Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform esterified azeotropically; | 72% |
With LEWATIT K2621 In toluene for 72h; Heating; | 58% |
With magnesium sulfate; toluene-4-sulfonic acid for 16h; Inert atmosphere; Reflux; | 36% |
thiocyanato-acetic acid ethyl ester
1-(ethoxycarbonylmethyl)pyridinium chloride
A
pyridinium cyanoi(ethoxycarbonyl)methylide
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A 63% B n/a |
thiocyanato-acetic acid ethyl ester
1-(2-oxopropyl)pyridinium chloride
A
Cyano-acetyl-pyridinium-methylid
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A 58% B n/a |
thiocyanato-acetic acid ethyl ester
1-ethoxycarbonylmethyl-4-methylpyridinium chloride
A
C11H12N2O2
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A 53% B n/a |
thiocyanato-acetic acid ethyl ester
1-Ethoxycarbonylmethyl-3,5-dimethyl-pyridinium; chloride
A
C12H14N2O2
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A 51% B n/a |
thiocyanato-acetic acid ethyl ester
1-(2-oxo-2-phenylethyl)pyridin-1-ium chloride
A
1-(1-cyano-2-oxo-2-phenyl-ethyl)-pyridinium betaine
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A 45% B n/a |
thiocyanato-acetic acid ethyl ester
1-acetonyl-3,5-dimethylpyridinium chloride
A
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A n/a B 42% |
thiocyanato-acetic acid ethyl ester
1-acetonyl-4-methylpyridinium chloride
A
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A n/a B 40% |
thiocyanato-acetic acid ethyl ester
1-[2-oxo-2-(phenyl)ethyl]-4-methylpyridinium chloride
A
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A n/a B 37% |
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A n/a B 28% |
thiocyanato-acetic acid ethyl ester
1-(cyanomethyl)-3,5-dimethylpyridinium chloride
A
3,5-dimethylpyridinium dicyanomethylide
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A 18% B n/a |
thiocyanato-acetic acid ethyl ester
A
4-methylpyridinium dicyanomethylide
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A 15% B n/a |
thiocyanato-acetic acid ethyl ester
2-pyridin-1-ium-1-ylacetonitrile chloride
A
pyridinium 1-dicyanomethylide
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In chloroform Ambient temperature; | A 7% B n/a |
Conditions | Yield |
---|---|
With phosphoric acid beim Destillieren; |
Conditions | Yield |
---|---|
With ethanol; 6-methyl-2,4-dinitrophenol durch Oxydations-Reduktionsfermente im Sonnenlicht bei pH 7.2; |
Conditions | Yield |
---|---|
zerfaellt in der Waerme; |
4,4-diethyl-3,5-dithia-heptanedioic acid diethyl ester
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
Destillation im Vakuum; | |
Destillation im Vakuum; |
4,4-dipropyl-3,5-dithia-heptanedioic acid diethyl ester
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
Destillation im Vakuum; |
4,4-dibutyl-3,5-dithia-heptanedioic acid diethyl ester
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
Destillation im Vakuum; |
formamide
ethyl bromoacetate
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With pyridine; phosphorous (V) sulfide anschliessend Behandeln mit Wasser; |
Conditions | Yield |
---|---|
Veresterung; |
Conditions | Yield |
---|---|
With ethanol; potassium hydrosulfide | |
With hydrosulfide exchange resin (from Amberlite IRA-400); triethylamine hydrochloride In methanol for 1h; Ambient temperature; | 97 % Chromat. |
Conditions | Yield |
---|---|
With ethanol |
1-(ethoxycarbonylmethylthio)-4-methylphthalazine
A
1-methyl-3,4-dihydro-4-oxophthalazine
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
