Conditions | Yield |
---|---|
With Lawessons reagent In tetrahydrofuran at 20℃; for 3h; Solvent; | 93% |
With Lawessons reagent In tetrahydrofuran at 20℃; for 0.166667h; | 87% |
With Lawessons reagent for 0.0333333h; microwave irradiation; | 87% |
Conditions | Yield |
---|---|
With aluminum oxide; diethyl dithiophosphate ammonium salt for 6h; Heating; | 90% |
Stage #1: acetonitrile With calcium hydride; tiolacetic acid at 50℃; for 1h; Stage #2: With water In ethyl acetate at 20℃; | 80% |
With diammonium sulfide In methanol at 80℃; for 0.25h; microwave irradiation; | 53% |
propan-1-ol
dipropyl thioacetimidoylphosphite
A
tri-n-propyl phosphite
B
thioacetamide
Conditions | Yield |
---|---|
In benzene | A 51% B 59.1% |
Conditions | Yield |
---|---|
In acetonitrile for 4h; Heating; | A 13.3% B 54.5% |
ethylene glycol
2,4-(4-phenoxyphenyl)-1,3-dithia-2λ(5),4λ(5)-diphosphetane 2,4-disulfides
A
thioacetamide
Conditions | Yield |
---|---|
In acetonitrile for 4h; Ambient temperature; | A 53.3% B 12.3% |
dipropyl thioacetimidoylphosphite
A
dipropyl phosphorochloridite
B
thioacetamide
Conditions | Yield |
---|---|
With hydrogenchloride In benzene | A 37% B 53% |
Conditions | Yield |
---|---|
In acetonitrile for 4h; Product distribution; Mechanism; Heating; other diols; also with p-phenoxyphenyl-(LR); variation of condition; | A 37.3% B 52% C 5.6% |
In acetonitrile for 5h; Heating; | A 37.3% B 52% C 5.6% |
triethylamine
dipropyl thioacetimidoylphosphite
A
diethyl-phosphoramidous acid dipropyl ester
B
thioacetamide
Conditions | Yield |
---|---|
In benzene at 55℃; for 0.333333h; | A 36.4% B 52% |
Conditions | Yield |
---|---|
In water at 80℃; for 6h; | 45% |
2,3-dimethyl-2,3-butane diol
2,4-(4-phenoxyphenyl)-1,3-dithia-2λ(5),4λ(5)-diphosphetane 2,4-disulfides
A
thioacetamide
Conditions | Yield |
---|---|
In acetonitrile for 4h; Ambient temperature; | A 35.3% B 41.6% |
Conditions | Yield |
---|---|
In acetonitrile for 3h; Heating; | A 41.3% B 31.1% C 12.5% |
Lawessons reagent
bis-(3,5-dichloro-2-hydroxy-phenyl)-(4-nitro-phenyl)-methane
acetonitrile
A
thioacetamide
Conditions | Yield |
---|---|
for 12h; Heating; | A n/a B 37% |
Butane-1,4-diol
2,4-(4-phenoxyphenyl)-1,3-dithia-2λ(5),4λ(5)-diphosphetane 2,4-disulfides
A
thioacetamide
Conditions | Yield |
---|---|
In acetonitrile for 2h; Heating; | A 29.3% B 8.13% |
Conditions | Yield |
---|---|
In acetonitrile for 4h; Heating; | A 18.6% B 26% |
Conditions | Yield |
---|---|
In acetonitrile at 25℃; for 12h; | A 20% B 23% |
Conditions | Yield |
---|---|
With ethanol; ammonia |
Conditions | Yield |
---|---|
With aluminum sulfide at 240℃; |
Conditions | Yield |
---|---|
With diethyl ether; hydrogen sulfide |
ethanol
diethyl thioacetimidoylphosphite
A
thioacetamide
B
triethyl phosphite
Conditions | Yield |
---|---|
In benzene | A 2.5 g B 41.4 g |
Conditions | Yield |
---|---|
at 326.9℃; Kinetics; Thermodynamic data; log A, Ea; temperatures: 645.2 - 704.2 K; |
Conditions | Yield |
---|---|
at 198.9 - 250.9℃; Kinetics; Arrhenius parameters; |
N-tert-butylethanethioamide
thioacetamide
Conditions | Yield |
---|---|
at 364.9 - 425.9℃; Kinetics; Arrhenius parameters; |
thioacetamide sulfoxide
