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642629

Sigma-Aldrich

Di-tert-butylmethylphosphine

97%

Synonym(s):

(t-Bu)2PMe, Bis(tert-butyl)methylphosphine

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About This Item

Linear Formula:
[(CH3)3C]2PCH3
CAS Number:
6002-40-0
Molecular Weight:
160.24
MDL number:
MFCD11869304
UNSPSC Code:
12352001
PubChem Substance ID:
24883212

Assay

97%

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

bp

58 °C/12 mmHg (lit.)

density

0.824 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CP(C(C)(C)C)C(C)(C)C

InChI

1S/C9H21P/c1-8(2,3)10(7)9(4,5)6/h1-7H3

InChI key

JURBTQKVGNFPRJ-UHFFFAOYSA-N

Application

Bulky phosphine used with various palladium complexes in cross-coupling catalysis.
Di-tert-butylmethylphosphine (PtBu2Me) when added as HBF4 salt, enhances the reactivity of palladium-catalyzed direct arylation of heterocylic arenes with aryl chlorides, bromides and azine N-oxides with aryl triflates to form the corresponding biaryl and 2-aryl azine N-oxides, respectively. It may be used in the preparation of CoCl2(PtBu2Me)2, a cobalt phosphine complex, which in combination with methylaluminoxane (MAO) catalyzes the butadiene polymerization to form predominantly the cis-1,4 polymer.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H250,H314

Hazard Classifications

Pyr. Liq. 1 - Skin Corr. 1B

Storage Class Code

4.2 - Pyrophoric and self-heating 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis, structure, and butadiene polymerization behavior of alkylphosphine cobalt (II) complexes.
Ricci G, et al.
J. Mol. Catal. A: Chem., 226(2), 235-241 (2005)
Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramolecular studies leading to new intermolecular reactions.
Campeau LC, et al.
Journal of the American Chemical Society, 128(2), 581-590 (2006)
Jae-Young Lee et al.
Journal of the American Chemical Society, 125(19), 5616-5617 (2003-05-08)
The first method for achieving Hiyama couplings of unactivated alkyl bromides and iodides is reported. The desired carbon-carbon bond formation proceeds under mild conditions (room temperature) with good functional-group tolerance.
Direct arylation of azine N-oxides with aryl triflates.
Schipper DJ, et al.
Tetrahedron, 65(26), 4977-4983 (2009)

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