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CAS No. : | 4746-63-8 | MDL No. : | MFCD04038827 |
Formula : | C10H8O3S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FVEJUHUCFCAYRP-UHFFFAOYSA-N |
M.W : | 240.30 | Pubchem ID : | 12723754 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
With diethyl ether Behandeln des Reaktionsprodukts mit wss. Salzsaeure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; acetic acid; tin(ll) chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With aluminium trichloride 1.) benzene, cooling bath 2.) reflux, 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With potassium hydroxide In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk. mit Methanol; | ||
Rk. mit Ethanol; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 53 percent / 15 °C 2: 49 percent / KOH / ethanol | ||
Multi-step reaction with 2 steps 2: diethyl ether / Behandeln des Reaktionsprodukts mit wss. Salzsaeure |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tin (II)-chloride; acetic acid; hydrogen chloride 2: isopropyl alcohol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tin (II)-chloride; acetic acid; hydrogen chloride 2: isopropyl alcohol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tin (II)-chloride; acetic acid; hydrogen chloride 2: isopropyl alcohol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tin (II)-chloride; acetic acid; hydrogen chloride 2: isopropyl alcohol / Behandeln des Reaktionsprodukts mit Methylbromid und Aethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In water; acetonitrile at 37℃; aq. phosphate buffer; | ||
With human recombinant cytochrome P450; NADPH aq. phosphate buffer; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21.31 g | With aluminum (III) chloride In benzene at 5℃; for 0.5h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate / cyclohexane / 80 - 85 °C / Large scale 1.2: 80 - 85 °C / Large scale 2.1: chloroform; acetonitrile / 25 - 30 °C / Large scale 2.2: 72 h / Large scale |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.05% | Stage #1: (R)-quinuclidin-3-ol With sodium methylate In cyclohexane at 80 - 85℃; Large scale; Stage #2: 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid In cyclohexane at 80 - 85℃; Large scale; | 2 Example-2: Preparation of l-azabicyclo[2.2.2]oct-3-ylhydroxy(dithiophen-2- yl)acetate Example-2: Preparation of l-azabicyclo[2.2.2]oct-3-ylhydroxy(dithiophen-2- yl)acetate To the 10 lit Cyclohexane added 0.638 kg (3R)-l-azabicyclo[2.2.2]octan-3-ol and 0.266 kg Sodium Methoxide Powder and heated upto 80-85° C. Simultaneously distilled out slowly 5.0 lit Cyclohexane and added 5.0 lit Cyclohexane and again distilled out by azeotrophically slowly 8.0 lit. Added 8.01it L Fresh Cyclohexane and stirred for 3-4 hr at 80-85° C. Added 1.0 kg of methyl hydroxy (dithiophen-2-yl) acetate lot wise over a period of 20-30 min. Stirred and maintained for 3-4 hrs at 80-85° C. Cyclohexane Distilled out and degased completely under vacuum at below 85° C. Added 10. L DM- Water at 25-30° C and stirred for lhr. Filtered and washed with 2.0 L DM water and slurry washed with 4.01it Cyclohexane two time. Filtered the product, suck dried and washed with 1.0 L Cyclohexane and suck dried for 10-15 min to get 89.05% titled product. HPLC purity: 97.68% |
79.9% | Stage #1: 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 15 - 25℃; for 1h; Stage #2: (R)-quinuclidin-3-ol In N,N-dimethyl-formamide at 30 - 35℃; for 12h; | 1.1 Preparation of 2,2-dithienyl-2-hydroxyacetic acid-R-quinuclidin-3-yl ester 50 g of 2,2-dithienyl-2-hydroxyacetic acid (0.21 mol) and 500 ml of DMF were added to the reaction flask, and CDI (0.23 mol) solid 37.45 g was slowly added, and stirred at 15 to 25 ° C for 1 hour. Then, 26.7 g of R-3-quinolol (0·21 mol) was added, and the mixture was stirred at 30 to 35 ° C for 12 hours. The reaction was completely monitored by TLC, and then cooled to 0 to 5 ° C in an ice bath, and slowly dripped. 500 ml of water was added, and after stirring, it was stirred at 0 to 10 ° C for 0.5 hour, filtered, and dried under vacuum at 60 ° C and -0.08 MPa to obtain 58.1 g of a white solid, yield 79.9%, purity HPLC: 98.5 % . