1-PHENYL-1H-INDOLE

Base Information

• Chemical Name: 1-PHENYL-1H-INDOLE
• CAS No.: 16096-33-6
• Molecular Formula: C14H11N
• Molecular Weight: 193.248
• Hs Code.: 2933990090
• Mol file: 16096-33-6.mol

Synonyms:1-Phenylindole;N-Phenylindole;Indole,1-phenyl- (7CI,8CI);1-Phenyl-1H-indole;

Chemical Property of 1-PHENYL-1H-INDOLE

Chemical Property:

• Vapor Pressure: 0.000187mmHg at 25°C
• Melting Point: 60-62℃
• Refractive Index: 1.608
• Boiling Point: 328.618 °C at 760 mmHg
• Flash Point: 152.543 °C
• PSA: 4.93000
• Density: 1.055 g/cm³
• LogP: 3.63050

Purity/Quality:

97% ^*data from raw suppliers

1-Phenyl-1H-indole >98.0%(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 1-Phenyl-1H-indole (also known as N-phenylindole) is an indole derivative where a phenyl group is attached to the nitrogen atom of the indole ring. In the context of the study, it serves as a key substrate for investigating regioselective palladation, demonstrating that the N-phenyl substituent influences the formation of either C2-Pd or C3-Pd bonds under varying reaction conditions, such as base or acid mediation. The research highlights its role in forming tetranuclear palladacycles, with selectivity dependent on factors like the protective group and reaction medium. (Note: The paragraph summarizes the compound's relevance to the study's mechanistic insights without detailing the literature itself.)

Technology Process of 1-PHENYL-1H-INDOLE

There total 95 articles about 1-PHENYL-1H-INDOLE 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: 100.0%

indole (120-72-9) + iodobenzene (591-50-4) → 1-phenyl-1H-indole (16096-33-6)

Guidance literature:

With copper(I) bromide; sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 170 ℃; for 6h;

DOI:10.1016/S0014-827X(99)00043-9

Reference yield: 100.0%

indole (120-72-9) + bromobenzene (108-86-1,52753-63-6) → 1-phenyl-1H-indole (16096-33-6)

Guidance literature:

With palladium diacetate; sodium hydroxide; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; In 1,4-dioxane; at 100 ℃; for 1h;

DOI:10.1021/jo010613+

Reference yield: 96.0%

N-Phenyl-2,3-dihydroindole (25083-11-8) → 1-phenyl-1H-indole (16096-33-6)

Guidance literature:

With aluminum oxide; In N,N-dimethyl-formamide; at 120 ℃; for 5h; Inert atmosphere;

DOI:10.1002/adsc.201300453

upstream raw materials:

1-phenyl-1,3-dihydro-indol-2-one

1-phenylindoline-2-thione

1-phenyl-4,5,6,7-tetrahydro-1H-indole

diphenylamino-N-acetaldehyde

Downstream raw materials:

(1-phenyl-indol-3-yl)-glyoxylic acid dimethylamide

1-Phenyl-3-(2-pyridin-4-yl-ethyl)-1H-indole

2-Brom-N-methyl-3-(1-phenyl-2-indolyl)maleinimid

2-Brom-3-(3-brom-1-phenyl-2-indolyl)-N-methylmaleinimid

Refernces

Mechanistic insight into the regioselective palladation of indole derivatives: Tetranuclear indolyl palladacycles with high C2-Pd or C3-Pd bond selectivity

10.1021/om300284t

The research focuses on the regioselective palladation of indole derivatives, aiming to understand the factors influencing the selectivity of C2?Pd or C3?Pd bond formation. The experiments involved the palladation of N-phenylindole (1a) and N-methylindole (1b) under different reaction conditions to capture both C2?Pd and C3?Pd intermediates. Key reactants included [Pd(OAc)2] (2a) as the palladium source, sodium pivalate (PivONa) as a base for C3 palladation, and PivOH with NaCl for C2 palladation. The experiments were designed to investigate the effect of N-substituted protective groups and the acidity of the reaction medium on the regioselectivity. Analytical techniques used included X-ray crystallography for structural characterization of the synthesized tetranuclear indolyl palladacycles, which provided insights into the regioselective palladation mechanism and the influence of reaction conditions on the C2?Pd or C3?Pd bond selectivity.