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337455

(1,5-Cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate

97%

Synonym(s):

[Ir(PMePh2)2COD]+ PF6-, [Ir(cod)(PPh2Me)2]PF6, {Ir(COD)[PCH3(C6H5)2]2}PF6

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About This Item

Empirical Formula (Hill Notation):
C34H38F6IrP3
CAS Number:
38465-86-0
Molecular Weight:
845.79
NACRES:
NA.22
PubChem Substance ID:
24860482
UNSPSC Code:
12161600
MDL number:
MFCD00064800
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Quality Level

100

assay

97%

reaction suitability

core: iridium, reagent type: catalyst

mp

224 °C (dec.) (lit.)

SMILES string

[Ir+].F[P-](F)(F)(F)(F)F.C1CC=CCCC=C1.CP(c2ccccc2)c3ccccc3.CP(c4ccccc4)c5ccccc5

InChI

1S/2C13H13P.C8H12.F6P.Ir/c2*1-14(12-8-4-2-5-9-12)13-10-6-3-7-11-13;1-2-4-6-8-7-5-3-1;1-7(2,3,4,5)6;/h2*2-11H,1H3;1-2,7-8H,3-6H2;;/q;;;-1;+1/b;;2-1-,8-7-;;

InChI key

LXKHQEQLBSJJCO-JXNOXZOESA-N

Application

(1,5-Cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate is an air-stable cationic iridium complex, generally employed in allyl isomerization reactions. Upon bubbling hydrogen into the solution of [Ir(cod)(PPh2Me)2]PF6, preferably in tetrahydrofuran, results in the formation of active catalyst [IrH2(solv)2(PPh2Me)2]PF6 which can be used in the isomerization of 3-(silyloxy)-1-propenylboronates to (γ-(silyloxy)allyl)boronic esters; diallyl ethers to allyl (E)-vinyl ethers and 1-alkenylboronates to corresponding 3-alkoxyallylboronates.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT5855
MKCR2227
MKCQ3638
MKCP4453
MKCL4193

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Isomerisation of allyl ethers catalysed by the cationic iridium complex [Ir (cyclo-octa-1, 5-diene)(PMePh 2) 2] PF 6. A highly stereoselective route to trans-propenyl ethers.
Baudry D, et al.
Journal of the Chemical Society. Chemical Communications, (16), 694-695 (1978)
Oltvoort, J. J.; Van Boeckel, C. A. A. et al.
Synthesis, 305-305 (1981)
Intramolecular allylboration of γ-(?-formylalkoxy) allylboronates for syntheses of trans-or cis-2-(ethenyl) tetrahydropyran-3-ol and 2-(ethenyl) oxepan-3-ol.
Yamamoto Y, et al.
Tetrahedron, 59(4), 537-542 (2003)
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Global Trade Item Number

SKUGTIN
337455-500MG04061826743584
337455-50MG04061833279502