2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl CAS 213697-53-1

Introduction：Basic information about 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl CAS 213697-53-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

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

• Product Name: 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl
• Synonyms: DAVEPHOS;2-DICYCLOHEXYLPHOSPHINO-2'-(N,N-DIMETHY&;2-(DICYCLOHEXYLPHOSPHINO)-2'-(DIMETHYLAMINO)BIPHENYL;2-Dicyclohexylphosphino-2'-(N,;2-(Dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl,98%DavePhos;2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)-;[1,1''-BIPHENYL]-2-AMINE, 2''-(DICYCLOHEXYLPHOSPHINO)-N,N-DIMETHYL-;2-Dicgclohexylphosphino-2’-(N,N-dimethylamino)biphenyl
• CAS: 213697-53-1
• MF: C26H36NP
• MW: 393.54
• EINECS: 606-749-5
• Product Categories: Buchwald Ligands&Precatalysts;Achiral Phosphine;Aryl Phosphine;Buchwald Ligands Series;Phosphines;Biphenyl & Diphenyl ether;Phosphine Ligands;Synthetic Organic Chemistry
• Mol File: 213697-53-1.mol

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

• Melting point: 121-124 °C(lit.)
• Boiling point: 539.6±43.0 °C(Predicted)
• storage temp.: Keep in dark place,Sealed in dry,Room Temperature
• form: crystal
• pka: 5.04±0.18(Predicted)
• color: white
• Water Solubility: Insoluble
• Sensitive: Air Sensitive
• InChI: InChI=1S/C26H36NP/c1-27(2)25-19-11-9-17-23(25)24-18-10-12-20-26(24)28(21-13-5-3-6-14-21)22-15-7-4-8-16-22/h9-12,17-22H,3-8,13-16H2,1-2H3
• InChIKey: ZEMZPXWZVTUONV-UHFFFAOYSA-N
• SMILES: C1(C2=CC=CC=C2P(C2CCCCC2)C2CCCCC2)=CC=CC=C1N(C)C
• CAS DataBase Reference: 213697-53-1(CAS DataBase Reference)

Safety Information

• Hazard Codes: Xi,Xn
• Risk Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• TSCA: No
• HazardClass: AIR SENSITIVE
• HS Code: 29310099
• Storage Class: 11 - Combustible Solids

2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl Usage And Synthesis

Reaction

1. Ligand used in the Pd-catalyzed Suzuki coupling and animation of unactivated aryl chlorides. The reactions generally occur at room temperature and give high yields of product.
2. Ligand used in Pd-catalyzed C-N bond formation. A general synthesis of N6-aryl-2'deoxyadenosine analogues.
3. Ligand used in Pd-catalyzed N-arylation of indoles.
4. Ligand used in Pd-catalyzed synthesis of aryl-tert-butyl ethers.
5. Effective ligand in the Pd-catalyzed arylation of ester enolates.
6. Ligand employed in arylation of ketone enolates using ortho-halo nitrobenezenes.
7. Ligand employed in the amination of aryl nonaflates using Pd catalysts.
8. Ligand used for cascade alkenyl amination/Heck reaction for the synthesis of indoles.
9. Ligand used in Pd-catalyzed Kumada-Corriu cross coupling at low temperatures.
10. Ligand used in Rh-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.
11. Ligand used in Au-catalyzed cycloisomerization of allenes.

Description

2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl is a potent inhibitor of the enzyme bromodomain. Bromodomain has been implicated in cancer and other diseases. It binds to the bromodomain in a covalent manner, blocking the ATP site and inhibiting bromodomain function. This inhibition has been shown to be selective for bromodomains over other domains.

Chemical Properties

white to light yellow crystals or

Uses

suzuki reaction

Uses

Effective ligand in the Pd-catalyzed arylation of ester enolates

Uses

2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl can act as ligand used in the palladium-catalyzed Suzuki coupling and amination of unactivated aryl chlorides.

Application

2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenylacts as a growth regulator by binding to Toll-like receptor 4 (TLR4), which is important in cytokine signaling. It also inhibits allyl carbonate production and cross coupling reactions between aryl chlorides and nitrogen atoms or amines. It has an inhibitory effect on depression, but this effect is not related to its inhibitory effect on bromodomains.

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Hydroaminations
reagent type: ligand
reaction type: Kumada Coupling
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl Preparation Products And Raw materials

• Raw materials: Ethyl acetate-->Diethyl ether-->Tetrahydrofuran-->Dichloromethane-->Ammonium hydroxide-->Dimethyl sulfate-->Iodomethane-->Magnesium-->Phosphorus trichloride-->Copper(I) chloride-->Diethylamine-->Cyclohexane-->1,2-Dibromoethane-->2-Chloroaniline-->4-Bromotoluene-->Chlorocyclohexane-->Bromocyclohexane-->2-Bromochlorobenzene-->2-Bromoaniline-->5-Bromo-m-xylene