172222-30-9 Usage
Description
Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium, also known as Phenylmethylenebis(tricyclohexylphosphorus)ruthenium dichloride, is a ruthenium catalyst that exists as a bright purple powder. It is highly resistant to polar monomers, which allows for the polymerization of various polar monomers to produce cyclic olefin copolymers. These copolymers have a wide range of applications in the manufacturing of optical, information, electrical, and medical materials.
Uses
1. Used in Organic Synthesis:
Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium is used as a catalyst in organic synthesis, specifically for the Suzuki reaction. It facilitates the formation of carbon-carbon bonds, which are crucial in the synthesis of various organic compounds.
2. Used in Catalysis of Olefin Metathesis:
This ruthenium catalyst is employed in the catalysis of olefin metathesis, which includes ring-closing of dienes, cross metathesis, and ring-opening metathesis polymerizations (ROMP). It is the first metathesis catalyst to be widely used in organic synthesis, making it a valuable tool for various applications.
3. Used in Acyclic Diene Metathesis Polymerization (ADMET):
Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium is used as a catalyst in ADMET, a process that involves the polymerization of acyclic dienes to form polymers with potential applications in various industries.
4. Used in Ring-Opening Metathesis Polymerization (ROMP):
This catalyst is also used in ROMP, a process that involves the polymerization of strained cyclic olefins to produce polymers with unique properties and potential applications in various fields.
5. Used in Ring Opening Metathesis (ROM):
Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium is used as a catalyst in ROM, a reaction that involves the opening of a cyclic olefin ring to form a linear product.
6. Used in Olefin Cross Metathesis (CM):
This ruthenium catalyst is used in CM, a reaction that involves the exchange of olefin groups between two molecules, leading to the formation of new carbon-carbon double bonds.
7. Used in Ring Closing Metathesis (RCM) of Terminal Olefins:
Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium is used as a catalyst in RCM, a reaction that involves the formation of a cyclic olefin from a terminal olefin, which is essential in the synthesis of various complex organic molecules.
Synthesis
Add 4.0 grams of dichlorotris(triphenylphosphine) ruthenium to the 250mL branch-necked bottle, feed nitrogen to replace the air in the branch-necked bottle, and inject 40mL into the branch-necked bottle through three times of liquid nitrogen freezing. Re-thaw the treated dichloromethane; place the side-necked flask in a cold bath at -78°C, and add a pentane solution of phenyldiazomethane with a mass concentration of -50°C of 98.5 mg/mL under stirring conditions 10 mL was mixed, and the phenyldiazomethane in the pentane solution of phenyldiazomethane was the phenyldiazomethane prepared above; the obtained mixture was stirred at -70 °C for 10 min, and then added 40 mL, -50 °C The mass concentration of 0.064 g/mL tricyclohexylphosphine in dichloromethane solution was carried out at 25 °C for 30 min. After the reaction, the obtained reaction solution was filtered to remove insolubles, the filtered reaction solution was concentrated to 10 mL and then filtered again, and 100 mL of methanol that had undergone three liquid nitrogen freeze-thaw treatments was added to the obtained filtered product for precipitation. , the obtained precipitate was first washed three times with methanol and then twice with acetone, and the washed precipitate was vacuum-dried for 3 hours to obtain 2.1 g of Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium.
Purification Methods
Wash it repeatedly with Me2CO and MeOH and dry it in a vacuum. Alternatively dissolve it in CH2Cl2, concentrate it to half its volume, filter, add MeOH to precipitate it as purple microcrystals. Filter these off, wash several times with Me2CO and MeOH and dry them in a vacuum for several hours. [Scwab et al. J Am Chem Soc 118 100 1996, Miller et al. J Am Chem Soc 118 9606 1996, Furstner & Langermann J Am Chem Soc 119 9130 1997.] § A polymer supported version is available [Schwab et al. Angew Chem (Intl Edn) 34 2039 1995.].
Check Digit Verification of cas no
The CAS Registry Mumber 172222-30-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,2,2,2 and 2 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 172222-30:
(8*1)+(7*7)+(6*2)+(5*2)+(4*2)+(3*2)+(2*3)+(1*0)=99
99 % 10 = 9
So 172222-30-9 is a valid CAS Registry Number.
InChI:InChI=1/2C18H33P.C7H6.2ClH.Ru/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-7-5-3-2-4-6-7;;;/h2*16-18H,1-15H2;1-6H;2*1H;/q;;;;;+2/p-2/r2C18H33P.C7H6Cl2Ru/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;8-10(9)6-7-4-2-1-3-5-7/h2*16-18H,1-15H2;1-6H
172222-30-9Relevant articles and documents
Cross-Metathesis of Vinylsilanes with Styrene Catalyzed by Ruthenium-Carbene Complexes
Pietraszuk, Cezary,Marciniec, Bogdan,Fischer, Helmut
, p. 913 - 917 (2000)
The cross-metathesis of styrene with various vinylsilanes, H2C=C(H)SiR3, catalyzed by [Cl2(PCy3)2Ru=CHPh] (1) to give (E)-silylstyrene, (E)-Ph(H)C=C(H)SiR3, and ethylene is reported. The reaction proceeds even at room temperature and is highly selective. Very high conversions are observed when R = OEt, OSiMe3 (≥95%, 6 h, 2 mol % of 1). The conversion significantly decreases with increasing substitution of Me for OR′. The metathesis is reversible. Therefore, removal of ethylene is critical for achieving high conversions. From the study of stoichiometric reactions of 1 with vinylsilanes it follows that in the series SiR3 = Si(OEt)3, SiMe(OEt)2, SiMe2OEt, SiMe3 and SiR3 = Si(OSiMe3)3, SiMe(OSiMe3)2, SiMe2-(OSiMe3), SiMe3 the conversion rate increases, but simultaneously the selectivity of the metathesis decreases. The decreasing selectivity readily accounts for the decreasing efficiency in the catalytic metathesis. The product distribution of reactions of styrene-d8 with H2C= C(H)SiR3 (R = OEt, OSiMe3) in the presence of 1 provides evidence for a metallacarbene mechanism involving [Ru]=CHPh and [Ru]=CH2 species.
IR-Thermographic Screening of Thermoneutral or Endothermic Transformations: The Ring-Closing Olefin Metathesis Reaction
Reetz, Manfred T.,Becker, Michael H.,Liebl, Monika,Fuerstner, Alois
, p. X1236-1239 (2007/10/03)
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