Basic information Organic reagents Chemical properties Uses Production method Safety Related Supplier
Thioacetamide Chemical Properties
- Melting point:108-112 °C(lit.)
- Boiling point:111.7±23.0 °C(Predicted)
- Density 1.37
- refractive index 1.5300 (estimate)
- storage temp. Store at RT.
- solubility passes test2%
- form Liquid
- color Off-white to slightly beige
- PH5.2 (100g/l, H2O, 20℃)
- PH Range5.2
- Water Solubility 16.3 g/100 mL (25 ºC)
- Merck 14,9319
- BRN 506006
- Stability:Stability Incompatible with water, mineral acids.
- CAS DataBase Reference62-55-5(CAS DataBase Reference)
- IARC2B (Vol. 7, Sup 7) 1987
- NIST Chemistry ReferenceEthanethioamide(62-55-5)
- EPA Substance Registry SystemThioacetamide (62-55-5)
Thioacetamide Usage And Synthesis
- Organic reagentsThioacetamide is organic reagent, it is colorless or white crystalline flake. It is dissolved in water, ethanol, very slightly soluble in benzene, ether, the aqueous solution at room temperature or 50~60℃ is fairly stable, when placed 2 to 3 weeks, it is not change, but when hydrogen ions is in the presence, it quickly decomposes into hydrogen sulfide , but hydrolysis increases with alkalinity or acidity of the solution and the temperature rises quickly. Hydrolysis equations solution of thioacetamide in acidic and basic is:
Acidic solution: CH3CSNH2 + 2H2O----(NH4 +) + CH3COO-+ H2S
Alkaline solution: CH3CSNH2 + 2OH-----NH3 + CH3COO-+ HS-
Since H2S or HS-can generate for hydrolysis in acidic or alkaline solution, so in analytical chemistry, it is often used in place of toxic and odor H2S, as the metal cation group reagents or precipitation reagents. The property of resulting precipitate is good, easy to separate. In addition, it can also be used for bismuth measurement reagent. Preparation method: It can be prepared by heating the acetamide with aluminum sulfide, hydrogen sulfide reacting with acetonitrile, or acetamide reacting with K3PS4.
- Chemical propertiesIt is colorless or white crystals. Mp is 113-114℃, the solubility in water is 16.3g/100ml at 25℃, ethanol 26.4g/100ml. It is slightly soluble in benzene, ether. Their solution is quite stable at room temperature or 50-60℃, but when hydrogen ions exists, it can generate thiosulfate hydrogen and decompose quickly. New product sometimes has mercaptan odor, slight moisture absorption.
The above information is edited by the chemicalbook of Wang Xiaodong.
- Uses1. It can be used for the production of catalysts, stabilizers, polymerization inhibitors, electroplating additives, photographic chemicals, pesticides, dyeing auxiliary and processing agents. It can be also used as polymer curing agents, crosslinking agents, rubber additives and pharmaceutical raw materials.
2. It can be also used as vulcanizing agent and crosslinking agent of polymer, rubber additives, pharmaceutical raw materials, etc.
3. It can be also used as analytical reagents.
- Production methodThioacetamide can be obtained by the reaction of acetonitrile with hydrogen sulfide, or acetamide with phosphorus pentasulfide.
- Chemical PropertiesWhite solid
- Chemical PropertiesThioacetamide is combustible, crystalline compound. Slight mercaptan odor.
- UsesIt is used as an intermediate in organicsynthesis.
- UsesSulfide generation
- UsesSubstitute for H2S in laboratory qualitative analyses.
- DefinitionChEBI: A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.
- General DescriptionWhite crystals with a mercaptan odor.
- Air & Water ReactionsSlightly water soluble.
- Reactivity ProfileThioacetamide reacts with aqueous acid to generate hydrogen sulfide. Forms addition compounds and sulfides with salts of heavy metals. Hydrolyzed by acids or bases .
- HazardToxic by ingestion and inhalation, a possible carcinogen.
