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GRUBBS CATALYST 2ND GENERATION
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High Quality Oled CAS 246047-72-3 Ruthenium,[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)-,(SP-5-41)-
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246047-72-3 Usage

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.

246047-72-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (569747)  GrubbsCatalyst,2ndGeneration   246047-72-3 569747-100MG 755.82CNY Detail
Aldrich (569747)  GrubbsCatalyst,2ndGeneration   246047-72-3 569747-500MG 2,331.81CNY Detail
Aldrich (569747)  GrubbsCatalyst,2ndGeneration   246047-72-3 569747-2G 6,598.80CNY Detail
Aldrich (569747)  GrubbsCatalyst,2ndGeneration   246047-72-3 569747-10G 20,369.70CNY Detail

246047-72-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium,tricyclohexylphosphane

1.2 Other means of identification

Product number -
Other names Grubbs catalyst,2nd Generation

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:246047-72-3 SDS

246047-72-3Synthetic route

Grubbs catalyst first generation

Grubbs catalyst first generation

1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene
173035-11-5

1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Glovebox;94%
1,3-di(2,4,6-trimethylphenyl)-2-(pentafluorophenyl)-2,4,5-trihydroimidazole
782479-45-2

1,3-di(2,4,6-trimethylphenyl)-2-(pentafluorophenyl)-2,4,5-trihydroimidazole

Grubbs catalyst first generation

Grubbs catalyst first generation

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In toluene mixt. of Ru complex and imidazolidine in toluene was heated at 60°C for 4 h;91%
Grubbs catalyst first generation

Grubbs catalyst first generation

1,3-bis(2,4,6-trimethylphenyl)-2-(trichloromethyl)imidazolidine
260054-47-5

1,3-bis(2,4,6-trimethylphenyl)-2-(trichloromethyl)imidazolidine

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In toluene mixt. of Ru complex and imidazolidine in toluene was heated at 60°C for 4 h;87%
In toluene byproducts: PCy3, CHCl3; (N2); using Schlenk techniques; mixing of (Mes2C3N2H5)(CCl3) and (PCy3)2Cl2Ru(CHPh) in toluene; heating at 60°C for 90 min; cooling to room temp., removal of solvent under vac., washing with methanol and pentane, drying under vac. for 12 h;84%
RuCl2(sIMes)(CHPh)(pyridine)2

RuCl2(sIMes)(CHPh)(pyridine)2

tris(cyclohexyl)phosphonium tetrafluoroborate
58656-04-5

tris(cyclohexyl)phosphonium tetrafluoroborate

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In toluene byproducts: pyridinium tetrafluoroborate, pyridine; 1.1 equiv. of phosphonium salt; passage through silica plug;80%
Grubbs catalyst first generation

Grubbs catalyst first generation

1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride
173035-10-4

1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
With KO(C(CH3)3) In hexane byproducts: KCl, C(CH3)3OH, PCy3; using Schlenk techniques; mixing of (Mes2C3N2H5)(Cl), KO(t-Bu) and (PCy3)2Cl2Ru(CHPh) in anhyd. hexane; degassing of soln. by pulling vac. for afew minutes, heating at 60°C for 24 h in vac. with very vigorous stirring; cooling to room temp., opening the flask to air, addn. of 1:1 2-propanol:water; stirring in air for 30 min, filtration, washing with 2-propanol:water and with hexane, drying under vac. overnight, elem. anal.;75%
With potassium tert-butylate In hexane at 60℃; for 24h; Schlenk technique;75%
With KOC(CH3)3 In toluene mixing N compd., Ru complex, K compd. in toluene at 50°C;
Grubbs catalyst first generation

Grubbs catalyst first generation

N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate

N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
Stage #1: N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere;
Stage #2: Grubbs catalyst first generation In benzene at 80℃; for 1.5h; Schlenk technique; Inert atmosphere;
56%
With KO(C(CH3)3) In benzene byproducts: KBF4, C(CH3)3OH, PCy3; (N2); using Schlenk techniques; mixing of (Mes2C3N2H5)(BF4), KO(t-Bu) and THF; stirring for 1 h; addn. of (PCy3)2Cl2Ru(CHPh) in benzene; heatingat 80°C for 30 min; removal of volatiles under vac., suspending in benzene, filtration over Celite, concn., addn. of methanol, pptn., washing with methanol, pentaneand then drying under vac.;45%
RuCl2(sIMes)(CHPh)(pyridine)2

