380237

Tebbe reagent solution

0.5 M in toluene

• Synonym(s): Bis(cyclopentadienyl)-μ-chloro­(dimethylaluminum)-μ-methylenetitanium
• Empirical Formula (Hill Notation): C₁₃H₁₈AlClTi
• CAS Number: 67719-69-1
• Molecular Weight: 284.58
• MDL number: MFCD00151575
• UNSPSC Code: 12352101
• PubChem Substance ID: 24863730
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 100
• reaction suitability: reaction type: C-C Bond Formation
• concentration: 0.5 M in toluene
• density: 0.927 g/mL at 25 °C
• SMILES string: [CH]1[CH][CH][CH][CH]1.[CH]2[CH][CH][CH][CH]2.C[Al](C)C[Ti]Cl
• InChI: 1S/2C5H5.2CH3.CH2.Al.ClH.Ti/c2*1-2-4-5-3-1;;;;;;/h2*1-5H;2*1H3;1H2;;1H;/q;;;;;;;+1/p-1
• InChI key: QEJAQNUJXFLWSP-UHFFFAOYSA-M

Description

General description

Tebbe 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.

Application

Tebbe 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.

Packaging

The 25 mL Sure/Seal^™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Safety Information

• pictograms: GHS02,GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H225,H304,H314,H336,H361d,H373,H412
• pcodes: P210 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3
• target_organs: Central nervous system, Respiratory system
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 39.2 °F - closed cup
• flash_point_c: 4 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter