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791016

RockPhos

Name: RockPhos
Brand: ALDRICH

97%

Synonym(s):

2-Di(tert-butyl)phosphino-2′,4′,6′-triisopropyl-3-methoxy-6-methylbiphenyl, Di-tert-butyl(2′,4′,6′-triisopropyl-3-methoxy-6-methyl-[1,1′-biphenyl]-2-yl)phosphine

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About This Item

Empirical Formula (Hill Notation):

C₃₁H₄₉OP

CAS Number:

1262046-34-3

Molecular Weight:

468.69

MDL number:

MFCD20922895

UNSPSC Code:

12352112

PubChem Substance ID:

329768254

NACRES:

NA.22

Quality Level

100

Assay

97%

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: ligand
reaction type: Cross Couplings

mp

121-131 °C

functional group

phosphine

storage temp.

15-25°C

SMILES string

CC1=C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)C(P(C(C)(C)C)C(C)(C)C)=C(OC)C=C1

InChI

1S/C31H49OP/c1-19(2)23-17-24(20(3)4)28(25(18-23)21(5)6)27-22(7)15-16-26(32-14)29(27)33(30(8,9)10)31(11,12)13/h15-21H,1-14H3

InChI key

CVLLAKCGAFNZHJ-UHFFFAOYSA-N

Related Categories

Buchwald Catalysts & Ligands

Phosphine Ligands

Application

RockPhos is a biphenyl-based phosphine ligand used with Pd(0) catalyst for carbon-carbon and carbon-heteroatom bond formation reactions.
It can also be employed in the:

2-fluroethoxylation of bromo-chalcones in the presence of palladium catalyst.
Conversion of aryl chlorides into aryl methoxides using RockPhos Pd G3 as a catalyst.

Storage Class Code

11 - Combustible Solids

WGK

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’.

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A general and efficient Pd-catalyzed rapid 2-fluoroethoxylation of bromo-chalcones

Rangarajan TM, et al.

Journal of Fluorine Chemistry, 186(10), 101-110 (2016)

An Improved Synthesis of BrettPhos-and RockPhos-Type Biarylphosphine Ligands

Hoshiya N and Buchwald SL

Advanced Synthesis & Catalysis, 354(10), 2031-2037 (2012)

P-chlorobenzyl ether: A p-methoxybenzyl ether in disguise

Viuff AH, et al.

Organic Letters, 18(22), 5773-5775 (2016)