4-Hydroxymethyl-1-tosylindole

Base Information

• Chemical Name: 4-Hydroxymethyl-1-tosylindole
• CAS No.: 71516-38-6
• Molecular Formula: C16H15NO3S
• Molecular Weight: 301.366
• DSSTox Substance ID: DTXSID50502327
• Wikidata: Q82355249
• Mol file: 71516-38-6.mol

Synonyms:4-hydroxymethyl-1-tosylindole;71516-38-6;SCHEMBL9839131;DTXSID50502327;RSTLWAHATMQENR-UHFFFAOYSA-N;[1-(4-Methylbenzene-1-sulfonyl)-1H-indol-4-yl]methanol

Chemical Property of 4-Hydroxymethyl-1-tosylindole

Chemical Property:

• PSA: 67.68000
• LogP: 3.75980
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 301.07726451
• Heavy Atom Count: 21
• Complexity: 451

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=CC3=C(C=CC=C32)CO

Technology Process of 4-Hydroxymethyl-1-tosylindole

There total 5 articles about 4-Hydroxymethyl-1-tosylindole 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: 92.0%

4-methoxycarbonyl-1-<(4-methylphenyl)sulfonyl>-1H-indole (31271-85-9) → 4-(hydroxymethyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole (71516-38-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 3.16667h;

Reference yield:

methyl 1H-indole-4-carboxylate (39830-66-5) → 4-(hydroxymethyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole (71516-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92.4 percent / K₂CO₃ / butan-2-one / 24 h / Heating

2: 85.3 percent / lithium aluminium hydride / tetrahydrofuran / 0.75 h / 0 - 5 °C

With lithium aluminium tetrahydride; potassium carbonate; In tetrahydrofuran; butanone;

DOI:10.1016/0040-4020(84)80018-6

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 4-(hydroxymethyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole (71516-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92.4 percent / K₂CO₃ / butan-2-one / 24 h / Heating

2: 85.3 percent / lithium aluminium hydride / tetrahydrofuran / 0.75 h / 0 - 5 °C

With lithium aluminium tetrahydride; potassium carbonate; In tetrahydrofuran; butanone;

DOI:10.1016/0040-4020(84)80018-6

upstream raw materials:

4-methoxycarbonyl-1-<(4-methylphenyl)sulfonyl>-1H-indole

methyl 1H-indole-4-carboxylate

p-toluenesulfonyl chloride

Downstream raw materials:

1-[(4-methyl-phenyl)-sulfonyl]-1H-indol-4-carboxaldehyde

4-(bromomethyl)-1-(p-tolylsulfonyl)indole

<3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole

<3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole