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

Reaction

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

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