700762

(S)-SIPHOS-PE

97%

• Synonym(s): (11aS)-(−)-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]-[(S)-1,1′-spirobiindane-7,7′-diyl]-phosphoramidite
• Empirical Formula (Hill Notation): C₃₃H₃₂NO₂P
• CAS Number: 500997-70-6
• Molecular Weight: 505.59
• MDL number: MFCD08459342
• UNSPSC Code: 12352005
• PubChem Substance ID: 329762229
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 97%
• form: powder
• optical activity: [α]22/D −65.0°, c = 1 in chloroform
• mp: 120-125 °C
• functional group: amine; phenyl
• storage temp.: −20°C
• SMILES string: C[C@@H](N([C@H](C)c1ccccc1)P2Oc3cccc4CCC5(CCc6cccc(O2)c56)c34)c7ccccc7
• 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

Description

Application

(S)-SIPHOS-PE is a chiral spiro phosphoramidate ligand that can be used to synthesize:

• Spiroindolenines by Pd-catalyzed intramolecular dearomative arylation of haloaryl-3-substituted indoles.
• Enantioselective conjugate addition compound by Cu-catalyzed 1,4-addition of diethylzinc (Et₂Zn) to cyclic enones.
• Octaketide natural products via rhodium-phosphoramidite catalyzed alkene hydroacylation.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves