animal. Typical metals salts are derived from cobalt, copper, iron, manganese, and zinc. The objective of supplementation with trace minerals is to avoid a variety of deficiency diseases. Trace minerals carry out key functions in relation to many metabolic processes, most notably as cofactors for enzymes and hormones, and are essential for optimum health, growth and productivity. For example, supplementary minerals help ensure good growth, bone development, feathering in birds, hoof, skin and hair quality in mammals, enzyme structure and functions, and appetite. Deficiency of trace minerals affect many metabolic processes and so may be manifested by different symptoms, such as poor growth and appetite, reproductive failures, impaired immune responses, and general ill-thrift. From the 1950s to the 1990s most trace mineral supplementation of animal diets was in the form of inorganic minerals, and these largely eradicated associated deficiency diseases in farm animals. The role in fertility and reproductive diseases of dairy cattle highlights that organic forms of Zn are retained better than inorganic sources and so may provide greater benefit in disease prevention, notably mastitis and lameness.
Norbormide is a toxic compound used as a rodenticide. It has several mechanisms of action, acting as a vasoconstrictor and calcium channel blocker, but is selectively toxic to rats and has relatively low toxicity to other species, due to a species specific action of opening the permeability transition pores in rat mitochondria.
α-Naphthylthiourea (ANTU) is an organosulfur compound with the formula C10H7NHC(S)NH2. This a white, crystalline powder although commercial samples may be off-white. It is used as a rodenticide and as such is fairly toxic. Naphthylthiourea is available as 10% active baits in suitable protein- or carbohydrate-rich materials and as a 20% tracking powder.
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