Dichloro[1,3-bis(2,6-diisopropylphenyl)imidazolyl-2-idene](3-chloropyridyl)palladium - ≥98% , CAS No.905459-27-0

CAS: 905459-27-0 Cat. No.: P139415 Peso molecular: 679.46 Número EC: 664-484-0 PubChem CID: 16218181

GRADE & PURITY ≥98%

Synonyms

Pd(PEPPSI)IPr | (1,3-BIS(2,6-DIISOPROPYLPHENYL)IMIDAZOLIDENE) (3-CHLOROPYRIDYL) PALLADIUM(II) DICHLORIDE | PEPPSI-SIPr catalyst | BLDKGTGQENJFON-UHFFFAOYSA-L | (1,3-Bis(2,6-diisopropylphenyl)imidazolidene) ( 3-chloropyridyl) palladium(II) dichloride | A8

Storage

Room temperature

Shipped In

Normal

Descripción general

Product class
M-P, Homogeneous Catalysts, M-N, N-Heterocyclic Carbene Ligands, M-C, IPr, PEPPSI Ligands, Pyridyl Ligands, Bidentate Ligands

Reaction type
Cross Coupling Reactions with Arenes, Amination, Buchwald-Hartwig Aminaton, CH-Activation, Kumada Coupling Reaction, Negishi Coupling Reaction, Oxidation, Sonogashira-Hagihara Coupling Reaction, Suzuki-Miyaura Coupling Reaction

Chemical properties

Chemical formula

C32H40N3Cl3Pd

Empirical formula

[(IPr)Pd(3-Cl-py)Cl2]

Molecular weight

679.47

Metal

Pd

Theoretical metal content

16

Physical state

crystalline

Color

yellow

Application

• Catalyst for Kumada-Tamao-Corriu (KTC) reaction[1] (eq. 1)

• Catalyst for Negishi coupling reaction[2] (eq. 2)

• Catalyst for Suzuki coupling reaction[3] (eq. 3)

• Catalyst for Buchwald-Hartwig amination reaction[4] (eq. 4)

Applications & references

Preparation of substituted heterobicyclic carboxylic acids, as well N-oxides and agriculturally accepted salts, which are applied in controlling plant growth.

Reference: WO2011045561

Manufacture of pyrazol derivatives as modulators of cannabinoid receptors, which are useful in the treatment of obesity and overweight.

Reference: WO2008 074982

Novel synthetic approach of glycine transport GT1 inhibitor sacrosine.

Reference: WO2007 060203

Intramolecular direct arylation of aryl chlorides.

Reference: Synth. Comm. 2011, 41, 41 (DOI: 10.1080/00397910903531755)

Oxidation of secondary alcohols.

Reference: J. Org. Chem. 2011, 76, 1390 (DOI: DOI: 10.1021/jo102385u)

Suzuki-Miyaura coupling reaction.

Reference: Org. Lett. 2011, 13, 146 (DOI: 10.1021/ol1027283)

Negishi coupling reactions.

Reference: Chem. Eur. J. 2006, 12, 4749 (DOI: 10.1002/chem.20060020) ; Org. Lett. 1999, 1, 1323 (DOI: 10.1021/ol9907872); J. Org. Chem. 2002, 67, 79 (DOI: 10.1021/jo0105787)

Palladium catalyzed anaerobic oxidation of secondary alcohols under mild reaction conditions.

Reference: J. Org. Chem. 2011, 76, 1390 (DOI: 10.1021/jo102385u)

Specifications

Sinónimos

Pd(PEPPSI)IPr | (1, 3-BIS(2, 6-DIISOPROPYLPHENYL)IMIDAZOLIDENE) (3-CHLOROPYRIDYL) PALLADIUM(II) DICHLORIDE | PEPPSI-SIPr catalyst | BLDKGTGQENJFON-UHFFFAOYSA-L | (1, 3-Bis(2, 6-diisopropylphenyl)imidazolidene) ( 3-chloropyridyl) palladium(II) dichloride | A8

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504768325
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504768325
• Sonrisas canónicas: CC(C)C1=C(C(=CC=C1)C(C)C)N2CN(C=C2)C3=C(C=CC=C3C(C)C)C(C)C.C1=CC(=CN=C1)Cl.Cl[Pd]Cl
• IUPAC Name: 1,3-bis[2,6-di(propan-2-yl)phenyl]-2H-imidazole;3-chloropyridine;dichloropalladium
• InChIKey: BLDKGTGQENJFON-UHFFFAOYSA-L
• INCHI: 1S/C27H38N2.C5H4ClN.2ClH.Pd/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;6-5-2-1-3-7-4-5;;;/h9-16,18-21H,17H2,1-8H3;1-4H;2*1H;/q;;;;+2/p-2
• Isómeros SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2CN(C=C2)C3=C(C=CC=C3C(C)C)C(C)C.C1=CC(=CN=C1)Cl.Cl[Pd]Cl
• WGK Alemania: 3
• PubChem CID: 16218181
• Peso molecular: 679.46

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Cumenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Cumenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Cumenes
• Alternative Parents: Phenylpropanes Aniline and substituted anilines Pyridines and derivatives Aryl chlorides Imidazolines Heteroaromatic compounds Tertiary amines Organic transition metal salts Organic metal halides Enamines Azacyclic compounds Organochlorides Organic chloride salts Hydrocarbon derivatives Organic cations
• Molecular Framework: Not available
• Substituents: Cumene - Phenylpropane - Aniline or substituted anilines - Aryl chloride - Aryl halide - Pyridine - Heteroaromatic compound - 4-imidazoline - Tertiary amine - Organoheterocyclic compound - Organic transition metal salt - Organic metal salt - Azacycle - Enamine - Organic metal halide - Organic salt - Amine - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic nitrogen compound - Organic chloride salt - Organic cation - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Punto de fusión (°C): 230°C
• Peso molecular: 681.500 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 679.148 Da
• Monoisotopic Mass: 679.148 Da
• Topological Polar Surface Area: 19.400 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 515.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3