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (S)-quinuclidin-3-ol With sodium methylate In cyclohexane at 80 - 85℃; Large scale; Stage #2: 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid In cyclohexane at 80 - 85℃; Large scale; | 10 Example 10: Preparation of (S)-l-azabicyclo [2.2.2] oct-3-ylhy droxy(dithiophen-2- yl)acetate Example 10: Preparation of (S)-l-azabicyclo [2.2.2] oct-3-ylhy droxy(dithiophen-2- yl)acetate To the 10 L Cyclohexane added 0.638 kg (3S)-Azabicyclo Compound and 0.266 kg Sodium Methoxide Powder and heatedupto 80-85° C. Simultaneously 5.0 lit Cyclohexane distilled out slowly and added 5.0 lit Cyclohexane and again distilled out by azeotrophically slowly 8.0 lit. Added S.Olit L Fresh Cyclohexane andstirred for 3-4 hr at 80-85° C. Added 1.0 kg of methyl hydroxy (dithiophen-2-yl) acetate lot wise over a period of 20-30 min. Stirred and maintained for 3-4 hrs at 80-85° C. Cyclohexane distilled out and degased completely under vacuum at below 85° C. Added 10. L DM- Water at 25-30° C stirred for lhr. Filtered and washed with 2.0 L DM water and slurry washed with 4.01it Cyclohexane two time. Filtered the product, sucked dry and washed with 1.0 L Cyclohexane and sucked dry for 10-15 min to get 80% titled compound. HPLC Purity: 90.42% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.166667h; Stage #2: C22H27NO3 In dichloromethane at 0 - 20℃; for 3h; | 6 Example 6: Esterification of alcohol with Acid (Steglich esterification) A solution of 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid 6.79 gm (1.0 equiv) in drydichloromethane were added DCC 5.84 gm (1.2 equiv) and p-dimethylaminopyridine 1.72gm (0. 5 equiv). The resulting mixture was stirred at 0 C for 10 mm and then a solution of alcohol 10 gm (1.0 equiv) was added at the same temperature and the mixture was stirred for 3 h at room temperature. The precipitated dicyclohexylurea was removed by filtration through a fritted Bhner funnel. The filtrate was dried over anhydrous sodium sulfate and concentrated on a rotary eJaporator. The crude product was purified by silica gel column chromatography (ethyl acetate: hexane, 2:8) to give the pure ester compound of Formula 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | Stage #1: 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester With sodium hydride In toluene for 0.0833333h; Stage #2: 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid In toluene at 155℃; for 1h; | 1.2 Step 2: tert-butyl 2-[2-hydroxy-2,2-bis(2-thienyl)acetyl]oxy-7-azaspiro[3.5]nonane-7-carboxylate (1c) Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate (1c) (0.482 g, 2 mmol) was dissolved in toluene (10ml), to which sodium hydride (0.024 g, 1 mmol) was added, followed by stirring for 5 min. 2-hydroxy-2,2-bis(2-thienyl)acetate(0.508 g, 2 mmol) was added thereto, and the temperature was elevated to 155°C to allow a reaction to proceedfor 1 h. The reaction was quenched by addition of water, extracted with ethyl acetate (20 mL32), washed with a saturatedsodium chloride solution (20 mL31), dried over anhydrous sodium sulfate, and filtered, and the filtrate was concentratedunder reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/petroleumether (v/v) = 1/100 to 1/20), to obtain the title compound tert-butyl 2-[2-hydroxy-2,2-bis(2-thienyl)acetyl]oxy-7-azaspiro[3.5]nonane-7-carboxylate (1c) as a light yellow solid (0.23 g, yield: 25%).1H NMR (400 MHz, CDCl3) δ 7.29 (dd, 2H), 7.17 (dd, 2H), 6.98 (dd, 2H), 5.25 - 5.05 (m, 1H), 4.66 (s, 1H), 3.32 (dd, 2H),3.29 - 3.23 (m, 2H), 2.41 - 2.30 (m, 2H), 1.88 (dd, 2H), 1.54 - 1.50 (m, 2H), 1.47 (d, 2H), 1.44 (s, 9H).LCMS m/z =486.3[M+23]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | With potassium carbonate In acetonitrile at 50℃; for 2h; | 8-12 Example 9: Preparation of methyl bis(2-dithienyl)glycolate: In a three-necked flask, bis(2-dithienyl)glycolic acid (4.8 g, 20 mmol) and potassium carbonate (8.26 g, 60 mmol) were dissolved in acetonitrile (80 mL), and iodomethane (4.25 g, 30 mmol) was added dropwise. After dripping, the temperature was raised to 50 °C and the reaction was stirred for 2 hours.After completion of the reaction, the filtrate was filtered, and the solvent was removed from the filtrate under reduced pressure. The obtained solid was added to isopropanol (60 mL), heated until completely dissolved, and then cooled in an ice-water bath for crystallization. After filtration, white crystals of methyl bis(2-dithienyl)glycolate were obtained with a yield of 96.5% and a purity of 99.93%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.2% | With potassium permanganate In acetone at 50℃; for 2h; | 5-7 Example 5: Preparation of bis(2-dithienyl)glycolic acid: In a three-necked flask, 1,1-bis(2-thienyl)prop-2-yn-1-ol (2.2g, 10mmol) was dissolved in acetone (50mL), acidic potassium permanganate solution (5%, 7 mL) was added, the temperature was raised to 50 °C. and the reaction was stirred for 2 hours. After the reaction was completed, dichloromethane (100 mL) was added, washed with saturated brine (100 mL×2), and the organic phase was dried over anhydrous sodium sulfate, Concentrated to dry solvent to obtain bis(2-dithienyl)glycolic acid with a yield of 94.2% and a purity of 99.84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: indium(III) bromide / 5,5-dimethyl-1,3-cyclohexadiene / 20 °C 2: potassium permanganate / acetone / 2 h / 50 °C |
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