A
acetamide
B
thioacetamide
C
acetonitrile
Conditions | Yield |
---|---|
With sodium NADH*4H2O In water-d2 at 37℃; for 24h; Yield given. Yields of byproduct given; | |
With sodium NADPH In water-d2 at 37℃; for 96h; Yield given. Yields of byproduct given; |
O,O'-tetramethylene bis(hydrogen methylphosphonodithioate)
acetonitrile
thioacetamide
Conditions | Yield |
---|---|
In tetrachloromethane Ambient temperature; investigation of intermediate, stability of the product, oligomerization; |
Conditions | Yield |
---|---|
at 224.9℃; Rate constant; Thermodynamic data; Mechanism; Ea, var. temp.; |
hydrogenchloride
diethyl ether
isothiocyanatobenzene
acetonitrile
thioacetamide
Conditions | Yield |
---|---|
bei Einw. von Saeuren; |
hydrogenchloride
diethyl ether
thioacetanilide
acetonitrile
thioacetamide
Conditions | Yield |
---|---|
bei Einw. von Saeuren; |
Conditions | Yield |
---|---|
at 80℃; under 6251820 Torr; |
hydrogenchloride
diethyl ether
N-Phenylbenzothioamide
acetonitrile
A
N-phenyl benzoyl amide
B
thioacetamide
Conditions | Yield |
---|---|
bei Einw. von Saeuren; |
thioacetamide
2-Bromo-4'-methoxyacetophenone
methyl 4-(2-methyl-1,3-thiazol-4-yl)phenyl ether
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 100% |
In ethylene glycol at 20℃; for 0.0833333h; | 97% |
With 1,3-di-n-butyl-imidazolium tetrafluoroborate at 20℃; for 0.25h; | 96% |
2-Bromo-2',4'-dimethoxyacetophenone
thioacetamide
4-(2,4-dimethoxy-phenyl)-2-methyl-thiazole
Conditions | Yield |
---|---|
In ethanol for 2h; Heating / reflux; | 100% |
thioacetamide
5-Acetoxy-3-chloropentan-2-one
acetic acid 2-(2,4-dimethylthiazol-5-yl)-ethyl ester
Conditions | Yield |
---|---|
at 110 - 120℃; for 0.5h; | 100% |
at 110 - 120℃; for 0.5h; | 100% |
at 110 - 120℃; for 0.5h; | 100% |
3-chloro-1,6,6-trimethyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile
thioacetamide
1-amino-5,8,8-trimethyl-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxamide
Conditions | Yield |
---|---|
With potassium carbonate In ethanol for 4h; Heating / reflux; | 100% |
thioacetamide
Conditions | Yield |
---|---|
With ammonium hydroxide; ammonium chloride In water NiCl2*6H2O dissolved in distilled water with NH4OH and NH4Cl buffer soln. adjusted the pH to 9.9 at 60°C; | A 0% B 100% C 0% D 0% |
With ammonium hydroxide; ammonium chloride In water NiCl2*6H2O dissolved in distilled water with NH4OH and NH4Cl buffer soln. adjusted the pH to 9.9 at 70°C; | A 0% B 100% C 0% D 0% |
With sodium hydroxide In water NiCl2*6H2O dissolved in distilled water with NaOH, thioacetamide added at 40°C, quickly mixed, boiled at 100°C for 1 h, refluxed at 60-80°C for 12 h; filtered, washed, dried at 120°C; | A 0% B 0% C 100% D 0% |
methyltriphenylbismuthonium tetrafluoroborate
thioacetamide
A
1-(methylthio)ethyleneiminium tetrafluoroborate
B
triphenylbismuthane
Conditions | Yield |
---|---|
In chloroform-d1 mixt. (Ph3BiMe)(BF4), thioacetamide, and CDCl3 was allowed to react at room temp. for 1 min; detn. by NMR; | A 100% B 100% |
1-(4-fluorophenyl)-3-(phenylsulfanyl)prop-2-yn-1-ol
thioacetamide
4-(4-fluorobenzyl)-2-methyl-5-(phenylsulfanyl)-thiazole
