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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

380237-100ML:4548173141978
380237-BULK:
380237-4X25ML:4548173913179
380237-VAR:
380237-25ML:4548173141985

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Certificates of Analysis (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

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Reagents for C–C Bond Formation

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