2-(Dicyclohexylphosphino)biphenyl supplier

Name
2-(Dicyclohexylphosphino)biphenyl
EINECS 480-030-2
CAS No. 247940-06-3
Article Data11
CAS DataBase
Density
Solubility
Melting Point 102-106 °C(lit.)
Formula C₂₄H₃₁P
Boiling Point 499.5 °C at 760 mmHg
Molecular Weight 350.484
Flash Point 271.7 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 36/37/39-26
Risk Codes 36/37/38-22
Molecular Structure
Hazard Symbols Xn
Synonyms (1,1'-Biphenyl-2-yl)dicyclohexylphosphine;(2-Biphenyl)dicyclohexylphosphine;2-(Dicyclohexylphosphino)-1,1'-biphenyl;2-Dicyclohexylphosphinyl-1,1'-biphenyl;Biphenyl-2-yl(dicyclohexyl)phosphine;Dicyclohexyl(o-biphenyl)phosphine;o-(Dicyclohexylphosphino)biphenyl;
PSA 13.59000
LogP 7.12620

Synthetic route

: 67-56-1
methanol

: 1186392-99-3
(2-biphenyl)dicyclohexylphosphane-borane(1:1)

A: 121-43-7
Trimethyl borate

B: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
In toluene at 100℃; Inert atmosphere;	A n/a B 97%

...Expand

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

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
With 1,3-diphenyl-disiloxane In toluene at 110℃; Sealed tube; chemoselective reaction;	93%
With diisobutylaluminium hydride In various solvent(s) at 125℃; for 4h;
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 1 h / 20 °C / Schlenk technique; Inert atmosphere; Sealed tube 2: hexachlorodisilane / dichloromethane-d2 / 0.08 h / 20 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme

: 2052-07-5
2-Bromobiphenyl

: 829-84-5
dicyclohexylphosphane

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); potassium hydroxide In water at 100℃; Inert atmosphere;	81%

: 591-50-4
iodobenzene

: 1417911-72-8
dicyclohexyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]phosphine borane

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
Stage #1: iodobenzene; dicyclohexyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]phosphine borane With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium hydroxide In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃; Inert atmosphere;	81%

: 17763-65-4
biphenyl-2-yl trifluoromethanesulfonate

: 829-84-5
dicyclohexylphosphane

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In N,N-dimethyl-formamide at 100℃; for 18.67h; Product distribution / selectivity;	77%
With 1,4-diaza-bicyclo[2.2.2]octane; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In N,N-dimethyl-formamide at 100℃; for 18.67h; Product distribution / selectivity;	8 %Chromat.
With 1,8-diazabicyclo[5.4.0]undec-7-ene; nickel dichloride In water; N,N-dimethyl-formamide at 100℃; for 18.67h; Product distribution / selectivity;	90 %Chromat.

: 2052-07-5
2-Bromobiphenyl

: 16523-54-9
chlorodicyclohexylphosphane

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
Stage #1: 2-Bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Metallation; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at -78 - 0℃; for 14h; Condensation;	71%
Stage #1: 2-Bromobiphenyl With n-butyllithium In diethyl ether; hexane at 0℃; for 2h; Stage #2: chlorodicyclohexylphosphane In diethyl ether; hexane at 20℃; for 1h;

: 64-17-5
ethanol

: 1186392-99-3
(2-biphenyl)dicyclohexylphosphane-borane(1:1)

A: 150-46-9
triethyl borate

B: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
Inert atmosphere; Reflux;	A n/a B 52%

...Expand

: 583-55-1
1-Bromo-2-iodobenzene

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,2-dimethoxyethane / 5 h / 80 °C / Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / 2 h / 0 °C 2.2: 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,2-dimethoxyethane; water / 5 h / 80 °C / Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / 2 h / 0 °C 2.2: 1 h / 20 °C View Scheme

: 98-80-6
phenylboronic acid

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,2-dimethoxyethane / 5 h / 80 °C / Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / 2 h / 0 °C 2.2: 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,2-dimethoxyethane; water / 5 h / 80 °C / Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / 2 h / 0 °C 2.2: 1 h / 20 °C View Scheme

: 2052-07-5
2-Bromobiphenyl

Cy2P-Hal: Cy2P-Hal

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
Stage #1: 2-Bromobiphenyl With n-butyllithium In diethyl ether; hexane at 0℃; for 2h; Stage #2: Cy2P-Hal In diethyl ether; hexane at 20℃; for 1h;

: 1-chloro-3-methyl-1-phenyl-2-phospholenium chloride

: 247940-06-3
CyJohnPhos

Conditions

Conditions	Yield
With hexachlorodisilane In dichloromethane-d2 at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Glovebox;	333 mg

: 247940-06-3
CyJohnPhos

: 1186392-99-3
(2-biphenyl)dicyclohexylphosphane-borane(1:1)

Conditions

Conditions	Yield
Stage #1: CyJohnPhos With dimethylsulfide borane complex In dichloromethane at 20℃; Inert atmosphere; Stage #2: With ammonium chloride In dichloromethane; water	100%

