Dimethylbisdiphenylphosphinoxanthene supplier

Name
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
EINECS 605-249-4
CAS No. 161265-03-8
Article Data17
CAS DataBase
Density
Solubility
Melting Point 224-228 °C(lit.)
Formula C₃₉H₃₂OP₂
Boiling Point 665.7 °C at 760 mmHg
Molecular Weight 578.63
Flash Point 449.9 °C
Transport Information
Appearance white to light yellow crystals
Safety 37/39-26
Risk Codes 37-20/22
Molecular Structure
Hazard Symbols Xn
Synonyms 9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthene;9,10a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-8aH-xanthene;Phosphine,(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[diphenyl- (9CI);(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[diphenylphosphine];4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene;9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene;Xantphos;
PSA 36.41000
LogP 7.63460

Synthetic route

: 9,9-dimethyl-4,6-bis(diphenyloxyphosphino)xanthene

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

Conditions

Conditions	Yield
With tributylphosphine; iodine In tetrahydrofuran; acetonitrile at 20℃; for 0.166667h; Inert atmosphere;	95%

: 67-64-1
acetone

: 166330-10-5
bis[2-(diphenylphosphino)phenyl] ether

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In toluene at 200℃; for 16h; Temperature; Inert atmosphere;	95%

: 808142-24-7
1,1'-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis-1,1-diphenylphosphine oxide

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

Conditions

Conditions	Yield
With bis(2-chlorophenyl)borinic acid; phenylsilane In toluene at 80℃; for 18h; Inert atmosphere;	89%
With 1,3-diphenyl-disiloxane In toluene at 110℃; Sealed tube; chemoselective reaction;	79%

: 19814-75-6
9,9-dimethylxanthene

: 1079-66-9
chloro-diphenylphosphine

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

Conditions

Conditions	Yield
Stage #1: 9,9-dimethylxanthene With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tert-butyl methyl ether; cyclohexane at 6 - 10℃; Stage #2: In cyclohexane; water at 20℃; for 14h; Stage #3: chloro-diphenylphosphine In cyclohexane; water at 10 - 20℃; for 5.16667h;	88%
Stage #1: 9,9-dimethylxanthene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -78 - 25℃; for 17h; Stage #2: chloro-diphenylphosphine In hexane at 25℃; for 16h; Cooling with ice;	84%
Stage #1: 9,9-dimethylxanthene With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tert-butyl methyl ether; cyclohexane at 10 - 20℃; for 16h; Stage #2: chloro-diphenylphosphine In cyclohexane; water at 20℃; for 5.75h;	77%

: 19814-75-6
9,9-dimethylxanthene

: diphenylphosphonium chloride

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

Conditions

Conditions	Yield
Stage #1: 9,9-dimethylxanthene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -78 - 25℃; for 17h; Stage #2: diphenylphosphonium chloride In hexane at 25℃; for 16h; Cooling with ice;	84%

: 19814-75-6
9,9-dimethylxanthene

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

Conditions

Conditions	Yield
Stage #1: 9,9-dimethylxanthene With bis 1,2-(dimethylamino)ethylene; sec.-butyllithium In tert-butyl methyl ether at 10 - 20℃; for 16h; Stage #2: With chloro-diphenylphosphine at 20℃; for 6.25h;

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 808142-24-7
1,1'-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis-1,1-diphenylphosphine oxide

Conditions

Conditions	Yield
With dihydrogen peroxide In dichloromethane at 0℃; for 2h;	100%
With dihydrogen peroxide In dichloromethane; water at 0℃; for 4h;	99%
With dihydrogen peroxide In 1,4-dioxane; water for 2h;	95%

: 15555-77-8, 86470-43-1
dichlorotetrakis(triphenylphosphine)ruthenium(II)

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 1579977-69-7
RuCl2(PPh3)(Xantphos)

Conditions

Conditions	Yield
In (2)H8-toluene for 3h; Inert atmosphere; Schlenk technique; Reflux;	100%
In (2)H8-toluene for 5h; Inert atmosphere; Schlenk technique; Reflux;	100%

: iron(dichloride)*1.5(tetrahydrofuran)

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: FeCl2(Xantphos)

Conditions

Conditions	Yield
In toluene at 60℃; for 4h;	100%

: 142-71-2
copper diacetate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: C43H38CuO5P2

Conditions

Conditions	Yield
In tetrahydrofuran	100%

: 598-54-9, 142-71-2, 4180-12-5, 24381-58-6, 66760-61-0, 66760-62-1
copper (I) acetate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: Cu(OAc)(Xantphos)

Conditions

Conditions	Yield
In tetrahydrofuran	100%
In tetrahydrofuran at 20℃; for 4h; Schlenk technique; Inert atmosphere; Glovebox;	74%

: tetrakis(acetonitrile)copper(I)tetrafluoroborate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: [Cu(NCMe)2(Xantphos)]BF4

Conditions

Conditions	Yield
In dichloromethane for 2h;	100%

: 7681-65-4
copper(l) iodide

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 1218788-80-7
Cu[9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene]I

Conditions

Conditions	Yield
In acetonitrile	99%
In CH2Cl2	99%
In acetonitrile at 50℃; for 2h;	99%

: tetrakis(acetonitrile)copper(I)tetrafluoroborate

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 1251536-86-3
[Cu(2,9-dimethyl-1,10-phenanthroline)(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)](BF4)

Conditions

Conditions	Yield
Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dichloromethane at 20℃; for 1h; Stage #2: 2.9-dimethyl-1,10-phenanthroline In dichloromethane for 1h;	99%
In dichloromethane Cu complex added to a soln. of (CH3)2C13H6O(P(C6H5)2)2, C12H6N2(CH3)2 added; pptd. with Et2O, filtered, dried (vac.);	70%
Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dichloromethane at 20℃; for 1h; Stage #2: 2.9-dimethyl-1,10-phenanthroline In dichloromethane at 20℃; for 1h;	46%

...Expand

: C24H26N2O6Pd2S2

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: C51H45NO4P2PdS

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	99%

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: [Cu(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)(CH3CN)2]PF6

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	99%
Inert atmosphere; Schlenk technique;
In dichloromethane at 20℃; for 0.25h; Darkness;

: tetrakis(acetonitrile)copper(I)tetrafluoroborate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 72914-19-3
4,4'-di-tert-butyl-2,2'-bipyridine

: C57H56CuN2OP2(1+)*BF4(1-)

Conditions

Conditions	Yield
Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dichloromethane at 20℃; for 1h; Stage #2: 4,4'-di-tert-butyl-2,2'-bipyridine In dichloromethane at 20℃; for 1h;	99%

...Expand

: tetrakis(acetonitrile)copper(I)tetrafluoroborate

: 17217-57-1
4,4'-Dimethoxy-2,2'-bipyridin

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: C51H44CuN2O3P2(1+)*BF4(1-)

Conditions

Conditions	Yield
Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dichloromethane at 20℃; for 1h; Stage #2: 4,4'-Dimethoxy-2,2'-bipyridin In dichloromethane at 20℃; for 1h;	99%

...Expand

: 21264-30-2, 90243-59-7, 14592-56-4
dichloro bis(acetonitrile) palladium(II)

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 205319-10-4
dichloro[9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene]palladium (II)

Conditions

Conditions	Yield
In benzene at 110℃; for 48h; Schlenk technique; Reflux; Inert atmosphere;	98%
In benzene at 110℃; for 48h; Inert atmosphere; Schlenk technique;	98%
In benzene at 110℃; for 48h; Schlenk technique; Inert atmosphere;

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 517919-24-3
4,4'-bis(4-chlorophenyl)-6,6'-dimethyl-2,2'-bipyridine

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: C63H50Cl2CuN2OP2(1+)*F6P(1-)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1.5h;	98%

...Expand

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 1427205-00-2
4,4’-di(4-bromophenyl)-6,6’-dimethyl-2,2’-bipyridine

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: C63H50Br2CuN2OP2(1+)*F6P(1-)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1.5h;	98%

...Expand

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 6-phenyloxy-2,2'-bipyridine

: C55H44CuN2O2P2(1+)*F6P(1-)

Conditions

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dichloromethane at 20℃; for 0.5h; Stage #2: 6-phenyloxy-2,2'-bipyridine In dichloromethane at 20℃; for 1h;	98%

...Expand

: 52522-40-4
tris(dibenzylideneacetone)dipalladium(0) chloroform complex

: 874-60-2
4-methyl-benzoyl chloride

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: (Xantphos)Pd(CO(C6H4CH3))(Cl)

Conditions

Conditions	Yield
In benzene at 20℃; for 18h; Glovebox; Inert atmosphere;	98%

...Expand

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: C20H20N2

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: C59H52CuN2OP2(1+)*F6P(1-)

Conditions

Conditions	Yield
Stage #1: C20H20N2; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In dichloromethane at 20℃; for 0.5h; Stage #2: tetrakis(actonitrile)copper(I) hexafluorophosphate In dichloromethane at 20℃; for 1h;	98%

...Expand

: dichlorotetrakis(dimethylsulfoxide)ruthenium(II)

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 1313371-86-6
Ru(P,O,P-xantphos)(S-dmso)Cl2

Conditions

Conditions	Yield
In dichloromethane mixt. of Ru complex and xantphos (1 equiv.) in CH2Cl2 refluxed; evapn. under vac., washed with Et2O, recrystn. from CH2Cl2; elem. anal.;	97.8%

: 12080-32-9
dichloro( 1,5-cyclooctadiene)platinum(ll)

: 75-09-2
dichloromethane

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: Pt(xantphos)Cl2*(dichloromethane)

Conditions

Conditions	Yield
In chloroform Pt complex and ligand dissolved in CHCl3, stirred at room temp. for 1.5 h; evapd. (vac.), washed (hexane/CH2Cl2), dried; elem. anal.;	97%

...Expand

: di(rhodium)tetracarbonyl dichloride

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 1241951-62-1
[Rh(CO)(4,5-bis(diphenylphosphino)-9,9'-dimethylxanthene)Cl]

