Crabtree's catalyst

Base Information

• Chemical Name: Crabtree's catalyst
• CAS No.: 64536-78-3
• Molecular Formula: C31H50F6IrNP2-
• Molecular Weight: 804.903
• Hs Code.: 29310099
• European Community (EC) Number: 636-356-4
• UNII: 816RS2NBPN
• DSSTox Substance ID: DTXSID10370362
• Wikipedia: Crabtree%27s_catalyst,Crabtree's_catalyst
• Wikidata: Q27269216
• Mol file: 64536-78-3.mol

Synonyms:Crabtree's catalyst;64536-78-3;Felkin-crabtree catalyst;Crabtree's catalyst [MI];(1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(i) hexafluorophosphate;UNII-816RS2NBPN;816RS2NBPN;Crabtree's catalyst (hexafluorophosphate);(1,5-Cyclooctadiene)pyridine(tricyclohexylphosphine)iridium hexafluorophosphate;(1Z,5Z)-cycloocta-1,5-diene;iridium;pyridine;tricyclohexylphosphane;hexafluorophosphate;1,5-CYCLOOCTADIENE(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE;((1,2,5,6-eta)-1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(1+) hexafluorophosphate(1-);Iridium(1+), ((1,2,5,6-eta)-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)-, hexafluorophosphate(1-) (1:1);(1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)-iridium(I) hexafluorophosphate;(TRICYCLOHEXYLPHOSPHINE)(1,5-CYCLOOCTADIENE)(PYRIDINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE;IRIDIUM(I) HEXAFLUOROPHOSPHATE;MFCD00075097;DTXSID10370362;WLRQNTYCIFESRH-KJWGIZLLSA-N;[Ir(cod)(Py)(PCy3)]+PF6-;AMY11738;SC10616;C2824;A914115;Q27269216;(1,5-cycloocta-diene)(pyridine)(tricyclohexylphosphine)iridium(i) hexafluorophosphate;(1,5-cyclooctadiene)(pyridine) (tricyclohexylphosphine)iridium (i) hexafluorophosphate;(1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)-iridium(I) hexafluorophosphate, 85%;((1,2,5,6-.ETA.)-1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(1+) HEXAFLUOROPHOSPHATE(1-);(1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)-iridium(I) hexafluorophosphate, >=99.0% (C);(Tricyclohexylphosphine)(1,5-cyclooctadiene)(pyridine)iridiuM(I) hexafluorophosphate CRABTREE'S CATALYST;[(1,2,5,6-?)-1,5-Cyclooctadiene](pyridine)(tricyclohexylphosphine)iridium(1+) hexafluorophosphate(1-) (1:1);[(1,2,5,6-Eta)-1,5-Cyclooctadiene](pyridine)(tricyclohexylphosphine)iridium(1+) hexafluorophosphate(1-) (1:1);IRIDIUM(1+), ((1,2,5,6-.ETA.)-1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)-, HEXAFLUOROPHOSPHATE(1-) (1:1)

Chemical Property of Crabtree's catalyst

Chemical Property:

• Melting Point: 175 °C (dec.)(lit.)
• PSA: 40.07000
• Density: 1.67 g/cm3
• LogP: 13.60320
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Slightly)
• Water Solubility.: Slightly soluble in acetone, dichloromethane, ethanol and diethyl ether. Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 805.29519
• Heavy Atom Count: 41
• Complexity: 368

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) Hexafluorophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3.C1CC=CCCC=C1.C1=CC=NC=C1.F[P-](F)(F)(F)(F)F.[Ir]
• Isomeric SMILES: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3.C1/C=C\CC/C=C\C1.C1=CC=NC=C1.F[P-](F)(F)(F)(F)F.[Ir]
• Uses: 1,5-Cyclooctadiene(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate is used as a catalyst for hydrogenation of mono-, di-, tri-, and tetra-substituted substrates and the isomerization and hydroboration of alkenes. It is also used in isotope exchange reactions, especially the direct exchange of a hydrogen atom with its isotopes deuterium and tritium. Carbonyl groups are also known to direct the hydrogenation by the Crabtree catalyst is highly regioselective.

Technology Process of Crabtree's catalyst

There total 1 articles about Crabtree's catalyst which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

(1,5-cyclooctadiene)bis(pyridine)iridium(I) hexafluorophosphate (56678-60-5) + tricyclohexylphosphine (2622-14-2) → Crabtree's catalyst (64536-78-3)

Guidance literature:

In methanol; at 25 ℃; for 1h;

DOI:10.1002/chem.201504825

Reference yield:

Crabtree's catalyst (64536-78-3) + hydrogen (1333-74-0) → IrH7(pyridine)2(tricyclohexylphosphine)3(1+) + Ir3H7(pyridine)3(tricyclohexylphosphine)3(1+) + [Ir4H10(tricycloexylphosphine)4(pyridine)](2+)

Guidance literature:

In dichloromethane-d2; hydrogenation of Ir complex; monitored by (1)H NMR; detd. by ES-MAS;

DOI:10.1002/anie.200804484

Reference yield:

Crabtree's catalyst (64536-78-3) + sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (79060-88-1) → (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (900161-50-4)

Guidance literature:

In dichloromethane; water; reaction of iridium compd. and borate deriv. in CH2Cl2/water mixt.; chromy. (silica, CH2Cl2), crystn. (ethanol/ether), X-ray anal.;

DOI:10.1139/v11-119

upstream raw materials:

(1,5-cyclooctadiene)bis(pyridine)iridium(I) hexafluorophosphate

tricyclohexylphosphine

Downstream raw materials:

(1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

Refernces