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29590

Sigma-Aldrich

(1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)-iridium(I) hexafluorophosphate

≥99.0% (C)

Sinónimos:

(1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)-Ir(I) PF6, Crabtree’s catalyst

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About This Item

Fórmula empírica (notación de Hill):
C31H50F6IrNP2
Número de CAS:
64536-78-3
Peso molecular:
804.89
MDL number:
MFCD00075097
UNSPSC Code:
12161600
PubChem Substance ID:
57648382
NACRES:
NA.22

Quality Level

100

assay

≥99.0% (C)

reaction suitability

core: iridium
reagent type: catalyst

mp

175 °C (dec.) (lit.)

SMILES string

[Ir+].c1ccncc1.F[P-](F)(F)(F)(F)F.C2CC=CCCC=C2.C3CCC(CC3)P(C4CCCCC4)C5CCCCC5

InChI

1S/C18H33P.C8H12.C5H5N.F6P.Ir/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2-4-6-8-7-5-3-1;1-2-4-6-5-3-1;1-7(2,3,4,5)6;/h16-18H,1-15H2;1-2,7-8H,3-6H2;1-5H;;/q;;;-1;+1/b;2-1-,8-7-;;;

InChI key

UJXHUUQZACSUOG-KJWGIZLLSA-N

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Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Catalyst for the homogeneous hydrogenation of olefins

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
BCCL9368
BCCH2295
BCCF8530
BCCD0401
BCBV7578

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Krel, M.; Lallemand, J.-Y.; Guillou, C.
Synlett, 2043-2043 (2005)
Barry M Trost et al.
Journal of the American Chemical Society, 127(13), 4763-4776 (2005-03-31)
A wide variety of diynols containing tertiary, secondary, and primary propargylic alcohols undergo a cycloisomerization reaction to form dienones and dienals in the presence of a catalytic amount of [CpRu(CH(3)CN)(3)]PF(6). The formation of five- and six-membered rings is possible using
R.H. Crabtree et al.
Journal of the American Chemical Society, 104, 6994-6994 (1982)
J.M. Brown
Angewandte Chemie (International Edition in English), 99, 169-169 (1987)
Eric Clot et al.
Journal of the American Chemical Society, 126(28), 8795-8804 (2004-07-15)
[H2Ir(OCMe2)2L2]BF4 (1) (L = PPh3), a preferred catalyst for tritiation of pharmaceuticals, reacts with model substrate 2-(dimethylamino)pyridine (py-NMe2; py = 2-pyridyl) to give chelate carbene [H2Ir(py-N(Me)CH=)L2]BF4 (2a) via cyclometalation, H2 loss, and reversible alpha-elimination. Agostic intermediate [H2Ir(py-N(Me)CH2-H)L2]BF4) (4a), seen by
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Contenido relacionado

Crabtree Group – Professor Product Portal

The Crabtree Group developed the [(cod)IrLL']PF6 series of catalysts, where L is a P-donor such as PCy3 and L' and N-donor such as pyridine. These are very active in the hydrogenation of sterically hindered alkenes. The catalyst also shows directing effects as a result of binding of the catalyst to suitable functional groups on the substrate, followed by addition of H2 from the same side of the substrate that the functional group is located. Two versions of the catalyst are available from us one with PF6 and the other with BArF4 counteranion.

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