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Basic Information
CAS No.: 251320-86-2
Name: 2-(Dicyclohexylphosphino)-2'-methylbiphenyl
Article Data: 5
Molecular Structure:
Molecular Structure of 251320-86-2 (2-(Dicyclohexylphosphino)-2'-methylbiphenyl)
Formula: C25H33P
Molecular Weight: 364.511
Synonyms: MePhos;2-Dicyclohexylphosphino-2'-methylbiphenyl;
EINECS: 607-557-4
Melting Point: 107-111 °C
Boiling Point: 499.3 °C at 760 mmHg
Flash Point: 271.5 °C
Solubility: insoluble in water
Appearance: White crystals or crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 37/39-26
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
ConditionsYield
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
ConditionsYield
Multistep reaction.;59%
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
ConditionsYield
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%
19493-31-3

2-chloro-2'-methyl-1,1'-biphenyl

16523-54-9

chlorodicyclohexylphosphane

251320-86-2

2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions
ConditionsYield
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
ConditionsYield
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%
931-51-1

cyclohexylmagnesiumchloride

251320-86-2

2-(dicyclohexylphosphino)-2'-methylbiphenyl

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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
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
ConditionsYield
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%
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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