RuCl2(sIMes)(CHPh)(pyridine)2

tricyclohexylphosphine
2622-14-2

tricyclohexylphosphine

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
With C5((2)H)5N In not given under Ar or N2; Ru complex reacts instantaneously with the phosphine; addn. of an excess of C5((2)H)5N leads to a formation of the bis(pyridine-d5) complex; evapn. of volatiles in vac. leads to a reformation of the phosphine complex;
Grubbs catalyst first generation

Grubbs catalyst first generation

bis[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)ruthenium(II)

bis[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)ruthenium(II)

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In benzene-d6 (N2); using Schlenk techniques; charging of NMR tube with Ru(CHPh)Cl2(C3N2H4Mes2)2, (PCy3)2(Cl)2Ru(CHPh) (1 equiv.) and C6D6; heating at 70°C for 47 h; monitoring by NMR;
bis[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)ruthenium(II)

bis[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)ruthenium(II)

tricyclohexylphosphine
2622-14-2

tricyclohexylphosphine

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In benzene-d6 (N2); using Schlenk techniques; charging of NMR tube with Ru(CHPh)Cl2(C3N2H4Mes2)2, PCy3 (excess) and C6D6; heating at 80°C for 36 h; monitoring by NMR;
styrene
292638-84-7

styrene

[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II)

[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II)

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In tetrahydrofuran excess styrene;0%
In toluene excess styrene;0%
(N,N'-dimesityl-N,N'-dimethylformamidin-2-ylidene)(1,3-dimesitylimidazolin-2-ylidene)Cl2Ru=CHPh

(N,N'-dimesityl-N,N'-dimethylformamidin-2-ylidene)(1,3-dimesitylimidazolin-2-ylidene)Cl2Ru=CHPh

tricyclohexylphosphine
2622-14-2

tricyclohexylphosphine

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In benzene-d6 100°C, 8 h;
(N,N'-bis(2,6-di-isopropylphenyl)-N,N'-dimethylformamidin-2-ylidene)(1,3-dimesitylimidazolin-2-ylidene)Cl2Ru=CHPh

(N,N'-bis(2,6-di-isopropylphenyl)-N,N'-dimethylformamidin-2-ylidene)(1,3-dimesitylimidazolin-2-ylidene)Cl2Ru=CHPh

tricyclohexylphosphine
2622-14-2

tricyclohexylphosphine

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In benzene-d6 100°C, 2 h;
2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: isopropyl alcohol; water / 24 h / 0 - 20 °C
2: sodium tetrahydroborate; hydrogenchloride / water; tetrahydrofuran / 0 - 20 °C
3: formic acid / 5 h / 120 °C / Inert atmosphere
4: potassium tert-butylate / hexane / 24 h / 60 °C / Schlenk technique
View Scheme
N,N'-bis(2,4,6-trimethylphenyl)ethanediimine
56222-36-7

N,N'-bis(2,4,6-trimethylphenyl)ethanediimine

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; hydrogenchloride / water; tetrahydrofuran / 0 - 20 °C
2: formic acid / 5 h / 120 °C / Inert atmosphere
3: potassium tert-butylate / hexane / 24 h / 60 °C / Schlenk technique
View Scheme
N1,N2-dimesitylethane-1,2-diaminium chloride
258278-23-8

N1,N2-dimesitylethane-1,2-diaminium chloride

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: formic acid / 5 h / 120 °C / Inert atmosphere
2: potassium tert-butylate / hexane / 24 h / 60 °C / Schlenk technique
View Scheme
(SIMes)Ru(S-DMSO)(CHPh)Cl2

(SIMes)Ru(S-DMSO)(CHPh)Cl2

tricyclohexylphosphine
2622-14-2

tricyclohexylphosphine

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
for 0.5h; Inert atmosphere; Schlenk technique;
dichloro(1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylylidene)(benzylidene)bis(pyridine)ruthenium(II)

dichloro(1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylylidene)(benzylidene)bis(pyridine)ruthenium(II)

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaN(Si(CH3)3)2 / toluene
2: benzene-d6
View Scheme
1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride
173035-10-4

1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hexamethylsilazane / toluene / 1 h / 20 °C / Inert atmosphere; Schlenk technique
2: toluene / Schlenk technique; Inert atmosphere
View Scheme
Grubbs catalyst first generation

Grubbs catalyst first generation

1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene

1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Conditions
ConditionsYield
In toluene Schlenk technique; Inert atmosphere;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

