380237

Tebbe reagent solution

0.5 M in toluene

• Synonyme(s) : Bis(cyclopentadienyl)-μ-chloro­(dimethylaluminum)-μ-methylenetitanium
• Formule empirique (notation de Hill) : C₁₃H₁₈AlClTi
• Numéro CAS: 67719-69-1
• Poids moléculaire : 284.58
• Numéro MDL: MFCD00151575
• Code UNSPSC : 12352101
• ID de substance PubChem : 24863730
• Nomenclature NACRES : NA.22

Propriétés

• Forme: liquid
• Capacité de réaction: reaction type: C-C Bond Formation
• Concentration: 0.5 M in toluene
• Densité: 0.927 g/mL at 25 °C
• Chaîne SMILES: [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
• Clé InChI: QEJAQNUJXFLWSP-UHFFFAOYSA-M

Description

Description générale

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.[1][2]

Application

Tebbe reagent can be used:     

• For the conversion of carbonyl groups of chlorophyll derivatives into the corresponding exo-methylene (or vinylidene) groups.[2]
• In the synthesis of β-C-glycosides from 3-OH glycol esters.[3]
• 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.[4]
• To olefinate aldehydes.[5]
• To methylenate a chiral polyhydroxyketone with high diasteroselctivity.[6]

Conditionnement

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

Informations légales

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

Informations sur la sécurité

• Pictogrammes: GHS02,GHS08,GHS05,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H225,H304,H314,H336,H361d,H373,H412
• Conseils de prudence: P210 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Classification des risques: Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3
• Organes cibles: Central nervous system, Respiratory system
• Code de la classe de stockage: 3 - Flammable liquids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 39.2 °F - closed cup
• Point d'éclair (°C): 4 °C - closed cup
• Équipement de protection individuelle: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter