Methyl 4-oxotetrahydrothiophene-3-carboxylate

Methyl 4-oxotetrahydrothiophene-3-carboxylate Basic information
Product Name:Methyl 4-oxotetrahydrothiophene-3-carboxylate
Synonyms:4-CARBOMETHOXYTETRAHYDRO-3-THIOPHENONE;AKOS 92615;tetrahydro-4-oxo-3-thiophenecarboxylicacimethylester;METHYL 4-OXOTETRAHYDROTHIOPHENE-3-CARBOXYLATE;methyl tetrahydro-4-oxo-3-thenoate;4-Oxo-Tetrahydro-Thiophene-3-CarboxylicAcidMethylEster;4-CARBOMETHOXYTETRAHYDRO-3-THIOPHENE;Methyl 4-oxotetrahydrothiophene-3-carboxylate, 95+%
CAS:2689-68-1
MF:C6H8O3S
MW:160.19
EINECS:220-256-9
Product Categories:Esters;Thiophenes & Benzothiophenes;Thiophenes & Benzothiophenes
Mol File:2689-68-1.mol
Methyl 4-oxotetrahydrothiophene-3-carboxylate Structure
Methyl 4-oxotetrahydrothiophene-3-carboxylate Chemical Properties
Melting point 37-38 °C
Boiling point 95 °C
density 1.309±0.06 g/cm3(Predicted)
storage temp. 2-8°C(protect from light)
solubility Chloroform
form Solid
pka10.52±0.20(Predicted)
color Light Yellow
InChIInChI=1S/C6H8O3S/c1-9-6(8)4-2-10-3-5(4)7/h4H,2-3H2,1H3
InChIKeyLEAKUJFYXNILRB-UHFFFAOYSA-N
SMILESC1SCC(=O)C1C(OC)=O
EPA Substance Registry System3-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester (2689-68-1)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39
HazardClass IRRITANT
HS Code 29339900
MSDS Information
Methyl 4-oxotetrahydrothiophene-3-carboxylate Usage And Synthesis
Chemical PropertiesWhite solid
UsesMethyl 4-oxotetrahydrothiophene-3-carboxylate is used in the preparation of a new class of neuroleptic agents.
Synthesis2,3,4,5-Tetrahydro-4-oxo-3-thiophene carboxylic acid, methyl ester (L75a): 25.3 g (1.1 mol) of sodium were implemented in 190 mL abs. methanol to methylate. To methylate solution 70 g (0.360 mol) (L74) was added dropwise at the boiling point and the reaction mixture was heated for 45 min under reflux. The cooling mixture was poured onto a mixture of 500 mL ice and 300 mL water, acidified with 100 mL conc. HCl and the oily precipitating product was brought to crystallize under cooling with ice/sodium chloride bath. The crystals were sucked off, resumed in 100 mL methylene chloride and dried over sodium sulfate and evaporated. There were obtained 16.7 g of pale beige crystals. The aqueous phase was extracted three times with 100 mL of methylene chloride, the organic phase dried over sodium sulfate and evaporated. 30 g of crystalline product Methyl 4-oxotetrahydrothiophene-3-carboxylate was obtained. Yield: 46.7 g of light beige crystals (81 % of theory). mp 29-31 degC. TLC: Bz:MeOH:AcOH = 45:8:4, Rf = 0.75.
Methyl 4-oxotetrahydrothiophene-3-carboxylate synthesis
HYDROXYECTOINE TERT-BUTYL 4-OXOCYCLOHEXANECARBOXYLATE 2-METHYL-1-BUTANETHIOL 4-METHYLTETRAHYDROTHIOPHEN-3-ONE METHYL 4-(METHYLTHIO)BUTYRATE 4-OXOTETRAHYDROTHIOPHENE-2,3-DICARBOXYLIC ACID DIMETHYL ESTER 1-(Methylthio)-2-butanone Methyl 4-oxotetrahydrothiophene-3-carboxylate METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE 3-Methylthiolane 3-MERCAPTOISOBUTYRIC ACID 4-Mercapto-2-butanone Tetrahydrothiophen-3-one Tetrahydrothiophene

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