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Merck
CN

665479

(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
UNSPSC Code:
12352005
PubChem Substance ID:
24884739
MDL number:
MFCD08276865

Key Documents

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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

SMILES string

C1CCN(CC1)P2Oc3ccc4ccccc4c3-c5c(O2)ccc6ccccc56

InChI key

ZYDGLCZCEANEHK-UHFFFAOYSA-N

assay

97%

form

solid

mp

206-213 °C

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

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
01203CE

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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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