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CAS No. : | 1918-79-2 | MDL No. : | MFCD00005439 |
Formula : | C6H6O2S | Boiling Point : | No data available |
Linear Structure Formula : | CH3C4H2SCOOH | InChI Key : | VCNGNQLPFHVODE-UHFFFAOYSA-N |
M.W : | 142.18 | Pubchem ID : | 74713 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sulfuric acid; for 72h;Reflux; | delta-Methyl-thiophene^-carboxylic acid (30.5 mmol) is dissolved in Ethanol (53 ml), H2SO4 (0.5 eq) is added and the reaction is heated to reflux for 3 days. The solvent is removed in vacuo and the remaining material dissolved in Dichloromethane. The organic layer is extracted with saturated NaHCO3 and washed with brine. The organic layer is dried over IS^SO4 and the solvent removed in vacuo. 5-Methyl- thiophene-2-carboxylic acid ethyl ester is obtained as brown oil in a yield of 67 percent. HPLC (Method A): 3.36 min, LCMS (Method A): 2.20 min, 171.2 m/z (MH+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5-Bromomethyl-2-carbomethoxythiophene (III-3). This compound was prepared from 5-methylthiophene-2-carboxylic acid by the method of Gogte et al, Tetrahedron, 23, 2443-51 (1967). | ||
Synthesis Example 14-1: Synthesis of 2-bromomethyl-5-methoxy carbonylthiophene (Compound IV-4) 2.05 g of commercially available 5-methylthiophene carboxylic acid was dissolved in 60 ml of methanol, and then a hydrochloric acid gas was brown into the solution for 5 minutes. After 23 hours, the reaction solution was concentrated, and then a 1 mol/l sodium hydroxide aqueous solution was added thereto, followedbyextractionwithchloroform. An organic layer was washed with a saturated salt solution and was then dried with anhydrous sodium sulfate and concentrated. 500 mg of the resulting residue was dissolved in 10 ml of carbon tetrachloride, followed by the addition of 570 mg of N-bromosuccinimide and 53 mg of azobisisobutyronitrile. After the resultant solution was stirred in oil bath for 20 hours at 70C, the reaction solution was filtrated, and then the filtrate thereof was then concentrated. The resulting residue was purified by means of silica gel column chromatography (15 g, hexane/ethyl acetate = 8/1). Consequently, 516.1 mg of the above-mentioned compound was obtained as light-yellow syrup. MS(EI,Pos.):m/z=233,235[M+1]+ 1H-NMR(500MHz,CDCl3):delta=3.89(3H,s),4.68(2H,s),7.10(1H,d,J=3.7Hz),7.64(1H,d,J=3.7Hz). | ||
With N-Bromosuccinimide; dibenzoyl peroxide; In methanol; tetrachloromethane; methyl 5-methylthiophene-2-carboxylate; | (ii) 5-bromomethyl-2-carbomethoxythiophene A solution of 5-methyl-2-thiophene carboxylic acid (25 g, 0.176 mol) in 500 ml of methanol was saturated with gaseous hydrochloric acid at 0 C. The reaction mixture was stirred at room temperature for 18 hours and then refluxed for 48 hours. The solvent was removed in vacuo and the crude methyl 5-methyl-2-thiophene carboxylate was used without further purification. The methyl ester prepared above (11.07 g, 0.071 mol) was dissolved in 200 ml of carbon tetrachloride under argon. N-bromosuccinimide (13.25 g, 0.074 mol) and dibenzoyl peroxide were then added. The reaction mixture was refluxed for 2 hours and allowed to stand at room temperature for 18 hours. The solids were collected and the filtrate was concentrated in vacuo to give 19 g of 5-bromomethyl-2-carbomethoxythiophene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sulfuric acid; In ethanol; | Part 1 5-methyl-thiophene-2-carboxylic acid ethyl ester A solution of 5-methyl-thiophene-2-carboxylic acid (25.2 g, 177 mmol) in EtOH (500 mL) is treated with conc. H2SO4 (15 mL) and heated to a gentle reflux for 72 h. The solution is partially concentrated and poured into water (500 mL) and extracted with Et2O (3*). The combined extracts are washed with