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700770

Sigma-Aldrich

(R)-SIPHOS-PE

97%

Synonym(s):

(11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1′, 7′-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine, N-Di[(R)-1-phenylethyl]-[(R)-1,1′-spirobiindane-7,7′-diyl]-phosphoramidite

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About This Item

Empirical Formula (Hill Notation):
C33H32NO2P
CAS Number:
500997-69-3
Molecular Weight:
505.59
MDL number:
MFCD08459342
UNSPSC Code:
12352005
PubChem Substance ID:
329762230

Assay

97%

form

powder

optical activity

[α]22/D +337°, c = 1 in chloroform

mp

90-96 °C

storage temp.

−20°C

InChI

1S/C33H32NO2P/c1-23(25-11-5-3-6-12-25)34(24(2)26-13-7-4-8-14-26)37-35-29-17-9-15-27-19-21-33(31(27)29)22-20-28-16-10-18-30(36-37)32(28)33/h3-18,23-24H,19-22H2,1-2H3/t23-,24-,33?/m1/s1

InChI key

ZXLQLIDJAURBDD-HRPAVAKOSA-N

Application

(R)-SIPHOS-PE can be used as:
  • A catalyst in the preparation of tricyclic alkaloid (+)-aphanorphine via asymmetric carboamination and Friedel−Crafts reaction.
  • A ligand in the synthesis of chiral ketones via hydroacylation of olefins using salicylaldehyde derivatives.
  • A ligand in the enantioselective synthesis of substituted pyrrolidine derivatives via Pd-catalyzed alkene aminoarylation reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

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

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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Regio-and enantioselective intermolecular hydroacylation: Substrate-directed addition of salicylaldehydes to homoallylic sulfides
Coulter MM, et al.
Journal of the American Chemical Society, 132(46), 16330-16333 (2010)
Recent developments in palladium-catalyzed alkene aminoarylation reactions for the synthesis of nitrogen heterocycles
Schultz DM and Wolfe JP
Synthesis, 44(03), 351-361 (2012)
Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination
Mai DN, et al.
Organic Letters, 13(11), 2932-2935 (2011)

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