(4-isopropoxy-3-vinyl-phenyl)dimethyl-phosphoramidate ethyl ester

(4-isopropoxy-3-vinyl-phenyl)dimethyl-phosphoramidate ethyl ester

1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-isopropoxy)-5-(N,N-dimethylamino-ethylphosphite)phenyl]methyleneruthenium(II) dichloride

1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-isopropoxy)-5-(N,N-dimethylamino-ethylphosphite)phenyl]methyleneruthenium(II) dichloride

Conditions
ConditionsYield
With copper(l) chloride In dichloromethane at 30℃; for 1h; Schlenk technique;100%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

(IMesH2)(C7H10N2)2(Cl)2Ru=CHPh

(IMesH2)(C7H10N2)2(Cl)2Ru=CHPh

Conditions
ConditionsYield
In toluene at 20 - 25℃; for 12h;99%
In neat (no solvent) for 0.333333h; Milling;87%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

hydrogen
1333-74-0

hydrogen

ethylenediamine
107-15-3

ethylenediamine

[RuHCl(NH2CH2CH2NH2)(P(C6H11)3)(C3H4N2(C6H2(CH3)3)2)]

[RuHCl(NH2CH2CH2NH2)(P(C6H11)3)(C3H4N2(C6H2(CH3)3)2)]

Conditions
ConditionsYield
In sodium hydroxide under H2 (1 atm.); NMR;99%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

(4-isopropoxy-3-vinylphenyl)(diphenyl)methanol
934165-44-3

(4-isopropoxy-3-vinylphenyl)(diphenyl)methanol

((2,4,6-trimethylphenyl)2(C3H4N2))Cl2Ru(CH(C6H3)(OC3H7)(5-C(OH)Ph2))

((2,4,6-trimethylphenyl)2(C3H4N2))Cl2Ru(CH(C6H3)(OC3H7)(5-C(OH)Ph2))

Conditions
ConditionsYield
With copper(l) chloride In dichloromethane carbene complex (0.075 mmol), CuCl (0.09 mmol), and CH2Cl2 (4 ml) placedin Schlenk tube; styrene (0.09 mmol) in CH2Cl2 added; stirred (under Ar , 40°C, 1 h); concd. (vac.); column chromy. (silica gel, cyclohexane/ethyl acetate 3:1); green band removed; evapd.; washed with min. amt. of cold n-pentane; dried (vac.);99%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

1-(4-isopropoxy-3-vinylphenyl)-pyridinium hexafluorophosphate

1-(4-isopropoxy-3-vinylphenyl)-pyridinium hexafluorophosphate

(C3H4N2(C6H2(CH3)3)2)RuCl2(CHC6H3(NC5H5)OCH(CH3)2)(1+)*PF6(1-)=((C3H4N2(C6H2(CH3)3)2)RuCl2(CHC6H3(NC5H5)OCH(CH3)2))PF6

(C3H4N2(C6H2(CH3)3)2)RuCl2(CHC6H3(NC5H5)OCH(CH3)2)(1+)*PF6(1-)=((C3H4N2(C6H2(CH3)3)2)RuCl2(CHC6H3(NC5H5)OCH(CH3)2))PF6

Conditions
ConditionsYield
With copper(l) chloride In dichloromethane under Ar; soln. of pyridinium compd. in CH2Cl2 added to Ru complex and CuCl (molar ratio 1.2:1:1.5) in CH2Cl2; stirred at 45°C for 15 min; under air; concd. in vac.; EtOAc added; soln. filtered off; solvent removed; washed with cold n-pentane; dried under vac.;99%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

C2H4OS2(2-)*2Li(1+)

C2H4OS2(2-)*2Li(1+)

[ruthenium(III)(O(CH2CH2S)2)(CHPh)(1,3-bis-(2,4,6-trimethylphenyl)-4,5-dihydroimidazole)]

[ruthenium(III)(O(CH2CH2S)2)(CHPh)(1,3-bis-(2,4,6-trimethylphenyl)-4,5-dihydroimidazole)]

Conditions
ConditionsYield
In tetrahydrofuran for 16h; Inert atmosphere; Schlenk technique;99%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

(LiSCH2CH2)2O·2THF

(LiSCH2CH2)2O·2THF

Ru(Mes2Im)(=CHPh)[O(CH2CH2S)2]

Ru(Mes2Im)(=CHPh)[O(CH2CH2S)2]

Conditions
ConditionsYield
In toluene; acetonitrile for 16h; Inert atmosphere; Schlenk technique; Glovebox;99%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

2C4H8O*C4H8S3(2-)*2Li(1+)

