6943-01-7

Basic information

• Product Name: 1H-Indole-3-ethanol,6-methyl-(9CI)
• Synonyms: 1H-Indole-3-ethanol,6-methyl-(9CI);1H-INDOLE-3-ETHANOL,6-METHYL-
• CAS NO: 6943-01-7
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• Product Categories: INDOLE
• Mol File: 6943-01-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 360.8°C at 760 mmHg
• Flash Point: 172°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 7.8E-06mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: 1H-Indole-3-ethanol,6-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-ethanol,6-methyl-(9CI)(6943-01-7)
• EPA Substance Registry System: 1H-Indole-3-ethanol,6-methyl-(9CI)(6943-01-7)

Safety Data

• Hazardous Substances Data: 6943-01-7(Hazardous Substances Data)

Usage

Derivative of

Tryptophan

Occurrence

Naturally occurring intermediate in the biosynthesis of melatonin and other important molecules in the body

Potential use

Pharmacological and medical applications, including as a sedative and hypnotic agent

Investigation for treatment

Various neurological and psychiatric disorders

Interest

Potential therapeutic benefits and role in the body's biochemical processes

InChI:InChI=1/C11H13NO/c1-8-2-3-10-9(4-5-13)7-12-11(10)6-8/h2-3,6-7,12-13H,4-5H2,1H3

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 637-04-7 (3-methylphenyl)hydrazine hydrochloride 
• 195455-54-0 trifluoromethanesulfonic acid 4-methyl-2-nitrophenyl ester 
• 3420-02-8 6-methylindole 
• 408356-30-9 methyl 2-(6-methyl-1H-indol-3-yl)oxoacetate 

Relevant articles and documents

Enantioselective Construction of Spirooxindole-Fused Cyclopentanes

The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.

A convenient synthesis of indole and 1,4-dihydropyridine hybrid macromolecules by dimerization of [2-(1h-indol-3-yl)ethyl]pyridinium salts

The design and synthesis of a novel type of macrocyclic compounds containing indole and 1,4-dihydropyridine heterocyclic subunits is presented. The key reaction involved in the synthesis was a base-mediated dimerization of [2-(1H-indol-3-yl)ethyl]pyridinium salts. The structure of the macrocycles was unambiguously confirmed by NMR and HRMS spectroscopic and X-ray single crystal diffraction.

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-Hamination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N-heterocyclization process are reported.