- Health HazardThe toxicity of this compound is moderatein rats; an oral lethal dose is 200 mg/kg.Oral administration of thioacetamide causedliver cancer in rats and mice. It is, however, a weak liver carcinogen. Malvaldi and associates (1988) investigated the mechanism of its carcinogenic activity on rat liver.Whereas the initiating ability of this compound is quite low, its promoting effect isstrong. Thus thioacetamide is a very effectivepromoter of the liver carcinogenesis. A similar promoting activity of liver carcinogenesishas been observed with other thioamide substances, such as thiobenzamide (Malvaldi et al. 1986). Low et al. (2004) have proposed a modelto explain thioacetamide-induced hepatotoxicity and cirrhosis in rat livers. The pathways of thioacetamide-induced liver fibrosiswere found to be initiated by thioacetamideS-oxide derived from the biotransformationof thioacetamide by the microsomal flavinadenine nucleotide containing monooxygenase and cytochrome P450 systems andinvolve oxidative stress and depletion ofsuccinyl-CoA, thus affecting heme and ironmetabolism. Karabay et al. (2005) observedsuch hepatic damage in rats with elevationof total nitrite level in livers and decrease inarginase activity. The authors have reportedthat nitrosative stress was essentially the critical factor in thioacetamide-induced hepaticfailure in rats.Pretreatment of rats with jigrine exhibited hepatoprotective action againstthioacetamide-induced toxicity (Ahmed et al.1999). Thioacetamide decreased the concentration of glutathione in the liver of rats.Jigrine pretreatment, however, restored theglutathione levels to the near normal values.The authors claimed that the effects of jigrinewere comparable to that of silymarin. Thehepatotoxicity in rats was found to potentiatefollowing pretreatment with phenobarbital.Al-Bader et al. (2000) investigated thetoxicity of thioacetamide in the spleen inexperimental animals. The authors foundan intimate association between the levelsof trace metals and spleen pathology, asobserved in studies of other organs.
- Fire HazardFlash point data on Thioacetamide are not available; Thioacetamide is probably combustible.
- Safety ProfileConfirmed carcinogen with experimental carcinogenic, neoplas tigenic, tumorigenic, and teratogenic data. Poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. Human mutation data reported. An experimental teratogen. Experimental reproductive effects. Exposure has caused liver damage. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also SULFIDES and MERCAPTANS.
- Potential ExposureThioacetamide is used as a replacement for hydrogen sulfide in qualitative analyses. Thioacetamide has been used as an organic solvent in the leather, textile, and paper industries; as an accelerator in the vulcanization of buna rubber; and as a stabilizer of motor fuel.
- CarcinogenicityThioacetamide is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
- ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
- Purification MethodsCrystallise the amide from absolute diethyl ether or *benzene. Dry it at 70o in a vacuum and store it over P2O5 at 0o under nitrogen. (It develops an obnoxious odour on storage, and absorption at 269nm decreases, hence it should be freshly recrystallised before use). [Beilstein 2 IV 565.]
- IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
- Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Treatment in an incinerator, boiler or cement kiln.
Thioacetamide Preparation Products And Raw materials
- Preparation Products3-(2-METHYL-1,3-THIAZOL-4-YL)BENZOIC ACID2-(2,5-DIMETHYL-1,3-THIAZOL-4-YL)ACETIC ACIDMETHYL 2-(2,5-DIMETHYL-1,3-THIAZOL-4-YL)ACETATE2,4-Dimethylthiazole-5-carboxylic acidAspoxicillin2-Methyl-1,3-thiazole-4-carboxylic acidETHYL 2-METHYLTHIAZOLE-4-CARBOXYLATE
- Raw materialsPhosphorus pentasulfideAcetamide
- 3-AMINO-2-BUTENETHIOAMIDE, 98 N,N'-BIS(2-HYDROXYETHYL)DITHIOOXAMIDE N-(1-NAPHTHYL)THIOACETAMIDE N-Phenyl-thioacetamid N.N'-DIBENZYLDITHIOOXAMIDE N,N'-DICYCLOHEXYLDITHIOOXAMIDE DITHIOURACIL THIOISONICOTINAMIDE 1-CYANO-N-METHYLTHIOFORMAMIDE 6-THIOXANTHINE Thioacetamide 2-HYDROXYACETAMIDE 2-[(Diphenylmethyl)thio]acetamide Dithiooxamide DIACETAMIDE N,N-Dimethylacetamide ACETYLTHIOCHOLINE IODIDE 2-Cyanothioacetamide
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