In 1,4-dioxane; water at 25℃; Rate constant; var. pH; |
(1-Hydroxy-2-oxo-2-phenyl-ethylsulfanyl)-acetic acid ethyl ester
A
2,2-dihydroxy-1-phenyl-ethanone
B
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In water; acetonitrile at 30℃; Equilibrium constant; |
thiocyanato-acetic acid ethyl ester
phosphoric acid
water
ethyl 2-sulfanylacetate
2-(acetylthio)acetate ethyl ester
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With water |
A
diethyl 2,2'-disulfanediyldiacetate
B
ethyl 2-sulfanylacetate
C
[5,6]fullerene-C70
Conditions | Yield |
---|---|
at 50℃; Temperature; |
2-chloro-3-pyridinecarbonitrile
ethyl 2-sulfanylacetate
ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.25h; Stage #2: 2-chloro-3-pyridinecarbonitrile In dimethyl sulfoxide; mineral oil at 20℃; for 3h; | 100% |
With sodium carbonate In ethanol at 90℃; for 2.5h; | 94% |
With sodium carbonate In ethanol for 4.5h; Heating / reflux; | 93.2% |
N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine
ethyl 2-sulfanylacetate
2-ethoxycarbonyl-5-trifluoroacetyl-3-trifluoromethylnaphtho<1,2-b>thiophene
Conditions | Yield |
---|---|
In acetonitrile for 2h; Heating; | 100% |
3-bromo-2-thiophenecarboxaldehyde
ethyl 2-sulfanylacetate
ethyl thieno[3,2,-b]thiophene-2-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 25 - 30℃; Inert atmosphere; Large scale; | 97.9% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h; | 91% |
2,3-Dichloro-1,4-naphthoquinone
ethyl 2-sulfanylacetate
ethyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetate
Conditions | Yield |
---|---|
With water at 50℃; for 2h; | 100% |
In water at 50℃; for 2h; | 100% |
In ethanol at 80 - 90℃; | 97% |
4-chloro-3-cyano-5-fluoropyridine
ethyl 2-sulfanylacetate
3-amino-7-fluoro-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 40℃; for 1h; | 100% |
2-fluoro-5-nitrobenzonitrile
ethyl 2-sulfanylacetate
ethyl (3-amino-5-nitrobenzothiophen)-2-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide | 100% |
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.333333h; Stage #2: 2-fluoro-5-nitrobenzonitrile In dimethyl sulfoxide; mineral oil at 20℃; for 3h; | 93% |
With triethylamine In dimethyl sulfoxide at 20℃; for 3h; | 90% |
1-benzoyl-4-oxo-piperidine-3-carboxylic acid methyl ester
ethyl 2-sulfanylacetate
A
1-benzoyl-4-ethoxycarbonylmethylsulfanyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
B
5-benzoyl-3-hydroxy-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
In ethanol | A n/a B 100% |
ethyl 2-sulfanylacetate
6-amino-5-bromo-pyridine-2-carboxylic acid methyl ester
methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 6-amino-5-bromo-pyridine-2-carboxylic acid methyl ester In N,N-dimethyl-formamide at 20℃; | 100% |
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 6-amino-5-bromo-pyridine-2-carboxylic acid methyl ester In N,N-dimethyl-formamide at 20℃; for 16h; | |
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 1h; Stage #2: 6-amino-5-bromo-pyridine-2-carboxylic acid methyl ester In DMF (N,N-dimethyl-formamide) at 20℃; for 16h; |
allyldimethylethoxysilane
ethyl 2-sulfanylacetate
[3-(ethoxydimethylsilanyl)propylsulfanyl]acetic acid ethyl ester
Conditions | Yield |
---|---|
at 100℃; for 16h; Inert atmosphere; | 100% |
3-bromo-6-(furan-2-yl)pyrazine-2-carbonitrile
ethyl 2-sulfanylacetate
ethyl 7-amino-2-(furan-2-yl)thieno[2,3-b]pyrazine-6-carboxylate
Conditions | Yield |
---|---|
With sodium carbonate In ethanol at 20 - 50℃; for 3h; | 100% |
With sodium carbonate In ethanol at 20 - 50℃; for 3h; | 10% |
