Key Documents

740845

5-[Di(1-adamantyl)phosphino]-1′,3′,5′-triphenyl-1′H-[1,4′]bipyrazole

Name: 5-[Di(1-adamantyl)phosphino]-1&#8242;,3&#8242;,5&#8242;-triphenyl-1&#8242;<I>H</I>-[1,4&#8242;]bipyrazole
Brand: ALDRICH

97%, solid

Synonym(s):

Ad-BGPhos, 5-[Bis(1-adamantyl)phosphino]-1′,3′,5′-triphenyl-1,4′-bi-1H-pyrazole, Adamantyl-BippyPhos

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About This Item

Empirical Formula (Hill Notation):

C₄₄H₄₇N₄P

CAS Number:

1239478-87-5

Molecular Weight:

662.84

UNSPSC Code:

12161600

PubChem Substance ID:

329765445

NACRES:

NA.22

MDL number:

MFCD22200502

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Properties

Product Name

5-[Di(1-adamantyl)phosphino]-1′,3′,5′-triphenyl-1′H-[1,4′]bipyrazole, 97%

Quality Level

100

assay

97%

form

solid

reaction suitability

reagent type: ligand

mp

295-300 °C

storage temp.

2-8°C

SMILES string

C1[C@@H]2C[C@@H]3C[C@H]1C[C@](C2)(C3)P(c4ccnn4-c5c(nn(-c6ccccc6)c5-c7ccccc7)-c8ccccc8)[C@@]9%10C[C@@H]%11C[C@@H](C[C@@H](C%11)C9)C%10

InChI

1S/C44H47N4P/c1-4-10-36(11-5-1)40-42(41(37-12-6-2-7-13-37)47(46-40)38-14-8-3-9-15-38)48-39(16-17-45-48)49(43-24-30-18-31(25-43)20-32(19-30)26-43)44-27-33-21-34(28-44)23-35(22-33)29-44/h1-17,30-35H,18-29H2/t30-,31+,32-,33-,34+,35-,43-,44-

InChI key

IHFBOUNFWVRWAQ-GOSCEEDCSA-N

Description

Application

5-[Di(1-adamantyl)phosphino]-1′,3′,5′-triphenyl-1′H-[1,4′]bipyrazole (Ad-BippyPhos) is an effective ligand that catalyzes C-O coupling reactions of aryl and heteroaryl bromides/chlorides with primary aliphatic alcohols. It can also be used as a catalyst in the synthesis of fluorinated anilines by coupling fluoroalkylamines with aryl bromides and chlorides.

Other Notes

Store at 2-8 °C.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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A general and efficient catalyst for palladium-catalyzed C? O coupling reactions of aryl halides with primary alcohols.

Gowrisankar S, et al.

Journal of the American Chemical Society, 132(33), 11592-11598 (2010)

S. Gowrisankar, et al.

Chemistry (Weinheim An Der Bergstrasse, Germany), 2498-2502 (2012)

Palladium-catalyzed arylation of fluoroalkylamines.

Brusoe A T and Hartwig J F

Journal of the American Chemical Society, 137(26), 8460-8468 (2015)

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Global Trade Item Number

SKU	GTIN
740845-5G	04061833339008
740845-1G	04061826549452
740845-250MG	04061826549469