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740845

Sigma-Aldrich

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

97%

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
MDL number:
MFCD22200502
UNSPSC Code:
12161600
PubChem Substance ID:
329765445
NACRES:
NA.22

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

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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.

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR2582
MKCS2443
MKCQ7513
MKCP9079
MKCP0943

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Palladium-Catalyzed C?O Coupling of a Sterically Hindered Secondary Alcohol with an Aryl Bromide and Significant Purity Upgrade in the API Step.
Young I S, et al.
Organic Process Research & Development, 22(5), 585-594 (2018)
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)
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)
Saravanan Gowrisankar et al.
Journal of the American Chemical Society, 132(33), 11592-11598 (2010-08-03)
An efficient procedure for palladium-catalyzed coupling reactions of (hetero)aryl bromides and chlorides with primary aliphatic alcohols has been developed. Key to the success is the synthesis and exploitation of the novel bulky di-1-adamantyl-substituted bipyrazolylphosphine ligand L6. Reaction of aryl halides
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