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337498

Sigma-Aldrich

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

85%

Synonym(s):

(1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)-Ir(I) PF6, Crabtree’s catalyst, Iridium(I) hexafluorophosphate (1,5-Cyclooctadiene)-(pyridine)-(tricyclohexylphosphine) complex, [Ir(cod)(PCy3)(py)]PF6

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About This Item

Empirical Formula (Hill Notation):
C31H50F6IrNP2
CAS Number:
64536-78-3
Molecular Weight:
804.89
MDL number:
MFCD00075097
UNSPSC Code:
12161600
PubChem Substance ID:
24860483
NACRES:
NA.22

Assay

85%

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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Application

Catalyst for alkene hydrogenation, isomerization, and hydroboration; also for hydrogen isotope exchange reaction.
Homogeneous hydrogenation catalyst hydroboration catalyst.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Evans, D. A.; Fu, G. C.
Journal of the American Chemical Society, 113, 4042-4042 (1991)
Chemical Reviews, 93, 1331-1331 (1993)
Song, Z.; Hsung, R. P. et al.
Journal of Labelled Compounds & Radiopharmaceuticals, 50, 519-519 (2007)
Journal of the American Chemical Society, 114, 6671-6671 (1992)
Stereoselective synthesis of Boc-protected cis and trans-4-trifluoromethylprolines by asymmetric hydrogenation reactions.
Juan R Del Valle et al.
Angewandte Chemie (International ed. in English), 41(9), 1600-1602 (2002-05-03)

Related Content

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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