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665290

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

97%

Synonym(s):

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

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100 mg
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$98.60
500 mg
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$460.00

About This Item

Empirical Formula (Hill Notation):
C36H30NO2P
CAS Number:
380230-02-4
Molecular Weight:
539.60
NACRES:
NA.22
PubChem Substance ID:
24884726
UNSPSC Code:
12352005
MDL number:
MFCD04117688

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Quality Segment

assay

97%

form

solid

reaction suitability

reagent type: chrial catalyst

mp

88-89 °C

functional group

amine, phenyl

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-/m0/s1

InChI key

LKZPDRCMCSBQFN-UIOOFZCWSA-N

Application

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.
DSM MonoPhos Family of Highly Efficient Privileged Ligands
The product may be used as a ligand in:
  • Iridium-catalyzed allylic etherification of acyclic, achiral allylic carbonates with potassium silanolates to form chiral allylic alcohols.
  • Palladium-catalyzed asymmetric allylic cyclisation of N-tosyl and N-benzyl carbonates to form the corresponding pyrrolidine and piperidine derivatives, respectively.
  • Intramolecular iridium-catalyzed allylic cyclizationof (E)-allylic methyl carbonates to form 2,5-trans/cis pyrrolidine derivatives.

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.

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This Item
665347668192665355
(S,S,S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a’]dinaphthalen-4-yl)bis(1-phenylethyl)amine 97%

Sigma-Aldrich

665290

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

(S,R)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)-(1-phenylethyl)amine 96%

Sigma-Aldrich

665347

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

(S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a;3,4- a′]dinaphthalen-4-yl)dimethylamine 97%

Sigma-Aldrich

668192

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

(S)-(+)-Benzyl(3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a′]dinaphthalen-4-yl)methylamine 97%

Sigma-Aldrich

665355

(S)-(+)-Benzyl(3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a′]dinaphthalen-4-yl)methylamine

description

97%

description

96%

description

97%

description

97%

assay

97%

assay

96%

assay

97%

assay

97%

form

solid

form

solid

form

solid

form

solid

functional group

amine, phenyl

functional group

-

functional group

amine

functional group

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

88-89 °C

mp

213-220 °C

mp

190 °C (dec.)

mp

155-159 °C

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Gloves, type N95 (US)

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