Conditions

Conditions	Yield
In ethanol using Schlenk techniques; addn. of xantphos to stirred soln. of (RhCl(CO)2)2 in EtOH, pptn., stirring for 10 min; collection on a sinter, washing with ice-cold EtOH and Et2O;	97%

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 25005-97-4
2,3,5,6-tetrakis(2-pyridyl)pyrazine

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: [Cu2(2,3,5,6-tetra(pyridin-2-yl)pyrazine)(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)2][PF6]2

Conditions

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dichloromethane for 2h; Stage #2: 2,3,5,6-tetrakis(2-pyridyl)pyrazine In dichloromethane for 2h;	97%

...Expand

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 54015-97-3
6-eethoxy-2,2'-bipyridine

: C51H44CuN2O2P2(1+)*F6P(1-)

Conditions

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dichloromethane at 20℃; for 0.5h; Stage #2: 6-eethoxy-2,2'-bipyridine In dichloromethane at 20℃; for 1h;	97%

...Expand

: 225931-80-6
bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II)

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: C47H54OP2PdSi2

Conditions

Conditions	Yield
In tetrahydrofuran for 0.0833333h; Solvent; Temperature; Milling;	97%

: 52409-22-0, 51364-51-3
tris-(dibenzylideneacetone)dipalladium(0)

: ethyl 4-bromo-1-ethyl-5-nitro-1H-pyrrole-2-carboxylate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: C48H43BrN2O5P2Pd

Conditions

Conditions	Yield
In benzene-d6 at 20℃; for 24h;	96%

...Expand

: 6-(naphthalen-2-yl)-2,2′-bipyridine

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: [Cu(2-Naphbpy)(xantphos)][PF6]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	96%

...Expand

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 49669-22-9
6,6'-Dibromo-2,2'-bipyridine

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: [Cu(xantphos)(6,6′-dibromo-2,2′-bipyridine)][PF6]

Conditions

Conditions	Yield
In dichloromethane for 2h;	96%

...Expand

: 96-45-7
N,N'-ethylenethiourea

: 7681-65-4
copper(l) iodide

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 905816-32-2
iodo(4,5-bis(diphenylphosphano)-9,9-dimethylxanthene)(imidazolidine-2-thione)copper(I)

Conditions

Conditions	Yield
In acetonitrile diphosphine added to suspn. of CuI in dry MeCN; stirred at 50°C for 2 h; soln. of thione in small amt. of MeOH added; heated under refluxfor 2 h; soln. filtered; left to evapd. at ambient temp. for several d; filtered;solid dried in vac.; elem. anal.;	95%

...Expand

: 15529-49-4, 41756-81-4
tris(triphenylphosphine)ruthenium(II) chloride

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: RuCl2(xantphos)PPh3

Conditions

Conditions	Yield
In chloroform for 3h; Inert atmosphere; Reflux;	95%

Dimethylbisdiphenylphosphinoxanthene Chemical Properties

Molecule structure of Dimethylbisdiphenylphosphinoxanthene (CAS NO.161265-03-8):

Molecular Weight: 578.6183 g/mol
Molecular Formula: C₃₉H₃₂OP₂
Melting Point: 224-228 °C(lit.)
Boiling Point: 665.7 °C at 760 mmHg
Flash Point: 449.9 °C
Enthalpy of Vaporization: 94.35 kJ/mol
Vapour Pressure: 7.61E-17 mmHg at 25 °C
InChI: InChI=1/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
InChIKey: CXNIUSPIQKWYAI-UHFFFAOYAQ
Product Categories: Phosphines; Amino Acid Derivatives; Phosphine Ligands; Synthetic Organic Chemistry

Dimethylbisdiphenylphosphinoxanthene Uses

Dimethylbisdiphenylphosphinoxanthene (CAS NO.161265-03-8) is used as a ligand for Buchwald, Suzuki and other coupling reactions

Dimethylbisdiphenylphosphinoxanthene Safety Profile

Hazard Codes: Harmful Xn
Risk Statements: 37-20/22
R37:Irritating to respiratory system
R20/22:Harmful by inhalation and if swallowed.
Safety Statements: 37/39-26
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3

Dimethylbisdiphenylphosphinoxanthene Specification

Dimethylbisdiphenylphosphinoxanthene (CAS NO.161265-03-8) is also named as (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) ; [5-(Diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl](diphenyl)phosphine ; phosphine, 1,1'-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenyl- ; Xanthene, 4,5-bis(diphenylphosphino)-9,9-dimethyl- ; 4,5-Bis(diphenylphosphino)-9,9-Dimethylxanthene . Dimethylbisdiphenylphosphinoxanthene (CAS NO.161265-03-8) is white to light yellow crystals.

Product Name

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

Synthetic route

Dimethylbisdiphenylphosphinoxanthene Chemical Properties

Dimethylbisdiphenylphosphinoxanthene Uses

Dimethylbisdiphenylphosphinoxanthene Safety Profile

Dimethylbisdiphenylphosphinoxanthene Specification

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