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
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)
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.
N-Bromosuccinimide Price
- Product number
- 650633
- Product name
- Methyl 3-oxotetrahydrothiophene-2-carboxylate
- Purity
- 96%
- Packaging
- 1g
- Price
- $159
- Updated
- 2025/07/31
- Product number
- 650633
- Product name
- Methyl 3-oxotetrahydrothiophene-2-carboxylate
- Purity
- 96%
- Packaging
- 250mg
- Price
- $58.5
- Updated
- 2023/01/07
- Product number
- 2452AB
- Product name
- Methyl 3-oxotetrahydrothiophene-2-carboxylate
- Packaging
- 1g
- Price
- $185
- Updated
- 2021/12/16
- Product number
- OR932444
- Product name
- Methyl 3-oxotetrahydrothiophene-2-carboxylate
- Purity
- 95%
- Packaging
- 1g
- Price
- $395
- Updated
- 2021/12/16
- Product number
- CHM0097369
- Product name
- METHYL TETRAHYDRO-3-OXO-2-THENOATE
- Purity
- 95.00%
- Packaging
- 250MG
- Price
- $617.3
- Updated
- 2021/12/16
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
- 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
- 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