2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl

Base Information

• Chemical Name: 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl
• CAS No.: 213697-53-1
• Molecular Formula: C26H36NP
• Molecular Weight: 393.552
• Hs Code.: 29310099
• UNII: 9877ONU78F
• DSSTox Substance ID: DTXSID20370171
• Nikkaji Number: J1.009.873D,J3.446.379D
• Wikidata: Q27272096
• Mol file: 213697-53-1.mol

Synonyms:213697-53-1;2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl;DavePhos;2'-(DICYCLOHEXYLPHOSPHINO)-N,N-DIMETHYL-[1,1'-BIPHENYL]-2-AMINE;2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline;2'-(dicyclohexylphosphino)-n,n-dimethylbiphenyl-2-amine;2-dicyclohexylphosphino-2'-(dimethylamino)biphenyl;MFCD02183572;2'-(dicyclohexylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine;2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl;Davephos phosphine ligand [MI];9877ONU78F;2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethyl-aniline;2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl;[1,1'-BIPHENYL]-2-AMINE, 2'-(DICYCLOHEXYLPHOSPHINO)-N,N-DIMETHYL-;Buchwald phosphine ligands, davephos phosphine ligand-;Dicyclohexyl(2'-(dimethylamino)biphenyl-2-yl)phosphine;(2-Dimethylamino-1,1'-biphenyl-2-yl)dicyclohexylphosphine;2'-(dicyclohexylphosphanyl)-N,N-dimethylbiphenyl-2-amine;(1,1'-Biphenyl)-2-amine, 2'-(dicyclohexylphosphino)-N,N-dimethyl-;2'-[dicyclohexylphosphino]-N,N-dimethylbiphenyl-2-amine;DavePhos, 97%;SCHEMBL21788;UNII-9877ONU78F;C26H36NP;(2'-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethylamine;2'-Dicyclohexylphosphino-2-(N,N-Dimethylamino)Biphenyl;2-dicyclohexylphosphino-2'-dimethylamino-1,1'-biphenyl;2-(dicyclohexylphosphino)-2'-(n,n-dimethylamino)biphenyl;DTXSID20370171;ZEMZPXWZVTUONV-UHFFFAOYSA-N;BCP22492;BBL102734;STL556540;AKOS015840828;AC-1365;AM86755;CS-W002925;GC10130;AS-71532;BP-11086;SY009088;D3389;FT-0650142;A25280;EN300-153020;2-dicyclohexylphosphanyl-2'-dimethylaminobiphenyl;2-dicyclohexylphosphino-2'-dimethylaminobiphenyl;2-dimethylamino-2'-dicyclohexylphosphino-biphenyl;2-dicyclohexylphospino-2'-(dimethylamino)biphenyl;2'-(Dimethylamino)biphenyl-2-yldicyclohexylphosphine;dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl;J-509270;Y-200003;(2'-dicyclohexylphosphanylbiphenyl-2-yl)-dimethylamine;(2'-dicyclohexylphosphanylbiphenyl-2-yl)dimethylamine;2-(dimethylamino)-2'-(dicyclohexylphosphino)biphenyl;2-(N,N-dimethylamino)-2'-dicylohexylphosphinobiphenyl;2-dicyclohexylphosphino 2'(N,N-dimethylamino)biphenyl;2-dicyclohexylphosphino-2'(N,N-dimethylamino)biphenyl;2-dicyclohexylphosphino-2'-(n,n-dimethyl)aminobiphenyl;2-dicyclohexylphospino-2'-(N,N-dimethylamino)biphenyl;dicyclohexylphosphino-2'-(N,N -dimethylamino)biphenyl;Q27272096;(2'-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine;(2'-dicyclohexylphosphanyl-biphenyl-2-yl)dimethyl-amine;[2'-(dicyclohexylphosphanyl)-2-biphenylyl]dimethylamine;2'-(dicyclohexylphosphanyl)-N,N-dimethyl-2-biphenylamine;2'-(dicyclohexylphosphino)-N,N-dimethyl-2-biphenylamine;2-(N,N-dimethylamino)-2'-dicyclohexylphosphinobiphenyl;2-di-cyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl;2-dicyclohexylphosphino -2'-(N,N-dimethylamino)biphenyl;2-dicyclohexylphosphino-2' (N,N-dimethylamino)biphenyl;2-dicyclohexylphosphino-2'-(N,N'-dimethylamino)biphenyl;2-dicyclohexylphosphino-2'-(N,N-dimethyl amino)biphenyl;2-dicyclohexylphosphino-2'-(N,N-dimethyl-amino)biphenyl;2-dicyclohexylphosphino-2'-(N,N-dimethylamino) biphenyl;2-dicyclohexylphospino-2'-(N,N-dimethylamino) biphenyl;F0001-0764;(2'-dicyclohexylphosphanyl -biphenyl-2-yl)-dimethyl-amine;(aR)-2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl;2'-(dicyclohexyl phosphino)-N,N-dimethylbiphenyl-2-amine;2'-(dicyclohexylphosphino)-N, N-dimethylbiphenyl-2-amine;2-(N,N-Dimethylamino)-2'-(dicyclohexylphosphino)biphenyl;2-dicyclohexylphosphino-2'-(N, N-dimethyl amino)biphenyl;2-dicyclohexylphosphino-2'-(N,N'-dimethylamino) biphenyl;2'-(dicyclohexylphosphino)-N,N-dimethyl-1,1'-biphenyl-2-amine;2'-(dicyclohexylphosphino)-N,N-dimethyl-[1,1-biphenyl]-2-amine;2'-(dicyclohexylphosphino)-N,N-dimethyl[1,1'-biphenyl]-2-amine;N-[2'-(dicyclohexylphoshino)(1,1'-biphenyl)-2-yl]-N,N-dimethylamine;N-[2'-(dicyclohexylphosphino)-1,1'-biphenyl-2-yl]-N,N-dimethylamine;N-[2'-(dicyclohexylphosphino)[1,1'-biphenyl]-2-yl]-N,N-dimethylamine;2-Dicyclohexylphosphino-2 inverted exclamation marka-(N,N-dimethylamino)biphenyl;2-(Dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl

