1H-Indole-2-methanol

Base Information

• Chemical Name: 1H-Indole-2-methanol
• CAS No.: 24621-70-3
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 2933990090
• European Community (EC) Number: 625-794-1
• NSC Number: 165230
• DSSTox Substance ID: DTXSID00179366
• Nikkaji Number: J1.035.661J
• ChEMBL ID: CHEMBL4522775
• Mol file: 24621-70-3.mol

Synonyms:(1H-Indol-2-yl)methanol;24621-70-3;1H-Indole-2-methanol;1H-indol-2-ylmethanol;(1H-Indol-2-yl)-methanol;2-(Hydroxymethyl)indole;indole-2-methanol;MFCD00030195;hydroxymethylindol;2-Indolemethanol;2-hydroxymethylindole;NSC 165230;(1h-indol-2-yl) methanol;SCHEMBL1442945;1H-Indole-2-methanol, 90%;CHEMBL4522775;DTXSID00179366;XEEANGGQJOWRTG-UHFFFAOYSA-N;AMY14082;NSC165230;AKOS015898490;CS-W004828;DS-1823;NSC-165230;SB74076;7-Bromo-6-hydroxyindole-3-acetonitrile;SY045599;BB 0265965;FT-0716202;EN300-159658;A817762;A877857;J-015594;1227565-88-9

Chemical Property of 1H-Indole-2-methanol

Chemical Property:

• Vapor Pressure: 7.89E-06mmHg at 25°C
• Melting Point: 72-78 °C
• Refractive Index: 1.705
• Boiling Point: 360.6 °C at 760 mmHg
• PKA: 14.86±0.10(Predicted)
• Flash Point: 171.9 °C
• PSA: 36.02000
• Density: 1.272 g/cm³
• LogP: 1.66020
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

98.0%Min ^*data from raw suppliers

(1H-Indol-2-yl)methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)CO
• 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

Technology Process of 1H-Indole-2-methanol

There total 10 articles about 1H-Indole-2-methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

6H,13H-pyrazino<1,2-a:4,5-a'>diindole-6,13-dione (58881-41-7) → 1H-indol-2-ylcarboxaldehyde (19005-93-7) + 2-(hydroxymethyl)indole (24621-70-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 2h;

Reference yield: 83.0%

1,2,3,4-tetrahydropyrazino[1,2-a]indole-1,4-dione (174418-78-1) → 1H-indol-2-ylcarboxaldehyde (19005-93-7) + 2-(hydroxymethyl)indole (24621-70-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield: 69.0%

2,2,2-trifluoro-N-(2-(3-hydroxyprop-1-ynyl)phenyl)acetamide (148564-88-9) + diethylamine (109-89-7) → 2-(hydroxymethyl)indole (24621-70-3) + N-((1H-indol-2-yl)methyl)-N-ethylethanamine (3978-16-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 1.5h; Reagent/catalyst; Solvent; Time; Temperature; Inert atmosphere;

DOI:10.1021/jo401456x

upstream raw materials:

1-methoxyindole-2-carboxaldehyde

propargyl alcohol

2,2,2-trifluoro-N-(2-iodophenyl)acetamide

1-methoxymethoxyindole-2-carboxaldehyde

Downstream raw materials:

2-phenylthiomethyl-1H-indole

2,3-Dihydro-1H-indol-2-ylmethanol

(+/-) 4-fluoro-N-methyl-N-(6,7,8,9-tetrahydropyrido[1,2-a]indol-7-yl)benzenesulfonamide

(+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate

Refernces

• 1、 Cacchi, Sandro,Fabrizi, Giancarlo,Iazzetti, Antonia,Molinaro, Carmela,Verdiglione, Rosanna,Goggiamani, Antonella. "Synthesis of free NH 2-(aminomethyl)indoles through copper-catalyzed reaction of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols with amines and palladium/copper- cocatalyzed domino three-component Sonogashira cross-coupling/cyclization/substitu". supporting information. p. 1053 - 1059. Retrieved 2015/03/30.
• 2、 Akeng'a,Read. "Synthesis of indoles: Tetrahydropyrazino[1,2-a]indole-1,4-dione and pyrazino[1,2-a]indole-6,13-diones from piperazine-2,5-diones". . p. 93 - 97. Retrieved 2007/10/03.