[1-(Benzenesulfonyl)indol-5-yl]methanol

Base Information

• Chemical Name: [1-(Benzenesulfonyl)indol-5-yl]methanol
• CAS No.: 182187-39-9
• Molecular Formula: C15H13 N O3 S
• Molecular Weight: 287.339
• DSSTox Substance ID: DTXSID10379890
• Wikidata: Q82169910
• Mol file: 182187-39-9.mol

Synonyms:182187-39-9;1-Phenylsulfonylindole-5-methanol;[1-(benzenesulfonyl)indol-5-yl]methanol;(1-(Phenylsulfonyl)-1H-indol-5-yl)methanol;[1-(phenylsulfonyl)-1H-indol-5-yl]methanol;1H-Indole-5-methanol,1-(phenylsulfonyl)-;[1-(benzenesulfonyl)-1H-indol-5-yl]methanol;SCHEMBL8932772;DTXSID10379890;MFCD03086086;AKOS015912275;benzenesulfonyl(1H-indol-5-yl)methanol;FT-0605388;A812661

Chemical Property of [1-(Benzenesulfonyl)indol-5-yl]methanol

Chemical Property:

• Vapor Pressure: 4.84E-12mmHg at 25°C
• Boiling Point: 529.5°Cat760mmHg
• Flash Point: 274°C
• PSA: 67.68000
• Density: 1.32g/cm³
• LogP: 3.45140
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 287.06161445
• Heavy Atom Count: 20
• Complexity: 425

Purity/Quality:

98%min ^*data from raw suppliers

1-PHENYLSULFONYLINDOLE-5-METHANOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi:Irritant
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)N2C=CC3=C2C=CC(=C3)CO

Technology Process of [1-(Benzenesulfonyl)indol-5-yl]methanol

There total 4 articles about [1-(Benzenesulfonyl)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: 85.0%

methyl 1-(benzenesulfonyl)-1H-indole-5-carboxylate → [1-(benzenesulfonyl)-1H-indol-5-yl]methanol (182187-39-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm300069y

Reference yield:

5-methoxycarbonylindole (1011-65-0) → [1-(benzenesulfonyl)-1H-indol-5-yl]methanol (182187-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.67 h / 25 °C / Inert atmosphere

1.2: 18 h / 25 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / 25 °C / Inert atmosphere

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm300069y

Reference yield:

benzenesulfonyl chloride (98-09-9) → [1-(benzenesulfonyl)-1H-indol-5-yl]methanol (182187-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.67 h / 25 °C / Inert atmosphere

1.2: 18 h / 25 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / 25 °C / Inert atmosphere

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm300069y

upstream raw materials:

5-methoxycarbonylindole

benzenesulfonyl chloride

1H-Indole-5-carboxylic acid

Downstream raw materials:

5-(bromomethyl)-1-(phenylsulfonyl)-1H-indole

Refernces

• 1、 Rueeger, Heinrich,Lueoend, Rainer,Rogel, Olivier,Rondeau, Jean-Michel,M?bitz, Henrik,MacHauer, Rainer,Jacobson, Laura,Staufenbiel, Matthias,Desrayaud, Sandrine,Neumann, Ulf. "Discovery of cyclic sulfone hydroxyethylamines as potent and selective β-site APP-cleaving enzyme 1 (BACE1) inhibitors: Structure-based design and in vivo reduction of amyloid β-peptides". supporting information; experimental part. p. 3364 - 3386. Retrieved 2012/06/01.