ChemicalBook > CAS DataBase List > METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE

METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE

Product Name: METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE
CAS No.: 2689-69-2
Chemical Name: METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE
Synonyms: methyl 3-oxothiolane-2-carboxylate;methyl tetrahydro-3-oxo-2-thenoate;METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBO&;methyl tetrahydrothiophen-3-one-2-carboxylate;METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE;tetrahydro-3-oxo-2-thiophenecarboxylicacimethylester;3-Oxotetrahydrothiophene-2-carboxylic acid methyl ester;3-ketotetrahydrothiophene-2-carboxylic acid methyl ester;Tetrahydro-3-oxo-2-thiophenecarboxylic acid methyl ester
CBNumber: CB3360723
Molecular Formula: C6H8O3S
Formula Weight: 160.19
MOL File: 2689-69-2.mol

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METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE Property

Melting point:: 38 °C (lit.)
Boiling point:: 232-254 °C/0.1 mmHg (lit.)
Density: 1.281 g/mL at 1.281 °C (lit.)
refractive index: n20/D 1.511(lit.)
Flash point:: >230 °F
storage temp.: 2-8°C
form: Liquid
pka: 11.11±0.20(Predicted)
Appearance: Off-white to light yellow <38°C Solid,>38°C Liquid
Water Solubility: Slightly soluble in water.
EPA Substance Registry System: 2-Thiophenecarboxylic acid, tetrahydro-3-oxo-, methyl ester (2689-69-2)

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Safety

Hazard Codes: Xn
Risk Statements: 22-36
Safety Statements: 26-36/37
WGK Germany: 3
HS Code: 2934999090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 650633
Product name: Methyl 3-oxotetrahydrothiophene-2-carboxylate
Purity: 96%
Packaging: 1g
Price: $159
Updated: 2025/07/31

Sigma-Aldrich

Product number: 650633
Product name: Methyl 3-oxotetrahydrothiophene-2-carboxylate
Purity: 96%
Packaging: 250mg
Price: $58.5
Updated: 2023/01/07

AK Scientific

Product number: 2452AB
Product name: Methyl 3-oxotetrahydrothiophene-2-carboxylate
Packaging: 1g
Price: $185
Updated: 2021/12/16

Apolloscientific

Product number: OR932444
Product name: Methyl 3-oxotetrahydrothiophene-2-carboxylate
Purity: 95%
Packaging: 1g
Price: $395
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0097369
Product name: METHYL TETRAHYDRO-3-OXO-2-THENOATE
Purity: 95.00%
Packaging: 250MG
Price: $617.3
Updated: 2021/12/16

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METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE Chemical Properties,Usage,Production

Uses

Methyl 3-oxotetrahydrothiophene-2-carboxylate is used in the production of dihydro-thiophen-3-one.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 2229, 1946 DOI: 10.1021/ja01215a034

Synthesis

7400-45-5

2689-69-2

2689-68-1

Step 1: Under vigorous stirring, 1.1 g of sodium metal pre-sliced into thin slices was slowly added to 11 ml of methanol. The resulting solution was heated to reflux followed by the slow addition of 3.0 g of methyl 3-[(2-methoxy-2-oxoethyl)thio]propionate (completed in about 10 minutes). After maintaining the reflux state for 30 minutes, the solution was allowed to cool to room temperature. The reaction mixture was poured into about 100 ml of ice water under continuous stirring, continued for 30-40 min and acidified with concentrated hydrochloric acid to pH 2. The aqueous phase was extracted five times with dichloromethane, the organic phases were combined and concentrated by rotary evaporation after drying to afford 1.7 g of the crude product in the form of an oil.GC-MS analysis showed that the crude product contained about 3% of the isomer (tetrahydro-3-oxa-2- methyl thiophenecarboxylate) (HPLC retention time = 2.53 min). The crude product was purified using a Flash Master Personal system and a STRATA column pre-filled with Phenomenex silica (20 g). The crude product was dissolved in a dichloromethane:hexane (1:1) solvent mixture, dried, upsampled and eluted with the same ratio of solvent mixture. Finally 1.12 g of white solid product was obtained in 54% yield.

References

[1] Patent: US2008/275023, 2008, A1. Location in patent: Page/Page column 9
[2] Patent: WO2006/97449, 2006, A1. Location in patent: Page/Page column 24-25
[3] Tetrahedron, 1991, vol. 47, # 27, p. 4847 - 4860
[4] Patent: WO2013/50508, 2013, A1. Location in patent: Page/Page column 42; 55
[5] Organic Process Research and Development, 2016, vol. 20, # 5, p. 982 - 988

METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

Product: Methyl tetrahydro-3-oxo-2-thenoate 2689-69-2
Price: US $1.10-6.60/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 50kg
Release date: 2025-06-23

Career Henan Chemical Co

Product: Methyl tetrahydro-3-oxo-2-thenoate 2689-69-2
Price: US $1.00/KG
Min. Order: 1KG
Purity: Min98% HPLC
Supply Ability: g/kg/ton
Release date: 2020-01-08

2689-69-2, METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATERelated Search:

METHYL THIOPHENE-2-CARBOXYLATE Tetrahydrothiophene Methyl 4-oxotetrahydrothiophene-3-carboxylate 3-METHYLTHIO-2-BUTANONE 3-Oxo-tetrahydro-thiophene-2-carboxylic acid ethyl ester Tetrahydrothiophen-3-one 2-(ethylthio)propanoic acid METHYL 2-(METHYLTHIO)BUTYRATE METHYL 2-(METHYLTHIO)PROPIONATE 3-Mercapto-2-butanone Dihydro-2-methyl-3(2H)-thiophenone METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE

METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBOXYLATE

tetrahydro-3-oxo-2-thiophenecarboxylicacimethylester

methyl tetrahydro-3-oxo-2-thenoate

METHYL 3-OXOTETRAHYDROTHIOPHENE-2-CARBO&

3-Oxotetrahydrothiophene-2-carboxylic acid methyl ester

Tetrahydro-3-oxo-2-thiophenecarboxylic acid methyl ester

3-ketotetrahydrothiophene-2-carboxylic acid methyl ester

methyl 3-oxothiolane-2-carboxylate

methyl tetrahydrothiophen-3-one-2-carboxylate

2689-69-2

C6H8O3S

Building Blocks

Heterocyclic Building Blocks

Thiophenes

Building Blocks

Heterocyclic Building Blocks

Thiophenes