680184

(S)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

96%

• Synonym(s): (11bS)-4-Hydroxy-2,6-bis(triphenylsilyl)dinaphtho-[2,1-d1′,2′f]-[1,3,2]-dioxaphosphepin 4-oxide, MacMillan TiPSY catalyst
• Empirical Formula (Hill Notation): C₅₆H₄₁O₄PSi₂
• CAS Number: 929097-92-7
• Molecular Weight: 865.07
• MDL number: MFCD09265079
• UNSPSC Code: 12352005
• PubChem Substance ID: 24885544
• NACRES: NA.22

Properties

• assay: 96%
• form: solid
• optical activity: [α]22/D +210°, c = 1 in chloroform
• mp: 188-193 °C
• SMILES string: OP1(=O)Oc2c(cc3ccccc3c2-c4c(O1)c(cc5ccccc45)[Si](c6ccccc6)(c7ccccc7)c8ccccc8)[Si](c9ccccc9)(c%10ccccc%10)c%11ccccc%11
• InChI: 1S/C56H41O4PSi2/c57-61(58)59-55-51(62(43-25-7-1-8-26-43,44-27-9-2-10-28-44)45-29-11-3-12-30-45)39-41-23-19-21-37-49(41)53(55)54-50-38-22-20-24-42(50)40-52(56(54)60-61)63(46-31-13-4-14-32-46,47-33-15-5-16-34-47)48-35-17-6-18-36-48/h1-40H,(H,57,58)
• InChI key: BDQOCXQVIFQJRK-UHFFFAOYSA-N

Description

Application

(S)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate can be used as a catalyst:

• In the synthesis of 1,3-dioxolochroman skeletons by reacting 3-methyl-2-vinylindoles with ortho-quinone methides.
• In the exo-selective cyclization of mupirocin methyl ester.
• In the kinetic resolution of cyclic aliphatic syn-1,3-diols, which are used as valuable building blocks.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• 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