3-bromobenzo[b]thiophene-2-carbaldehyde
ethyl 2-sulfanylacetate
ethyl thieno[3,2-b][1]benzothiophene 2-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 50h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 72h; | 92% |
With potassium carbonate In N,N-dimethyl-formamide | |
With potassium carbonate In N,N-dimethyl-formamide |
3-nitro-4-fluorobenzoic acid
ethyl 2-sulfanylacetate
4-ethoxycarbonylmethylsulfanyl-3-nitrobenzoic acid
Conditions | Yield |
---|---|
With sodium acetate In water at 90℃; for 24h; Inert atmosphere; | 100% |
(2-amino-3-methylphenyl) (benzotriazole-1-yl)methanone
ethyl 2-sulfanylacetate
ethyl 2-(2-amino-3-methylbenzoylthio)acetate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; | 100% |
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethylguanidine In N,N-dimethyl-formamide at 23℃; for 16h; | 100% |
3-bromo-5-(4-methoxyphenyl)thiophene-2-carbaldehyde
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 50h; | 100% |
3-bromo-5-(4-(trifluoromethyl)phenyl)thiophene-2-carbaldehyde
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 50h; | 100% |
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; | 100% |
With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h; | 100% |
ethyl 2-sulfanylacetate
2-bromo-4-methyl-5-nitrobenzaldehyde
ethyl 6-methyl-5-nitrobenzo[b]thiophene-2-carboxylate
Conditions | Yield |
---|---|
With sodium In ethanol for 3h; Inert atmosphere; Reflux; | 99.8% |
With sodium ethanolate 1.) EtOH, 5 deg C, 20 min, 2.) EtOH, reflux, 3 h; Yield given. Multistep reaction; |
ethyl 2-sulfanylacetate
dimethyl N-cyanodithioiminocarbonate
ethyl 4-amino-2-(methylthio)thiazol-5-carboxylate
Conditions | Yield |
---|---|
With diisopropylamine In N,N-dimethyl-formamide at 100℃; for 5h; | 99% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; | 89% |
With triethylamine In N,N-dimethyl-formamide | |
With triethylamine In N,N-dimethyl-formamide at 100℃; for 2h; |
cyclohexane-1,2-epoxide
ethyl 2-sulfanylacetate
trans-2-hydroxycyclohexyl(carboethoxy)methyl sulfide
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 25h; Heating; | 99% |
2-((R)-oxiran-2-ylmethoxy)tetrahydro-2H-pyran
ethyl 2-sulfanylacetate
[(R)-2-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-propylsulfanyl]-acetic acid ethyl ester
Conditions | Yield |
---|---|
sodium ethanolate In ethanol at 22℃; | 99% |
ethyl 2-sulfanylacetate
α-bromoacetophenone
ethyl 2-((2-oxo-2-phenylethyl)thio)acetate
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 20℃; Inert atmosphere; | 99% |
With sodium hydroxide In methanol for 4h; | 60% |
With sodium carbonate In ethanol at 20℃; |
[Bis(methylthio)methylene]malononitrile
ethyl 2-sulfanylacetate
3-amino-4-cyano-5-(methylthio)thiophene-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine In methanol for 2h; Reflux; | 99% |
With triethylamine In methanol for 2h; Reflux; | 99% |
With triethylamine In ethanol at 0 - 20℃; for 12h; | 72.6% |
3-chloroisonicotinic acid ethyl ester
ethyl 2-sulfanylacetate
ethyl 3-hydroxythieno [2,3-c]pyridine-2-carboxylate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 5 - 20℃; for 18.67h; | 99% |
In N,N-dimethyl-formamide; mineral oil at 20℃; for 3.25h; Cooling with ice; | 70% |
2-fluoro-6-(trifluoromethyl)benzonitrile
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; | 99% |
With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h; | 99% |
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: N-(benzyloxy)formimidoyl chloride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; | 99% |
