(1H-indol-5-yl)methanol

Base Information

• Chemical Name: (1H-indol-5-yl)methanol
• CAS No.: 1075-25-8
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 2933990090
• European Community (EC) Number: 688-376-8
• DSSTox Substance ID: DTXSID40378472
• Wikidata: Q72483041
• ChEMBL ID: CHEMBL1650258
• Mol file: 1075-25-8.mol

Synonyms:1075-25-8;Indole-5-methanol;(1H-indol-5-yl)methanol;1H-indol-5-ylmethanol;1H-Indole-5-methanol;5-Hydroxymethylindole;MFCD02179594;5-(Hydroxymethyl)indole;5-(HYDROXYMETHYL)-1H-INDOLE;(1H-Indol-5-yl)-methanol;SCHEMBL951685;indole-5-methanol, AldrichCPR;CHEMBL1650258;DTXSID40378472;ZSHFWQNPJMUBQU-UHFFFAOYSA-N;STK360679;AKOS000321461;AB11366;PS-3333;BB 0254647;CS-0091638;FT-0633303;EN300-370665;A801719;W-200768;Z1201621651

Chemical Property of (1H-indol-5-yl)methanol

Chemical Property:

• Appearance/Colour: Brown powder
• Vapor Pressure: 7.89E-06mmHg at 25°C
• Melting Point: 66-70 °C
• Refractive Index: 1.705
• Boiling Point: 360.6 °C at 760 mmHg
• PKA: 14.52±0.10(Predicted)
• Flash Point: 171.9 °C
• PSA: 36.02000
• Density: 1.272 g/cm³
• LogP: 1.66020
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• 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%,99%, ^*data from raw suppliers

Indole-5-methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2)C=C1CO

Technology Process of (1H-indol-5-yl)methanol

There total 7 articles about (1H-indol-5-yl)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: 93.0%

1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0) → indole-5-methanol (1075-25-8)

Guidance literature:

1H-Indole-5-carboxylic acid; With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; Reflux;

With water; sodium hydroxide; In tetrahydrofuran;

Reference yield: 93.0%

1H-indole-5-carboxaldehyde (1196-69-6) → indole-5-methanol (1075-25-8)

Guidance literature:

With methanol; sodium tetrahydroborate; for 1.5h; Cooling with ice; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.202107438

Reference yield: 82.0%

5-methoxycarbonylindole (1011-65-0) → indole-5-methanol (1075-25-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

upstream raw materials:

1H-indole-5-carboxaldehyde

5-methoxycarbonylindole

1H-Indole-5-carboxylic acid

methyl 3-methyl-4-nitrobenzoate

Downstream raw materials:

1-(tert-butoxycarbonyl)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-indol-2-ylboronic acid

1H-indole-5-carboxaldehyde

1-(5-(((tert-butyldimethylsilyl)oxy)methyl)-1H-indol-3-yl)-2-chloro-2-phenylethanone

5-methoxycarbonylindole

Refernces

• 1、 Holoidovsky, Lara,Meijler, Michael M.. "Synthesis and Evaluation of Indole-Based Autoinducers on Quorum Sensing in Vibrio cholerae". . p. 572 - 576. Retrieved 2020.
• 2、 Fleischer, Steffen,Zhou, Shaolin,Junge, Kathrin,Beller, Matthias. "General and highly efficient iron-catalyzed hydrogenation of aldehydes, ketones, and α,β-unsaturated aldehydes". . p. 5120 - 5124. Retrieved 2013/06/27.