213697-53-1

Basic information

• Product Name: 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl
• Synonyms: DAVEPHOS;2-(DICYCLOHEXYLPHOSPHINO)-2'-(DIMETHYLAMINO)BIPHENYL;2-DICYCLOHEXYLPHOSPHINO-2'-(N,N-DIMETHYLAMINO)BIPHENYL;2-DICYCLOHEXYLPHOSPHINO-2'-(N,N-DIMETHY&;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-
• CAS NO: 213697-53-1
• Molecular Formula: C₂₆H₃₆NP
• Molecular Weight: 393.54
• EINECS: 1312995-182-4
• Product Categories: Phosphines;Biphenyl & Diphenyl ether;Phosphine Ligands;Synthetic Organic Chemistry;Achiral Phosphine;Aryl Phosphine;Buchwald Ligands Series;Buchwald Ligands&Precatalysts
• Mol File: 213697-53-1.mol

Chemical Properties

• Melting Point: 121-124 °C(lit.)
• Boiling Point: 539.6 °C at 760 mmHg
• Flash Point: 280.1 °C
• Appearance: white/crystal
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 5.04±0.18(Predicted)
• Water Solubility: Insoluble
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl(213697-53-1)
• EPA Substance Registry System: 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl(213697-53-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• TSCA: No
• HazardClass: AIR SENSITIVE
• Hazardous Substances Data: 213697-53-1(Hazardous Substances Data)

Usage

Uses

Used in the Chemical Industry:
2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl is used as a ligand in the palladium-catalyzed Suzuki coupling reaction for the formation of carbon-carbon bonds. This reaction is a widely employed method in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl is also used as an effective ligand in the Pd-catalyzed arylation of ester enolates. This application is significant in the synthesis of complex organic molecules and the development of new chemical compounds.
Furthermore, 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl can act as a ligand in the palladium-catalyzed amination of unactivated aryl chlorides. This reaction is crucial for the synthesis of various nitrogen-containing compounds, which are essential in the pharmaceutical and chemical industries.

Reaction

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. Ligand used in Pd-catalyzed C-N bond formation. A general synthesis of N6-aryl-2'deoxyadenosine analogues. Ligand used in Pd-catalyzed N-arylation of indoles. Ligand used in Pd-catalyzed synthesis of aryl-tert-butyl ethers. Effective ligand in the Pd-catalyzed arylation of ester enolates. Ligand employed in arylation of ketone enolates using ortho-halo nitrobenezenes. Ligand employed in the amination of aryl nonaflates using Pd catalysts. Ligand used for cascade alkenyl amination/Heck reaction for the synthesis of indoles. Ligand used in Pd-catalyzed Kumada-Corriu cross coupling at low temperatures. Ligand used in Rh-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines. Ligand used in Au-catalyzed cycloisomerization of allenes.

Upstream product

• 694-80-4 2-bromo-1-chlorobenzene 
• 542-18-7 cyclohexyl chloride 
• 698-01-1 1-chloro-2-(dimethylamino)benzene 
• 16523-54-9 chlorodicyclohexylphosphane 
• 698-00-0 2-bromo-N,N-dimethylaniline 
• 931-51-1 cyclohexylmagnesiumchloride 
• 95-51-2 o-chloroaniline 

Downstream Products

• 582292-77-1 2-amino-4-p-tolyl-quinoline-3-carbonitrile 
• 552331-81-4 5-(4-methoxy-benzyloxy)-2-pyridin-4-yl-[1,7]naphthyridine 
• 535936-23-3 benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate 
• 503612-54-2 1-(4-methoxyphenyl)-6-[4-(2-oxo-1-piperidinyl)phenyl]-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one 
• 474645-91-5 (R)-3-((4-(trifluoromethyl)phenyl)amino)pentanenitrile 
• 444343-50-4 (3,5-dinitrophenyl)-2-pyridylamine 
• 142557-76-4 4-acetyl-4'-trifluoromethylbiphenyl 
• 601513-26-2 2-[2-chloro-4-(trifluoromethyl)phenyl]acetic acid 
• 601513-27-3 2-chloro-4-(trifluoromethyl)phenylacetic acid tert-butyl-ester 
• 10282-31-2 4-morpholinobenzonitrile 
• 81693-80-3 1-hexyl-4-methoxybenzene 

Relevant articles and documents

A Mild One-Pot Reduction of Phosphine(V) Oxides Affording Phosphines(III) and Their Metal Catalysts

The metal-free reduction of a range of phosphine(V) oxides employing oxalyl chloride as an activating agent and hexachlorodisilane as reducing reagent has been achieved under mild reaction conditions. The method was successfully applied to the reduction of industrial waste byproduct triphenylphosphine(V) oxide, closing the phosphorus cycle to cleanly regenerate triphenylphosphine(III). Mechanistic studies and quantum chemical calculations support the attack of the dissociated chloride anion of intermediated phosphonium salt at the silicon of the disilane as the rate-limiting step for deprotection. The exquisite purity of the resultant phosphine(III) ligands after the simple removal of volatiles under reduced pressure circumvents laborious purification prior to metalation and has permitted the facile formation of important transition metal catalysts.

Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account

The palladium-catalyzed coupling of amines and aryl halides or aryl alcohol derivatives has matured from an exotic small-scale transformation into a very general, efficient and robust reaction during the last ten years. This article reports several applications of this method from an industrial vantage point, including ligand synthesis, synthesis of arylpiperazines, arylhydrazines and diarylamines. Much emphasis in placed on issues of scale-up and safety to underline the potential of C-N couplings as solutions for industrial-scale synthetic problems.

Ligands for metals and improved metal-catalyzed processes based thereon

One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

Ligands for metals and improved metal-catalyzed processes based thereon

One aspect of the present invention relates to novel ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

The Use of Catalytic Amounts of CuCl and Other Improvements in the Benzyne Route to Biphenyl-Based Phosphine Ligands

Biphenyl-based phosphine ligands can be prepared on a significantly larger scale than previously possible as a result of the following discoveries and improvements to the original experimental procedure: the finding that CuCl catalyzes the coupling of hindered dialkylchlorophosphines with Grignard reagents; the development of conditions that permit ClPCy2 to be prepared and utilized in situ; the development of a more reliable large-scale preparation of 2-dimethylaminophenylmagnesium halide.

An Improved Synthesis of Functionalized Biphenyl-Based Phosphine Ligands

Functionalized dicyclohexyl- and di-tert-butylphosphinobiphenyl ligands are prepared by the reaction of arylmagnesium halides with benzyne, followed by the addition of a chlorodialkylphosphine. This one-pot procedure is considerably less expensive and time-consuming than the method used previously to prepare such ligands. The cost of introducing the dicyclohexylphosphine group can be decreased by preparing chlorodicyclohexylphosphine from PCl3 and cyclohexylmagnesium chloride, and using the reagent without further purification. The new method is significant, as a variety of ligands can be produced in useful amounts by a procedure that is simple, with starting materials that are relatively inexpensive, and, in most cases, without chromatographic purification.