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CAS No.: | 657408-07-6 |
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Name: | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl |
Article Data: | 7 |
Molecular Structure: | |
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: | Xn |
Risk Codes: | 40 |
Safety: | 24/25-36/37 |
PSA: | 32.05000 |
LogP: | 7.14340 |
chlorodicyclohexylphosphane
2'-bromo-2,6-dimethoxybiphenyl
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
Conditions | Yield |
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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 |
2-bromo-1-chlorobenzene
1,3-Dimethoxybenzene
chlorodicyclohexylphosphane
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
Conditions | Yield |
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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% |
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
Conditions | Yield |
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With 1,3-diphenyl-disiloxane In toluene at 110℃; Sealed tube; chemoselective reaction; | 87% |
2'-chloro-2,6-dimethoxy-1,1'-biphenyl
chlorodicyclohexylphosphane
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
Conditions | Yield |
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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% |
2-bromo-1-chlorobenzene
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
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 |
1,3-Dimethoxybenzene
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
Conditions | Yield |
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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 |
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
(2,6-dimethoxyphenyl)boronic acid
1,2-dichloro-benzene
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
Conditions | Yield |
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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 |
1,3-Dimethoxybenzene
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
Conditions | Yield |
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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 |
chlorobenzene
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane
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 |
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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 (CAS NO.657408-07-6) has been used as a ligand for Buchwald and Suzuki coupling reaction.
Hazard Codes of 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (CAS NO.657408-07-6): 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 , 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.