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate; scandium tris(trifluoromethanesulfonate) In nitromethane; water for 0.166667h; Reflux; regioselective reaction; | 100% |
thioacetamide
3-chloro-4-(bromoacetyl)nitrobenzene
Conditions | Yield |
---|---|
Stage #1: thioacetamide; 3-chloro-4-(bromoacetyl)nitrobenzene In ethanol at 85℃; for 1h; Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In ethanol; water for 1h; Reflux; Stage #3: With potassium hydroxide In ethanol; water at 0℃; | 100% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 60℃; for 1h; Hantzsch Thiazole Synthesis; Sealed tube; | 99% |
With tert-butylammonium hexafluorophosphate(V) In methanol at 20℃; for 0.25h; | 95% |
With 1,3-di-n-butyl-imidazolium tetrafluoroborate at 20℃; for 0.166667h; | 94% |
thioacetamide
3'-nitro-2-bromoacetophenone
2-methyl-4-(3-nitrophenyl)-thiazole
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 99% |
In ethanol for 1.5h; Heating; | 83% |
Conditions | Yield |
---|---|
With calcium oxide; palladium; triphenylphosphine In N,N-dimethyl-formamide at 60℃; for 3h; Product distribution; molar ratio of each component, 1,1'-bis(diphenylphosphino)ferrocene (dppf) ligand, reation time; | 99% |
With calcium oxide; palladium; triphenylphosphine In N,N-dimethyl-formamide at 60℃; for 3h; | 99 % Chromat. |
thioacetamide
2-[2-Bromo-3-[4-chloro-2-(2-fluorobenzoyl)phenyl]-3-oxopropyl]-1H-isoindole-1,3(2H)-dione
2-{4-[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-2-methyl-thiazol-5-ylmethyl}-isoindole-1,3-dione
Conditions | Yield |
---|---|
With sulfur dioxide In N,N-dimethyl-formamide for 1h; Heating; | 99% |
thioacetamide
(2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine
(2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-methylthiazol-4'-yl)pyrrolidine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol Condensation; Heating; | 99% |
With sodium hydrogencarbonate In ethanol for 2h; Heating; | 99% |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 98℃; for 20h; | 99% |
Conditions | Yield |
---|---|
In water at 160℃; for 12h; High pressure; Autoclave; | 99% |
With layryl mercaptane In ethane-1,2-diol Sonication; thioacetamide in ethanediol heated to 65°C,, then SnCl4 in ethanediol and lauryl mercaptane added; sonicated for 0.5 h; mixt. injected into thioacetamide within 40 min; cooled down to room temp.; EtOH added; centrifuged; washed 3 times with EtOH; | |
With cetyltrimethylammonium bromide In ethanol High Pressure; cetyltrimethylammonium bromide, SnCl4*5H2O and thioacetamide added into Schlenk flask; sealed by Teflon screw cap; heated at 40, 80 or 120°C for 2, 4, 6, 8 or 10 h under inert atm.; allowed to cool naturally to room temp.; filtered out, washed with water for sseveral times; dispersed in Et2O/EtOH (1:1) via sonication, centrifuged; dried overnight under high vac. at40°C; |
thioacetamide
Conditions | Yield |
---|---|
In ethanol at 80℃; for 12h; Sealed tube; | 99% |
thioacetamide
2-bromo-3'-methoxyacetophenone
4-(3-methoxyphenyl)-2-methylthiazole
Conditions | Yield |
---|---|
In toluene for 24h; Heating / reflux; | 98.5% |
In ethanol at 80℃; for 1h; | 90% |
In ethanol at 80℃; for 1h; | 90% |
Conditions | Yield |
