4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

Product Information

Molecular Formula:
C39H32OP2
Molecular Weight:
578.62
Description
Ligand used in a synthesis of heterocycles by palladium-catalyzed C-N cross coupling of 3-bromothiophenes with 2-aminopyridines. Also used in a ruthenium-catalyzed alkylation of active methylene compounds with alcohols. Metal chelating ligand for catalysis.
Synonyms
(5-diphenylphosphino-9,9-dimethyl-4-xanthenyl)-diphenylphosphine; (5-diphenylphosphanyl-9,9-dimethylxanthen-4-yl)-diphenylphosphane
IUPAC Name
(5-diphenylphosphanyl-9,9-dimethylxanthen-4-yl)-diphenylphosphane
Canonical SMILES
CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
InChI
InChI=1S/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3
InChI Key
CXNIUSPIQKWYAI-UHFFFAOYSA-N
Boiling Point
665 ℃ / 760 mmHg
Melting Point
224-230 ℃
Flash Point
450 ℃ (C.C)
Purity
97 %
Appearance
White to light yellow powder to crystal
LogP
7.63460

Safety Information

Precautionary Statement
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning

Computed Properties

XLogP3
9.7
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
6
Exact Mass
578.19283964 g/mol
Monoisotopic Mass
578.19283964 g/mol
Topological Polar Surface Area
9.2Ų
Heavy Atom Count
42
Formal Charge
0
Complexity
731
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes

Patents

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CN-114105922-A Synthesis method of hydroxypropyl tetrahydropyrane triol 2021-12-03
CN-114105958-A Hydroximic acid-containing 2-phenylamino pyrimidine derivatives and application thereof 2021-12-03
CN-114105890-A 3-cyanophenyl-6, 7-dimethoxy-quinazoline and preparation method and application thereof 2021-11-30

Literatures

PMID Publication Date Title Journal
22905711 2012-09-07 Room temperature, palladium-mediated P-arylation of secondary phosphine oxides Organic letters
22864631 2012-08-28 Hydrogenolysis of β-O-4 lignin model dimers by a ruthenium-xantphos catalyst Dalton transactions (Cambridge, England : 2003)
22524250 2012-05-10 Imidazolopiperazines: lead optimization of the second-generation antimalarial agents Journal of medicinal chemistry
22462662 2012-04-18 Intramolecular oxycyanation of alkenes by cooperative Pd/BPh3 catalysis Journal of the American Chemical Society
22407928 2012-04-16 Synthesis of hindered anilines: copper-catalyzed electrophilic amination of aryl boronic esters Angewandte Chemie (International ed. in English)
22589910 2012-04-01 4,6-Bis(diphenyl-phosphan-yl)-2,8-di-methyl-phenoxathiin dichloro-methane monosolvate Acta crystallographica. Section E, Structure reports online
22266830 2012-02-20 An efficient mixed-ligand Pd catalytic system to promote C-N coupling for the synthesis of N-arylaminotriazole nucleosides Chemistry (Weinheim an der Bergstrasse, Germany)
22238020 2012-02-13 Constrained digold(I) diaryls: syntheses, crystal structures, and photophysics Chemistry (Weinheim an der Bergstrasse, Germany)
22111927 2011-12-22 Structure-guided evolution of potent and selective CHK1 inhibitors through scaffold morphing Journal of medicinal chemistry
22091952 2011-12-16 Synthesis of rhodamines from fluoresceins using Pd-catalyzed C-N cross-coupling Organic letters
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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