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ALD00386

Sigma-Aldrich

Fe(dibm)3

greener alternative

Synonym(s):

Baran Olefin Cross-Coupling Catalyst, Iron tris(diisobutyrylmethane)

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About This Item

Empirical Formula (Hill Notation):
C27H45FeO6
CAS Number:
24444-72-2
Molecular Weight:
521.49
UNSPSC Code:
12161600
PubChem Substance ID:
329772664
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

core: iron
reagent type: catalyst

greener alternative product characteristics

Catalysis
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Greener Alternative Product

mp

96-102 °C

greener alternative category

Aligned,

SMILES string

O=C([CH-]C(C(C)C)=O)C(C)C.O=C([CH-]C(C(C)C)=O)C(C)C.O=C([CH-]C(C(C)C)=O)C(C)C.[Fe+3]

InChI

1S/3C9H15O2.Fe/c3*1-6(2)8(10)5-9(11)7(3)4;/h3*5-7H,1-4H3;/q3*-1;+3

InChI key

LKNJSJQVZKKQHU-UHFFFAOYSA-N

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Green Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

Iron tris(diisobutyrylmethane) was reported by Baran and coworkers to be an effective catalyst in the cross-coupling of olefins. In the presence of phenylsilane (Aldrich 335150), several highly substituted and novel functionalized C-C bonds can be formed using simple and mild reaction conditions.

Other Notes

The Baran Laboratory Blog: Functionalized Olefin Cross-Coupling
Functionalized olefin cross-coupling to construct carbon–carbon bonds

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

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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Baran Group – Professor Product Portal

The Baran Group works with Sigma-Aldrich in providing a portfolio of zinc-based reagents promoting difluoromethylation, trifluoromethylation, trifluoroethylation and isopropylation of aryl and heteroaryl motifs. Baran’s lab has also helped introduce a portable desaturase (Tz0Cl), which promotes the installation of alcohol and amine groups and leaves behind a highly useful tosyl group for further transformations.

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