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ChemicalBook > CAS DataBase List > (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE

(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE

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Product Name
(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE
CAS No.
500997-69-3
Chemical Name
(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE
Synonyms
(R)-SIPHOS-PE;(S)-SIPHOS-PE;(RA,R,R)-SIPHOS-PE;(R)-SIPHOS-PE 97%;(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE;1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE;N-DI[(R)-1-PHENYLETHYL]-[(S)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE;N-DI[(R)-1-PHENYLETHYL]-[(R)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE;N-Di[(R)-1-phenylethyl]-[(R)-1,1'-spirobiindane-7,7'-diyl]-phosphoramidite ,98%;N,N-bis[(1R)-1-phenylethyl]-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-12-amine
CBNumber
CB4471613
Molecular Formula
C33H32NO2P
Formula Weight
505.59
MOL File
500997-69-3.mol
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(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE Property

Melting point:
98-100°C
alpha 
+300° (c 1.0, CH2Cl2)
Boiling point:
617.8±65.0 °C(Predicted)
storage temp. 
-20°C
pka
0.40±0.20(Predicted)
form 
solid
color 
white
optical activity
[α]22/D +337°, c = 1 in chloroform
Sensitive 
moisture sensitive
InChIKey
ZXLQLIDJAURBDD-HRPAVAKOSA-N
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36/37
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
700770
Product name
(R)-SIPHOS-PE
Purity
97%
Packaging
50mg
Price
$190
Updated
2022/05/15
Strem Chemicals
Product number
15-5162
Product name
(11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine, min. 98% (R)-SIPHOS-PE
Packaging
100mg
Price
$160
Updated
2024/03/01
Strem Chemicals
Product number
15-5162
Product name
(11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine, min. 98% (R)-SIPHOS-PE
Packaging
500mg
Price
$632
Updated
2024/03/01
ChemScene
Product number
CS-0037331
Product name
(R)-SIPHOS-PE
Purity
≥97.0%
Packaging
50mg
Price
$95
Updated
2021/12/16
ChemScene
Product number
CS-0037331
Product name
(R)-SIPHOS-PE
Purity
≥97.0%
Packaging
100mg
Price
$185
Updated
2021/12/16
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(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE Chemical Properties,Usage,Production

Reaction

  1. Chiral ligands for copper-catalyzed asymmetric allylic alkylation with dialkylzincs.
  2. Chiral ligands for copper-catalyzed asymmetric conjugate addition of diethylzinc to enones.
  3. Chiral ligands for palladium-catalyzed asymmetric hydrosilylation of styrenes
  4. Chiral ligands for copper-catalyzed asymmetric ring-opening of oxabicyclic alkenes with Grignard reagents.
  5. Chiral ligands for nickel-catalyzed asymmetric hydrovinylation of α-alkyl vinylarenes.
  6. Chiral ligands for iridium-catalyzed asymmetric hydrogenation of cyclic enamines.
  7. Chiral ligands for iridium-catalyzed asymmetric hydrogenation of cyclic imines.
  8. Chiral ligands for gold-catalyzed asymmetric [2 + 2] cycloaddition reaction.
  9. Chiral ligands for rhodium-catalyzed asymmetric hydroacylation of salicylaldehydes to homoallylic sulfides.
  10. Chiral ligands for palladium-catalyzed asymmetric carboamination reactions. 



Uses

(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.

(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE Preparation Products And Raw materials

Raw materials

CALCIUM HYDRIDE Benzyl chloride (R,R)-(+)-BIS(ALPHA-METHYLBENZYL)AMINE HYDROCHLORIDE Ethanol Acetone Sodium bromide Methanesulfonic acid Hydrogen peroxide Sodium chloride Toluene N,N-Diisopropylethylamine Nickel (R,R)-(+)-BIS(ALPHA-METHYLBENZYL)AMINE HYDROCHLORIDE Cinchonidine Triethylamine Boron tribromide Palladium 3-Hydroxybenzaldehyde Phosphorus trichloride (R)-1,1'-SPIROBIINDANE-7,7'-DIOL Tetrahydrofuran Ethyl acetate Hydrochloric acid Sodium bicarbonate Hydrogen Dichloromethane Sodium hydroxide PETROLEUM ETHER n-Butyllithium

Preparation Products

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(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE Suppliers

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500997-69-3, (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINERelated Search:

(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE 3A,4,7,7A-TETRAHYDROINDENE (R,R)-(+)-BIS(ALPHA-METHYLBENZYL)AMINE HYDROCHLORIDE (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-DIMETHYLAMINE

  • (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE
  • (11AS)-(-)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1-PHENYLETHYL]AMINE
  • (S)-SIPHOS-PE
  • (R)-SIPHOS-PE
  • N-DI[(R)-1-PHENYLETHYL]-[(R)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE
  • N-DI[(R)-1-PHENYLETHYL]-[(S)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE
  • (11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine,min.98%(R)-SIPHOS-PE
  • N-Di[(R)-1-phenylethyl]-[(R)-1,1'-spirobiindane-7,7'-diyl]-phosphoramidite ,98%
  • (11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine
  • (11aR)-10,11,12,13-tetrahydro-N,N-bis[(1R)-1-phenylethyl]-Diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-aMine
  • (R)-SIPHOS-PE 97%
  • 1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE
  • (11aR)-10,11,12,13-Tetrahydro-N,N-bis[(1R)-1-phenylethyl]-diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-amine,99%e.e.
  • (RA,R,R)-SIPHOS-PE
  • N,N-bis[(1R)-1-phenylethyl]-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-12-amine
  • (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE
  • Diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-amine,10,11,12,13-tetrahydro-N,N-bis[(1R)-1-phenylethyl]-, (11aR)-
  • (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
  • (R)-SIPHOS-PE,(R,R,R)-SIPHO,N-Di[(R)-1-phenylethyl]-[(R)-1,1′-spirobiindane-7,7′-diyl]-phosphoramidite
  • (11aR)-10,11,12,13-Tetrahydro-N,N-bis[(1R)-1-phenylethyl]diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-amine
  • 500997-69-3
  • Chiral Phosphine
  • Chiral Spiro Ligand
  • CPN