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With Trimethylsilanol; (S)-N-(2-pyridinesulfonyl)-(6-methoxyquinolin-4-yl)(8-vinylquinuclidin-2-yl)methanamine In toluene at -80℃; for 8h; Inert atmosphere; enantioselective reaction; | 99% |
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With Trimethylsilanol; (S)-N-(2-pyridinesulfonyl)-(6-methoxyquinolin-4-yl)(8-vinylquinuclidin-2-yl)methanamine In toluene at -80℃; for 8h; Inert atmosphere; enantioselective reaction; | 99% |
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With Trimethylsilanol; (S)-N-(2-pyridinesulfonyl)-(6-methoxyquinolin-4-yl)(8-vinylquinuclidin-2-yl)methanamine In toluene at -80℃; for 8h; Inert atmosphere; enantioselective reaction; | 99% |
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
With Trimethylsilanol; (S)-N-(2-pyridinesulfonyl)-(6-methoxyquinolin-4-yl)(8-vinylquinuclidin-2-yl)methanamine In toluene at -80℃; for 8h; Inert atmosphere; enantioselective reaction; | 99% |
The Acetic acid,2-mercapto-, ethyl ester, with the CAS registry number 623-51-8, is also known as Thioglycolic acid ethyl ester. Its EINECS number is 210-800-3. This chemical's molecular formula is C4H8O2S and molecular weight is 120.17. What's more, its systematic name is ethyl sulfanylacetate. It is air sensitive. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, static electricity and fire. It is used as a reagent to determinate iron content.
Physical properties of Acetic acid,2-mercapto-, ethyl ester are: (1)ACD/LogP: 1.18; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.18; (4)ACD/LogD (pH 7.4): 1.14; (5)ACD/BCF (pH 5.5): 4.66; (6)ACD/BCF (pH 7.4): 4.21; (7)ACD/KOC (pH 5.5): 104.72; (8)ACD/KOC (pH 7.4): 94.67; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 51.6 Å2; (13)Index of Refraction: 1.452; (14)Molar Refractivity: 30.25 cm3; (15)Molar Volume: 112 cm3; (16)Polarizability: 11.99×10-24cm3; (17)Surface Tension: 32.6 dyne/cm; (18)Density: 1.072 g/cm3; (19)Flash Point: 47.8 °C; (20)Enthalpy of Vaporization: 39.45 kJ/mol; (21)Boiling Point: 157.8 °C at 760 mmHg; (22)Vapour Pressure: 2.7 mmHg at 25°C.
Preparation: this chemical can be prepared by thioglycollicacid and ethanol by heating. This reaction will need solvent sulfuric acid with the reflux time of 24 hours. The product is gained by collecting the cut fraction of the temperature of 155-158 °C at atmospheric fractionation.
Uses of Acetic acid,2-mercapto-, ethyl ester: it can be used to produce (2-cyano-ethylsulfanyl)-acetic acid ethyl ester at the ambient temperature. It will need reagent sodium ethoxide with the reaction time of 14 hours. The yield is about 90%.
When you are using this chemical, please be cautious about it as the following:
This chemical is flammable, so you should keep it away from sources of ignition - No smoking. It is toxic if swallowed. It is irritating to eyes and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)InChI: InChI=1S/C4H8O2S/c1-2-6-4(5)3-7/h7H,2-3H2,1H3
(2)InChIKey: PVBRSNZAOAJRKO-UHFFFAOYSA-N
(3)Canonical SMILES: CCOC(=O)CS
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 100mg/kg (100mg/kg) | National Technical Information Service. Vol. AD277-689. | |
rat | LD50 | intraperitoneal | 176mg/kg (176mg/kg) | Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974. | |
rat | LD50 | oral | 178mg/kg (178mg/kg) | Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974. |
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