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
• Article Data: 6

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

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.

Chemical Properties

white to light yellow crystals or

Uses

Different sources of media describe the Uses of 213697-53-1 differently. You can refer to the following data:
1. suzuki reaction
2. Effective ligand in the Pd-catalyzed arylation of ester enolates
3. 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl can act as ligand used in the palladium-catalyzed Suzuki coupling and amination of unactivated aryl chlorides.

Upstream product

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

Downstream Products

• 444343-50-4 (3,5-dinitrophenyl)-2-pyridylamine 
• 142557-76-4 4-acetyl-4'-trifluoromethylbiphenyl 
• 700844-86-6 tert-butyl (2E)-3-{6-cyano-7-[(2,4-dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridin-2-yl}prop-2-enoate 
• 863615-26-3 rac.-[Ru(η6:η1-2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl)Cl2] 
• 1132754-54-1 [PdCl((eta.5-C5H5)Fe((η5-C5H3)-N2C4H(CH3)2)(2-(dicyclohexylphosphanyl)-2'-(N,N-dimethylamino)biphenyl)] 
• 1268489-10-6 [IrCl(COD)(2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl)] 
• 1445085-87-9 C₂₆H₃₆NP*C₁₃H₁₃NO₃PdS 
• 1196707-11-5 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)-1,1'-biphenylgold⁽¹⁾ chloride 
• 10282-31-2 4-morpholinobenzonitrile 
• 601513-26-2 2-[2-chloro-4-(trifluoromethyl)phenyl]acetic acid 
• 601513-27-3 2-chloro-4-(trifluoromethyl)phenylacetic acid tert-butyl-ester 
• 474645-91-5 (R)-3-((4-(trifluoromethyl)phenyl)amino)pentanenitrile 
• 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 
• 535936-23-3 benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate 

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.

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.

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.