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CAS No. : | 15774-06-8 | MDL No. : | MFCD20661296 |
Formula : | C10H11NS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CLQAPWVEHNTJLC-UHFFFAOYSA-N |
M.W : | 177.27 | Pubchem ID : | 12244279 |
Synonyms : |
|
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P264-P270-P280-P305+P351+P338-P310-P330-P403-P501 | UN#: | 3077 |
Hazard Statements: | H302-H318-H411 | Packing Group: | Ⅲ |
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 toluene-4-sulfonic acid In benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk. m. Acetessigsaeure-methylester Bildung (IIa); | ||
Rk. m. Ethyl-β-oxovaleriat Bildung (IIb); | ||
Rk. m. Ethyl-β-oxocapronat Bildung (IIc); |
Rk. m. Ethyl-propiolat Bildung (IId) od. (XIII); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Thiosulfat (VIII), H3PO4; | ||
Indol, Thiiran; | ||
Disulfid (IV), LiAlH4; |
3.2 g (100%) | 2-(1H-Indol-3-yl)-ethanethiol 2-(1H-Indol-3-yl)-ethanethiol Thiosulfuric acid S-[2-(1H-indol-3-yl)-ethyl]ester, O-sodium salt (5.04 g, 18 mmol) was suspended in 105 ml of 50% phosphoric acid and covered with a layer of 160 ml of ether. The mixture was refluxed for 6 hours. After cooling, the phases were separated and the aqueous phase was extracted with ether and the organic phases were concentrated to dryness by evaporation. The crude product was obtained in a yield of 3.2 g (100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: TsOH / benzene 2: (i) NaH, benzene, DMF, (ii) /BRN= 1209223/ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; for 92h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphoric acid; acetic acid In water at 4 - 20℃; for 20h; | ||
Stage #1: 4-dimethylamino-4-phenylcyclohexanone; 2-(1H-indol-3-yl)ethane-1-thiol With trimethylsilyl methanesulfonate In dichloromethane at 20℃; for 96h; Stage #2: With sodium hydroxide In ethanol; dichloromethane; water at 20℃; for 1.5h; Heating / reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 20℃; for 96h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: 3-dimethylaminomethyl-4-(3-fluorophenyl)-4-hydroxy-cyclohexanone; 2-(1H-indol-3-yl)ethane-1-thiol With phosphoric acid; acetic acid at 20℃; for 24h; Stage #2: With sodium hydroxide In water | |
With sodium hydroxide; phosphoric acid In dichloromethane; acetic acid | 13 1,1-(2-(Dimethylaminomethyl)-3-hydroxy-3-(3-fluorophenyl)-pentamethylene)-1,3,4,9-tetrahydro-2-thia-9-aza-fluorene 1,1-(2-(Dimethylaminomethyl)-3-hydroxy-3-(3-fluorophenyl)-pentamethylene)-1,3,4,9-tetrahydro-2-thia-9-aza-fluorene 3-Dimethylaminomethyl-4-(3-fluorophenyl)-4-hydroxy-cyclohexanone (1.0 g, 3.8 mmol) and 2-(1H-indol-3-yl)-ethanethiol (670 mg, 3.8 mmol) were dissolved in 17 ml of glacial acetic acid. 4 ml of phosphoric acid were added dropwise at 5° C., and stirring was carried out for 24 hours at RT. 130 ml of 1M sodium hydroxide solution and 100 ml of dichloromethane were added at 5° C., and stirring was carried out for 2 hours at RT. The phases were separated and the aqueous phase was extracted with dichloromethane. After concentration of the solvent, 839 mg (52%) of the crude product were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: 3-dimethylaminomethyl-4-phenyl-4-hydroxy-cyclohexanone; 2-(1H-indol-3-yl)ethane-1-thiol With phosphoric acid; acetic acid at 20℃; for 24h; Stage #2: With sodium hydroxide In water | |
