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643777

Sigma-Aldrich

Di-tert-butyl(methyl)phosphonium tetrafluoroborate

97%

Sinonimo/i:

(t-Bu)2PMeHBF4, Bis(1,1-dimethylethyl)methylphosphine tetrafluoroborate

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About This Item

Formula empirica (notazione di Hill):
C9H22BF4P
Numero CAS:
479094-62-7
Peso molecolare:
248.05
Numero MDL:
MFCD03840579
Codice UNSPSC:
12352101
ID PubChem:
24883295
NACRES:
NA.22

Livello qualitativo

100

Saggio

97%

Stato

solid

Impiego in reazioni chimiche

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

pH

1.79 (1% in solution)

Punto di fusione

>230 °C (lit.)

Gruppo funzionale

phosphine

Stringa SMILE

F[B-](F)(F)F.C[PH+](C(C)(C)C)C(C)(C)C

InChI

1S/C9H21P.BF4/c1-8(2,3)10(7)9(4,5)6;2-1(3,4)5/h1-7H3;/q;-1/p+1
BRDLRXCAHKUWJS-UHFFFAOYSA-O

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Categorie correlate

Applicazioni

Di-tert-butyl(methyl)phosphonium tetrafluoroborate may be used in the preparation of a precursor for nantenine analogs bearing a C4 phenyl substituent, which shows an affinity for 5-HT2B receptor. It may also be used in the palladium-catalyzed borylation of primary alkyl electrophiles (bromides, iodides or tosylates) using bis(pinacolato)diboron or bis(neopentyl glycolato)diboron as the boron source.
The phosphonium salt is used for Pd catalyzed cross coupling reaction.

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314

Classi di pericolo

Eye Dam. 1 - Skin Corr. 1B

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificati d'analisi (COA)

Lot/Batch Number
MKCP9136
SHBJ8156
SHBG6822V
SHBF0723V
SHBC1832V

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Jian-Xin Wang et al.
Organic letters, 10(14), 2923-2926 (2008-06-26)
A general and efficient synthesis of 5-aryl imidazo[1,5- a]pyrazines by palladium-catalyzed coupling of the corresponding 8-substituted derivatives with aryl halides is described. The scope of this new reaction for the imidazo[1,5- a]pyrazine ring system was explored using three readily available
Laurence Caron et al.
Organic letters, 10(20), 4533-4536 (2008-09-25)
Direct arylation reactions of nitrobenzenes and aryl halides occur in good yield and high ortho regioselectivity. These reactions can be performed on gram scale with as few as 3 equiv of the nitro arene relative to the aryl halide. The
C4 phenyl aporphines with selective h5-HT 2B receptor affinity.
Kapadia N and Harding WW.
Bioorganic & Medicinal Chemistry Letters, 25(17), 3451-3454 (2015)
Palladium-catalyzed borylation of primary alkyl bromides.
Joshi-Pangu A, et al.
The Journal of Organic Chemistry, 77(15), 6629-6633 (2012)
Marc Lafrance et al.
Journal of the American Chemical Society, 128(27), 8754-8756 (2006-07-06)
Penta-, tetra-, tri-, and difluorobenzenes undergo direct arylation with a wide range of arylhalides in high yield. Inverse reactivity is observed compared to the common electrophilic aromatic substitution pathway since electron-deficient, C-H acidic arenes react preferentially. Computational studies indicate that

Global Trade Item Number

SKUGTIN
643777-5G4061833357194
643777-1G4061826733219

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