Key Documents

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine]

Name: (<I>R</I>)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-<I>tert</I>-butylphenyl)phosphine]
Brand: ALDRICH

≥97%, optical purity ee: ≥99%

Synonym(s):

(R)-2,2′-Bis[bis(3,5-di-tert-butyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl, (R)-3,5-t-Bu-MeOBIPHEP, SL-A121-1

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About This Item

Empirical Formula (Hill Notation):

C₇₀H₉₆O₂P₂

CAS Number:

192138-05-9

Molecular Weight:

1031.46

NACRES:

NA.22

PubChem Substance ID:

329753371

UNSPSC Code:

12352112

MDL number:

MFCD09753001

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Quality Level

100

assay

≥97%

optical purity

ee: ≥99%

functional group

phosphine

SMILES string

COc1cccc(P(c2cc(cc(c2)C(C)(C)C)C(C)(C)C)c3cc(cc(c3)C(C)(C)C)C(C)(C)C)c1-c4c(OC)cccc4P(c5cc(cc(c5)C(C)(C)C)C(C)(C)C)c6cc(cc(c6)C(C)(C)C)C(C)(C)C

InChI

1S/C70H96O2P2/c1-63(2,3)45-33-46(64(4,5)6)38-53(37-45)73(54-39-47(65(7,8)9)34-48(40-54)66(10,11)12)59-31-27-29-57(71-25)61(59)62-58(72-26)30-28-32-60(62)74(55-41-49(67(13,14)15)35-50(42-55)68(16,17)18)56-43-51(69(19,20)21)36-52(44-56)70(22,23)24/h27-44H,1-26H3

InChI key

PBYRAYONARLAQJ-UHFFFAOYSA-N

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This Item	29517	29516
Sigma-Aldrich 29524 (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine]	Sigma-Aldrich 29517 (S)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-dimethylphenyl)phosphine]	Sigma-Aldrich 29516 (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-dimethylphenyl)phosphine]
assay ≥97%	assay ≥97%	assay ≥97% (³¹P-NMR)
functional group phosphine	functional group phosphine	functional group phosphine
Quality Level 100	Quality Level 100	Quality Level 100
optical purity ee: ≥99%	optical purity ee: ≥99%	optical purity ee: ≥99%

General description

sold in collaboration with Solvias AG

Application

Atropisomeric MeOBIPHEP ligands

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] can be used as a ligand to prepare:

1,2-Dihydropyridines through Rh-catalyzed cycloaddition of diynes to sulfonimines.
Enantiorich disubstituted γ-lactams via intramolecular allylic alkylation reaction using Pd catalyst.
A Ru-metal complex, which acts as a hydrogenation catalyst applicable in the synthesis of an organic building block (S)-3-fluoromethyl-γ-butyrolactone.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Enantioselective γ-lactam synthesis via palladium-catalyzed intramolecular asymmetric allylic alkylation

Bantreil X, et al.

Synlett, 2009(09), 1441-1444 (2009)

Highly enantioselective rhodium-catalyzed [2+2+2] cycloaddition of diynes to sulfonimines

Amatore M, et al.

Journal of the American Chemical Society, 135(12), 4576-4579 (2013)

Development of a scalable synthesis of (S)-3-fluoromethyl-γ-butyrolactone, building block for Carmegliptin′s lactam moiety

Adam J-M, et al.

Organic Process Research & Development, 15(3), 515-526 (2011)

Articles

MeOBIPHEP

Solvias MeOBIPHEP Ligands: State-of-the-art atropisomeric MeOBIPHEP ligands, also referred to as MeO-BIPHEP, originally developed by Roche, have an extraordinarily broad performance profile for many synthetic applications due to their modular ligand design.

Global Trade Item Number

SKU	GTIN
29524-500MG	04061832622873
29524-5G	04061832622880
29524-100MG	04061832622866
29524-1G	04061826094808

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