2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl supplier

Name
2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
EINECS 613-838-2
CAS No. 657408-07-6
Article Data7
CAS DataBase
Density
Solubility
Melting Point 164-166 °C
Formula C₂₆H₃₅O₂P
Boiling Point 513.3 °C at 760 mmHg
Molecular Weight 410.536
Flash Point 330.7 °C
Transport Information
Appearance
Safety 24/25-36/37
Risk Codes 40
Molecular Structure
Hazard Symbols Xn
Synonyms (2,6-Dimethoxy-1,1'-biphenyl-2-yl)dicyclohexylphosphine;2-(Dicyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl;Dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine;S-Phos;
PSA 32.05000
LogP 7.14340

Synthetic route

: 16523-54-9
chlorodicyclohexylphosphane

: 755017-61-9
2'-bromo-2,6-dimethoxybiphenyl

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
Stage #1: 2'-bromo-2,6-dimethoxybiphenyl With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Cooling with acetone-dry ice; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran at 20 - 45℃; Inert atmosphere;	88%
Stage #1: 2'-bromo-2,6-dimethoxybiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at -78 - 20℃;	3.32 g

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

: 151-10-0
1,3-Dimethoxybenzene

: 16523-54-9
chlorodicyclohexylphosphane

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
Stage #1: 1,3-Dimethoxybenzene With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 3.5h; Stage #2: 2-bromo-1-chlorobenzene In tetrahydrofuran at 0℃; for 0.5h; Stage #3: chlorodicyclohexylphosphane	36%

...Expand

: (2’,6’-dimethoxy-[1,1’-biphenyl]-2-yl)dicyclohexylphosphine oxide

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
With 1,3-diphenyl-disiloxane In toluene at 110℃; Sealed tube; chemoselective reaction;	87%

: 1380028-15-8
2'-chloro-2,6-dimethoxy-1,1'-biphenyl

: 16523-54-9
chlorodicyclohexylphosphane

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
Stage #1: 2'-chloro-2,6-dimethoxy-1,1'-biphenyl With sec.-butyllithium In diethyl ether; cyclohexane at -78 - -45℃; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In diethyl ether; cyclohexane at -78℃; Inert atmosphere;	48%

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

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 5 h / 0 - 20 °C 1.2: 81 percent / tetrahydrofuran; hexane / 0.25 h / 0 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 3.32 g / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

: 151-10-0
1,3-Dimethoxybenzene

4-methoxy-trans(?)-cinnamic acid: 4-methoxy-trans(?)-cinnamic acid

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 5 h / 0 - 20 °C 1.2: 81 percent / tetrahydrofuran; hexane / 0.25 h / 0 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 3.32 g / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

: potassium phosphate

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: 23112-96-1
(2,6-dimethoxyphenyl)boronic acid

: 95-50-1
1,2-dichloro-benzene

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane / toluene / 70 °C / Inert atmosphere 2.1: sec.-butyllithium / diethyl ether; cyclohexane / -78 - -45 °C / Inert atmosphere 2.2: -78 °C / Inert atmosphere View Scheme

: 151-10-0
1,3-Dimethoxybenzene

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,2,6,6-tetramethylpiperidinyl-lithium / diethyl ether; tetrahydrofuran / 36 h / -45 °C / Inert atmosphere; Sealed tube 2: diethyl ether / -78 °C / Inert atmosphere; Sealed tube View Scheme

: 108-90-7
chlorobenzene

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,2,6,6-tetramethylpiperidinyl-lithium / diethyl ether; tetrahydrofuran / 36 h / -45 °C / Inert atmosphere; Sealed tube 2: diethyl ether / -78 °C / Inert atmosphere; Sealed tube View Scheme

: 13732-86-0
2,6-dimethoxybiphenyl

: 16523-54-9
chlorodicyclohexylphosphane

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions

Conditions	Yield
In diethyl ether at -78℃; Inert atmosphere; Sealed tube;	1.3 g

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

: 854045-95-7
chloro(dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine)gold(I)

Conditions

Conditions	Yield
In dichloromethane for 1.75h;	100%
In dichloromethane at 20℃; for 1h; Darkness;