2C4H8O*C4H8S3(2-)*2Li(1+)

Ru(Mes2Im)(=CHPh)[O(CH2CH2S)2]

Ru(Mes2Im)(=CHPh)[O(CH2CH2S)2]

Conditions
ConditionsYield
In tetrahydrofuran98%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi

2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi

(SIMes)Ru(CHPh)(SCH2CH2)2S

(SIMes)Ru(CHPh)(SCH2CH2)2S

Conditions
ConditionsYield
In toluene; acetonitrile for 16h; Inert atmosphere; Schlenk technique; Glovebox;98%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

Vinylidene fluoride
75-38-7

Vinylidene fluoride

1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene-dichloro(phenylmethylene)-(tricyclohexyl-phosphine)difluoromethylene ruthenium

1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene-dichloro(phenylmethylene)-(tricyclohexyl-phosphine)difluoromethylene ruthenium

Conditions
ConditionsYield
In benzene under 1140.08 Torr; for 12h; Heating;98%
In benzene soln. of Ru(Cl)2(P(C6H11)3)(CH(C6H5))(C3H5N2(C6H2(CH3)3)2) in dry degassed benzene in thick-walled glass ampule put under approx. 1.5 atm of 1,1-difluoroethylene; mixt. heated at 60°C for 12 h; color changed from reddish to brown; soln. concd. and purifed by column chromy. in air (silica gel, 5:1 pentane:THF); orange fraction stripped of solvent; dried under vac.;86%
In benzene-d6 at 60℃; under 760.051 Torr; for 12h;
In benzene-d6 at 60℃; under 760.051 Torr; for 12h;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

p-phenylpyridine
939-23-1

p-phenylpyridine

(IMesH2)(C11H9N)2(Cl)2Ru=CHPh

(IMesH2)(C11H9N)2(Cl)2Ru=CHPh

Conditions
ConditionsYield
In toluene at 20 - 25℃; for 12h;97%
In toluene at 20 - 25℃; for 12h;97%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

C21H23NO3S

C21H23NO3S

C42H49Cl2N3O3RuS

C42H49Cl2N3O3RuS

Conditions
ConditionsYield
In dichloromethane at 45℃;97%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

2-methyl-8-vinylquinoline
261899-66-5

2-methyl-8-vinylquinoline

[RuCl2(ImH2Mes)((2-methyl-8-quinolinyl)methylene)]

[RuCl2(ImH2Mes)((2-methyl-8-quinolinyl)methylene)]

Conditions
ConditionsYield
With copper(l) chloride In dichloromethane at 30℃; for 1.5h;96%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

(IMesH2)(C12H8N2)(Cl)2Ru=CHPh

(IMesH2)(C12H8N2)(Cl)2Ru=CHPh

Conditions
ConditionsYield
In toluene at 20 - 25℃; for 12h;96%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

acetonitrile
75-05-8

acetonitrile

[(MeCN)3(H2IMes)(benzylidene)ruthenium](triflate)2

[(MeCN)3(H2IMes)(benzylidene)ruthenium](triflate)2

Conditions
ConditionsYield
In chloroform byproducts: AgCl, PCy3; using standard Schlenk techniques; mixt. of Ru complex and Ag salt (2 equiv.) in CHCl3 stirred in presence of MeCN (3 equiv.) at 25°C for30 min; filtered; n-pentane added to filtrate; filtered; ppt. washed with n-pentane; dried under vac.; elem. anal.;96%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

C16H14FNO

C16H14FNO

C36H38Cl2FN3ORu

C36H38Cl2FN3ORu

Conditions
ConditionsYield
With copper(l) chloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere;96%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

iodine
7553-56-2

iodine

5I(1-)*C2H6*C46H64Cl2N2PRu(1+)*I5(1-)

5I(1-)*C2H6*C46H64Cl2N2PRu(1+)*I5(1-)

Conditions
ConditionsYield
In dichloromethane at 25℃; for 0.5h; Inert atmosphere;95%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

(2R,4aR,5aS,10aR,11R,11aS)-2-(naphthalen-2-yl)-4,4a,5a,6,9,10a,11,11a-octahydro-[1,3]dioxino[40,50:5,6]pyrano[3,2-b]oxepin-11-ol
784157-67-1

(2R,4aR,5aS,10aR,11R,11aS)-2-(naphthalen-2-yl)-4,4a,5a,6,9,10a,11,11a-octahydro-[1,3]dioxino[40,50:5,6]pyrano[3,2-b]oxepin-11-ol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 5h;95%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

acetonitrile
75-05-8

acetonitrile

C32H38Cl2N4Ru

C32H38Cl2N4Ru

Conditions
ConditionsYield
With copper(l) chloride at 20℃; for 3h;95%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

