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CAS No. : | 7333-07-5 | MDL No. : | MFCD00173678 |
Formula : | C10H6O2S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 222.28 g/mol | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332 | Packing Group: | N/A |
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 |
---|---|---|
With potassium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With samarium; potassium iodide; copper(l) chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | Typical Procedure for the Self-Condensation of Aromatic Aldehydes General procedure: Benzaldehyde (0.4 mL, 4 mmol) was added to a mixture of Sm powder (0.3 g, 2 mmol), CuCl (0.2 g, 2 mmol), and KI (0.33 g, 2 mmol) in anhydrous tetrahydrofuran (THF, 10 mL) at room temperature under a nitrogen atmosphere with magnetic stirring. After completion of the reaction (about 2 h, monitored by TLC), dilute hydrochloric acid (2 M, 5 mL) was added and the resulting mixture was extracted with ethyl acetate (320 mL). The combined organic layer was washed with brine and saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product were purified with flash chromatography (silica/hexane-ethyl acetate 5:1 v/v) to afford 0.36 g of the corresponding benzoin (2a) with 84% yield. |
70% | With carbon dioxide; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; potassium carbonate; dimethyl sulfoxide at 55℃; for 24h; | |
21% | With sodium hydroxide; vitamin B1 In methanol for 720h; pH 9.0; |
Multi-step reaction with 2 steps 1: Thiamine hydrochloride; triethylamine / ethanol / 24 h / 20 °C / Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 6 h | ||
Multi-step reaction with 2 steps 1: vitamin B1; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 5 h / 60 °C / Inert atmosphere 2: copper(ll) sulfate pentahydrate / acetonitrile; water; triethylamine / 0.17 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper diacetate; palladium diacetate; silver carbonate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 120℃; for 14h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With indium; acetic acid; In methanol; for 0.333333h;Reflux; Inert atmosphere; | General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With indium; acetic acid; In methanol; for 0.333333h;Reflux; Inert atmosphere; | General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With indium; acetic acid; In methanol; for 0.0833333h;Reflux; Inert atmosphere; | General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With indium; acetic acid; In methanol; for 0.333333h;Reflux; Inert atmosphere; | General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.8% | With acetic acid at 40℃; for 12h; | 3.2 (2) To 250 ml single-port flask is sequentially added in the compound (IIIc) (3.0 g, 6 . 15 mmol), thiophene acyloin (1.0 g, 6 . 77 mmol) and glacial acetic acid (40 ml). The oil bath heated to 40 °C stirring reaction 12 h, filtered to get yellow solid. Ethanol recrystallize to get yellow needle-like solid compound (IVc) 2.31 g, yield 76.8%. |
68% | With toluene-4-sulfonic acid In methanol for 15h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid for 72h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | General procedure: 5,6-Diaminouracil sulphate (1.31 mmol, 1 eq.) was suspended in water (35 mL). The mixture wasmade alkaline using a methanolic solution of NaOH (0.65M, 3 eq.) and heated to 90 C for 15 min.A solution of diketone (1.96 mmol, 1.5 eq.) in a mixture of THF (40 mL) and water (15 mL) was addedand the mixture was stirred at 90 C for 45 min. The reaction mixture was acidified glacial acetic acid(15 mL) and heated at 90 C for another 20 h. The reaction mixture was subsequently concentrated toapproximately 1/3 of the volume, cooled in the freezer and the as-obtained suspension was filteredand the solid fraction was washed with cold water (30 mL) and cold ethanol (20 mL) to yield the crudeflavin derivative. The crude product was purified by digestion in boiling methanol. The digestedflavin derivative was further subjected to vacuum sublimation to yield the final target compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium hydroxide; In ethanol; at 70℃; for 3h;Inert atmosphere; | (2) Intermediate product 2 (3.69 g, 10 mmol), thiophene acetoin (Compound 3) (2.2 g, 10 mmol) and potassium hydroxide (0.168 g, 3 mmol) were added to the reaction flask, pumped three times, solvent ethanol (30mL) was added under nitrogen protection and refluxed at 70 C for three hours. After the reaction, the reaction flask was cooled in an ice bath and precipitated to obtain the product. The product was washed with cold ethanol and dried to give red powder product 4 (compound 4). Yield 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.9% | With iron(III) chloride In nitromethane; chlorobenzene at 20℃; for 12h; |