MilliporeSigma
All Photos(4)

Documents

740845

Sigma-Aldrich

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

97%

Sign Into View Organizational & Contract Pricing

Synonym(s):
Ad-BGPhos, 5-[Bis(1-adamantyl)phosphino]-1′,3′,5′-triphenyl-1,4′-bi-1H-pyrazole, Adamantyl-BippyPhos
Empirical Formula (Hill Notation):
C44H47N4P
CAS Number:
Molecular Weight:
662.84
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
319856799718903124
Acetophenone-(phenyl-d5) 99 atom % D

319856

Acetophenone-(phenyl-d5)

AlPhos

799718

AlPhos

(Ad−BippyPhos)2PdCl2

903124

(Ad−BippyPhos)2PdCl2

reaction suitability

reagent type: ligand

reaction suitability

-

reaction suitability

-

reaction suitability

-

form

solid

form

-

form

powder

form

powder or crystals

storage temp.

2-8°C

storage temp.

-

storage temp.

−20°C

storage temp.

-

mp

295-300 °C

mp

19-20 °C (lit.)

mp

218-223 °C

mp

263 °C (Decomp)

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Gowrisankar, S.; et al.
ChemCatChem, 3, 1439-1441 (2011)
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 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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service