24621-70-3

Basic information

• Product Name: 1H-INDOL-2-YLMETHANOL
• Synonyms: 1H-INDOL-2-YLMETHANOL;2-HYDROXYMETHYLINDOLE;1H-Indole-2-methanol;NSC 165230;indol-2-ylmethan-1-ol
• CAS NO: 24621-70-3
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• Product Categories: Heterocyclic Compounds
• Mol File: 24621-70-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 72-78 °C
• Boiling Point: 360.6 °C at 760 mmHg
• Flash Point: 171.9 °C
• Appearance: /
• Density: 1.272 g/cm³
• Vapor Pressure: 7.89E-06mmHg at 25°C
• Refractive Index: 1.705
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 14.86±0.10(Predicted)
• CAS DataBase Reference: 1H-INDOL-2-YLMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOL-2-YLMETHANOL(24621-70-3)
• EPA Substance Registry System: 1H-INDOL-2-YLMETHANOL(24621-70-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 24621-70-3(Hazardous Substances Data)

Usage

Uses

Reactant for the synthesis of:Oxazino[4,3-a]indoles2-arylsulfonylmethyl-3-piperazinylmethylindole derivatives as 5-HT6 receptor ligandsSR13668 designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signalingAzido- and isothiocyanato-substituted indoles as melatoninergic agents

InChI:InChI=1/C9H9NO/c11-6-8-5-7-3-1-2-4-9(7)10-8/h1-5,10-11H,6H2

Upstream product

• 3289-87-0 1-methoxyindole-2-carboxaldehyde 
• 107-19-7 propargyl alcohol 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 174418-78-1 1,2,3,4-tetrahydropyrazino[1,2-a]indole-1,4-dione 
• 86531-02-4 1H-indol-1-yl benzoate 
• 3289-82-5 1-hydroxyindole 
• 144219-54-5 1-methoxymethoxyindole 
• 134792-59-9 1-(t-butyldimethylsilyloxy)indole 
• 148564-88-9 2,2,2-trifluoro-N-(2-(3-hydroxyprop-1-ynyl)phenyl)acetamide 
• 109-89-7 diethylamine 
• 58881-41-7 6H,13H-pyrazino<1,2-a:4,5-a'>diindole-6,13-dione 
• 144393-28-2 1-methoxymethoxyindole-2-carboxaldehyde 

Downstream Products

• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 143232-23-9 2-phenylthiomethyl-1H-indole 
• 42136-84-5 for 3e 
• 27640-31-9 2,3-Dihydro-1H-indol-2-ylmethanol 
• 1424168-16-0 (S,Z)-tert-butyl 2-((p-tolylsulfinylimino)methyl)-1H-indole-1-carboxylate 
• 1424168-18-2 tert-butyl 2-((R)-5-(allyloxy)-4-diazo-1-((S)-4-methylphenylsulfinamido)-3,5-dioxopentyl)-1H-indole-1-carboxylate 
• 114604-96-5 tert-butyl 2-formyl-1H-indole-1-carboxylate 
• 1415114-81-6 tert-butyl 2-(2-((3-(phenylmethylsulfonamido)phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate 
• 1579956-01-6 (E)-(1H-indol-2-yl)methyl 2-cyano-3-(3,4-dihydroxyphenyl)acrylate 
• 33553-29-6 1,2,4-triphenyl-9H-carbazole 
• 1616101-34-8 1,2-diphenyl-4-p-tolyl-9H-carbazole 
• 1616101-35-9 4-(4-methoxyphenyl)-1,2-diphenyl-9H-carbazole 
• 1616101-36-0 4-(3-chlorophenyl)-1,2-diphenyl-9H-carbazole 
• 1616101-37-1 4-(4-chlorophenyl)-1,2-diphenyl-9H-carbazole 

Relevant articles and documents

Lithiation of 1-alkoxyindole derivatives

Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.

Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from 3-(o -trifluoroacetamidoaryl)-1-propargylic alcohols and amines

A novel palladium-catalyzed approach to 2-(aminomethyl)indoles from 3-(o-trifluoroacetamidoaryl)-1-propargylic alcohols and amines has been developed.

Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones

o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.