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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Indole-3-Carbinol is a naturally occuring plant hormone found in cruciferous vegetables, which can both inhibit carcinogenesis in several animal species and enhance tumor incidence if administered at a post-initiation stage.
Synonyms: I3C; 3-Indolemethanol; NSC 525801
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 700-06-1 |
Formula : | C9H9NO |
M.W : | 147.17 |
SMILES Code : | OCC1=CNC2=C1C=CC=C2 |
Synonyms : |
I3C; 3-Indolemethanol; NSC 525801
|
MDL No. : | MFCD00005632 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P305+P351+P338 |
* 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 |
---|---|---|
88%Chromat. | With sodium hydroxide; In isopropyl alcohol; at 82℃; for 2h; | General procedure: In a typical procedure, a 5 mg (0.77 mol%) of RuO2/MWCNT and 80 mg (2 mmol) of NaOH were stirred with 5 mL of i-PrOH taken in an ace pressure tube equipped with a stirring bar. Then the substrate (1 mmol) was added to the stirring solution and then the mixture was heated at 82C. The completion of the reaction was monitored by GC. After the reaction, the catalyst was separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was alsocalculated. Finally, the separated RuO2/MWCNT was washed well with diethyl ether followed by drying in an oven at 60C for 5 h and it was reused for the subsequent transfer hydrogenation of carbonyl compounds to investigate the reusability of the RuO2/MWCNT. |
With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20℃; for 3h; | General procedure: To a solution of a compound 11a-11d (10 mmol) in 20 mL of DMF, phosphorus oxychloride (1.4 mL, 15 mmol) was added dropwise at 0C. Upon 2 h of the process at 55C, the mixture was poured into 150 mL of ice water. Then 20 % NaOH solution was added to adjust pH at 8.0. The crude product was filtered off and recrystallized from anhydrous ethanol to give the corresponding product. Compounds 12a-12d (10 mmol) were dissolved in 20 mL of EtOH/THF (1: 1), and sodium boron hydride was added to the reaction mixture in portions. Upon stirring the mixture for 3 h, 20 mL of saturated Na2CO3solution was added to quench the reaction. In 10 min the mixture was extracted by 30 mL of ethyl acetate, then the organic layer was washed with 30 mL of saturated sodium chloride solution. The organic layer was concentrated in vacuum to give the corresponding solid product 13a-13d. (1H-Indol-3-yl)methanol (13a). White solid, yield 91 %, mp 97-98C (lit. 99-100C). 1H NMR spectrum, delta, ppm: 4.64 d (J = 5.0 Hz, 2H, CH2), 4.74 t (J = 5.0 Hz, 1H, OH), 6.98 t (J = 7.5 Hz, 1H, ArH), 7.07 t (J = 7.5 Hz, 1H, ArH), 7.23 s (1H, CH-N), 7.35 d (J = 8.5 Hz, 1H, ArH), 7.59 d (J = 7.5 Hz, 1H, ArH), 10.90 s (1H, NH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium hydroxide; In water; for 1h;Heating / reflux; | (a) 3,3'-Diindolylmethane (55). Indole-3-carbinol (54) (1.0 g, 6.79 mmol) in 10% aqueous NaOH solution (100 mL) was refluxed for 1 h. The solution was cooled, neutralized with carbon dioxide and the white precipitate was collected by filtration, which was then crystallized from toluene to yield 55 as a white solid (0.65 g, 77%): 1H NMR (300 MHz, CDCl3) delta 4.26 (s, 2, CH2), 6.94 (m, 2, PyH), 7.11 (m, 2, ArH), 7.21 (m, 2, ArH), 7.36 (m, 2, ArH), 7.64 (m, 2, ArH), 7.86 (br.s, 2, NH). |
With sodium hydroxide; In water; for 1h;Reflux; | Indole-3-carbinol (1.0 g, 6.79 mmol) in 10% aqueous NaOH solution (100 mL) was refluxed for 1 h. The solution was cooled, neutralized with carbon dioxide and the white precipitate was collected by filtration, which was then crystallized from toluene to yield 3,3'-Diindolylmethane as a white solid (0.65 g, 77%): 1H NMR (300 MHz, CDCl3) delta 4.26 (s, 2, CH2), 6.94 (m, 2, PyH), 7.11 (m, 2, ArH), 7.21 (m, 2, ArH), 7.36 (m, 2, ArH), 7.64 (m, 2, ArH), 7.86 (br. s, 2, NH). | |
