TEBBE REAGENT Property

Density 

0.96 g/mL at 20 °C

Flash point:

34 °F

storage temp. 

Refrigerator

form 

Solution

color 

Dark red to purple

Water Solubility 

Soluble in toluene, benzene, dichloromethane. Insoluble in water.

Sensitive 

Air & Moisture Sensitive

Merck 

9091

Exposure limits

ACGIH: TWA 20 ppm
OSHA: Ceiling 300 ppm; TWA 200 ppm
NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)

InChIKey

QEJAQNUJXFLWSP-UHFFFAOYSA-M

Safety

Hazard Codes 

F,C

Risk Statements 

11-34-48/20-63-65-67

Safety Statements 

26-36/37/39-45-62-16

RIDADR 

UN 2924 3/PG 2

WGK Germany 

2

F 

1-10

HazardClass 

4.3

PackingGroup 

II

HS Code 

29310099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H261In contact with water releases flammable gas

H302Harmful if swallowed

H304May be fatal if swallowed and enters airways

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

H333May be harmful if inhaled

H336May cause drowsiness or dizziness

H361Suspected of damaging fertility or the unborn child

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

TEBBE REAGENT Chemical Properties,Usage,Production

Chemical Properties

Dark red to purple solution

Chemical Properties

The Tebbe reagent is the organometallic compound with the formula (CH)TiCHClAl(CH). It is used in the methylenation of carbonyl compounds, that is it converts organic compounds containing the RC=O group into the related RC=CH derivative.It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research. Tebbe's reagent contains two tetrahedral metal centers linked by a pair of bridging ligands. The titanium has two cyclopentadienyl ([CH]-, or Cp) rings and aluminium has two methyl groups. The titanium and aluminium atoms are linked together by both a methylene bridge (-CH-) and a chloride atom in a nearly square-planar (Ti–CH–Al–Cl) geometry.The Tebbe reagent was the first reported compound where a methylene bridge connects a transition metal (Ti) and a main group metal (Al).Preparation The Tebbe reagent is synthesized from titanocene dichloride and trimethylaluminium in toluene solution.

Uses

μ-Chloro-μ-methylenebis(cyclopentadienyl)titaniumdimethylaluminum is used in organic synthesis for carbonyl methylenation, 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. Tebbe reagent can be used to olefinate aldehydes, to methylenate a chiral polyhydroxyketone with high diasteroselctivity.

Uses

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.

Uses

Reagent for the methylenation of carbonyl groups.

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.