Methyl 4-oxotetrahydrothiophene-3-carboxylate supplier

Name
METHYL 4-OXOTETRAHYDROTHIOPHENE-3-CARBOXYLATE
EINECS 220-256-9
CAS No. 2689-68-1
Article Data22
CAS DataBase
Density 1.31 g/cm³
Solubility
Melting Point 37-38 °C
Formula C₆H₈O₃S
Boiling Point 248.4 °C at 760 mmHg
Molecular Weight 160.194
Flash Point 116.7 °C
Transport Information
Appearance Slight yellow to yellow crystalline powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 4-Carbomethoxy-2,3,4,5-tetrahydro-3-thiophenone;4-Carbomethoxy-3-thiophanone;4-Oxotetrahydrothiophene-3-carboxylic acid methylester;Methyl 4-oxo-2,3,4,5-tetrahydrothiophene-3-carboxylate;Methyl4-oxotetrahydrothienyl-3-carboxylate;Methyltetrahydro-4-oxo-3-thiophenecarboxylate;NSC 127560;Tetrahydro-4-oxo-3-thiophenecarboxylicacid methyl ester;Methyl 4-oxotetrahydrothiophene-3-carboxylate;
PSA 68.67000
LogP 0.09150

Synthetic route

: C6H7O3S(1-)*Li(1+)

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With hydrogenchloride In water pH=Ca. 5;	82%

: 3-Methoxycarbonylthiopropanoic acid methyl ester

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With lithium methanolate; acetic acid In methanol; hexane; water	81%

: 7400-45-5
dimethyl-3-thiaadipate

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With pyridine In toluene at 80℃; for 2.5h;	80%
With lithium methanolate In methanol; toluene at 70 - 110℃;	53.7%
Stage #1: dimethyl-3-thiaadipate With sodium methylate In tetrahydrofuran at 20℃; for 2.08333h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water	39%

: 2365-48-2
Methyl thioglycolate

: 292638-85-8
acrylic acid methyl ester

A: 2689-69-2
methyl tetrahydrothiophen-3-one-2-carboxylate

B: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With sodium hydride at -40℃; for 5h;	A 57% B 42%
With sodium hydride at -40℃; for 5h; Product distribution; var.: temp.: 0 degC;	A 57% B 42%

...Expand

: 7400-45-5
dimethyl-3-thiaadipate

A: 2689-69-2
methyl tetrahydrothiophen-3-one-2-carboxylate

B: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With sodium methylate In methanol for 0.666667h; Heating / reflux;	A n/a B 54%
With methanol; sodium for 0.666667h; Heating / reflux;	A n/a B 54%
With sodium methylate In diethyl ether for 3h; Heating;	A 44% B 18%
With lithium methanolate In toluene at 70 - 110℃; for 18.5h;	A n/a B 33%
With sodium hydride In 1,2-dimethoxyethane at -40℃; Inert atmosphere;

: 292638-85-8
acrylic acid methyl ester

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
Stage #1: Methyl thioglycolate With sodium methylate In methanol at 20℃; for 3h; Stage #2: acrylic acid methyl ester In dimethyl sulfoxide at 0 - 20℃; for 18h; Michael addition; Dieckmann cyclization; Stage #3: With hydrogenchloride In water; dimethyl sulfoxide	48%

: 16002-29-2
dimethyl thiodiglycolate

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil for 5h; Reflux;	35%

3-butoxycarbonylmethylsulfanyl-propionic acid methyl ester: 3-butoxycarbonylmethylsulfanyl-propionic acid methyl ester

A: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

B: 3-oxo-tetrahydro-thiophene-2-carboxylic acid butyl ester

Conditions

Conditions	Yield
With sodium; benzene

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 58230-46-9
4-hydroxyimino-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; barium carbonate In methanol Heating / reflux;	98%
With hydroxylamine hydrochloride; barium carbonate In methanol for 12h; Reflux;	98%

: 186581-53-3, 908094-01-9
diazomethane

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 22097-91-2
methyl 2,5-dihydro-4-methoxythiophene-3-carboxylate

