methyl4-aminothiophene-3-carboxylateHCl
Methyl 4-aminothiophene-3-carboxylate hydrochloride
CAS: 39978-14-8
Molecular Formula: C6H8ClNO2S
methyl4-aminothiophene-3-carboxylateHCl - Names and Identifiers
methyl4-aminothiophene-3-carboxylateHCl - Physico-chemical Properties
| Molecular Formula | C6H8ClNO2S |
| Molar Mass | 193.65 |
| Melting Point | 203-204°C |
| Appearance | Shape Powder, color Brown |
| Storage Condition | under inert gas (nitrogen or Argon) at 2–8 °C |
| Use | Application 3-aminothiophene-4-carboxylic acid methyl ester hydrochloride is a pharmaceutical intermediate, which can be prepared by three-step reaction of methyl acrylate and methyl mercaptoacetate as raw materials. There are reports that it can be used to prepare compounds for the treatment of metastatic malignant melanoma and other cancers. |
methyl4-aminothiophene-3-carboxylateHCl - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
methyl4-aminothiophene-3-carboxylateHCl - Upstream Downstream Industry
| Downstream Products | METHYL 4-AMINOTHIOPHENE-3-CARBOXYLATE |
methyl4-aminothiophene-3-carboxylateHCl - Nature
| Sensitivity | Hygroscopic |
Last Update：2024-04-10 22:29:15
methyl4-aminothiophene-3-carboxylateHCl - Preparation
Step a:
Methyl 3[(methoxycarbonyl) methylthio] propionate: At room temperature, add methyl acrylate (4.25g,49.5mmol) dropwise to a continuously stirred solution of methyl mercaptoacetate (5g,47.16mmol) and piperidine (0.10mL) for more than 20min. After about half of the acrylate is converted, piperidine (0.10mL) is added. After the addition of the acrylate, the resulting reaction mixture was continuously stirred for 1h at room temperature. The resulting mixture was diluted with 100mL chloroform. Wash off the chloroform layer with water, salt water, and dry with sodium sulfate. The obtained solution was filtered and the solvent was evaporated to obtain an oily product (9g,100%).
Step B:
methyl 4-oxygen -2,3, 5-trihydroxythiophene-3-carboxylate: at room temperature, a dry THF(15mL) solution of demethyl-3-thiohexane standard (5g,26.03mmol) was added to a continuously stirred dry THF(15mL) slurry of sodium methoxide (1.68g,31.25mmol) for a total time of 5min. The obtained reaction mixture is heated and refluxed for 2h, then cooled to room temperature, then added with ice-cold water, and acidified with dilute HCl. The resulting solution is extracted with chloroform, then the bound chloroform layer is washed away with water and salt water, and the sodium sulfate is dried. The resulting solution was filtered and the solvent evaporated. The obtained residue was subjected to silica gel column chromatography, in which hexane-ethyl acetate (95: 5) was used as the elution solution to obtain a light yellow oily product (1.6g,39%).
step c:
3-Aminothiophene-4-carboxylic acid methyl ester hydrochloride: Stir and mix 4-oxo-3-methoxycarbonylthiophene tetrahydrate (6.5g,40.62mmol), hydroxylamine hydrochloride (2.84g,40.62mmol) and acetonitrile (30mL), and then refluxed for 1h. The resulting mixture was cooled, the solids were separated by filtration, and after washing with dry ether, 3-aminothiophene-4-carboxylic acid methyl ester hydrochloride (4.9g,62%) was obtained with a melting point of 192-196°C.
Last Update：2024-04-10 22:29:15
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