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695874

Sigma-Aldrich

2-Di-tert-butylphosphino-2′-(N,N-dimethylamino)biphenyl

Sinonimo/i:

tBuDavePhos

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About This Item

Formula empirica (notazione di Hill):
C22H32NP
Numero CAS:
224311-49-3
Peso molecolare:
341.47
Numero MDL:
MFCD03426986
Codice UNSPSC:
12352116
ID PubChem:
329761782
NACRES:
NA.22

Forma fisica

solid

Livello qualitativo

100

Impiego in reazioni chimiche

reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-X Bond Formation

Punto di fusione

114-118 °C

Gruppo funzionale

phosphine

Stringa SMILE

CN(C)c1ccccc1-c2ccccc2P(C(C)(C)C)C(C)(C)C

InChI

1S/C22H32NP/c1-21(2,3)24(22(4,5)6)20-16-12-10-14-18(20)17-13-9-11-15-19(17)23(7)8/h9-16H,1-8H3
PHLPNEHPCYZBNZ-UHFFFAOYSA-N

Categorie correlate

Applicazioni

Learn more about Buchwald Phosphine Ligands

Dialkylbiaryl phosphine ligand often used for Pd-catalyzed reactions in a range of contexts.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335,H413

Classi di pericolo

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand
Ruben Martin et al.
Accounts of chemical research, 41(11), 1461-1473 (2008-07-16)
The cores of many types of polymers, ligands, natural products, and pharmaceuticals contain biaryl or substituted aromatic structures, and efficient methods of synthesizing these structures are crucial to the work of a broad spectrum of organic chemists. Recently, Pd-catalyzed carbon-carbon

Articoli

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Contenuto correlato

Buchwald Group – Professor Product Portal

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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