Skip to Content
Merck
CN

Key Documents

View All Documentation

380237

Tebbe reagent solution

0.5 M in toluene

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C13H18AlClTi
CAS Number:
67719-69-1
Molecular Weight:
284.58
NACRES:
NA.22
PubChem Substance ID:
24863730
UNSPSC Code:
12352101
MDL number:
MFCD00151575
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

form

liquid

Quality Segment

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

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

signalword

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

3 - Flammable liquids

wgk

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library