Chemical Property of 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl

Chemical Property:

• Appearance/Colour: white to light yellow crystals
• Melting Point: 121-124 °C(lit.)
• Boiling Point: 539.6 °C at 760 mmHg
• PKA: 5.04±0.18(Predicted)
• Flash Point: 280.1 °C
• PSA: 16.83000
• LogP: 7.19220
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 393.258537150
• Heavy Atom Count: 28
• Complexity: 433

Purity/Quality:

98% ^*data from raw suppliers

DavePhos ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4
• Uses: suzuki reaction Effective ligand in the Pd-catalyzed arylation of ester enolates 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl can act as ligand used in the palladium-catalyzed Suzuki coupling and amination of unactivated aryl chlorides.

Technology Process of 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl

There total 9 articles about 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

2-bromo-1-chlorobenzene (694-80-4) + 2-bromo-N,N-dimethylaniline (698-00-0) + chlorodicyclohexylphosphane (16523-54-9) → DavePhos (213697-53-1)

Guidance literature:

2-bromo-N,N-dimethylaniline; With magnesium; In tetrahydrofuran; Heating;

2-bromo-1-chlorobenzene; In tetrahydrofuran; at 60 ℃; for 2.25h;

chlorodicyclohexylphosphane; With copper(l) chloride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 1h; Further stages.;

DOI:10.1002/1615-4169(20011231)343:8<789::AID-ADSC789>3.0.CO;2-A

Reference yield: 55.0%

2-bromo-1-chlorobenzene (694-80-4) + 1-chloro-2-(dimethylamino)benzene (698-01-1) + chlorodicyclohexylphosphane (16523-54-9) → DavePhos (213697-53-1)

Guidance literature:

1-chloro-2-(dimethylamino)benzene; With magnesium; ethylene dibromide; In tetrahydrofuran; for 29.5h; Heating;

2-bromo-1-chlorobenzene; In tetrahydrofuran; at 60 ℃; for 2h;

chlorodicyclohexylphosphane; With copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 9h; Further stages.;

DOI:10.1021/jo000691h

Reference yield: 52.0%

2-bromo-1-chlorobenzene (694-80-4) + cyclohexyl chloride (542-18-7) + 1-chloro-2-(dimethylamino)benzene (698-01-1) → DavePhos (213697-53-1)

Guidance literature:

Multistep reaction.;

DOI:10.1021/jo000691h

upstream raw materials:

2-bromo-1-chlorobenzene

cyclohexyl chloride

1-chloro-2-(dimethylamino)benzene

chlorodicyclohexylphosphane

Downstream raw materials:

4-acetyl-4'-trifluoromethylbiphenyl

2-[2-chloro-4-(trifluoromethyl)phenyl]acetic acid

2-chloro-4-(trifluoromethyl)phenylacetic acid tert-butyl-ester

[(η3-allyl)Pd(2-(dicyclohexylphosphino)-2'-(dimethylamino)biphenyl)]SbF6

Refernces

• 1、 Buchwald, Stephen L.,Mauger, Christelle,Mignani, Gerard,Scholz, Ulrich. "Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account". . p. 23 - 39. Retrieved 2007/10/03.
• 2、 Kaye, Steven,Fox, Joseph M.,Hicks, Frederick A.,Buchwald, Stephen L.. "The Use of Catalytic Amounts of CuCl and Other Improvements in the Benzyne Route to Biphenyl-Based Phosphine Ligands". . p. 789 - 794. Retrieved 2007/10/03.