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665479

Sigma-Aldrich

(S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)piperidine

97%

Synonym(s):

(S)-(+)-4-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-piperidine, (S)-PipPhos

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About This Item

Empirical Formula (Hill Notation):
C25H22NO2P
Molecular Weight:
399.42
MDL number:
MFCD08276865
UNSPSC Code:
12352005
PubChem Substance ID:
24884739

Assay

97%

form

solid

mp

206-213 °C

SMILES string

C1CCN(CC1)P2Oc3ccc4ccccc4c3-c5c(O2)ccc6ccccc56

InChI

1S/C25H22NO2P/c1-6-16-26(17-7-1)29-27-22-14-12-18-8-2-4-10-20(18)24(22)25-21-11-5-3-9-19(21)13-15-23(25)28-29/h2-5,8-15H,1,6-7,16-17H2

InChI key

ZYDGLCZCEANEHK-UHFFFAOYSA-N

Application

DSM MonoPhos Family of Highly Efficient Privileged Ligands
Asymmetric hydrogenation of N-aryl imines
Phosphoramidite ligand used in a rhodium-catalyzed enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds.

Legal Information

Sold under license from DSM for research purposes only.

Storage Class Code

13 - Non 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

665479-100MG:
665479-2G:
665479-BULK:
665479-VAR:
665479-500MG:

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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Natasa Mrsić et al.
Journal of the American Chemical Society, 131(24), 8358-8359 (2009-06-18)
Asymmetric hydrogenation of N-aryl acetophenone imines using iridium/PipPhos leads to very high enantioselectivities up to >99% depending on the presence of electron-donating substituents in the 2-, 3-, and 5-position of the aryl ring. If the substituent is 2-methoxy, the resultant
Journal of Organometallic Chemistry, 692, 428-428 (2007)

Articles

DSM MonoPhos™ Ligands

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