4,6-Bis(diphenylphosphino)phenoxazine

Base Information

• Chemical Name: 4,6-Bis(diphenylphosphino)phenoxazine
• CAS No.: 261733-18-0
• Molecular Formula: C₃₆H₂₇NOP₂
• Molecular Weight: 551.564
• European Community (EC) Number: 812-116-6
• DSSTox Substance ID: DTXSID70390703
• Nikkaji Number: J1.229.013F
• Wikidata: Q72445457
• Mol file: 261733-18-0.mol

Synonyms:261733-18-0;4,6-Bis(diphenylphosphino)phenoxazine;4,6-Bis(diphenylphosphino)-10H-phenoxazine;NIXANTPHOS;N-XantPhos;(6-diphenylphosphanyl-10H-phenoxazin-4-yl)-diphenylphosphane;10H-Phenoxazine, 4,6-bis(diphenylphosphino)-;MFCD03788937;Bis(diphenylphosphino)phenoxazine;4,6-bis(diphenylphosphanyl)-10H-phenoxazine;NiXanthphos;C36H27NOP2;N-XantPhos, 97%;SCHEMBL2440624;DTXSID70390703;HSWZLYXRAOXOLL-UHFFFAOYSA-N;(6-diphenylphosphanyl-10H-phenoxazin-4-yl)-diphenyl-phosphane;AMY19721;AKOS015840598;4,6-bis(diphenylphosphino)-phenoxazine;CS-W009604;PB42421;SC11333;AS-66127;SY022700;B2717;FT-0707208;F15028;A855237;EN300-19632070;J-016299;4,6-bis(diphenylphosphino)-10H-phenoxazine;4,6-BIS(DIPHENYLPHOSPHINO)-10H-PHENOXAZINE;4,6-BIS(DIPHENYLPHOSPHINO)PHENOXAZINE

Chemical Property of 4,6-Bis(diphenylphosphino)phenoxazine

Chemical Property:

• Vapor Pressure: 2.1E-17mmHg at 25°C
• Melting Point: 256-262ºC
• Boiling Point: 662.1 °C at 760 mmHg
• PKA: 1.34±0.20(Predicted)
• Flash Point: 354.3 °C
• PSA: 48.44000
• LogP: 7.19030
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Miscible with water.
• XLogP3: 8.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 551.15678848
• Heavy Atom Count: 40
• Complexity: 671

Purity/Quality:

98+% ^*data from raw suppliers

4,6-Bis(Diphenylphosphino)phenoxazine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC4=C3OC5=C(N4)C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7
• Uses: 4,6-Bis(Diphenylphosphino)phenoxazine is used as a palladium catalyst in reactions involving the synthesis of triarylmethanes. 4,6-Bis(diphenylphosphino)phenoxazine used as an intermediate in the manufacture of pharmaceuticals, agrochemicals, dyestuffs, fine chemicals, medical and material synthesis. N-XantPhos is a deprotonatable chelating aryldiphosphine ligand that can be used in:The preparation of Pd-NiXantphos catalyst system for the room temperature cross-coupling reactions of unactivated aryl chlorides.The synthesis of cinchonine iridium(III) cyclometalated complex that exhibits luminescence and good quantum efficiency.N-XantPhos and N-modified counterparts are also used in the preparation of rhodium based catalysts for hydroformylation reaction.

Technology Process of 4,6-Bis(diphenylphosphino)phenoxazine

There total 2 articles about 4,6-Bis(diphenylphosphino)phenoxazine 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: 92.0%

bis[2-(diphenylphosphino)phenyl] ether (166330-10-5) → nixantphos (261733-18-0)

Guidance literature:

bis[2-(diphenylphosphino)phenyl] ether; With tert.-butylhydroperoxide; sodium azide; copper(I) bromide; In water; acetonitrile; at 30 ℃; for 12h; Inert atmosphere;

With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In water; acetonitrile; at 100 ℃; for 18h; Temperature; Inert atmosphere;

Reference yield: 88.0%

C40H33NO5P2Pd (1602922-02-0) → nixantphos (261733-18-0)

Guidance literature:

With depe; at 24 ℃; for 0.666667h; Inert atmosphere; Glovebox;

DOI:10.1021/ja411855d

Reference yield: 98.0%

chloro(dimethylsulfide) gold(I) (29892-37-3) + dichloromethane (75-09-2) + nixantphos (261733-18-0) → [AuI(4,6-bis(diphenylphosphino)phenoxazine)Cl]*0.085CH2Cl2

Guidance literature:

for 0.0666667h; Milling;

DOI:10.1039/d1dt01751a

upstream raw materials:

C₄₀H₃₃NO₅P₂Pd

bis[2-(diphenylphosphino)phenyl] ether

Downstream raw materials:

(nixantphos)Rh(CO)2H

(nixantphos)Rh(CO)H(PPh₃)

[(2′-phenyl-9-O-benzyl-10,11-dihydrocinchonine-C₂,N)₂Ir(4,6-bis(diphenylphosphino)phenoxazine)][PF₆]

[(2-phenylquinolinato-C₂,N)₂Ir(4,6-bis(diphenylphosphino)phenoxazine)][PF₆]

Refernces

• 1、 Zhang, Jiadi,Bellomo, Ana,Trongsiriwat, Nisalak,Jia, Tiezheng,Carroll, Patrick J.,Dreher, Spencer D.,Tudge, Matthew T.,Yin, Haolin,Robinson, Jerome R.,Schelter, Eric J.,Walsh, Patrick J.. "NiXantphos: A deprotonatable ligand for room-temperature palladium-catalyzed cross-couplings of aryl chlorides". supporting information. p. 6276 - 6287. Retrieved 2014/05/20.