With sodium hydroxide; phosphoric acid In dichloromethane; acetic acid | 8 1,1-(2-(Dimethylaminomethyl)-3-hydroxy-3-phenyl-pentamethylene)-1,3,4,9-tetrahydro-2-thia-9-aza-fluorene 1,1-(2-(Dimethylaminomethyl)-3-hydroxy-3-phenyl-pentamethylene)-1,3,4,9-tetrahydro-2-thia-9-aza-fluorene 3-Dimethylaminomethyl-4-phenyl-4-hydroxy-cyclohexanone (1.4 g, 5.7 mmol) and 2-(1H-indol-3-yl)-ethanethiol (1.0 g, 5.7 mmol) were dissolved in 26 ml of glacial acetic acid. 6 ml of phosphoric acid were added dropwise at about 10° C., and stirring was carried out for 24 hours at RT. 190 ml of 1M sodium hydroxide solution and 150 ml of dichloromethane were added at 0° C., and stirring was carried out for 30 minutes at RT. The phases were separated and the aqueous phase was extracted with dichloromethane. After concentration of the solvent, 1.35 g (59%) of the crude product were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | Stage #1: 3-dimethylaminomethyl-4-(2-methylphenyl)-4-hydroxy-cyclohexanone; 2-(1H-indol-3-yl)ethane-1-thiol With phosphoric acid; acetic acid at 20℃; for 20h; Stage #2: With sodium hydroxide In water at 5℃; for 1h; | |
541 mg (35%) | With phosphoric acid In dichloromethane; acetic acid | 23 1,1-(2-(Dimethylaminomethyl)-3-hydroxy-3-(2-methylphenyl)-pentamethylene)-1,3,4,9-tetrahydro-2-thia-9-aza-fluorene 1,1-(2-(Dimethylaminomethyl)-3-hydroxy-3-(2-methylphenyl)-pentamethylene)-1,3,4,9-tetrahydro-2-thia-9-aza-fluorene 3-Dimethylaminomethyl-4-(2-methylphenyl)-4-hydroxy-cyclohexanone (980 mg, 3.7 mmol) and 2-(1H-indol-3-yl)-ethanethiol (660 mg, 3.7 mmol) were dissolved in 17 ml of glacial acetic acid. 4 ml of 85% phosphoric acid were added dropwise at 5° C., and stirring was carried out for 20 hours at RT. 100 ml of dichloromethane were added at 5° C., the pH was adjusted to 9 with 5M sodium hydroxide solution, and then stirring was carried out for one hour. The phases were separated and the aqueous phase was extracted with dichloromethane. After removal of the solvent by distillation, the crude product was obtained in a yield of 541 mg (35%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: 3-dimethylaminomethyl-4-(4-methylthio-phenyl)-4-hydroxy-cyclohexanone; 2-(1H-indol-3-yl)ethane-1-thiol With phosphoric acid; acetic acid at 20℃; for 20h; Stage #2: With sodium hydroxide In water at 10℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With phosphoric acid In diethyl ether; water for 6h; Heating / reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; toluene-4-sulfonic acid In water; benzene | 3 1-METHYL-1,3,4,9-TETRAHYDROTHIOPYRANO[3,4-b]INDOLE-1-ACETIC ACID (I; R1 = CH3, R2, R3, R4, R5, R6 AND R7 = H, X = S, Y = CH2 CO AND Z = OH) EXAMPLE 3 1-METHYL-1,3,4,9-TETRAHYDROTHIOPYRANO[3,4-b]INDOLE-1-ACETIC ACID (I; R1 = CH3, R2, R3, R4, R5, R6 AND R7 = H, X = S, Y = CH2 CO AND Z = OH) Indole-3-ethanethiol (1.5 g.) and methyl acetoacetate are mixed with 50 ml. of benzene and the solution heated for 30 min. (bath temperature 70° - 80°C.). p-Toluenesulfonic acid (0.15 g.) is added and the reaction mixture is subjected to reflux and stirring for 12 hours. Water formed in the reaction mixture during this period is collected by a water separator. After cooling the benzene solution is washed with a 10% solution of sodium bicarbonate, water, saturated brine and dried over sodium sulfate. Evaporation of the benzene solution yields the ester, 1-methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid methyl ester as a semi-solid, ννCHCl 3 1715 cm-1. This ester is then treated with aqueous alcoholic KOH in the manner described for the esters in Example 1 and 2 to afford the title compound, m.p. 147° - 149°C., nmr (CDCl3) δ1.86 (S, 3H), 3.06 and 8.12 (6H), 7.35 (multiplet, 4H), 8.71 (1H), 10.31 (1H), after recrystallization from benzene-hexane. | |
