Name | 2-Hydroxymethyl indole |
Synonyms | NSC 165230 1H-Indole-2-methanol 1H-INDOL-2-YLMETHANOL indol-2-ylmethan-1-ol 2-HYDROXYMETHYLINDOLE 2-Hydroxymethyl indole 2-(Hydroxymethyl)-1H-indole |
CAS | 24621-70-3 |
Molecular Formula | C9H9NO |
Molar Mass | 147.17 |
Density | 1.272±0.06 g/cm3(Predicted) |
Melting Point | 72-78°C |
Boling Point | 360.6±17.0 °C(Predicted) |
pKa | 14.86±0.10(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2–8 °C |
Hazard Symbols | Xi - Irritant |
Risk Codes | 41 - Risk of serious damage to eyes |
Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
Background | hydroxyindole compounds are the starting materials for the synthesis of many natural compounds, indole is often found as a significant structural unit in many natural products and pharmaceutical active compounds, methods for the synthesis of this framework in order to obtain new forms of substitution are currently a major goal of organic synthesis. |
Application | indole derivatives such as 2-methylhydroxyindole are also important organic chemical raw materials and pharmaceutical intermediates, can be used to synthesize dyes, spices and some drugs, can also be used as auxin, feed additives. In particular, 2-methylhydroxyindole is an important intermediate in the synthesis of Pindolol, a drug for treating angina pectoris, and dimethylhydroxytryptamine, a drug for treating psychosis. |
preparation | a 100L reactor with stirring device was charged with 20 kg4-oxindole, 4kg Pd content of 5% Pd/C catalyst (Palladium carbon catalyst), 60L diethylene glycol dimethyl ether as solvent, to the reactor sandwich steam heating, stirring, the catalytic dehydrogenation reaction was carried out at T = 150-160 ℃. After the dehydrogenation reaction is completed, the Pd/C catalyst is separated by filtration, and the separated Pd/C catalyst can be recycled. The separated filtrate is pumped to a 100L distillation kettle and subjected to vacuum distillation, collect the diethylene glycol dimethyl ether fraction (can be applied continuously), and then collect 11kg of the product 2-methylhydroxyindole fraction, with a mass yield of 55% and a content of ≥ 99.0%. |