---|---|
In further solvent(s) Sonication; Cd salt and thioacetamide slowly dissolved 1-ethyl-3-methylimidazolium ethyl sulfate under stirring at room temp., sonicated for 60 min; centrifuged, washed 3 times (H2O, EtOH), dried at 50°C for 24 h; | 98.2% |
In water Sonication; Cd salt and thioacetamide slowly dissolved in H2O/1-ethyl-3-methylimidazolium ethyl sulfate (1:1) under stirring at room temp., sonicated for 60min; centrifuged, washed 3 times (H2O, EtOH), dried at 50°C for 24 h; | 89.8% |
In water Sonication; Cd salt and thioacetamide slowly dissolved in H2O under stirring at roomtemp., sonicated for 60 min; centrifuged, washed 3 times (H2O, EtOH), dried at 50°C for 24 h; | 82% |
thioacetamide
2-[2-Bromo-3-[4-chloro-2-(2-chlorobenzoyl)phenyl]-3-oxopropyl]-1H-isoindole-1,3(2H)-dione
2-{4-[4-Chloro-2-(2-chlorobenzoyl)phenyl-2-methyl]-5-thiazolyl-methyl}-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With sulfur dioxide In N,N-dimethyl-formamide for 1h; Heating; | 98% |
With sulfur dioxide In methanol; dichloromethane; N,N-dimethyl-formamide |
2-Chloroacrylic acid
thioacetamide
S-(2-Carboxy-2-chlorethyl)thioacetamid-hydrochlorid
Conditions | Yield |
---|---|
With hydrogenchloride In acetonitrile for 4h; Ambient temperature; | 98% |
2-chloroacrylamide
thioacetamide
S-<2-Carbamoyl-2-chlorethyl>thioacetamid-hydrochlorid
Conditions | Yield |
---|---|
With hydrogenchloride In acetonitrile for 1h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
In 1,4-dioxane Ambient temperature; | 98% |
2-Bromo-1-(3,4-dimethoxyphenyl)ethanone
thioacetamide
4-(3,4-dimethoxyphenyl)-2-methylthiazole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 65℃; for 8h; | 98% |
In ethanol for 2h; Reflux; Inert atmosphere; | 87% |
In N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux; | 82% |
2-bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone
thioacetamide
4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methylthiazole
Conditions | Yield |
---|---|
In tetrahydrofuran for 6h; Heating / reflux; | 98% |
4-(1-hydroxy-1,3-diphenylprop-2-ynyl)benzonitrile
thioacetamide
4-((2-methyl-5-phenylthiazol-4-yl)methyl)benzonitrile
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 100℃; for 23h; Inert atmosphere; regioselective reaction; | 98% |
1,1,3-triphenylprop-2-yn-1-ol
thioacetamide
4-benzhydryl-2-methyl-5-phenylthiazole
Conditions | Yield |
---|---|
With 5 wtpercent H-USY zeolite In 1,2-dichloro-ethane at 100℃; for 16h; Concentration; | 98% |
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 100℃; for 5h; Inert atmosphere; regioselective reaction; | 90% |
1-(4-chlorophenyl)-1,3-diphenylprop-2-yn-1-ol
thioacetamide
4-((4-chlorophenyl)(phenyl)methyl)-2-methyl-5-phenylthiazole
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 100℃; for 2.5h; Inert atmosphere; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
In ethanol for 1h; Temperature; Solvent; Reflux; chemoselective reaction; | 98% |
In ethanol for 1h; Temperature; Reflux; | 98% |
thioacetamide
Methanesulfonyl azide
N-(methylsulfonyl)acetimidamide
Conditions | Yield |
---|---|
In ethanol for 1h; Solvent; Temperature; Reflux; chemoselective reaction; | 98% |