With sodium hydrogencarbonate; toluene-4-sulfonic acid In water; benzene | 3 1-Methyl-1,3,4,9-Tetrahydrothiopyrano[3,4-b]indole-1-Acetic Acid (I; R1 = CH3, R2, R3, R4, R5, R6 and R7 = H, X = S, Y = CH2 CO and Z = OH) EXAMPLE 3 1-Methyl-1,3,4,9-Tetrahydrothiopyrano[3,4-b]indole-1-Acetic Acid (I; R1 = CH3, R2, R3, R4, R5, R6 and R7 = H, X = S, Y = CH2 CO and Z = OH) Indole-3-ethanethiol (1.5 g.) and methyl acetoacetate are mixed with 50 ml. of benzene and the solution heated for 30 min. (bath temperature 70°-80° C.). p-Toluenesulfonic acid (0.15 g.) is added and the reaction mixture is subjected to reflux and stirring for 12 hours. Water formed in the reaction mixture during this period is collected by a water separator. After cooling the benzene solution is washed with a 10% solution of sodium bicarbonate, water, saturated brine and dried over sodium sulfate. Evaporation of the benzene solution yields the ester, 1-methyl-1, 3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid methyl ester as a semi-solid, γmaxCHCl3 1715 cm-1. This ester is then treated with aqueous alcoholic KOH in the manner described for the esters in Example 1 and 2 to afford the title compound, m.p. 147°-149° C., nmr (CDCl3) δ1.86 (S, 3H), 3.06 and 8.12 (6H), 7.35 (multiplet, 4H), 8.71 (1H), 10.31 (1H), after recrystallization from benzene-hexane. | |
With sodium hydrogencarbonate; toluene-4-sulfonic acid In water; benzene | 3 1-Methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid (VII; R1 = CH3, R2, R3, R4, R5, R6 and R7 = H, X = S and Z = CH2 COOH) EXAMPLE 3 1-Methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid (VII; R1 = CH3, R2, R3, R4, R5, R6 and R7 = H, X = S and Z = CH2 COOH) Indole-3-ethanethiol (1.5 g.) and methyl acetoacetate are mixed with 50 ml. of benzene and the solution heated for 30 min. (bath temperature 70° - 80° C.). p-Toluenesulfonic acid (0.15 g.) is added and the reaction mixture is subjected to reflux and stirring for 12 hours. Water formed in the reaction mixture during this period is collected by a water separator. After cooling the benzene solution is washed with 10% solution of sodium bicarbonate, water, saturated brine and dried over sodium sulfate. Evaporation of the benzene solution yields the ester, 1-methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid methyl ester as a semi-solid, νmaxCHCl3; 1715 cm-1. This ester is then treated with aqueous alcoholic KOH in the manner described for the esters in Examples 1 and 2 to afford the title compound, m.p. 147° - 149° C., nmr (CDCl3) δ1.86 (S, 3H), 3.06, 8.12 (6H), 7.35 (multiplet, 4H), 8.71 (1H), 10.31 (1H), after recrystallization from benzene-hexane. |
With sodium hydrogencarbonate; toluene-4-sulfonic acid In water; benzene | 3 1-METHYL-1,3,4,9-TETRAHYDROTHIOPYRANO[3,4-b]INDOLE-1-ACETIC ACID (I; R1 = CH3, R2, R3, R4, R5, R6 AND R7 = H, X = S, Y = CH2 CO AND Z = OH) EXAMPLE 3 1-METHYL-1,3,4,9-TETRAHYDROTHIOPYRANO[3,4-b]INDOLE-1-ACETIC ACID (I; R1 = CH3, R2, R3, R4, R5, R6 AND R7 = H, X = S, Y = CH2 CO AND Z = OH) Indole-3-ethanethiol (1.5 g.) and methyl acetoacetate are mixed with 50 ml. of benzene and the solution heated for 30 min. (bath temperature 70°-80°C.). p-Toluenesulfonic acid (0.15 g.) is added and the reaction mixture is subjected to reflux and stirring for 12 hours. Water formed in the reaction mixture during this period is collected by a water separator. After cooling the benzene solution is washed with a 10% solution of sodium bicarbonate, water, saturated brine and dried over sodium sulfate. Evaporation of the benzene solution yields the ester, 1-methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid methyl ester as the semi-solid, γmaxCHCl3 1715 cm-1. This ester is then treated with aqueous alcoholic KOH in the manner described for the esters in Example 1 and 2 to afford the title compound, m.p. 147°-149°C., nmr (CDCl3) δ1.86 (S, 3H), 3.06 and 8.12 (6H), 7.35 (multiplet, 4H), 8.71 (1H), 10.31 (1H), after recrystallization from benzene-hexane. | |
With sodium hydrogencarbonate; toluene-4-sulfonic acid In water; benzene | 3 1-METHYL-1,3,4,9-TETRAHYDROTHIOPYRANO[3,4-b]INDOLE-1-ACETIC ACID (VII: R1 = CH3, R2, R3, R4, R5, R6 AND R7 = H, X = S AND Z = CH2 COOH) EXAMPLE 3 1-METHYL-1,3,4,9-TETRAHYDROTHIOPYRANO[3,4-b]INDOLE-1-ACETIC ACID (VII: R1 = CH3, R2, R3, R4, R5, R6 AND R7 = H, X = S AND Z = CH2 COOH) Indole-3-ethanethiol (1.5 g.) and methyl acetoacetate are mixed with 50 ml. of benzene and the solution heated for 30 min. (bath temperature 70°-80° C.). p-Toluenesulfonic acid (0.15 g.) is added and the reaction mixture is subjected to reflux and stirring for 12 hours. Water formed in the reaction mixture during this period is collected by a water separator. After cooling the benzene solution is washed with 10% solution of sodium bicarbonate, water, saturated brine and dried over sodium sulfate. Evaporation of the benzene solution yields the ester, 1-methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid methyl ester as a semi-solid,γmaxCHCl3 1715 cm-1. This ester is then treated with aqueous alcoholic KOH in the manner described for the esters in Examples 1 and 2 to afford the title compound, m.p. 147°-149° C., nmr (CDCl3) δ1.86 (S, 3H), 3.06, 8.12 (6H), 7.35 (multiplet, 4H), 8.71 (1H), 10.31 (1H), after recrystallization from benzene-hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | Stage #1: 3-nitro-benzaldehyde; 2-(1H-indol-3-yl)ethane-1-thiol In toluene at 70℃; for 0.5h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In toluene for 14h; Reflux; | I-2 Preparation of 1-(3-nitrophenyl)-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole (6) Preparation of 1-(3-nitrophenyl)-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole (6). Thiotryptophol (200.3 mg, 1.13 mmol) and 3-nitrobenzaldehyde (204 mg, 1.35 mmol) were dissolved in anhydrous toluene under argon atmosphere and stirred at 70°C for 30 min. Para-toluenesulfonic acid monohydrate (106.5 mg, 0.56 mmol) was then added and the mixture was further refluxed for 14 h. Solvent evaporation under reduced pressure followed by chromatography on silica gel (cHex/AcOEt 10/0 to 7/3) afforded 6 as a white solid (109 mg, 31%). [0051] 1H RMN (400 MHz, CDCl3) δ 2.95-3.08 (m, 2H), 3.11-3.26 (m, 2H), 5.30 (s, 1H), 7.14-7.26 (m, 3H), 7.48 (t, J= 8.2 Hz, 1H), 7.55-7.59 (m, 3H), 8.13-8.15 (m, 2H). [0052] 13C RMN (100 MHz, CDCl3) δ 23.5, 25.6, 41.0, 111.0, 112.9, 118.7, 120.1, 123.0, 123.1, 123.3, 127.6, 129.4, 129.9, 134.4, 135.4, 144.1, 148.7. [0053] HPLC: tR = 9.63 min. [0054] MS: m/z 311 ([M+H]+). [0055] HRMS-ESI-TOF: m/z calculated 309.0698, found 309.0697 ([M-H]-) |
31% | Stage #1: 3-nitro-benzaldehyde; 2-(1H-indol-3-yl)ethane-1-thiol In toluene at 70℃; for 0.5h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In toluene for 14h; Reflux; | 6 Thiotryptophol (200.3 mg, 1.13 mmol) and 3-nitrobenzaldehyde (204 mg, 1.35 mmol) were dissolved in anhydrous toluene under argon atmosphere and stirred at 70°C for 30 min. Para-toluenesulfonic acid monohydrate (106.5 mg, 0.56 mmol) was then added and the mixture was further refluxed for 14 h. Solvent evaporation under reduced pressure followed by chromatography on silica gel (cHex/AcOEt 10/0 to 7/3) afforded 6 as a white solid (109 mg, 31%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-(2-bromoethyl)-1H-indole With sodium thiosulfate In ethanol; water Reflux; Stage #2: In isopropyl alcohol Reflux; Stage #3: With phosphoric acid In diethyl ether; water Reflux; | ||
Stage #1: 3-(2-bromoethyl)-1H-indole With thiourea In ethanol Reflux; Inert atmosphere; Stage #2: With water; sodium hydroxide In ethanol Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 306 mg 2: 182 mg | In dichloromethane at 20℃; for 96h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane / 20 °C / Inert atmosphere |