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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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5 TABS
€100.00
25 TABS
€347.00

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5 TABS
€100.00
25 TABS
€347.00

About This Item

Empirical Formula (Hill Notation):
C44H47N4P
CAS Number:
Molecular Weight:
662.84
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

€100.00


Please contact Customer Service for Availability

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Quality Level

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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1 of 4

This Item
5379744259931716
format

neat

format

neat

format

neat

format

neat

Quality Level

100

Quality Level

300

Quality Level

100

Quality Level

100

grade

analytical standard

grade

certified reference material, TraceCERT®

grade

analytical standard

grade

analytical standard

storage temp.

2-30°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

packaging

ampule of 10 mg

packaging

-

packaging

ampule of 50 mg

packaging

-

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[1] of aryl and heteroaryl bromides/chlorides with primary aliphatic alcohols.[2] It can also be used as a catalyst in the synthesis of fluorinated anilines by coupling fluoroalkylamines with aryl bromides and chlorides.[3]

Other Notes

Store at 2-8 °C.

related product

Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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)
    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)
    Palladium-catalyzed arylation of fluoroalkylamines.
    Brusoe A T and Hartwig J F
    Journal of the American Chemical Society, 137(26), 8460-8468 (2015)
    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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