In water at 20℃; for 15h; Solvent; Temperature; | 63% |
thioacetamide
Conditions | Yield |
---|---|
In methanol at 20 - 70℃; for 2h; Inert atmosphere; | 98% |
The molecular structure of thioacetamide (CAS NO.62-55-5):
IUPAC Name: ethanethioamide
Empirical Formula: C2H5NS
Molecular Weight: 75.1328
H bond acceptors: 1
H bond donors: 2
Freely Rotating Bonds: 0
Index of Refraction: 1.543
Molar Refractivity: 22.13 cm3
Molar Volume: 70.2 cm3
Surface Tension: 50.6 dyne/cm
Density: 1.07 g/cm3
Flash Point: 21.4 °C
Enthalpy of Vaporization: 35.03 kJ/mol
Boiling Point: 111.7 °C at 760 mmHg
Vapour Pressure: 22.5 mmHg at 25°C
EINECS: 200-541-4
Melting Point: 108-112 °C(lit.)
Product Categories: Sulphur Derivatives
Storage Temp: Store at RT
Water Solubility: 16.3 g/100 mL (25 ºC)
Merck: 14,9319
BRN: 506006
Stability: Stability Incompatible with water, mineral acids
Conditions to Avoid: Incompatible materials
Incompatibilities with Other Materials: Strong oxidizing agents, strong acids, strong bases
Hazardous Decomposition Products: Carbon monoxide, carbon dioxide, nitrogen oxides (NOx) and ammonia (NH3), hydrogen sulfide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Will not occur
Thioacetamide is prepared by treating acetamide with phosphorus pentasulfide as shown in the following idealized reaction:
CH3C(O)NH2 + 1/4 P4S10 → CH3C(S)NH2 + 1/4 P4S6O4
1. | mmo-smc 19,900 µmol/L | MGGEAE Molecular and General Genetics. 174 (1979),39. | ||
2. | otr-rat:emb 30 mg/L | JJIND8 JNCI, Journal of the National Cancer Institute. 67 (1981),1303. | ||
3. | orl-rat TDLo:7350 mg/kg/40W-C:CAR | JJIND8 JNCI, Journal of the National Cancer Institute. 79 (1987),1047. | ||
4. | orl-rat TD:5140 mg/kg/47W-C:ETA,TER | JPBAA7 Journal of Pathology and Bacteriology. 72 (1956),415. | ||
5. | orl-rat LD50:301 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 27 (1974),380. | ||
6. | ipr-mus LD50:300 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . | ||
7. | scu-mus LDLo:2000 mg/kg | AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 12 (1904),447. |
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, 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.
Hazard Codes: T
Risk Statements 45-22-36/38-52/53
R45:May cause cancer.
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements 53-45-61-99
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: 2811
WGK Germany: 3
RTECS: AC8925000
F: 10
HS Code 29309070
Thioacetamide , with CAS number of 62-55-5, can be called ethanethioamide ; Acetamide, thio- ; Acetic acid, thiono-, amide ; Acetimidic acid, thio- ; Acetimidic acid, thio- (7CI) . Thioacetamide (CAS NO.62-55-5) is a white solid, can be used as the production of catalysts, stabilizers, inhibitor, electroplating additives, photographic drugs, pesticides, dyeing auxiliary and ore dressing agent. Also used as a polymer curing agent, crosslinking agent, rubber additives and pharmaceutical raw materials. The production methods of Thioacetamide (CAS NO.62-55-5) is acetonitrile and hydrogen sulfide reaction or to acetamide with phosphorus pentasulfide reaction.
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