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380237

Sigma-Aldrich

Tebbe reagent solution

0.5 M in toluene

Synonym(s):

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

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About This Item

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

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

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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

Signal Word

Danger

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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

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