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657408-07-6

Basic Information
CAS No.: 657408-07-6
Name: Phosphine,dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)-
Molecular Structure:
Molecular Structure of 657408-07-6 (Phosphine,dicyclohexyl(2',6'-dimethoxy[1,1'-biphenyl]-2-yl)-)
Formula: C26H35O2P
Molecular Weight: 410.53
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;
EINECS: 613-838-2
Density:
Melting Point: 164-166 °C
Boiling Point: 513.3 °C at 760 mmHg
Flash Point: 330.7 °C
Solubility:
Appearance:
Hazard Symbols: HarmfulXn
Risk Codes: 40
Safety: 24/25-36/37
Transport Information:
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
ConditionsYield
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
ConditionsYield
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%

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

657408-07-6

dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0) In water; ethyl acetate; toluene96%
657408-07-6

dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

dihydrogen tetrachloropalladate(II)

7550-35-8

lithium bromide

[HSPhos]2[Pd2Br6]

Conditions
ConditionsYield
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%
657408-07-6

dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

C26H35O8PS2

Conditions
ConditionsYield
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
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0) In hexane; water; toluene95%
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
ConditionsYield
With nitrogen In tetrahydrofuran; methanol; dichloromethane95%
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
ConditionsYield
In further solvent(s) treatment of palladium compd. with chlorobenzene deriv. and phosphine deriv. in methyl tert-butyl ether at 55°C; recrystn.;94%
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
ConditionsYield
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
ConditionsYield
94%
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
ConditionsYield
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
ConditionsYield
In cyclohexane at 20℃; for 18h; Inert atmosphere; Glovebox;93%
657408-07-6

dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

C16H20I2N2Pd2

C34H45INO2PPd

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In dichloromethane at 20℃; for 48h; Inert atmosphere;92%
657408-07-6

dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

C20H24I2N2O4Pd2

C36H47INO4PPd

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With dihydrogen peroxide In dichloromethane90%
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
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0) In dichloromethane; water; ethyl acetate; toluene90%
657408-07-6

dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane

C22H18Cl2N4O2Pd2

C37H44ClN2O3PPd

Conditions
ConditionsYield
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
ConditionsYield
With sodium acetate In ethanol at 80℃; for 30h; Inert atmosphere;89%
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
ConditionsYield
In dichloromethane mixt. ligand and (CH3CN)2PdCl2 in CH2Cl2 was stirred; flash chromy. on silica;88%
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Chemistry

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

Uses

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

Safety Profile

Hazard Codes of 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (CAS NO.657408-07-6): HarmfulXn
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.

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.