67593-11-7

Basic information

• Product Name: (1-Tosyl-1H-Indol-3-Yl)Methanol
• Synonyms: (1-Tosyl-1H-Indol-3-Yl)Methanol;(1-Tosyl-1H-Indol-3-Yl)Methanol(WX640386);1H-Indole-3-methanol, 1-[(4-methylphenyl)sulfonyl]
• CAS NO: 67593-11-7
• Molecular Formula: C₁₆H₁₅NO₃S
• Molecular Weight: 301.3602
• Mol File: 67593-11-7.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1-Tosyl-1H-Indol-3-Yl)Methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Tosyl-1H-Indol-3-Yl)Methanol(67593-11-7)
• EPA Substance Registry System: (1-Tosyl-1H-Indol-3-Yl)Methanol(67593-11-7)

Safety Data

• Hazardous Substances Data: 67593-11-7(Hazardous Substances Data)

Usage

General Description

(1-Tosyl-1H-Indol-3-Yl)Methanol is a chemical compound that belongs to the class of tosylated indole derivatives. It is a white to light yellow solid with a molecular formula of C21H19NO3S and a molecular weight of 369.45 g/mol. (1-Tosyl-1H-Indol-3-Yl)Methanol is commonly used in organic synthesis as a versatile building block for the preparation of various pharmaceuticals and agrochemicals. It is also used as a reagent in the preparation of other functionalized indole derivatives through various chemical reactions. Additionally, (1-Tosyl-1H-Indol-3-Yl)Methanol has potential applications in medicinal chemistry, particularly in drug discovery and development due to its structural features and potential biological activities.

Upstream product

• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 
• 487-89-8 Indole-3-carboxaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 676-58-4 methylmagnesium chloride 
• 776-41-0 indole-3-carboxylic acid ethyl ester 

Downstream Products

• 1242306-27-9 1-p-toluenesulfonyl-1H-indole-3-carboxamide 
• 1313236-87-1 C₃₂H₃₂N₄O₄S 
• 1313236-63-3 C₃₃H₃₃N₅O₃S 
• 874911-14-5 (toluene-4-sulfonyl)-acetic acid 1-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester 
• 1349705-58-3 C₁₈H₁₆ClNO₄S 
• 874911-13-4 (toluene-4-sulfonyl)-acetic acid 1-(toluene-4-sulfonyl)-1H-indol-3-ylmethyl ester 
• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 
• 1228320-13-5 (1-p-toluenesulfonyl-1H-indol-3-yl)methyl acetate 
• 1616889-19-0 1-tosyl-3-(2,2,2-trifluoroethyl)-1H-indole 

Relevant articles and documents

Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides

We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed in situ from substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements in the presence of a rhodium and a copper catalyst, respectively. The combined experimental and density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving a metal-free ylide in the rhodium catalyzed reaction favoring [2,3]-rearrangement, and a metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates were also demonstrated.

A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study

Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

Chromium-Catalyzed Asymmetric Dearomatization-Addition Reactions of Halomethyloxazoles and Indoles

The asymmetric dearomatization-addition reaction of halomethyloxazoles and halomethylindoles with aldehydes is realized in the presence of a carbazole-based bisoxazoline CrCl 2 complex to afford the corresponding enantioenriched, hydroxylated oxazoline and indoline products. The observed excellent chemo-, regio-, diastereo- and enantioselectivities are notable advantages of this protocol. The strategy established in this study is expected to find application in the synthesis of azaheterocycles with biological significance and useful functionalities.