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate

Conditions

Conditions	Yield
Stage #1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane With sulfuric acid In dichloromethane at 0 - 40℃; for 24h; Stage #2: With sodium hydroxide In dichloromethane; water at 0℃; pH=~ 7.0; Cooling with ice;	99%
Stage #1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane With sulfuric acid In dichloromethane at 20℃; for 1h; Sealed tube; Stage #2: With sodium hydroxide In dichloromethane; water at 20℃; for 0.25h; pH=14; Sealed tube; Cooling with ice; regioselective reaction;	85%
Stage #1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane With sulfuric acid In dichloromethane at 0 - 40℃; for 24.7h; Inert atmosphere; Stage #2: With sodium hydroxide In dichloromethane; water at 0℃; pH=13;	62%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]

: Pd(π-cinnamyl)(SPhos)Cl

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Schlenk technique; Inert atmosphere;	99%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

: [PdCl2(N,N′-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene)(PCy2-(2',6'-oMe2-2-byphenyl))]

Conditions

Conditions	Yield
In tetrahydrofuran for 3h; Schlenk technique; Inert atmosphere; Glovebox;	98%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: bis(η3-allyl-μ-chloropalladium(II))

: Pd(π-allyl)(SPhos)Cl

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h; Schlenk technique; Inert atmosphere;	98%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	97.3%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: hydrogen tetrachloroaurate(III) tetrahydrate

: 854045-95-7
chloro(dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine)gold(I)

Conditions

Conditions	Yield
Stage #1: hydrogen tetrachloroaurate(III) tetrahydrate With propyl sulfide In ethanol at 40℃; for 0.166667h; Stage #2: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane In ethanol at 40℃; for 1h;	97%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: C12H10ClNPd

: 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Conditions

Conditions	Yield
In acetone at 25℃;	96%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: 1429471-42-0
4-chloro-2-(dibenzo[b,d]furan-4-yl)pyridine

: 126726-62-3
2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

: 1421361-86-5
2-(dibenzo[b,d]furan-4-yl)-4-(prop-1-en-2-yl)pyridine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0) In water; ethyl acetate; toluene	96%

...Expand

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: dihydrogen tetrachloropalladate(II)

: 7550-35-8
lithium bromide

: [HSPhos]2[Pd2Br6]

Conditions

Conditions	Yield
Stage #1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dihydrogen tetrachloropalladate(II) In acetone at 18 - 27℃; for 0.5h; Stage #2: lithium bromide In water; acetone	96%

...Expand

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: C26H35O8PS2

Conditions

Conditions	Yield
Stage #1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane With sulfuric acid In dichloromethane for 1.5h; Sealed tube; Stage #2: With fuming sulphuric acid In dichloromethane at 0 - 20℃; for 0.533333h; Sealed tube; regioselective reaction;	96%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: 84110-40-7
Dihydroxy-isobutyl-boran

: 73075-58-8
5,7-dichloro isoquinoline

: 1443013-08-8
5,7-diisobutylisoquinoline

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0) In hexane; water; toluene	95%

...Expand

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: 54879-20-8
2-bromo-3-methylaniline

: 1859-17-2
1-methylphenanthridin-6-amine

Conditions

Conditions	Yield
With nitrogen In tetrahydrofuran; methanol; dichloromethane	95%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

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

: 1028206-58-7
chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II)

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.;	94%

...Expand

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: 12112-67-3
bis(1,5-cyclooctadiene)diiridium(I) dichloride

: 1268489-06-0
[IrCl(COD)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)]

Conditions

Conditions	Yield
In toluene under Ar atm. using Schlenk techniques; mixt. of Ir complex and ligand in dry toluene was stirred at room temp. for 3 h; solvent evapd.; cold hexane added; suspn. filtered; washed (cold hexane); elem. anal.;	94%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: 1153-85-1
3-bromo-9-phenyl-9H-carbazole

: 108847-20-7
4-dibenzothiophene boronic acid

: 3-(dibenzo[b,d]thiophen-4-yl)-9-phenyl-9H-carbazole

Conditions

Conditions	Yield
	94%

...Expand

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

: 1445085-82-4
C26H35O2P*C13H13NO3PdS

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃;	93%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

