2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl supplier

Name
X-PHOS
EINECS 270-588-3
CAS No. 564483-18-7
Article Data5
CAS DataBase
Density
Solubility
Melting Point 187-190 °C(lit.)
Formula C₃₃H₄₉P
Boiling Point 569.762 °C at 760 mmHg
Molecular Weight 476.726
Flash Point 317.745 °C
Transport Information
Appearance White crystalline powder
Safety 37/39-26-36/37
Risk Codes 36/37/38-22-40
Molecular Structure
Hazard Symbols Xn
Synonyms 2,,4',6'-Diisopropyl-1,1'-biphenyl-2-yldicyclohexylphosphine;Dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine;X-Phos;[2',4',6'-Triisopropyl-1,1'-biphenyl-2-yl]dicyclohexylphosphine;2-(Dicyclohexylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl;
PSA 13.59000
LogP 10.49640

Synthetic route

: 462-06-6
fluorobenzene

: 717-74-8
1,3,5-triisopropyl benzene

: 16523-54-9
chlorodicyclohexylphosphane

: 564483-18-7
XPhos

Conditions

Conditions	Yield
Stage #1: fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran at 15℃; for 10h; Stage #3: 1,3,5-triisopropyl benzene With n-butyllithium; potassium tert-butylate In hexane at 30 - 60℃; for 16h; Reagent/catalyst; Temperature;	93%

...Expand

: 2'-chloro-2,4,6-triisopropylbiphenyl

: 16523-54-9
chlorodicyclohexylphosphane

: 564483-18-7
XPhos

Conditions

Conditions	Yield
Stage #1: 2'-chloro-2,4,6-triisopropylbiphenyl With n-butyllithium at 0℃; for 1h; Stage #2: chlorodicyclohexylphosphane at 20℃; for 2h; Temperature; Reagent/catalyst;	90%

: 21524-34-5
1-Bromo-2,4,6-triisopropylbenzene

: 16523-54-9
chlorodicyclohexylphosphane

: 583-53-9
1,2-dibromobenzene

: 564483-18-7
XPhos

Conditions

Conditions	Yield
Stage #1: 2,4,6-triisopropyl-1-bromobenzene With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 2,3-dibromobenzene In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #3: chlorodicyclohexylphosphane Further stages;	89%

...Expand

: 694-80-4
2-bromo-1-chlorobenzene

: 21524-34-5
1-Bromo-2,4,6-triisopropylbenzene

: 100384-03-0
dicyclohexylbromophosphine

: 564483-18-7
XPhos

Conditions

Conditions	Yield
Stage #1: 2,4,6-triisopropyl-1-bromobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: 2-bromo-1-chlorobenzene In tetrahydrofuran at 65℃; for 2h; Stage #3: dicyclohexylbromophosphine With copper(l) chloride In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;	86%

...Expand

: 694-80-4
2-bromo-1-chlorobenzene

: 21524-34-5
1-Bromo-2,4,6-triisopropylbenzene

: 16523-54-9
chlorodicyclohexylphosphane

: 564483-18-7
XPhos

Conditions

Conditions	Yield
Stage #1: 2,4,6-triisopropyl-1-bromobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 65℃; for 1h; Stage #2: 2-bromo-1-chlorobenzene In tetrahydrofuran at 65℃; for 1h; Stage #3: chlorodicyclohexylphosphane With copper(l) chloride In tetrahydrofuran at 20℃; for 20h;	83%
Stage #1: 2,4,6-triisopropyl-1-bromobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: 2-bromo-1-chlorobenzene In tetrahydrofuran at 65℃; for 2h; Stage #3: chlorodicyclohexylphosphane With copper(l) chloride In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;	83%
Stage #1: 2,4,6-triisopropyl-1-bromobenzene With magnesium; ethylene dibromide In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Industrial scale; Stage #2: 2-bromo-1-chlorobenzene With magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Industrial scale; Stage #3: chlorodicyclohexylphosphane With copper(l) chloride In tetrahydrofuran at 20℃; Thermodynamic data; Inert atmosphere; Industrial scale;	56%

...Expand

: 39929-21-0
(tetrahydrothiophene)gold(I) chloride

: 564483-18-7
XPhos

: 854045-94-6
chloro[2-dicyclohexyl(2′,4′,6′-triisopropylbiphenyl)phosphine]gold(I)

Conditions

Conditions	Yield
In dichloromethane for 1.75h;	99%
In toluene (N2); Au complex added to a soln. of ligand, stirred for 20 h; evapd. (vac.), pentane added, the solid collected, dried; elem. anal.;	91%
In dichloromethane Inert atmosphere;
In dichloromethane
In dichloromethane at 20℃; for 1h; Darkness;

: 1599466-80-4
N-phenyl-2-aminobiphenylpalladium methanesulfonate

: 564483-18-7
XPhos

: 1599466-82-6
C52H66NO3PPdS

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	99%

: 564483-18-7
XPhos

: 1234888-60-8
dicyclohexyl(2',6'-diisopropyl-4'-sulfobiphenyl-2-yl)phosphonium hydrogen sulfate

Conditions

Conditions	Yield
With sulfuric acid; sulfur trioxide at -40 - 20℃; Inert atmosphere;	98%

: 92-66-0
4-bromo-1,1'-biphenyl

: 108847-20-7
4-dibenzothiophene boronic acid

: 564483-18-7
XPhos

: 4-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0)	98%

...Expand

: C12H10ClNPd

: 564483-18-7
XPhos

: 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl

Conditions

Conditions	Yield
In acetone at 25℃;	97%

: bis(η3-allyl-μ-chloropalladium(II))

: 564483-18-7
XPhos

: [2,6-bis(2,4,6-triisopropylphenyl)phenyl(dicyclohexylphosphine)](allyl-η3)palladium(II) chloride

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h; Schlenk technique; Inert atmosphere;	97%
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	97%
In diethyl ether at 25℃; for 1h; Inert atmosphere; Schlenk technique;	53%

: 564483-18-7
XPhos

: dichloro[η6 :η1-dicyclohexyl-(2',4',6'-triisopropylbiphenyl-2-yl)phosphane]ruthenium(II)

Conditions

Conditions	Yield
With [RuCl2(cod)]n In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Inert atmosphere;	95%

: [Pd2(CH3CN)6][BF4]2

: 564483-18-7
XPhos

: C66H98P2Pd2(2+)*2BF4(1-)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	95%

: 564483-18-7
XPhos

: sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate

Conditions

Conditions	Yield
Stage #1: XPhos With sulfuric acid; sulfur trioxide In dichloromethane at 0 - 20℃; for 24h; Cooling with ice; Stage #2: With sodium hydroxide In dichloromethane; water at 0℃; pH=~ 7.0; Cooling with ice;	94%
Stage #1: XPhos With sulfuric acid In dichloromethane at 0℃; for 0.0833333h; Sealed tube; Schlenk technique; Inert atmosphere; Stage #2: With fuming sulphuric acid In dichloromethane at -10℃; for 0.216667h; Schlenk technique; Sealed tube; Inert atmosphere; Stage #3: With sodium hydroxide In dichloromethane; water for 0.283333h; pH=14; Cooling with ice; regioselective reaction;	77%
Stage #1: XPhos With sulfuric acid In dichloromethane at 0 - 20℃; for 24h; Stage #2: With sodium hydroxide In dichloromethane; water pH=13;	53%

: 1435520-65-2
(2'-amino-1,1'-biphenyl-2-yl)methanesulfonatopalladium(II) dimer

: 564483-18-7
XPhos

: 1445085-55-1, 1445085-72-2
((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃;	92%

: di(2-(2′-amino-1,1′-biphenyl))palladium(II) methanesulfonate dimer

: 564483-18-7
XPhos

: 1445085-55-1, 1445085-72-2
methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere;	92%

: 116724-06-2
N1,N1-diphenyl-1,3-phenylenediamine

: 113975-23-8
methyl(3-iodopyridin-2-yl)amine

: 865-48-5
sodium t-butanolate

: 564483-18-7
XPhos

: 1399050-27-1
N3-(3-(diphenylamino)phenyl)-N2-methylpyridine-2,3-diamine

Conditions

Conditions	Yield
With nitrogen In dichloromethane; ethyl acetate; toluene	91%

...Expand

: bis[(1,2,3-η)-2-butenyl]di(μ-chloro)palladium(II)

: 564483-18-7
XPhos

: chloro(crotyl)(2-dicyclohexylphosphino-2’,4’,6’-triisopropybiphenyl)palladium(II)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h; Schlenk technique; Inert atmosphere;	91%
In toluene at 20℃; for 2h; Inert atmosphere;	91%

: (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one palladium(II) complex

: 352-34-1
4-fluoro-1-iodobenzene

: 564483-18-7
XPhos

: (4-F-C6H4)Pd(XPhos)I

Conditions

Conditions	Yield
In toluene at 20℃; Inert atmosphere;	91%

...Expand

: dihydrogen tetrachloropalladate(II)

: 564483-18-7
XPhos

: [HXPhos]2[Pd2Cl6]

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 18 - 27℃; for 1h;	91%

: (N,N,N',N'-tetramethylethylenediamine)dimethylpalladium(II)

