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643777

Sigma-Aldrich

Di-tert-butyl(methyl)phosphonium tetrafluoroborate

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H22BF4P
CAS Number:
479094-62-7
Molecular Weight:
248.05
MDL number:
MFCD03840579
UNSPSC Code:
12352101
PubChem Substance ID:
24883295
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

reaction suitability

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)

mp

>230 °C (lit.)

functional group

phosphine

SMILES string

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

InChI key

BRDLRXCAHKUWJS-UHFFFAOYSA-O

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Application

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF3373V
WXBD8389V
MKCP9136
SHBJ8156
SHBG6822V

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Palladium-catalyzed borylation of primary alkyl bromides.
Joshi-Pangu A, et al.
The Journal of Organic Chemistry, 77(15), 6629-6633 (2012)
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
C4 phenyl aporphines with selective h5-HT 2B receptor affinity.
Kapadia N and Harding WW.
Bioorganic & Medicinal Chemistry Letters, 25(17), 3451-3454 (2015)
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
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

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