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510017

Sigma-Aldrich

(Oxydi-2,1-phenylene)bis(diphenylphosphine)

greener alternative

98%

Synonym(s):

Bis[(2-diphenylphosphino)phenyl] ether, DPEPhos

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About This Item

Linear Formula:
O[C6H4P(C6H5)2]2
CAS Number:
166330-10-5
Molecular Weight:
538.55
MDL number:
MFCD00233863
UNSPSC Code:
12352112
PubChem Substance ID:
24873467
NACRES:
NA.22

Quality Level

100

Assay

98%

reaction suitability

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Hydroaminations
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

184-187 °C (lit.)

functional group

phosphine

greener alternative category

, Aligned

SMILES string

O(c1ccccc1P(c2ccccc2)c3ccccc3)c4ccccc4P(c5ccccc5)c6ccccc6

InChI

1S/C36H28OP2/c1-5-17-29(18-6-1)38(30-19-7-2-8-20-30)35-27-15-13-25-33(35)37-34-26-14-16-28-36(34)39(31-21-9-3-10-22-31)32-23-11-4-12-24-32/h1-28H

InChI key

RYXZOQOZERSHHQ-UHFFFAOYSA-N

Related Categories

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

Ligand for ruthenium-catalyzed greener amine synthesis from amines and alcohols by hydrogen-borrowing.

Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Nicholas R Andreychuk et al.
Dalton transactions (Cambridge, England : 2003), 47(14), 4866-4876 (2018-03-16)
Palladium-catalyzed coupling of 1-adamantylamine (2 equiv.) with 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethylxanthene afforded the proligand 4,5-bis(1-adamantylamino)-2,7-di-tert-butyl-9,9-dimethylxanthene, H2[XAd] (1), which upon deprotonation with excess KH or KCH2Ph in THF or dme generated [{K(THF)3}2(XAd)] (2a) and [K2(XAd)(dme)] (2b). Subsequent reaction of in situ generated 2a or
Zihao Zhang et al.
ChemSusChem, 13(18), 4922-4928 (2020-07-17)
Catalytic deoxygenation of even-numbered fatty acids into odd-chain linear α-olefins (LAOs) has emerged as a complementary strategy to oligomerization of ethylene, which only affords even-chain LAOs. Although enzymes and homogeneous catalysts have shown promising potential for this application, industrial production
Mohammed Zain Aldin et al.
Dalton transactions (Cambridge, England : 2003), 47(39), 13926-13938 (2018-09-19)
The reaction of [RuCl2(p-cymene)]2 with potassium O-ethylxanthate and a set of nine representative Ph2P-X-PPh2 bidentate phosphines (dppm, dppe, dppp, dppb, dpppe, dppen, dppbz, dppf, and DPEphos) afforded monometallic [Ru(S2COEt)2(diphos)] chelates 1-9 in 62-96% yield. All the products were fully characterized
Helen Larson et al.
The Journal of organic chemistry, 84(20), 13092-13103 (2019-09-25)
This manuscript details the development of the nickel-catalyzed arylation of oxazoles and benzoxazoles with aryl halides. A series of aryl, heteroaryl, and druglike electrophiles relevant to pharmaceutical applications were surveyed. The desired arylated products were obtained in synthetically useful yields

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