titanium(4+) ion tetrakis(propan-2-olate)

• ChemBase ID: 295297
• Molecular Formular: C12H28O4Ti
• Molecular Mass: 284.21532
• Monoisotopic Mass: 284.14670568
• SMILES: CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]
• Canonical SMILES: [O-]C(C)C.[O-]C(C)C.[O-]C(C)C.[O-]C(C)C.[Ti+4]
• InChI: InChI=1S/4C3H7O.Ti/c4*1-3(2)4;/h4*3H,1-2H3;/q4*-1;+4
• InChIKey: VXUYXOFXAQZZMF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: titanium(4+) ion tetrakis(propan-2-olate)
• IUPAC Traditional name: titanium(4+) ion tetrakis(propan-2-olate)
• Synonyms: Tetraisopropoxytitanium(IV); Tetraisopropyl orthotitanate; Titanium(IV) isopropoxide; 四异丙醇钛(IV)

Database IDs

• CAS Number: 546-68-9
• EC Number: 208-909-6
• MDL Number: MFCD00008871
• Beilstein Number: 3679474
• Merck Index: 149480
• PubChem SID: 180680828
• PubChem CID: 11026

CALCULATED PROPERTIES

• Acid pKa: 17.262587
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.2548059
• LogD (pH = 7.4): 0.25480592
• Log P: 0.25480592
• Molar Refractivity: 27.979 cm^3
• Polarizability: 6.5838666 Å^3
• Polar Surface Area: 23.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Liquid
• Melting Point: 16-20°C
• Boiling Point: 232°C
• Flash Point: 46°C(115°F)
• Density: 0.955
• Refractive Index: 1.4640

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: NT8060000
• European Hazard Symbols: Irritant (Xi)
• UN Number: UN2413
• Hazard Class: 3
• Packing Group: III
• Risk Statements: 10-36
• Safety Statements: 26-60
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Hazard statements: H226-H319
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P403+P235-P501A

Product Information

• Purity: 95%; 99.995% (metals basis)

REFERENCES

• For use in the Sharpless enantioselective epoxidation of allylic alcohols, see tert-Butyl hydroperoxide, A13926. For analogous enantioselective oxidation of sulfides to sulfoxides, see Cumene hydroperoxide, L06866. Epoxy alcohols can also be obtained in high yield in one pot by hydroperoxidation of alkenes with singlet oxygen in the presence of Ti(O-i-Pr)₄: J. Am. Chem. Soc., 111, 203 (1989).
• Also catalyzes the ring-opening of 2,3-epoxy alcohols (e.g. from the above reactions) with various nucleophiles, including amines, thiols, thiolate anions, halides, carboxylates etc. The mild conditions result in increased regioselectivity: J. Org. Chem., 50, 1557 (1985).
• See also Dimethylamine hydrochloride, A12133.
• For conversion of epoxides to episulfides, see Thiourea, A12828. For use in reductive alkylation of amines, see Sodium cyanoborohydride, 87839. For use in enantioselective synthesis of homoallylic alcohols, see (R)-(+)-1,1'-Bi(2-naphthol), L08305. For reduction of amides to aldehydes, see Diphenylsilane, A10884.
• For a brief feature on uses of the reagent, see: Synlett, 2261 (2003).
• Catalyst for transesterification, avoiding acidic or basic conditions. The reaction is carried out such that one alcohol is removed to displace the equilibrium: Synthesis, 138 (1982); Org. Synth. Coll., 8, 201 (1993). For application to carbamates, including Boc to Cbz conversion, see: J. Org. Chem., 62, 7096 (1997).