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

: 247940-06-3
CyJohnPhos

: 854045-92-4
chloro([1,1'-biphenyl]-2-yldicyclohexylphosphine)gold(I)

Conditions

Conditions	Yield
In dichloromethane for 1.75h;	100%
In dichloromethane at 20℃;	46%
In dichloromethane at 20℃; for 1h; Darkness;

: 247940-06-3
CyJohnPhos

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

Conditions

Conditions	Yield
With dihydrogen peroxide In dichloromethane at 20℃; for 1h;	99%
With dihydrogen peroxide In water; acetone for 3h;	93%
With oxygen In toluene at 20℃; Product distribution; Further Variations:; Reagents; Temperatures;

: hydrogen tetrachloroaurate(III) tetrahydrate

: 247940-06-3
CyJohnPhos

: 854045-92-4
chloro([1,1'-biphenyl]-2-yldicyclohexylphosphine)gold(I)

Conditions

Conditions	Yield
Stage #1: hydrogen tetrachloroaurate(III) tetrahydrate With propyl sulfide In ethanol at 40℃; for 0.166667h; Stage #2: CyJohnPhos In ethanol at 40℃; for 1h;	97%

: 590417-55-3
4-bromo-1-methyl-1H-indole

: 247940-06-3
CyJohnPhos

: 4,4'-(2'-(dicyclohexylphosphino)biphenyl-2,6-diyl)bis(1-methyl-1H-indole)

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	96%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;	96%

: copper(II) tetrafluroborate hexahydrate

: 247940-06-3
CyJohnPhos

: BF4(1-)*C24H30P(1+)

Conditions

Conditions	Yield
In acetonitrile at 100℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;	96%

: 292638-85-8
acrylic acid methyl ester

: 247940-06-3
CyJohnPhos

: 2-(dicyclohexylphosphino)-2’-(3-methoxy-3-oxopropyl)biphenyl

Conditions

Conditions	Yield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); Trimethylacetic acid In toluene at 110℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;	96%

: copper(I) triflate benzene complex

: 247940-06-3
CyJohnPhos

: [(CyJohnPhos)Cu][OTf]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 12h; Inert atmosphere;	95%

: 623-00-7
4-bromobenzenecarbonitrile

: 247940-06-3
CyJohnPhos

: 2-dicyclohexylphosphino-2',6'-bis(4-cyanophenyl)biphenyl

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	95%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;	95%

: 141-32-2
acrylic acid n-butyl ester

: 247940-06-3
CyJohnPhos

: 2-(dicyclohexylphosphino)-2’-(3-n-butoxy-3-oxopropyl)biphenyl

Conditions

Conditions	Yield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); Trimethylacetic acid In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;	95%

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

: 247940-06-3
CyJohnPhos

: 1268489-02-6
[IrCl(COD)(2-(dicyclohexylphosphino)biphenyl)]

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.; acetone added; suspn. filtered; washed (acetone); elem. anal.;	94%

: 402-43-7
p-trifluoromethylphenyl bromide

: 247940-06-3
CyJohnPhos

: 2-dicyclohexylphosphino-2',6'-bis(4-trifluoromethylphenyl)biphenyl

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 150℃; for 36h; Temperature; Concentration; Schlenk technique; Inert atmosphere;	94%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	87%

: 328-70-1
3,6-bis(trifluoromethyl)bromobenzene

: 247940-06-3
CyJohnPhos

: 2-dicyclohexylphosphino-2',6'-bis(3,5-ditrifluoromethylphenyl)biphenyl

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 150℃; for 36h; Temperature; Concentration; Schlenk technique; Inert atmosphere;	94%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	89%

: 108-86-1
bromobenzene

: 247940-06-3
CyJohnPhos

: 2',6'-diphenylbiphenyl-2-yldicyclohexylphosphine

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	94%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Concentration; Temperature; Schlenk technique; Inert atmosphere;	94%

: C60H24Cl3F18N3Pd3

: 247940-06-3
CyJohnPhos

: C44H39ClF6NPPd

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	94%

: 15070-92-5
2,3,4,5-tetrakis(pentafluorophenyl)cyclopenta-2,4-dien-1-one

: 247940-06-3
CyJohnPhos

: C53H31F20OP

Conditions

Conditions	Yield
In toluene at 20℃; Inert atmosphere;	93%

: 106-38-7
para-bromotoluene

: 247940-06-3
CyJohnPhos

: 2-dicyclohexylphosphino-2',6'-bis(4-methylphenyl)biphenyl

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	93%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;	93%

: 4835-96-5
(-)-menthyl acrylate

: 247940-06-3
CyJohnPhos

: 2-(dicyclohexylphosphino)-2’-(3-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-3-oxopropyl)biphenyl

Conditions

Conditions	Yield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); Trimethylacetic acid In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;	93%

: 779344-65-9
trifluoro-methanesulfonic acid 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl ester

