Basic information
- CAS
1271-19-8- Standard SMILES
[Cl][Ti][Cl].[c-]1[c-][c-][cH-][c-]1.[c-]1[c-][c-][cH-][c-]1- InChIKey
DYUFLUNZOBVZGN-UHFFFAOYSA-L- Molecular formula
- C10H2Cl2Ti-10
- Average molar mass
- 240.89 g/mol
Names & identifiers
- Preferred name
- Bis(cyclopentadienyl)titanium(IV) chloride
- IUPAC
- bis(cyclopenta-1,3-diene);dichlorotitanium
- English name
- Titanocene dichloride
- Molecular formula
- C10H10Cl2Ti
- Molecular weight
- 248.96
Names & synonyms
NSC78453s10411WLN: L50J 0-TI-GG- 0L50JDichlorobis(.eta.(5)-cyclopentadienyl)titaniumBIS(CYCLOPENTADIENYL)TITANIUM(IV) CHLORIDECp2TiCl2BIS(CYCLOPENTADIENYL)TITANIUM DICHLORIDETDCDichlorotitanoceneBIS(CYCLOPENTADIENYL)TITANIUM(IV) DICHLORIDENCI-C04502titanium(2+)
Show more names
)titanium dichLtitaniumferroceneTitanocene dichlorid
Database identifiers
- CAS
1271-19-8- PubChem CID
- 416358
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- -10
- Complexity
- 163
Physicochemical properties
- Melting point
- 260 · 260-280 °C (dec.)(lit.)
- Boiling point
- 355.52 °C · 355.52°C (estimate)
- Density
- 1.6 g/mL · 1.6 g/mL at 25 °C(lit.)
- vapor pressure
- 0.002 Pa · 0.002Pa at 25℃
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 2 O, · slightly soluble in H2O, benzene; soluble in chloroform,ethanol, toluene
- form
- crystal
- Specific Gravity
- 1.6 · 1.6
- color
- red
- Water Solubility
- slow decomposition
- Sensitive
- Air & Moisture Sensitive
- Hydrolytic Sensitivity
- 4 · 4: no reaction with water under neutral conditions
- Merck
- 14 · 14,9482
- Stability
- Stable. Incompatible with strong oxidizing agents. Decomposes in water. Moisture sensitive.
- InChI
- 1S/2C5H5.2ClH.Ti/c2*1-2-4-5-3-1;;;/h2*1-5H;2*1H;/q;;;;+2/p-2
Safety & regulation
Safety data
- F
- 8-10-21
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- XR2050000
- ridadr
- UN3261
- hs_code
- 29310095
- Toxicity
- Titanocene dichloride may cause skin and mucous membrane irritation. The LD50 in mice has been reported as 60 mg/kg (i.p.) and 180 mg/kg (i.v.). In the rat, the LD50 is 25 mg/kg (i.p.).
- risk_code
- 37/38-61-40-34-33-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,T
- safety_code
- 36-7/8-6A-45-36/37/39-26
- hazard_class
- 8
- Storage Class
- 11 - Combustible Solids
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1STOT SE 3
- Precautionary statements
- P302+P352-P305+P351+P338
- Hazardous Substances Data
- 1271-19-8(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionTitanocene dichloride is an organotitanium compound with the chemical formula (η5-C5H5)2TiCl2, often written as Cp2TiCl2, which is a common reagent in organometallic chemistry and organic synthesis. Cp2TiCl2 does not form a "sandwich" structure like ferrocene, but a tetrahedral structure due to its four ligands around a metal center. Because of its anti-tumor activity, it has been used in clinical trials as a chemotherapeutic agent.
UsesTitanocene dichloride is used as an experimental cancer chemotherapeutic agent. It is used as a research chemical, as a catalyst in Ziegler–Natta polymerization reactions, and as an implant material in orthopedics, oral surgery, and neurosurgery.This metallocene is a common reagent in organometallic and organic synthesis. Titanocene dichloride is used to prepare titanocene pentasulfide. Used as an anticancer drug.
General DescriptionTitanocene dichloride appears as red to red-orange crystals. (NTP, 1992)
Preparation methods
PreparationCp2TiCl2 continues to be prepared similarly to its original synthesis by Wilkinson and Birmingham:2 NaC5H5 + TiCl4 → (C5H5)2TiCl2 + 2 NaClThe reaction is conducted in THF. Work-up entails extraction into chloroform/hydrogen chloride and recrystallization from toluene. In the original literature, the structure was poorly understood. Each of the two Cp rings are attached to Ti(IV) through all five carbon atoms. In organometallic chemical jargon, this bonding is referred to as η5 (see hapticity).
Upstream & downstream products
Upstream raw materials
Related reactions
4 records
Compound notes
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