aq Na2CO3, water, dried over Na2SO4, filtered and concentrated in vacuo. Vacuum distillation of the residue afforded 5-methyl-thiophene-2-carboxylic acid ethyl ester (25.6 g, 85percent): bp 98-99° C./9-10 mbar; 1H NMR (CDCl3, 300 MHz) delta7.6 (s, 1 H), 6.78 (s, 1 H), 4.30 (q, J=6.0 Hz, 2 H), 2.50 (s, 3 H), 1.34 (t, J=6.0 Hz, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 2h; | To a solution of commercially available 5-methylthiophene-2-carboxylic acid (SI-13) (1.0g, 7.04 mmol) and K2CO3 (1.94 g, 14.08 mmol) in DMF (10 mL), CH3CH2I (1.65 g, 10.56mmol) was added dropwise and the reaction mixture was stirred at room temperature for 2hours. Then, the reaction was quenched with water and extracted with EtOAc. The organiclayer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated togive compound SI-14 (400 mg, 34percent) as a pale yellow oil. ESI-MS m/z 171 [M+H]+ calc.for C8H10O2S. This intermediate was used in the next step without further purification orcharacterization. |
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | To a solution of commercially available 5-methylthiophene-2-carboxylic acid(9.2 g, 0.065 mol) in DMF (80 mL) was added K2003 (17.9 g, 0.13 mol), thencompound CH3CH2I (15.2 g, 0.98 mol) was added slowly. The reactionmixture was stirred at room temperature overnight. After TLC ( PE/ EtOAc =2:1 ) showed the starting material was consumed completely, the mixture was quenched with water and extracted with EtOAc, the organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give the crude reagent KR-39 (9.5 g, 86.3percent) as a pale yellow oil which was used for the next step without further purification. ESI-MS (Mi-i): 171.0 calc. forC8H1002S:170.0. | |
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | Preparation of reagent KR-5: ethyl 5-methylthiophene-2-carboxylate To a solution of commercially available 5-methylthiophene-2-carboxylic acid (9.2 g, 0.065 mol) in DMF (80 ml_) was added K2CO3 (17.9 g, 0.13 mol), then compound CH3CH2I (15.2 g, 0.98 mol) was added slowly. The reaction mixture was stirred at room temperature overnight. After TLC (PE/ EtOAc = 2:1 ) showed the starting material was consumed completely, the mixture was quenched with water and extracted with EtOAc, the organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give the crude reagent KR-5 (9.5 g, 86.3percent) as a pale yellow oil which was used for the next step without further purification. ESI-MS (M+1 ): 171 .0 calc. for C8H10O2S:170.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: Furan-2-carboxylic acid, thiophene-2-carboxylic acid, 5-methylthiophene-2-carboxylic acid, benzofuran-2-carboxylic acid, benzothiophene-2-carboxylic acid, and amino acid ester hydrochlorides were obtained from commercial supplies and were used without further purification. To a two-necked flask, an amino acid ester hydrochloride (1.1 mmol), 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride (EDC, 0.29 g, 1.5 mmol), HOBt (0.20 g, 1.5 mmol), Et3N (0.42 mL, 3.0 mmol), and CHCl3 or DMF (2.2 mL) were added, and the mixture was stirred at 0 C for 10 min. Furan-2-carboxylic acid or thiophene-2-carboxylic acid dissolved in DMF (2.2 mL) was added, and then stirred for 17 h. The reaction mixture was diluted with water and extracted with EtOAc (3 x 20 mL). The organic phase was then washed with 3 N HCl aq. (3 x 20 mL), saturated NaHCO3 aq. (3 x 20 mL), and brine (20 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/EtOAc = 1/1) to obtain the product. The purity of the product was confirmed by 1H-NMR. Stereochemistry of the final product was measured by high-performance liquid chromatography (HPLC) with a chiral column (Compound 16). The chart is shown in the supporting information. |
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