2-(Dicyclohexylphosphino)-2'-methylbiphenyl supplier

Name
2-(Dicyclohexylphosphino)-2'-methylbiphenyl
EINECS 607-557-4
CAS No. 251320-86-2
Article Data5
CAS DataBase
Density
Solubility insoluble in water
Melting Point 107-111 °C
Formula C₂₅H₃₃P
Boiling Point 499.3 °C at 760 mmHg
Molecular Weight 364.511
Flash Point 271.5 °C
Transport Information
Appearance White crystals or crystalline powder
Safety 37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms MePhos;2-Dicyclohexylphosphino-2'-methylbiphenyl;
PSA 13.59000
LogP 7.43460

Synthetic route

: 251320-87-3
2-bromo-2'-methylbiphenyl

: 16523-54-9
chlorodicyclohexylphosphane

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions

Conditions	Yield
Stage #1: 2-bromo-2'-methylbiphenyl With n-butyllithium In tetrahydrofuran at -78℃; for 1.16667h; Metallation; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran Condensation; a) -78 deg C, 20 min, b) 0 deg C, 20 min, c) RT, 18 h;	65%

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

: 95-49-8
2-methylchlorobenzene

: 931-51-1
cyclohexylmagnesiumchloride

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions

Conditions	Yield
Multistep reaction.;	59%

...Expand

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

: 95-46-5
2-methylphenyl bromide

: 16523-54-9
chlorodicyclohexylphosphane

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions

Conditions	Yield
Stage #1: 2-methylphenyl bromide With magnesium; ethylene dibromide In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Industrial scale; Stage #2: 2-bromo-1-chlorobenzene With magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Industrial scale; Stage #3: chlorodicyclohexylphosphane With copper(l) chloride In tetrahydrofuran at 20℃; Thermodynamic data; Inert atmosphere; Industrial scale;	55%

Yield

Stage #1: 2-methylphenyl bromide With magnesium; ethylene dibromide In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Industrial scale;
Stage #2: 2-bromo-1-chlorobenzene With magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Industrial scale;
Stage #3: chlorodicyclohexylphosphane With copper(l) chloride In tetrahydrofuran at 20℃; Thermodynamic data; Inert atmosphere; Industrial scale;

55%

...Expand

: 19493-31-3
2-chloro-2'-methyl-1,1'-biphenyl

: 16523-54-9
chlorodicyclohexylphosphane

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions

Conditions	Yield
Stage #1: 2-chloro-2'-methyl-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;	52%

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

: 33872-80-9
o-tolyl magnesium chloride

: 16523-54-9
chlorodicyclohexylphosphane

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions

Conditions	Yield
Stage #1: o-tolyl magnesium chloride With magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: 2-bromo-1-chlorobenzene In tetrahydrofuran for 2h; Heating; Stage #3: chlorodicyclohexylphosphane In tetrahydrofuran at 20℃; for 14h; Further stages.;	51%

...Expand

: 931-51-1
cyclohexylmagnesiumchloride

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: PCl3 / diethyl ether / -40 - 20 °C 2.1: Mg / tetrahydrofuran / 0.25 h / Heating 2.2: tetrahydrofuran / 2 h / Heating 2.3: 51 percent / tetrahydrofuran / 14 h / 20 °C View Scheme

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

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1.57 g / tetrakis(triphenylphosphine)palladium; Na2CO3 / 1,2-dimethoxy-ethane; H2O; ethanol / 42 h / 90 °C 2.1: n-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 65 percent / tetrahydrofuran / a) -78 deg C, 20 min, b) 0 deg C, 20 min, c) RT, 18 h View Scheme

: 16419-60-6
2-Methylphenylboronic acid

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1.57 g / tetrakis(triphenylphosphine)palladium; Na2CO3 / 1,2-dimethoxy-ethane; H2O; ethanol / 42 h / 90 °C 2.1: n-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 65 percent / tetrahydrofuran / a) -78 deg C, 20 min, b) 0 deg C, 20 min, c) RT, 18 h View Scheme
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

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

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

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

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

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: 1005420-86-9
dicyclohexyl(2'-methylbiphenyl-2-yl)phosphinegold(I) chloride

Conditions

Conditions	Yield
In dichloromethane for 1.75h;	100%
In toluene (N2); Au complex added to a soln. of ligand, stirred for 24 h under Ar; evapd. (vac.), pentane added, the solid collected, dried; elem. anal.;	97%

: dirhodium tetraacetate

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: C33H45O8PRh2

Conditions

Conditions	Yield
In toluene at 80℃; for 12h; Solvent; Inert atmosphere;	87%

: silver hexafluoroantimonate

: 15529-49-4, 41756-81-4
tris(triphenylphosphine)ruthenium(II) chloride

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: 569346-65-2, 568592-74-5
[Ru(η6:η1-2-(dicyclohexylphosphino)-2'-methylbiphenyl-P)(PPh3)Cl]SbF6

Conditions

Conditions	Yield
In chlorobenzene under N2 atm. to (Ru(PPh3)3Cl2) in chlorobenzene AgSbF6 and phosphine were added and refluxed for 3 h; solvent was distilled off, residue was washed with ether and dried in vacuo - diastereomers were not separated;	78%

