GRUBBS CATALYST 2ND GENERATION Chemical Properties

Melting point:

143.5-148.5 °C(lit.)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly, Heated)

form 

Solid

color 

Brown to Very Dark Brown to Very Dark Red

InChIKey

FCDPQMAOJARMTG-UHFFFAOYSA-L

EPA Substance Registry System

Ruthenium, [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)-, (SP-5-41)- (246047-72-3)

Safety Information

Hazard Codes 

F

Risk Statements 

36/37/38-11

Safety Statements 

26-36/37/39

RIDADR 

1325

WGK Germany 

3

F 

10-23

HazardClass 

4.1

PackingGroup 

Ⅱ

MSDS

• Language:English Provider:SigmaAldrich

GRUBBS CATALYST 2ND GENERATION Usage And Synthesis

Description

Grubbs catalysts are a series of transition metal carbene complexes used as catalyst for olefin metathesis.1 The Grubbs catalysts are based on a ruthenium atom surrounded by five ligands: two neutral electron-donating entities (e.g., trialkylphosphines, N-heterocyclic carbenes), two monoanionic groups (e.g., halides), and one alkylidene moiety (e.g., unsubstituted and substituted methylidenes). L2X2Ru=CHR complexes (where L is a phosphine ligand) were discovered first and are referred to as the first-generation Grubbs catalyst. (L)(L’)X2Ru=CHR complexes (where L is a phosphine ligand and L’ a saturated N-heterocyclic carbene or NHC ligand) are referred to as the second-generation Grubbs catalysts.
The first-generation Grubbs catalysts show attractive functional-group tolerance and handling properties and have been widely used as highly efficient promoters for ring opening metathesis polymerizations, ring-closing metathesis reactions to make disubstituted olefins, ethenolysis (i.e., cleavage of the carbon–carbon double bond), cross-metathesis of terminal olefins, and the preparation of 1,3-dienes via enyne metathesis. These catalysts and analogues are still widely used in important processes, including the ethenolysis of feedstocks derived from bio-renewable seed oils and the manufacture of macrocyclic hepatitis C therapeutics. Nevertheless, the first-generation Grubbs catalysts show limitations with electron-poor and electron-rich double bonds as well as with sterically hindered systems. The second-generation Grubbs catalysts with excellent metathesis activity while retaining the handling characteristics and broad functional-group tolerance of the earlier Grubbs catalysts are thereby developed. At the same time, the second-generation catalysts are stable against moisture and air.

Reference

M. L. Crawley, B. M. Trost, Applications of Transition Metal Catalysis in Drug Discovery and Development, 2012, ISBN 978-0-470-63132-4

Chemical Properties

pink-brown to red-purple crystals or powder

Characteristics

Grubbs catalyst is a kind of coordination compound used in olefin metathesis reaction, and the ligand in it has a great influence on the catalytic performance and stability of the catalyst. Grubbs second-generation catalysts are more active than first-generation catalysts and have a wider substrate range, including sterically demanding or deactivated olefins such as 1,1-disubstituted olefins and α,β-non- Saturated carbonyl compounds.

Uses

suzuki reaction

Uses

Grubbs Catalyst^? M204 can be used as a catalyst for ring-closing metathesis (RCM), cross-metathesis, and ring-opening metathesis polymerization (ROMP). It is also used to synthesize trisubstituted olefins with excellent functional group tolerance and selectivity via cross-metathesis and ring closing metathesis reactions.
It can also be used as a catalyst:

• To synthesize coumarins from phenolic compounds via RCM.
• To cleave secondary (E)-allyl vic-diols to aldehydes.

GRUBBS CATALYST 2ND GENERATION(246047-72-3)Related Product Information

• 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
• Hoveyda-Grubbs Catalyst 2nd Generation
• Dichloro(p-cymene)ruthenium(II) dimer
• Rhodium(II) acetate dimer
• Ruthenium(II) chloride mesitylene dimer
• Tris(triphenylphosphine)rhodiu
• Rhodium(III) 2,4-pentanedionate
• Bis(tricyclohexylphosphine)nickel(II) chloride, 99%
• Ruthenium(III) chloride hydrate
• (1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE
• DICHLORO-[1,3-BIS(DIISOPROPYLPHENYL)IMIDAZOLYLIDENE]-(3-CHLOROPYRIDYL)PALLADIUM(II)
• Dichloro[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene](benzylidene)bis(3-bromopyridine)ruthenium(II)
• DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)(TRICYCLOHEXYLPHOSPHINE)RUTHENIUM(II)
• Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium
• Ruthenium
• Tricyclohexyl phosphine
• GRUBBS CATALYST 2ND GENERATION
• Tricyclohexylphosphine[3-phenyl-1H-inden-1-ylidene][1,3-bis(2,4,6-triMethylphenyl)-4,5-dihydroiMidazol-2-ylidene]rutheniuM(II)