Conditions

Conditions	Yield
	97%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 1576-35-8
toluene-4-sulfonic acid hydrazide

: 152507-80-7
methyl 2,5-dihydro-4-(N'-tosylhydrazino)thiophene-3-carboxylate

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 0.5h; Ambient temperature;	95%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 99492-88-3
3-methylthio-5-methylamino-1H-1,2,4-triazole

: 119699-86-4
2-methylthio-9-methyl-5,7-dihydrothieno<3,4-e>-1,2,4-triazolo<1,5-a>pyrimidin-8(9H)-one

Conditions

Conditions	Yield
at 160℃; for 0.0833333h;	93%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 69363-85-5
methyl 4-aminothiophene-3-carboxylate

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In methanol for 1h; Reflux;	93%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 70-11-1
α-bromoacetophenone

: methyl 4-oxo-3-(2-oxo-2-phenylethyl)tetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone at 65℃; for 1h;	92%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 67525-75-1
methyl 2,5-dihydro-4-(p-toluenesulfonato)thiophene-3-carboxylate

Conditions

Conditions	Yield
With 4-methyl-morpholine In dichloromethane for 1.5h; Cooling with ice;	88.5%
With 4-methyl-morpholine In dichloromethane at 10℃; for 1.5h;	85%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 78-94-4
methyl vinyl ketone

: 85696-91-9
methyl 4-oxo-3-(3-oxobutyl)tetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
Stage #1: methyl 4-oxotetrahydrothiophene-3-carboxylate With iron(III) chloride hexahydrate In dichloromethane at 23℃; for 0.0833333h; Stage #2: methyl vinyl ketone In dichloromethane at 20℃; for 48h; Michael Addition;	88%
With triphenylphosphine In acetonitrile for 5h; Ambient temperature;	73%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 95-54-5
1,2-diamino-benzene

: 61325-23-3
3-(2-aminoanilino)-4-(carbomethoxy)-2,5-dihydrothiophene

Conditions

Conditions	Yield
With acetic acid In ethanol for 4h; Heating;	86%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

4-nitrobenzyl halide: 4-nitrobenzyl halide

: 84782-87-6
3-(4-Nitro-benzyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	86%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

p-NO2C6H4CH2-halide: p-NO2C6H4CH2-halide

: 84782-87-6
3-(4-Nitro-benzyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	86%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 65369-21-3
4-hydroxythiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With dihydrogen peroxide In methanol for 2h;	85%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

EtOCOCH2-halide: EtOCOCH2-halide

: 84790-04-5
3-Ethoxycarbonylmethyl-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	85%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 1071-37-0
2-ethylisothiourea hydrobromide

: 5719-20-0
5H,7H-2-ethylthiodihydrothieno<3,4-d>pyrimidin-4-one

Conditions

Conditions	Yield
With sodium carbonate In water at 25℃; for 18h; Darkness;	84.6%
With sodium carbonate for 12h; Ambient temperature;	83%
With sodium carbonate In water at 20℃; Darkness;

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 96-96-8
4-methoxy-2-nitroaniline

: 4-(4-Methoxy-2-nitro-phenylamino)-2,5-dihydro-thiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In toluene for 4h; Heating;	84%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 146496-36-8
4-(tert-Butyl-dimethyl-silanyloxy)-2,5-dihydro-thiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With triethylamine	82%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

CH2=CHCH2-halide: CH2=CHCH2-halide

: 84782-86-5
methyl 3-allyl-4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	81%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 4-ethoxycarbonyl-3-methyl-1-phenylaminocarbonyl-1,2-diaza-1,3-butadiene

: 1311296-62-4
3-ethyl 3a-methyl 1-[(anilinocarbonyl)amino]-6a-hydroxy-2-methyl-6,6a-dihydro-1H-thieno[3,4-b]pyrrole-3,3a(4H)-dicarboxylate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 5.5h;	81%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

benzyl halide: benzyl halide

: 84782-84-3
methyl 3-benzyl-4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	80%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

PhCH2-halide: PhCH2-halide

: 84782-84-3
methyl 3-benzyl-4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	80%

