38445-36-2

Basic information

• Product Name: 1,2-dimethyl-3-phenyl-1H-indole
• CAS NO: 38445-36-2
• Molecular Formula: C₁₆H₁₅N
• Molecular Weight: 221.297
• Mol File: 38445-36-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 376°C at 760 mmHg
• Flash Point: 181.2°C
• Density: 1.03g/cm³
• Vapor Pressure: 1.62E-05mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 1,2-dimethyl-3-phenyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dimethyl-3-phenyl-1H-indole(38445-36-2)
• EPA Substance Registry System: 1,2-dimethyl-3-phenyl-1H-indole(38445-36-2)

Safety Data

• Hazardous Substances Data: 38445-36-2(Hazardous Substances Data)

Usage

Physical state

Colorless to light yellow liquid

Odor

Strong, unpleasant

Natural occurrence

Found in feces, a byproduct of bacterial breakdown of tryptophan in the intestines

Production

Also produced in small quantities during the combustion of tobacco

Use

Used in some perfumes to impart a leather-like smell

Classification

Volatile organic compound

Environmental impact

Contributes to the odor of livestock manure and sewage

Health concerns

Linked to certain metabolic disorders and considered a potential environmental pollutant

Upstream product

• 38445-35-1 (1-methyl-3-phenyl-indol-2-yl)-acetic acid 
• 106032-42-2 Phenylaceton-methylphenylhydrazon 
• 875-79-6 1,2-dimethylindole 
• 28719-46-2 triphenylbismuth bis(trifluoroacetate) 
• 4757-69-1 2-methyl-3-phenyl-1H-indole 
• 74-88-4 methyl iodide 
• 100-63-0 phenylhydrazine 
• 77-78-1 dimethyl sulfate 
• 103-79-7 1-phenyl-acetone 
• 100-61-8 N-methylaniline 
• 10147-11-2 propargyl benzene 
• 618-40-6 1-Methyl-1-phenylhydrazine 
• 3920-67-0 2-methyl-2-phenyl-1,2-dihydro-3H-indol-3-one 
• 66152-09-8 (2R,3S)-2-Methyl-2-phenyl-2,3-dihydro-1H-indol-3-ol 

Downstream Products

• 75834-28-5 6-Methoxy-1,2-dimethyl-3-phenyl-1H-indole 
• 75834-30-9 2-Methoxy-3,4-dimethyl-2-phenyl-3,4-dihydro-2H-benzo[1,4]oxazine 

Relevant articles and documents

Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles

(Chemical Equation Presented) Indole click chemistry: The quest for better catalysts for the intermolecular hydrohydrazination to indoles leads to zinc salts. A simple one-pot synthesis forms indoles from arylhydrazines and terminal alkynes. The pharmacologically relevant indole building blocks are selectively formed in the presence of zinc triflate (Zn(OTf)2) or ZnCl 2 (see scheme).

A Copper-Catalyzed Aerobic [1,3]-Nitrogen Shift through Nitrogen-Radical 4-exo-trig Cyclization

A novel radical [1,3]-nitrogen shift catalyzed by copper diacetate under an oxygen atmosphere (1 atm) has been developed for the construction of a diverse range of indole derivatives from α,α-disubstituted benzylamine. In this reaction, oxygen was used as a clean terminal oxidant, and water was produced as the only by-product. Five inert bonds were cleaved, and two C?N bonds and one C?C double bond were constructed in one pot during this transformation. This unique method demonstrated broad application protential for the late-stage modification of biologically active natural products and drugs. Mechanistic investigations indicate that a unique 4-exo-trig cyclization of an aminyl radical onto a phenyl ring is involved in the catalytic cycle.

Rhodium(III)-catalyzed synthesis of indoles from 1-alkylidene-2- arylhydrazines and alkynes via C-H and N-N bond cleavages

1-Alkylidene-2-arylhydrazines undergo annulative coupling with internal alkynes in the presence of a rhodium(III) catalyst and a copper(II) salt. The reaction proceeds through cleavage of the C-H and N-N bonds of hydrazines to afford 1,2,3-trisubstituted indole derivatives.