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CAS No. : | 1075-26-9 | MDL No. : | MFCD02179595 |
Formula : | C9H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WRMZOPANDOHWJU-UHFFFAOYSA-N |
M.W : | 147.17 | Pubchem ID : | 2773459 |
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 |
---|---|---|
24% | Stage #1: With Dess-Martin periodane In dichloromethane for 1 h; Stage #2: With sodium hydroxide In dichloromethane; water for 0.5 h; |
a) 1 -Methyl- lH-indole-6-carbaldehyde; Dess-Martin periodane (2.56 g, 6.04 mmol) was dissolved into anhydrous CH2Cl2 (25 ml). (lH-Indol-6-yl)-methanol (883 mg, 6.04 mmol) in anhydrous CH2Cl2 (20 ml) was added and the mixture was stirred for 1 h. Aqueous sodium hydroxide (12 ml of IN solution) was added and the reaction was stirred for 30 min. The organic layer was separated and washed with water (10 ml), brine (10 ml), dried over MgSO4, filtered and concentrated to a thick brown oil. Purification by column chromatography (silica gel, gradient elution of 2percent MeOH/CH2Cl2 to 5percent MeOH/CH2Cl2) gave lH-indole-6-carbaldehyde (212 mg, 24percent) as a brown solid: 1H NMR (300 MHz, DMSO-d6) δ 11.67 (bs, IH), 9.99 (s, IH), 7.97 (s, IH), 7.70-7.65 (m, 2H), 7.54-7.50 (m, IH), 6.59-5.54 (m, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With manganese dioxide In dichloromethane | b. 6-Formylindole Manganese dioxide (240 g) was added to a mechanically stirred solution of 6-hydroxymethylindole (40.7 g) in methylene chloride (1.6 liter). The mixture was stirred for 18 hr, filtered through a pad of diatomaceous earth, the filter cake washed with methylene chloride and chloroform, and the filtrate evaporated to give 6-formylindole (30.55 g) as a yellow solid. The filter cake was washed with tetrahydrofuran and the washings evaporated to give a further crop of 6-formylindole (2.35 g, 82percent combined yield); partial NMR (250 MHz, DMSO-d6): 6.58(m, 1H, H3 -indole), 10.00(s, 1H, CHO), 11.71(br s, 1H, NH). |
56% | Stage #1: With Dess-Martin periodane In dichloromethane for 1 h; Stage #2: With sodium hydroxide In dichloromethane; water for 0.25 h; |
Dess-Martin periodinane (1.53 g, 2.6 mmol) was dissolved into methylene chloride (15 mL). Indol-6-yl-methanol (500 mg, 3.4 mmol) in methylene chloride (12 mL) was added and the mixture was stirred for 1 hr. Sodium hydroxide (5 mL of 1 N solution) was added and the reaction was stirred for 15 min. The organic layer was separated and washed with H20 (5 mL), brine (5 mL), dried over MGS04 and concentrated to afford the title compound as a brown solid (275 mg, 56percent). TH NMR (300 MHz, DMSO-D6) 8 11.7 (s, 1H), 9.98 (s, 1H), 7.97 (s, 1H), 7.70-7. 65 (m, 2H), 7.52 (dd, J= 8.2, 1.4 Hz, 1H), 6.57-6. 5 (m, 1H). |
[ 1349717-81-2 ]
(3-(1H-Indol-6-yl)phenyl)methanol
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