: 106-43-4
para-chlorotoluene

: C33H42ClO2PPd

Conditions

Conditions	Yield
In cyclohexane at 20℃; for 18h; Inert atmosphere; Glovebox;	93%

...Expand

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: C16H20I2N2Pd2

: C34H45INO2PPd

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	93%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: dihydrogen tetrachloropalladate(II)

: [HSPhos]2[Pd2Cl6]

Conditions

Conditions	Yield
In acetone at 18 - 27℃; for 1.16667h;	93%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

: 1599466-88-2
C45H52NO5PPdS

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	92%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: 105286-78-0
bis(pentafluorophenyl)(1,5-cyclo-octadiene)palladium(II)

: C38H35F10O2PPd

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 48h; Inert atmosphere;	92%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: C20H24I2N2O4Pd2

: C36H47INO4PPd

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	92%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

: C52H70O4P2Pd2(2+)*2BF4(1-)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.00166667h; Time;	91%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: (2’,6’-dimethoxy-[1,1’-biphenyl]-2-yl)dicyclohexylphosphine oxide

Conditions

Conditions	Yield
With dihydrogen peroxide In dichloromethane	90%
With oxygen In toluene at 20℃; Product distribution; Further Variations:; Reagents; Temperatures;
With dihydrogen peroxide In diethyl ether at 30℃; for 16h;

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: 84110-40-7
Dihydroxy-isobutyl-boran

: 1443013-16-8
4,6-dichloro-1-(3,5-dimethylphenyl)isoquinoline

: 1056451-68-3
1-(3,5-dimethylphenyl)isoquinoline

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0) In dichloromethane; water; ethyl acetate; toluene	90%

...Expand

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: C22H18Cl2N4O2Pd2

: C37H44ClN2O3PPd

Conditions

Conditions	Yield
In acetone at 20℃; for 0.5h;	90%

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

: ruthenium trichloride

: C53H46CuN4OP2(1+)*BF4(1-)

: C105H115Cl2CuN4O5P4Ru(1+)*BF4(1-)

Conditions

Conditions	Yield
With sodium acetate In ethanol at 80℃; for 30h; Inert atmosphere;	89%

...Expand

: 657408-07-6
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

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

: 848652-20-0
Pd(2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl)2Cl2

Conditions

Conditions	Yield
In dichloromethane mixt. ligand and (CH3CN)2PdCl2 in CH2Cl2 was stirred; flash chromy. on silica;	88%

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Chemical Properties

Empirical Formula: C₂₆H₃₅O₂P
Molecular Weight: 410.5287
Nominal Mass: 410 Da
Average Mass: 410.5287 Da
Monoisotopic Mass: 410.237466 Da
Flash Point: 330.7 °C
Enthalpy of Vaporization: 75.51 kJ/mol
Boiling Point: 513.3 °C at 760 mmHg
Vapour Pressure: 3.86E-10 mmHg at 25 °C
Melting point: 164-166 °C
Sensitive: Air sensitive
Structure of 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (CAS NO.657408-07-6):

Product Category of 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (CAS NO.657408-07-6): Phosphines

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Uses

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (CAS NO.657408-07-6) has been used as a ligand for Buchwald and Suzuki coupling reaction.

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Safety Profile

Hazard Codes of 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (CAS NO.657408-07-6): Harmful Xn
Risk Statements: 40
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 24/25-36/37
S24/25:Avoid contact with skin and eyes.
S36/37:Wear suitable protective clothing and gloves.

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Specification

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl , its cas register number is 657408-07-6. It also can be called (2,6-Dimethoxy-1,1'-biphenyl-2-yl)dicyclohexylphosphine ; Phosphine,dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)- ; and Dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine . It is an organophosphorus compound derived from biphenyl; and its palladium complexes exhibit high activity for Suzuki coupling reactions involving aryl chlorides.

Product Name

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Synthetic route

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Chemical Properties

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Uses

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Safety Profile

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl Specification

Related Products

Hot Products