800369-69-1

Basic information

• Product Name: 1H-Indole, 2-(diphenylphosphino)-3-methyl-
• CAS NO: 800369-69-1
• Molecular Formula: C21H18NP
• Molecular Weight: 315.354
• Mol File: 800369-69-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 2-(diphenylphosphino)-3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 2-(diphenylphosphino)-3-methyl-(800369-69-1)
• EPA Substance Registry System: 1H-Indole, 2-(diphenylphosphino)-3-methyl-(800369-69-1)

Safety Data

• Hazardous Substances Data: 800369-69-1(Hazardous Substances Data)

Upstream product

• 83-34-1 3-Methylindole 
• 105340-00-9 1-[(N,N-dimethylamino)methyl]-3-methylindole 
• 1079-66-9 chloro-diphenylphosphine 
• 1333165-62-0 N,N'-bis(2-(diphenylphosphino)-3-(methyl)indolyl)diethylaminophosphine 
• 65610-64-2 3-methyl-N-indolecarboxylic acid 

Downstream Products

• 1333165-62-0 N,N'-bis(2-(diphenylphosphino)-3-(methyl)indolyl)diethylaminophosphine 
• 1474029-01-0 dichloro(η⁶-p-cymene){diphenyl(3-methyl-2-indolyl)phosphine}ruthenium(II) 
• 1321502-81-1 Au₂(2-diphenylphosphino-3-methylindole^(1-))2 
• 1321502-93-5 Ag₂(2-diphenylphosphino-3-methylindole^(1-))2 
• 1321502-89-9 AuAg(2-diphenylphosphino-3-methylindole^(1-))2 
• 1321502-89-9 AuAg(2-diphenylphosphino-3-methylindole^(1-))2 
• 1321502-78-6 [Au(2-diphenylphosphino-3-methylindole)2]PF₆ 
• 1206804-50-3 tris(2-(diphenylphosphino)-3-methyl-1H-indol-1-yl)phosphine 
• 800369-72-6 Ru₃(CO)11[diphenyl-2-(3-methylindolyl)phosphine] 
• 828255-96-5 [Pd(diphenyl(3-methyl-2-indolyl)phosphine)Cl(mu.-Cl)]2 
• 1241376-26-0 [RhCl(2,5-norbornadiene)(diphenyl-2-(3-methyl)indolylphosphine)] 
• 1241376-25-9 [IrCl(1,5-cyclooctadiene)(diphenyl-2-(3-methyl)indolylphosphine)] 

Relevant articles and documents

Ethylene tri-/tetramerization catalysts supported by diphosphinoindole ligands

A new class of diphosphinoindole ligands have been developed. Upon activation with MMAO-3A, Cr catalysts supported by these bisphosphine ligands are active for ethylene tri-/tetramerization. The best result was achieved by using the bisphosphine ligand containing a phenyl group at C3 position of indole, giving a high activity of up to 364 kg/(g Cr/h) with a total selectivity of up to 72% toward 1-hexene (23.5%) and 1-octene (48.4%). A representative chromium tetracarbonyl complex was synthesized and structurally characterized by single-crystal X-ray diffraction.

Asymmetric hydrogenation with highly active IndolPhos-Rh catalysts: Kinetics and reaction mechanism

The mechanism of the IndolPhos-Rh-catalyzed asymmetric hydrogenation of prochiral olefins has been investigated by means of X-ray crystal structure determination, kinetic measurements, high-pressure NMR spectroscopy, and DFT calculations. The mechanistic study indicates that the reaction follows an unsaturate/dihydride mechanism according to Michaelis Menten kinetics. A large value of KM (KM = 5.01 ± 0.16 M) is obtained, which indicates that the Rh-solvate complex is the catalyst resting state, which has been observed by high-pressure NMR spectroscopy. DFT calculations on the substrate-catalyst complexes, which are undetectable by experimental means, suggest that the major substrate-catalyst complex leads to the product. Such a mechanism is in accordance with previous studies on the mechanism of asymmetric hydrogenation reactions with C1-symmetric heteroditopic and monodentate ligands.

Asymmetric synthesis of the Roche ester and its derivatives by rhodium-INDOLPHOS-catalyzed hydrogenation

(S)-3-Hydroxy-2-methylpropionate, known as the Roche ester, and several of its derivatives were successfully synthesized through asymmetric rhodium-catalyzed hydrogenation, using INDOLPHOS (diisopropyl{1-[(S)-3,5-dioxa- 4-phosphacyclohepta[ 2,1-a;3,4-a′]dinaphthalen-4-yl]-3-methyl-2-indolyl} phosphine) as the chiral ligand, in excellent yield and the highest ee reported up to now (TOF over 5500 h-1 at 25°C; up to 98% ee at -40°C).