Merck
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677264

Sigma-Aldrich

APhos

95%

Synonym(s):
(4-(N,N-Dimethylamino)phenyl)di-tert-butyl phosphine, A-taPhos, [4-(Dimethylamino)phenyl]bis(tert-butyl)phosphine
Empirical Formula (Hill Notation):
C16H28NP
CAS Number:
Molecular Weight:
265.37
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

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: catalyst
reagent type: ligand
reaction type: Cross Couplings

mp

57-61 °C

functional group

phosphine

SMILES string

CN(C)c1ccc(cc1)P(C(C)(C)C)C(C)(C)C

InChI

1S/C16H28NP/c1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8/h9-12H,1-8H3

InChI key

IQTHEAQKKVAXGV-UHFFFAOYSA-N

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This Item
901215901906759171
APhos 95%

Sigma-Aldrich

677264

APhos

Ephos ≥95%

Sigma-Aldrich

901215

Ephos

SPhos 95%

Sigma-Aldrich

901906

SPhos

CPhos 98%

Sigma-Aldrich

759171

CPhos

form

solid

form

powder or crystals

form

powder or crystals

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: catalyst, reagent type: ligand
reaction type: Cross Couplings

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: catalyst
reaction type: Cross Couplings, reagent type: ligand

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: catalyst
reaction type: Cross Couplings, reagent type: ligand

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

mp

57-61 °C

mp

161-162 °C

mp

164-166 °C (lit.), 165.5 °C

mp

108-113 °C

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

Application

Ligand used to prepare a palladium dichloride catalyst (678740) on treatment with PdCl2(COD). The catalyst effectively cross-couples aryl boronic acids with heteroaryl chlorides.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8B - Non-combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Anil S Guram et al.
Organic letters, 8(9), 1787-1789 (2006-04-21)
[reaction: see text] New air-stable PdCl(2){P(t)Bu(2)(p-R-Ph)}(2) (R = H, NMe(2), CF(3),) complexes represent simple, general, and efficient catalysts for the Suzuki-Miyaura cross-coupling reactions of aryl halides including five-membered heteroaryl halides and heteroatom-substituted six-membered heteroaryl chlorides with a diverse range of

Articles

An Introduction to A-Phos, its Applications and Advantages

Ligand used to prepare a palladium dichloride catalyst on treatment with PdCl2(COD). The catalyst effectively cross-couples aryl boronic acids with heteroaryl chlorides.

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