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642629

Di-tert-butylmethylphosphine

Name: Di-<I>tert</I>-butylmethylphosphine
Brand: ALDRICH

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

UNSPSC Code:

12352001

PubChem Substance ID:

24883212

MDL number:

MFCD11869304

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Properties

Quality Level

100

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

Description

Application

Di-tert-butylmethylphosphine (P^tBu₂Me) 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.

Bulky phosphine used with various palladium complexes in cross-coupling catalysis.

pictograms

GHS02,GHS05

signalword

Danger

hcodes

H250,H314

pcodes

P210 - P231 + P232 - P280 - P303 + P361 + P353 - P305 + P351 + P338 - P370 + P378

Hazard Classifications

Pyr. Liq. 1 - Skin Corr. 1B

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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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)

Room-temperature Hiyama cross-couplings of arylsilanes with alkyl bromides and iodides.

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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Global Trade Item Number

SKU	GTIN
642629-5G	04061838120434