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TEBBE REAGENT

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CAS:67719-69-1
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  • 2024-04-05
  • CAS:67719-69-1
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TEBBE REAGENT Basic information
Product Name:TEBBE REAGENT
Synonyms:Bis(cyclopentadienyl-micron-chloro(dimethylaluminum-micron-methylenetitanium;Chlorobishetacyclopentadienyldimethylammoniummumethyle;mu-Chlorobis(((heta)^5)-cyclopentadienyl)(dimethylammonium)-mu-methylene-titanium;Tebbe's reagent;μ-Chloro-μ-methylenebis(cyclopentadienyl)titaniumdimethylaluminum solution, 0.5M in toluene;BIS(CYCLOPENTADIENYL)-MU-CHLORO(DIMETHYLALUMINUM)-MU-METHYLENETITANIUM;MU-CHLOROBIS(CYCLOPENTADIENYL)(DIMETHYLALUMINUM)-MU-METHYLENETITANIUM;MU-CHLOROBIS(ETA5-CYCLOPENTADIENYL)(DIMETHYLALUMINUM)-MU-METHYLENETITANIUM
CAS:67719-69-1
MF:C13H4AlClTi
MW:270.47
EINECS:
Product Categories:Titanocene, etc.;Al (Alminum) Compounds;Classes of Metal Compounds;Metallocenes;Ti (Titanium) Compounds;Transition Metal Compounds;Typical Metal Compounds
Mol File:67719-69-1.mol
TEBBE REAGENT Structure
TEBBE REAGENT Chemical Properties
density 0.96 g/mL at 20 °C
Fp 34 °F
storage temp. Refrigerator
form Solution
color Dark red to purple
Water Solubility Soluble in toluene, benzene, dichloromethane. Insoluble in water.
Sensitive Air & Moisture Sensitive
Merck 9091
Exposure limitsACGIH: TWA 20 ppm
OSHA: Ceiling 300 ppm; TWA 200 ppm
NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)
InChIKeyQEJAQNUJXFLWSP-UHFFFAOYSA-M
Safety Information
Hazard Codes F,C
Risk Statements 11-34-48/20-63-65-67
Safety Statements 26-36/37/39-45-62-16
RIDADR UN 2924 3/PG 2
WGK Germany 2
1-10
HazardClass 4.3
PackingGroup II
HS Code 29310099
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
TEBBE REAGENT Usage And Synthesis
Chemical PropertiesDark red to purple solution
Chemical PropertiesThe Tebbe reagent is the organometallic compound with the formula (CH)TiCHClAl(CH). It is used in the methylenation of carbonyl compounds, that is it converts organic compounds containing the RC=O group into the related RC=CH derivative.It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research. Tebbe's reagent contains two tetrahedral metal centers linked by a pair of bridging ligands. The titanium has two cyclopentadienyl ([CH]-, or Cp) rings and aluminium has two methyl groups. The titanium and aluminium atoms are linked together by both a methylene bridge (-CH-) and a chloride atom in a nearly square-planar (Ti–CH–Al–Cl) geometry.The Tebbe reagent was the first reported compound where a methylene bridge connects a transition metal (Ti) and a main group metal (Al).Preparation The Tebbe reagent is synthesized from titanocene dichloride and trimethylaluminium in toluene solution.
UsesTebbe reagent can be used:?????
  • For the conversion of carbonyl groups of chlorophyll derivatives into the corresponding exo-methylene (or vinylidene) groups.
  • In the synthesis of β-C-glycosides from 3-OH glycol esters.
  • As a versatile methylenation reagent for the conversion of ketones and aldehydes to olefins. It offers facile reaction with hindered ketones and allows the conversion of esters to vinyl ethers.
  • To olefinate aldehydes.
  • To methylenate a chiral polyhydroxyketone with high diasteroselctivity.
Usesμ-Chloro-μ-methylenebis(cyclopentadienyl)titaniumdimethylaluminum is used in organic synthesis for carbonyl methylenation, A versatile methylenation reagent for the conversion of ketones and aldehydes to olefins, it offers facile reaction with hindered ketones and allows the conversion of esters to vinyl ethers. Tebbe reagent can be used to olefinate aldehydes, to methylenate a chiral polyhydroxyketone with high diasteroselctivity.
UsesReagent for the methylenation of carbonyl groups.
General DescriptionTebbe reagent is a Lewis acid stabilized organometallic compound, which is used to transform carbonyl groups into β-substituted methylenes. It also reacts with a wide range of carbonyl compounds, including esters, amides, and lactones to yield corresponding olefins.
TEBBE REAGENT Preparation Products And Raw materials
Tag:TEBBE REAGENT(67719-69-1) Related Product Information
Potassium sodium tartrate Nysted Reagent Lithium hydroxide 1,3-Cyclopentadiene GRUBBS-TEBBE REAGENT Trimethylaluminium TEBBE REAGENT NUGENT'S REAGENT titanocene