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Merck
CN

665363

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

95% (HPLC)

Synonym(s):

(+)-N,N-Bis[(1R)-1-phenylethyl]-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, (11bS)

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About This Item

Empirical Formula (Hill Notation):
C36H30NO2P
CAS Number:
497883-22-4
Molecular Weight:
539.60
NACRES:
NA.22
PubChem Substance ID:
24884733
UNSPSC Code:
12352005
MDL number:
MFCD08561138

Key Documents

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Product Name

(S,R,R)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)bis(1-phenylethyl)amine, 95% (HPLC)

InChI key

LKZPDRCMCSBQFN-CLJLJLNGSA-N

SMILES string

C[C@@H](N([C@H](C)c1ccccc1)P2Oc3ccc4ccccc4c3-c5c(O2)ccc6ccccc56)c7ccccc7

InChI

1S/C36H30NO2P/c1-25(27-13-5-3-6-14-27)37(26(2)28-15-7-4-8-16-28)40-38-33-23-21-29-17-9-11-19-31(29)35(33)36-32-20-12-10-18-30(32)22-24-34(36)39-40/h3-26H,1-2H3/t25-,26-/m1/s1

assay

95% (HPLC)

mp

102-103 °C

functional group

amine
phenyl

Quality Level

100

Related Categories

Application

DSM MonoPhos Family of Highly Efficient Privileged Ligands
Chiral phosphoramidite ligand used in a highly enantioselective copper-catalyzed conjugate addition of diakylzincs to a variety of Michael acceptors. Also used in a palladium-catalyzed diethylzinc mediated umpolung allylation.

Features and Benefits

Advantages of the MonoPhos® ligands:
  • Superior enantiocontrol in numerous transformations
  • High activities at low catalyst loadings
  • Hydrogenations under low-pressure conditions

Legal Information

Sold under license from DSM for research purposes only.
MonoPhos is a registered trademark of DSM IP Assets B.V.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ8748
MKCF5150
MKBK9889V
01103CE

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Jorge Esquivias et al.
The Journal of organic chemistry, 70(18), 7451-7454 (2005-08-27)
[reaction: see text] The enantioselective catalytic 1,4-addition to alpha,beta-unsaturated ketimines is an unprecedented process. Herein, we document the copper-catalyzed addition of dialkylzinc reagents to (2-pyridylsulfonyl)imines of chalcones. This process occurs rapidly in the presence of a chiral phosphoramidite ligand to
Organic & Biomolecular Chemistry, 4, 1278-1278 (2006)
Privileged Ligands
Aldrich Chemfiles, 6(8), 7-7 null
Oliver Knopff et al.
Organic letters, 4(22), 3835-3837 (2003-02-26)
[formula: see text] The zinc enolates, resulting from the copper-catalyzed enantioselective conjugate addition of dialkyl zinc reagents to cyclic and acyclic enones, could be trapped, quantitatively, as silyl enol ethers with TMSOTf in apolar solvents or with TMSCI and NEt3.
Synlett, 1375-1375 (2001)

Articles

DSM MonoPhos™ Ligands

DSM collaboration offers MonoPhos™ ligands for research, based on the BINOL platform by Feringa and co-workers.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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