...Expand

: 2680-03-7
N,N-Dimethylacrylamide

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: C30H42NOP

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;	78%

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

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: 1268489-04-8
[IrCl(COD)(2-dicyclohexylphosphino-2'-methylbiphenyl)]

Conditions

Conditions	Yield
In toluene under Ar atm. using Schlenk techniques; mixt. of Ir complex and ligand in dry toluene was stirred at 60°C for 8 h; volatiles evapd.; solid dissolved in acetone; tert-butylmethyl ether added; suspn. filtered; elem. anal.;	77%

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

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: 2-(dicyclohexylphosphino)-2'-(3-butoxy-3-oxopropyl)-6'-methyl-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;	76%

: 501-65-5
diphenyl acetylene

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: (E)-dicyclohexyl(2'-(1,2-diphenylvinyl)-6'-methyl-[1,1'-biphenyl]-2-yl)phosphane

Conditions

Conditions	Yield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); potassium acetate In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;	68%

: 14044-65-6
borane-THF

: 73183-34-3
bis(pinacol)diborane

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: C31H47B2O2P

Conditions

Conditions	Yield
Stage #1: bis(pinacol)diborane; 2-(dicyclohexylphosphino)-2'-methylbiphenyl With bis(1,5-cyclooctadiene)iridium(I) tetrafluoroborate; 8-(diisopropylsilyl)quinoline In 1,4-dioxane at 130℃; for 48h; Stage #2: borane-THF In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	54%

...Expand

: allyl palladium chloride dimer

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: C28H38BrPPd

Conditions

Conditions	Yield
In diethyl ether at 25℃; for 1h; Inert atmosphere; Schlenk technique;	37%

: 37366-09-9
dichloro(benzene)ruthenium(II) dimer

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: 568592-70-1
[Ru(η6:η1-2-(dicyclohexylphosphino)-2-methylbiphenyl-P)Cl2]

Conditions

Conditions	Yield
In N,N-dimethyl-formamide under N2 atm. (Ru(benzene)Cl2)2 and phosphine were stirred in DMF at 100°C for 10 min; solvent was distilled off in vacuo, residue was chromed. on silica (MeCOMe);	31%

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: C25H32(2)HP

Conditions

Conditions	Yield
Stage #1: 2-(dicyclohexylphosphino)-2'-methylbiphenyl With palladium diacetate; sodium tert-pentoxide In toluene at 80℃; for 1h; Stage #2: With para-chlorotoluene; morpholine-2,2,3,3,5,5,6,6-d8 In toluene at 80℃; for 8h;

: potassium phosphate

deoxygenated toluene: deoxygenated toluene

: 210628-07-2
4-chloro-2-methyl-indene

: 100379-00-8
2,6-dimethylbenzene boronic acid

: 3375-31-3
palladium diacetate

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: 2-methyl-4-(2,6-dimethylphenyl)indene

...Expand

: 251320-86-2
2-(dicyclohexylphosphino)-2'-methylbiphenyl

: 1005420-87-0
[(PCy2(2'-methylbiphenyl))AuBr]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene 2: dichloromethane; water View Scheme

2-(Dicyclohexylphosphino)-2'-methylbiphenyl Specification

The CAS register number of 2-(Dicyclohexylphosphino)-2'-methylbiphenyl is 251320-86-2. It also can be called as Phosphine,dicyclohexyl(2'-methyl[1,1'-biphenyl]-2-yl)- and the systematic name about this chemical is dicyclohexyl(2'-methylbiphenyl-2-yl)phosphane. The molecular formula about this chemical is C₂₅H₃₃P and molecular weight is 364.50. It belongs to the Biphenyl & Diphenyl ether.

Physical properties about 2-(Dicyclohexylphosphino)-2'-methylbiphenyl are: (1)ACD/LogP: 8.91; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 8.91; (4)ACD/LogD (pH 7.4): 8.91; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 1668082.63; (8)ACD/KOC (pH 7.4): 1668082.63; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 13.59Å²; (11)Flash Point: 271.5 °C; (12)Enthalpy of Vaporization: 73.85 kJ/mol; (13)Boiling Point: 499.3 °C at 760 mmHg; (14)Vapour Pressure: 1.3E-09 mmHg at 25°C.

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

You can still convert the following datas into molecular structure:
(1)SMILES: P(c2ccccc2c1ccccc1C)(C3CCCCC3)C4CCCCC4
(2)InChI: InChI=1/C25H33P/c1-20-12-8-9-17-23(20)24-18-10-11-19-25(24)26(21-13-4-2-5-14-21)22-15-6-3-7-16-22/h8-12,17-19,21-22H,2-7,13-16H2,1H3
(3)InChIKey: GPVWUKXZFDHGMZ-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C25H33P/c1-20-12-8-9-17-23(20)24-18-10-11-19-25(24)26(21-13-4-2-5-14-21)22-15-6-3-7-16-22/h8-12,17-19,21-22H,2-7,13-16H2,1H3
(5)Std. InChIKey: GPVWUKXZFDHGMZ-UHFFFAOYSA-N

Product Name

2-(Dicyclohexylphosphino)-2'-methylbiphenyl

Synthetic route

2-(Dicyclohexylphosphino)-2'-methylbiphenyl Specification

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