: 13078-80-3
2-(2-chlorophenyl)ethanamine

: 564483-18-7
XPhos

: 1028206-56-5
chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct

Conditions

Conditions	Yield
In further solvent(s) treatment of palladium compd. with chlorobenzene deriv. and phosphine deriv. in methyl tert-butyl ether at 55°C; recrystn.;	90%

...Expand

: bis(acetonitrile)(acetylacetonate)palladium(II) tetrafluoroborate

: 564483-18-7
XPhos

: (acetylacetonate-κ2O,O')(2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl-κP)palladium(II) tetrafluoroborate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	87.7%

: [Pd(η3-tBu-indenyl)(μ-Cl)]2

: 564483-18-7
XPhos

: C46H64ClPPd

Conditions

Conditions	Yield
at 20℃; for 1h; Inert atmosphere;	86%

: η3-1-tert-butylindenyl palladium chloride dimer

: 564483-18-7
XPhos

: C46H64ClPPd

Conditions

Conditions	Yield
In tetrahydrofuran for 1h; Inert atmosphere; Schlenk technique;	86%

: 1581285-85-9
(2′-methylamino-1,1′-biphenyl-2-yl)methanesulfonatopalladium(II) dimer

: 564483-18-7
XPhos

: 1599466-81-5
(2‑dicyclohexylphosphino‑2′,4′,6′‑triisopropyl‑1,1′‑biphenyl)[2‑(2′‑methylamino‑1,1′‑biphenyl)]palladium(II) methanesulfonate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	85%

: 591-50-4
iodobenzene

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

: 564483-18-7
XPhos

: C33H49P*C6H5(1-)*Pd(2+)*I(1-)

Conditions

Conditions	Yield
In pentane at 20℃; for 72h; Glovebox; Inert atmosphere;	85%

...Expand

: lithium tetrachloropalladate

: C49H38CuN3OP2

: 564483-18-7
XPhos

: C82H86ClCuN3OP3Pd

Conditions

Conditions	Yield
Stage #1: lithium tetrachloropalladate; C49H38CuN3OP2 With sodium acetate In methanol at 23℃; for 24h; Stage #2: XPhos In acetone at 25℃; for 3h;	85%

...Expand

: 90624-27-4
bis(μ-chloro)bis(η3-indenyl)dipalladium(II)

: 2923-28-6
silver trifluoromethanesulfonate

: 564483-18-7
XPhos

: (η3-indenyl)Pd(XPhos)(OTf)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h; Schlenk technique;	85%

...Expand

: 3375-31-3
palladium diacetate

: 90-41-5
2-phenylaniline

: lithium chloride

: 564483-18-7
XPhos

: 1310584-14-5
(chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II))

Conditions

Conditions	Yield
In toluene NH2C6H4C6H5 reacted with Pd salt in toluene at 60°C, reacted withLiCl in acetone at room temp., reacted with (C6H11)2PC6H4C6H2(CH(CH3)2) 3 at room temp.;	83%

...Expand

: [Pd(μ-Cl)(Cl)(N,N′-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene)]2

: 564483-18-7
XPhos

: [PdCl2(N,N′-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene)(PCy2(2',4',6'-iPr3-2-byphenyl))]

Conditions

Conditions	Yield
In tetrahydrofuran for 3h; Schlenk technique; Inert atmosphere; Glovebox;	83%

2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl Specification

The 2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl, with the CAS registry number 564483-18-7, is also known as Dicyclohexyl(2',4',6'-triisopropyl-2-biphenylyl)phosphine. This chemical's molecular formula is C₃₃H₄₉P and molecular weight is 476.72. What's more, its IUPAC name is called Dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane. It should be stored in a cool, dry and well-ventilated place. This chemical is an organophosphorus compound derived from biphenyl. Its palladium complexes exhibit high activity for Buchwald-Hartwig amination reactions involving aryl chlorides and aryl tosylates.

Physical properties about 2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl are: (1)ACD/LogP: 11.09; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 11.09; (4)ACD/LogD (pH 7.4): 11.09; (5)ACD/BCF (pH 5.5): 1000000.00; (6)ACD/BCF (pH 7.4): 1000000.00; (7)ACD/KOC (pH 5.5): 10000000.00; (8)ACD/KOC (pH 7.4): 10000000.00; (9)#H bond acceptors: 0; (10) #H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 13.59 Å²; (13)Flash Point: 317.745 °C; (14)Enthalpy of Vaporization: 82.298 kJ/mol; (15)Boiling Point: 569.762 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: P(c2ccccc2c1c(cc(cc1C(C)C)C(C)C)C(C)C)(C3CCCCC3)C4CCCCC4
(2) InChI: InChI=1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3
(3) InChIKey: UGOMMVLRQDMAQQ-UHFFFAOYSA-N

Product Name

X-PHOS

Synthetic route

2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl Specification

Related Products

Hot Products