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CAS No. : | 1968-05-4 | MDL No. : | MFCD00195766 |
Formula : | C17H14N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VFTRKSBEFQDZKX-UHFFFAOYSA-N |
M.W : | 246.31 | Pubchem ID : | 3071 |
Synonyms : |
DIM;Arundine;HB 236
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P273-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335-H412 | 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 |
---|---|---|
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. |