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657408-07-6

Basic Information
CAS No.: 657408-07-6
Name: 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
Article Data: 7
Molecular Structure:
Molecular Structure of 657408-07-6 (2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl)
Formula: C26H35O2P
Molecular Weight: 410.536
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
Melting Point: 164-166 °C
Boiling Point: 513.3 °C at 760 mmHg
Flash Point: 330.7 °C
Hazard Symbols: HarmfulXn
Risk Codes: 40
Safety: 24/25-36/37
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
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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.