: 5720-07-0
4-methoxyphenylboronic acid

: 247940-06-3
CyJohnPhos

: 779344-69-3
6-(4-Methoxy-phenyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

Conditions

Conditions	Yield
With potassium phosphate; palladium diacetate In toluene	92%

...Expand

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

: 247940-06-3
CyJohnPhos

: 1268489-02-6
(COD)Ir(2-(dicyclohexylphosphino)biphenyl)Cl

Conditions

Conditions	Yield
In dichloromethane at 20℃;	92%

: 108-90-7
chlorobenzene

: 247940-06-3
CyJohnPhos

: 2',6'-diphenylbiphenyl-2-yldicyclohexylphosphine

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 150℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique;	92%

: 460-00-4
1-Bromo-4-fluorobenzene

: 247940-06-3
CyJohnPhos

: 2-dicyclohexylphosphino-2',6'-bis(4-fluorophenyl)biphenyl

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	92%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;	92%

: 455-13-0
4-Iodobenzotrifluoride

: 247940-06-3
CyJohnPhos

: dicyclohexyl(4''-(trifluoromethyl)-[1,1':2',1''-terphenyl]-2-yl)phosphane

Conditions

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; iodine; potassium acetate; 1-amino-1-cyclopentanecarboxylic acid; acetylacetone In cyclohexane at 160℃; for 16h; Inert atmosphere; Sealed tube; Schlenk technique;	92%

: 586-77-6
4-bromo-N,N-dimethylaniline

: 247940-06-3
CyJohnPhos

: 2-dicyclohexylphosphino-2',6'-bis(4-dimethylaminophenyl)biphenyl

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	91%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;	91%

: 140-88-5
ethyl acrylate

: 247940-06-3
CyJohnPhos

: 2-(dicyclohexylphosphino)-2’-(3-ethoxy-3-oxopropyl)biphenyl

Conditions

Conditions	Yield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); Trimethylacetic acid In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;	91%

: 618-91-7
methyl 3-iodo-benzoate

: 247940-06-3
CyJohnPhos

: methyl 2''-(dicyclohexylphosphanyl)-[1,1':2',1''-terphenyl]-3-carboxylate

Conditions

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; iodine; potassium acetate; 1-amino-1-cyclopentanecarboxylic acid; acetylacetone In cyclohexane at 160℃; for 16h; Inert atmosphere; Sealed tube; Schlenk technique;	91%

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

: 247940-06-3
CyJohnPhos

: 692782-19-7
[(η3-syn-crotyl)PdCl(dicyclohexylphosphino-2-biphenyl)]

Conditions

Conditions	Yield
In tetrahydrofuran (N2); THF was added via syringe to mixt. of Pd compd. and P ligand in Schlenk flask; soln. was stirred at room temp. for 1 h; evapd. (vac.); washed (pentane); elem. anal.;	90%

: 556-96-7
5-bromo-1,3-xylene

: 247940-06-3
CyJohnPhos

: 2-dicyclohexylphosphino-2',6'-bis(3,5-dimethylphenyl)biphenyl

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Inert atmosphere; Schlenk technique;	90%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide In 1,4-dioxane at 140℃; for 36h; Schlenk technique; Inert atmosphere;	90%

2-(Dicyclohexylphosphino)biphenyl Specification

The Phosphine,[1,1'-biphenyl]-2-yldicyclohexyl-, with the CAS registry number 247940-06-3, is also known as 2-(Dicyclohexylphosphino)-1,1'-biphenyl. It belongs to the product categories of Phosphines; Ligand; Phosphine Ligands; Synthetic Organic Chemistry; Organophosphine ligand. This chemical's molecular formula is C₂₄H₃₁P and molecular weight is 350.48. What's more, its systematic name is biphenyl-2-yl(dicyclohexyl)phosphane. The product should be sealed and stored in containers with nitrogen gas which are placed in cool and dry places. Moreover, it should be protected from oxides and halogen. It is a ligand employed in an extremely general method for the Pd-catalyzed synthesis of aromaticamines using aryl chlorides, bromides and triflates.

Physical properties of Phosphine,[1,1'-biphenyl]-2-yldicyclohexyl- are: (1)ACD/LogP: 8.45; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 8.45; (4)ACD/LogD (pH 7.4): 8.45; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 937423.31; (8)ACD/KOC (pH 7.4): 937423.31; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 13.59 Å²; (13)Flash Point: 271.7 °C; (14)Enthalpy of Vaporization: 73.88 kJ/mol; (15)Boiling Point: 499.5 °C at 760 mmHg; (16)Vapour Pressure: 1.27E-09 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: P(c2ccccc2c1ccccc1)(C3CCCCC3)C4CCCCC4
(2)Std. InChI: InChI=1S/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2
(3)Std. InChIKey: LCSNDSFWVKMJCT-UHFFFAOYSA-N

Product Name

2-(Dicyclohexylphosphino)biphenyl

Synthetic route

2-(Dicyclohexylphosphino)biphenyl Specification

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