C17H17NO3S

C17H17NO3S

C37H41Cl2N3O3RuS

C37H41Cl2N3O3RuS

Conditions
ConditionsYield
In dichloromethane at 45℃;95%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

3-Bromopyridine
626-55-1

3-Bromopyridine

Grubbs catalyst third generation
477218-66-9

Grubbs catalyst third generation

Conditions
ConditionsYield
Inert atmosphere;94%
In not given byproducts: P(C6H11)3; within minutes; pptn. with pentane;89%
at 20 - 25℃; for 12h;86%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

2-(prop-1-enyl)phenol
6380-21-8

2-(prop-1-enyl)phenol

C46H64ClN2OPRu

C46H64ClN2OPRu

Conditions
ConditionsYield
With tricyclohexylphosphine In dichloromethane at 40℃; for 24h; Inert atmosphere; Schlenk technique;94%
With tricyclohexylphosphine In dichloromethane at 40℃; for 5h;72%
With tricyclohexylphosphine In dichloromethane at 40℃; for 5h;72%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

2-(prop-1-enyl)phenol
6380-21-8

2-(prop-1-enyl)phenol

tricyclohexylphosphine
2622-14-2

tricyclohexylphosphine

C46H64ClN2OPRu

C46H64ClN2OPRu

Conditions
ConditionsYield
In dichloromethane at 40℃; for 24h; Inert atmosphere;94%
N-(but-3-enyl)-4-methyl-N-(phenylethynyl)benzenesulfonamide
853688-25-2

N-(but-3-enyl)-4-methyl-N-(phenylethynyl)benzenesulfonamide

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

C40H45Cl2N3O2RuS

C40H45Cl2N3O2RuS

Conditions
ConditionsYield
In dichloromethane at 45℃;94%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

2,2'-biquinoline
119-91-5

2,2'-biquinoline

(IMesH2)(C18H12N2)2(Cl)2Ru=CHPh

(IMesH2)(C18H12N2)2(Cl)2Ru=CHPh

Conditions
ConditionsYield
In toluene at 20 - 25℃; for 12h;93%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

4-pyrrolidin-1-ylpyridine
2456-81-7

4-pyrrolidin-1-ylpyridine

(IMesH2)(C9H12N2)2(Cl)2Ru=CHP

(IMesH2)(C9H12N2)2(Cl)2Ru=CHP

Conditions
ConditionsYield
at 20 - 25℃; for 12h;93%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

ethyl vinyl ether
109-92-2

ethyl vinyl ether

RuCl2(ethoxymethylidene)(1-mesityl-3-mesityl-4,5-dihydroimidazol-2-ylidene)(PCy3)

RuCl2(ethoxymethylidene)(1-mesityl-3-mesityl-4,5-dihydroimidazol-2-ylidene)(PCy3)

Conditions
ConditionsYield
In dichloromethane ligand was added to CH2Cl2 soln. of Ru-complex, stirred at room temp. for 2 h under N2; solvent was evapd. under vac., washed with pentane and MeOH;93%
In benzene-d6 Kinetics; at 25°C; monitoring by NMR;
In toluene at 50℃; for 1h; Schlenk technique; Inert atmosphere;
In (2)H8-toluene at 30℃;
pyridine
110-86-1

pyridine

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

dichloro(1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylylidene)(benzylidene)bis(pyridine)ruthenium(II)

dichloro(1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylylidene)(benzylidene)bis(pyridine)ruthenium(II)

Conditions
ConditionsYield
In toluene at 20℃; for 0.5h; Inert atmosphere;92%
In toluene at 20℃; for 0.5h; Inert atmosphere; Glovebox;92%
In toluene at 20℃; for 0.5h; Inert atmosphere; Glovebox;92%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride
246047-72-3

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride

2-hydroxy-5-nitrostyrene
83520-63-2

2-hydroxy-5-nitrostyrene

C46H63ClN3O3PRu

C46H63ClN3O3PRu

Conditions
ConditionsYield
With tricyclohexylphosphine In dichloromethane at 40℃; for 24h; Inert atmosphere; Schlenk technique;92%
With tricyclohexylphosphine In dichloromethane at 40℃; for 1h;50%
With tricyclohexylphosphine In dichloromethane at 40℃; for 1h;50%
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