: 773837-37-9
sodium cyanide

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 155251-30-2
3-cyano-3-hydroxy-tetrahydrothiophene-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium hydrogensulfite In methanol; water at 20℃; for 16h; pH=7 - 8; Time;	80%
Stage #1: sodium cyanide With sodium hydrogensulfite In water Cooling with ice; Stage #2: methyl 4-oxotetrahydrothiophene-3-carboxylate In methanol; water at 20℃; for 16h;

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

: 88722-50-3
5-amino-1-(2-amino-4-trifluoromethylphenyl)-3-methylthio-1H-1,2,4-triazole

: 120929-95-5
4,5-dihydro-2-methylthio-8-trifluoromethyl-1,2,4-triazolo<1,5-a>-1,3,5-benzotriazepin-5(6H)-one

Conditions

Conditions	Yield
for 3h; Product distribution; Mechanism; Heating;	79%
for 3h; Heating;	79%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

HCCCH2-halide: HCCCH2-halide

: 84782-85-4
methyl 4-oxo-3-(propargyl)tetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	79%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

EtOCOCH=C(OEt)CH2-halide: EtOCOCH=C(OEt)CH2-halide

: 84782-88-7
3-((Z)-2-Ethoxy-3-ethoxycarbonyl-allyl)-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	79%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

prop-2-enyl halide: prop-2-enyl halide

: 84782-86-5
methyl 3-allyl-4-oxotetrahydrothiophene-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	78%

: 2689-68-1
methyl 4-oxotetrahydrothiophene-3-carboxylate

ethoxycarbonylmethyl halide: ethoxycarbonylmethyl halide

: 84790-04-5
3-Ethoxycarbonylmethyl-4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	78%

Methyl 4-oxotetrahydrothiophene-3-carboxylate Chemical Properties

IUPAC Name: methyl 4-oxothiolane-3-carboxylate
Empirical Formula: C₆H₈O₃S
Molecular Weight: 160.1909g/mol
EINECS: 220-256-9
Structure of 3-Thiophenecarboxylicacid, tetrahydro-4-oxo-, methyl ester (CAS NO.2689-68-1):

Index of Refraction: 1.528
Molar Refractivity: 37.69 cm³
Molar Volume: 122.3 cm³
Polarizability: 14.94×10^-24cm³
Surface Tension: 47.8 dyne/cm
Density: 1.309 g/cm³
Flash Point: 116.7 °C
Enthalpy of Vaporization: 48.56 kJ/mol
Boiling Point: 248.4 °C at 760 mmHg
Vapour Pressure: 0.0243 mmHg at 25°C
Product Categories: Esters;Thiophenes & Benzothiophenes;Thiophenes & Benzothiophenes
Canonical SMILES: COC(=O)C1CSCC1=O
InChI: InChI=1S/C6H8O3S/c1-9-6(8)4-2-10-3-5(4)7/h4H,2-3H2,1H3
InChIKey: LEAKUJFYXNILRB-UHFFFAOYSA-N

Methyl 4-oxotetrahydrothiophene-3-carboxylate Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
Hazard Note: Irritant

Methyl 4-oxotetrahydrothiophene-3-carboxylate Specification

3-Thiophenecarboxylicacid, tetrahydro-4-oxo-, methyl ester , its cas register number is 2689-68-1. It also can be called 4-Carbomethoxy-3-thiophanone ; EINECS 220-256-9 ; Methyl tetrahydro-4-oxo-3-thiophenecarboxylate ; NSC 127560 . 3-Thiophenecarboxylicacid, tetrahydro-4-oxo-, methyl ester (CAS NO.2689-68-1) is irritating to eyes, respiratory system and skin.

Product Name

METHYL 4-OXOTETRAHYDROTHIOPHENE-3-CARBOXYLATE

Synthetic route

Methyl 4-oxotetrahydrothiophene-3-carboxylate Chemical Properties

Methyl 4-oxotetrahydrothiophene-3-carboxylate Safety Profile

Methyl 4-oxotetrahydrothiophene-3-carboxylate Specification

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