bis(cyclopenta-2,4-dien-1-yl)titaniumbis(ylium) dichloride

• ChemBase ID: 295203
• Molecular Formular: C10H10Cl2Ti
• Molecular Mass: 248.9594
• Monoisotopic Mass: 247.96390198
• SMILES: C1=CC(C=C1)[Ti+2]C1C=CC=C1.[Cl-].[Cl-]
• Canonical SMILES: C1=CC(C=C1)[Ti+2]C1C=CC=C1.[Cl-].[Cl-]
• InChI: InChI=1S/2C5H5.2ClH.Ti/c2*1-2-4-5-3-1;;;/h2*1-5H;2*1H;/q;;;;+2/p-2
• InChIKey: XKLWATAZDMHTSH-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(cyclopenta-2,4-dien-1-yl)titaniumbis(ylium) dichloride
• IUPAC Traditional name: bis(cyclopenta-2,4-dien-1-yl)titaniumbis(ylium) dichloride
• Synonyms: Dichlorobis(cyclopentadienyl)titanium; Titanocene dichloride; Bis(cyclopentadienyl)titanium dichloride; 双(环戊二烯)二氯化钛

Database IDs

• CAS Number: 1271-19-8
• EC Number: 215-035-9
• MDL Number: MFCD00003723
• Merck Index: 149482
• PubChem SID: 180680734
• PubChem CID: 53384597

CALCULATED PROPERTIES

• Acid pKa: 6.2537427
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.9007231
• LogD (pH = 7.4): 0.7856822
• Log P: 1.9712
• Molar Refractivity: 47.9718 cm^3
• Polarizability: 19.448069 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Slightly soluble in water
• Apperance: Crystalline, Packaged under argon
• Melting Point: 289-290°C; ca 285°C dec.
• Density: 1.60

Safety Information

• Storage Warning: Air & Moisture Sensitive
• RTECS: XR2050000
• European Hazard Symbols: Corrosive (C); X
• UN Number: UN3096
• Hazard Class: 8
• Packing Group: II
• Risk Statements: 20/21/22-34-68; 20/22-37/38-41-68
• Safety Statements: 9-26-36/37/39; 9-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS08
• GHS Hazard statements: H301-H311-H332-H314-H318-H341; H301-H332-H315-H335-H318-H341
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A

Product Information

• Purity: 97%; 99+%

REFERENCES

• In combination with trimethyaluminum, generates an ylide (Tebbe reagent): J. Am. Chem. Soc., 100, 3611 (1978), which transfers a methylene group not only to aldehydes and ketones (cf Wittig reaction) but also to the carbonyl groups of esters and lactones: J. Am. Chem. Soc., 102, 3270 (1980):
  
• A similar reagent can be prepared by reaction with the Simmons-Smith adduct (see Diiodomethane, A15457) and used for the methylenation of ketones in excellent yields: Tetrahedron Lett., 24, 2043 (1983).
• Reacts with Grignard reagents with a ?-hydrogen atom (e.g. isobutyl or isopropyl) to form, in a catalytic cycle, a titanium hydride species, which reduces aldehydes, ketones and esters to alcohols: Tetrahedron Lett., 21, 2171, 2175 (1980). The same combination effects regioselective cis-hydromagnesation of alkynes to give alkenyl Grignard reagents: Tetrahedron Lett., 22, 85 (1981); J. Chem. Soc., Chem. Commun., 718 (1981). For application in a highly stereospecific synthesis of vinylsilanes in excellent yields, see: Tetrahedron Lett., 24, 1041 (1983):
  
• For further examples of the hydroxymagnesation of alkynes, see: Org. Synth. Coll., 8, 507 (1993). Similarly π-allyl complexes with 1,3-dienes can be generated, which react regio-and stereo-selectively with aldehydes to give homoallylic alcohols: J. Chem. Soc., Chem. Commun., 621 (1984):
  
• For use, in combination with Mg metal, in formation of titanocycle intermediates, see: J. Org. Chem., 63, 9285 (1998); for reaction scheme, see Triphosgene, A14932.