[(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol; chlorotitaniumylium; cyclopenta-2,4-dien-1-ide

• ChemBase ID: 135420
• Molecular Formular: C36H35ClO4Ti
• Molecular Mass: 614.9807
• Monoisotopic Mass: 614.17033358
• SMILES: CC1(O[C@@H]([C@H](O1)C(c1ccccc1)(c1ccccc1)O)C(c1ccccc1)(c1ccccc1)O)C.C1=C[CH-]C=C1.Cl[Ti+]
• Canonical SMILES: [CH-]1C=CC=C1.CC1(C)O[C@@H]([C@H](O1)C(c1ccccc1)(c1ccccc1)O)C(c1ccccc1)(c1ccccc1)O.Cl[Ti+]
• InChI: InChI=1S/C31H30O4.C5H5.ClH.Ti/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26;1-2-4-5-3-1;;/h3-22,27-28,32-33H,1-2H3;1-5H;1H;/q;-1;;+2/p-1/t27-,28-;;;/m0.../s1
• InChIKey: OQWVQKWVCAIVPK-HVVJQNAGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol; chlorotitaniumylium; cyclopenta-2,4-dien-1-ide
• IUPAC Traditional name: [(4S,5S)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol; chlorotitaniumylium; cyclopentadienide
• Synonyms: (S,S)-Duthaler-Hafner reagent; (4S,5S)-Chloro-cyclopentadienyl-[2,2-dimethyl-1,3-dioxolan-4,5-bis(diphenylmethoxy)]titanium; [(4S,5S)-2,2-Dimethyl-1,3-dioxolan-4,5-bis(diphenylmethoxy)]cyclopentadienyl-chlorotitanium; Chlorocyclopentadienyl[(4S,5S)-2,2-dimethyl-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium; (4S,5S)-氯-环戊二烯基-[2,2-二甲基,-1,3-二氧戊环-4,5-双(二苯基甲氧基)]钛; [(4S,5S)-2,2-二甲基-1,3-二氧戊环-4,5-双(二苯基甲氧基)]环戊二烯基-氯化钛; 氯环戊二烯基[(4S,5S)-2,2-二甲基-α,α,α′,α′-四苯基-1,3-二氧戊环-4,5-二甲醇酸根]钛

Database IDs

• CAS Number: 140462-73-3
• PubChem SID: 162229694; 24868490
• PubChem CID: 71309271

CALCULATED PROPERTIES

• Acid pKa: 12.106078
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.8206005
• LogD (pH = 7.4): 5.820592
• Log P: 5.8206005
• Molar Refractivity: 136.6576 cm^3
• Polarizability: 53.904915 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 209-213 °C(lit.)
• Optical Rotation: [α]20/D +246°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C36H33ClO4Ti

DETAILS

Sigma Aldrich - 449539

Packaging
100, 500 mg in glass bottle
Application
ApplicationA novel highly enantioselective allyl-transfer reagent. Excellent regio-, diastereo-, and enantioselectivities (usually >95% ee, >95% de) are obtained for the addition of allyl nucleophiles to aldehydes.1ium trichloride can be easily recovered.5117application