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2689-68-1

Basic Information
CAS No.: 2689-68-1
Name: METHYL 4-OXOTETRAHYDROTHIOPHENE-3-CARBOXYLATE
Article Data: 22
Molecular Structure:
Molecular Structure of 2689-68-1 (METHYL 4-OXOTETRAHYDROTHIOPHENE-3-CARBOXYLATE)
Formula: C6H8O3S
Molecular Weight: 160.194
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;
EINECS: 220-256-9
Density: 1.31 g/cm3
Melting Point: 37-38 °C
Boiling Point: 248.4 °C at 760 mmHg
Flash Point: 116.7 °C
Appearance: Slight yellow to yellow crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
PSA: 68.67000
LogP: 0.09150
Synthetic route

C6H7O3S(1-)*Li(1+)

2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

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

3-Methoxycarbonylthiopropanoic acid methyl ester

2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
With lithium methanolate; acetic acid In methanol; hexane; water81%
7400-45-5

dimethyl-3-thiaadipate

2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

Conditions
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium; benzene
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

58230-46-9

4-hydroxyimino-tetrahydro-thiophene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With hydroxylamine hydrochloride; barium carbonate In methanol Heating / reflux;98%
With hydroxylamine hydrochloride; barium carbonate In methanol for 12h; Reflux;98%
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

22097-91-2

methyl 2,5-dihydro-4-methoxythiophene-3-carboxylate

Conditions
ConditionsYield
97%
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Chemistry

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

Safety Profile

Hazard Codes: IrritantXi
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

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.