847616-85-7

Basic information

• Product Name: Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II)
• Synonyms: Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II);Di-μ-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II);Chloro(2'-aMino-1,1'-biphenyl-2-yl)palladiuM(II) diMer, Min. 98%;Di-Mu-chlorobis[2'-(aMino-N)[1,1'-biphenyl]-2-yl-C]dipalladiuM(II);Bis[2′-(amino-κN)[1,1′-biphenyl]-2-yl-κ;Di-μ-chlorobis[2′-(amino-N)[1,1′-biphenyl]-2-yl-C]dipalladium(II);Chloro(2'-amino-1,1'-biphenyl-2-yl)palladium(II)dimer,min.98%;-(amino-N)[1,1′
• CAS NO: 847616-85-7
• Molecular Formula: C₂₄H₂₀Cl₂N₂Pd₂
• Molecular Weight: 618.16
• Product Categories: Pd
• Mol File: 847616-85-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 207°C(lit.)
• Appearance: pale gray/Powder
• Sensitive: air sensitive
• CAS DataBase Reference: Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II)(CAS DataBase Reference)
• NIST Chemistry Reference: Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II)(847616-85-7)
• EPA Substance Registry System: Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II)(847616-85-7)

Safety Data

• Hazard Codes: Xn
• Statements: 19-36/37/38-40
• Safety Statements: 26-36/37
• RIDADR: UN 3175 4.1 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 847616-85-7(Hazardous Substances Data)

Usage

Description

Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II), with the CAS number 847616-85-7, is an organometallic compound that functions as a catalyst in various chemical reactions. It is characterized by its ability to facilitate α-arylations of methyl sulfones with aryl chlorides and cross-coupling reactions of aromatic boronic acids and acyl chlorides.

Uses

Used in Chemical Synthesis:
Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II) is used as a catalyst in the chemical synthesis industry for its ability to promote α-arylations of methyl sulfones with aryl chlorides. This application is crucial for the formation of new carbon-carbon bonds, which are essential in creating complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II) is utilized as a catalyst for cross-coupling reactions of aromatic boronic acids and acyl chlorides. This process is vital for the synthesis of various pharmaceutical compounds, as it allows for the efficient formation of specific molecular structures that can exhibit desired therapeutic properties.
Used in Material Science:
Di-Mu-chlorobis(2'-aMino-1,1'-biphenyl-2-yl-C,N)dipalladiuM(II) is also employed in material science as a catalyst for the synthesis of novel materials with unique properties. The cross-coupling reactions it facilitates enable the creation of materials with tailored characteristics, such as improved conductivity, stability, or specific optical properties, which can be applied in various technological applications.

Upstream product

• 90-41-5 2-phenylaniline 

Downstream Products

• 1375477-29-4 chloro[(di(1-adamantyl)-N-butylphosphine)-2-(2-aminobiphenyl)]palladium(II) 
• 847616-84-6 2'-(PdPCy₃Cl)-2-Aminobiphenyl 

Relevant articles and documents

Palladium-catalyzed primary amine-directed regioselective mono- and di-alkynylation of biaryl-2-amines

The first example of the palladium-catalyzed primary amine-directed C(sp2)-H alkynylation of biaryl-2-amines has been developed by using (bromoethynyl)triisopropylsilane as an alkynylating reagent. This protocol exhibits a broad substrate scope, excellent regioselectivity and gram-scale synthesis. Significantly, the versatility of this straightforward method was further demonstrated by controlled mono- and di-alkynylation.

The cyclopalladation reaction of 2-phenylaniline revisited

2-Phenylaniline reacted with Pd(OAc)2 in toluene at room temperature for 24 h in a one-to-one molar ratio and with the system PdCl 2, NaCl and NaOAc in a 1 (2-phenylaniline):1 (PdCl2):2 (NaCl):1 (NaOAc) molar ratio in methanol at room temperature for one week to give the dinuclear cyclopalladated compounds (μ-X)2[Pd{κ 2-N2′,C1-2-(2′-NH2C6H 4)C6H4}]2 [1a (X = OAc) and 1b (X = Cl)] in high yield. Moreover, the reaction between 2-phenylaniline and Pd(OAc)2 in one-to-one molar ratio in acid acetic at 60°C for 4 h, followed by a metathesis reaction with LiBr, allowed isolation of the dinuclear cyclopalladated compound (μ-Br)2[Pd{κ2- N2′,C1-2-(2′-NH2C6H4)C 6H4}]2 (1c) in moderate yield. A parallel treatment, but using monodeuterated acetic acid (DOAc) as solvent in the cyclopalladation reaction, allowed isolation of a mixture of compounds 1c, 1cd1 [Pd{κ2-N2′,C1-2-(2′-NH 2C6H4)C6H4](μ-Br) 2[Pd{κ2-N2′,C1-2-(2′-NH 2C6H4)-3-d-C6H3] and 1cd2 (μ-Br)2[Pd{κ2-N2′,C1-2- (2′-NH2C6H4)-3-d-C6H 3}]2 in moderate yield and with a deuterium content of ca. 60%. 1a and 1b reacted with pyridine and PPh3 affording the mononuclear cyclopalladated compounds [Pd{κ2-N2′,C1-2- (2′-NH2C6H4)C6H 4}(X)(L)] [2a (X = OAc, L = py), 2b (X = Cl, L = py), 3a (X = OAc, L = PPh3) and 3b (X = Cl, L = PPh3)] in a yield from moderate to high. Furthermore, 1a reacted with Na(acac) ? H2O to give the mononuclear cyclopalladated compound 4 [Pd{κ2- N2′,C1-2-(2′-NH2C6H4)C 6H4}(acac)] in moderate yield. 1H NMR studies in CDCl3 solution of 2a, 2b, 3a, 3b and 4 showed that 2a and 3a presented an intramolecular hydrogen bond between the acetato ligand and the amino group, and were involved in a dynamic equilibrium with water present in the CDCl3 solvent; and that the enantiomeric molecules of 2b and 4 were in a fast exchange at room temperature, while they were in a slow exchange for 2a, 3a and 3b. The X-ray crystal structures of 3b and 4 were determined. 3b crystallized in the triclinic space group P1? with a = 9.9170(10), b = 10.4750(10), c = 12.0890(10) A?, α = 98.610(10)°, β = 94.034(10)°and γ = 99.000(10)°and 4 in the monoclinic space group P21/a with a = 11.5900(10), b = 11.2730(10), c = 12.2150(10) A?, α = 90°, β = 107.6560(10)°and γ = 90°.