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380237

Sigma-Aldrich

Tebbe reagent solution

0.5 M in toluene

Sinonimo/i:

Bis(cyclopentadienyl)-μ-chloro­(dimethylaluminum)-μ-methylenetitanium

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About This Item

Formula empirica (notazione di Hill):
C13H18AlClTi
Numero CAS:
67719-69-1
Peso molecolare:
284.58
Numero MDL:
MFCD00151575
Codice UNSPSC:
12352101
ID PubChem:
24863730
NACRES:
NA.22

Forma fisica

liquid

Impiego in reazioni chimiche

reaction type: C-C Bond Formation

Concentrazione

0.5 M in toluene

Densità

0.927 g/mL at 25 °C

Stringa SMILE

[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
QEJAQNUJXFLWSP-UHFFFAOYSA-M

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Categorie correlate

Descrizione generale

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.

Applicazioni

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.

Confezionamento

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

Note legali

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

Avvertenze

Danger

Classi di pericolo

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

Organi bersaglio

Central nervous system, Respiratory system

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

39.2 °F - closed cup

Punto d’infiammabilità (°C)

4 °C - closed cup

Dispositivi di protezione individuale

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
SHBL0526
SHBF7171V
SHBC9497V
SHBC6639V
SHBB7786V

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Stereoselective synthesis of C-glycosides via Tebbe methylenation and Claisen rearrangement
Godage HY and Fairbanks AJ
Tetrahedron Letters, 41(39), 7589-7593 (2000)
Transformation of carbonyl to vinylidene groups in the pi-conjugated peripheral substituent of chlorophyll derivatives by Tebbe reagent
Tamiaki H, et al.
Tetrahedron Letters, 57(7), 788-790 (2016)
Xuequan Lu et al.
Organic letters, 7(8), 1645-1648 (2005-04-09)
[reaction: see text] A new analogue of (2S,3R)-ceramide (2) with a methylene group at C4 has been synthesized from d-tartaric acid (3) by using Tebbe methylenation as the key step. Compound 2 exhibited markedly higher antiproliferative activity on mouse embryonic
Ketone Methylenation Using the Tebbe and Wittig Reagents-A Comparison
Pine SH, et al.
Synthesis, 1991(2), 165-167 (1991)
Mauricio A Cuellar et al.
Bioorganic & medicinal chemistry, 11(12), 2489-2497 (2003-05-22)
The Diels-Alder reaction between two polygodial-derived dienes and simple quinones to yield substituted naphtho- and anthraquinones, is described. The in vitro trypanocide activity for the series was determined. Two of the new compounds showed an activity ten and two times

Articoli

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

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