With hydrogen chloride; In d(4)-methanol; for 0.0833333h;Conversion of starting material; | OSU- A9 resists acid-catalyzed dimerization. We used a nuclear magnetic resonance (NMR) technique to analyze the chemical stability of OSU-A9 versus indole-3- carbinol in 0.1 N HCl by monitoring changes in the proton signal associated with CH2OH. Individual compounds (20 mg) were dissolved in 1 ml of deuterium-labeled methanol (CD3OD). The NMR spectra revealed signals for the methylene protons (indicated by *) at 4.73 ppm and 4.74 ppm for <strong>[700-06-1]indole-3-carbinol</strong> and OSU-A9, respectively (upper spectra, left and right panels). Addition of 100 mul of 0.1 N deuterium-labeled HCl to <strong>[700-06-1]indole-3-carbinol</strong> resulted in an immediate shift of the CH2 signal from 4.73 ppm to 4.66 ppm (t = 5 min), indicating the chemical transformation of <strong>[700-06-1]indole-3-carbinol</strong> to an acid reaction mixture consisting of DIM and other <n="38"/>oligomeric products. On the other hand, no appreciable change in the spectrum was noted after exposure of OSU- A9 to HCl for up to 8 h, indicating its significantly greater chemical stability. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With LACTIC ACID; dihydrogen peroxide; at 30℃; for 7h; | General procedure: A mixture of alcohol (1 mmol) and lactic acid (1 mL) was charged in 25 mL round bottom flask subjected to constant magnetic stirring at room temperature (30C). The reaction mixture was further activated by addition of 30% H2O2 (1.07 equiv.). The reaction progress was monitored by GC. After completion of the reaction, Dichloromethane (2×6 mL) was added to the reaction mixture and then washed with distilled water (2×2mL). The organic layer was separated and dried over Na2SO4 and removed under reduced pressure. The crude product was obtained by evaporation method and again purified by column chromatography using ethyl acetate and n-hexane as eluting system. |
82% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; In water; acetonitrile; at 20℃; for 6h;Green chemistry; | General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)2 (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH3CN/H2O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product. |
72% | With magnetic polydopamine-wrapped Fe3O4 core-shell submicrosphere-supported nano-palladium; air; In o-xylene; at 120℃; for 24h;Sonication; | General procedure: Approximately 0.1 g of Fe3O4(at)PDAPd catalyst (2 mol% of Pd) was used. The aforementioned solidand liquor were separated using a magnet and placed under ultrasonic washing using 10 mL 3O-xylene. Then, 1 mmol of benzyl alcohol derivative and 5 mL of O-xylene were successively added and blended under ultrasonic conditions. The mixture was then magnetically stirred for 24 h under 120 C. After the reaction ended, the solid and liquor were separated using a magnet. The liquor wasconcentrated, and the dehydrogenation product could be obtained after purification through column chromatography (petroleum ether/ethyl acetate). |
43% | With 4,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluorescein disodium salt; oxygen; ammonium thiocyanate; In acetonitrile; at 20℃; for 20h;Irradiation; | General procedure: A glass vial fitted with magnetic stirrer and a magnetic bar containing a reaction mixture of alcohol (0.1 mmol), NH4SCN (3 eq.), catalyst (5 mol%) and 2 ml of solvent. The vial was closed with rubber septum and O2 was bubbling for 15 minutes using needles. The reaction mixture was irradiated under a 23W CFL lamp for a certain time period. Reaction progress was monitored by TLC. After, completion of the reaction, a yellow solid was formed. The reaction mixture of three vials with the same content were combined and filter it through whatman filter paper. The mixture was evaporated under reduced pressure and purified by column chromatography using hexane/ethyl acetate as eluent. Further, the reaction mixture was run on a GC-MS instrument for characterisation. Yield, conversion and selectivity were calculated using following equations. |