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683175

Sigma-Aldrich

Chiralyst P374

Umicore

Synonym(s):

Bis(norbornadiene)rhodium(I) tetrafluoroborate, Bis(bicyclo[2.2.1]hepta-2,5-diene)rhodium tetrafluoroborate, Bis(norbornadiene)(tetrafluoroborato)rhodium, Rh(nbd)2BF4, Rh(nbd)2BF4

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About This Item

Linear Formula:
[Rh(NBD)BF4
CAS Number:
36620-11-8
Molecular Weight:
373.99
MDL number:
MFCD00671775
UNSPSC Code:
12161600
PubChem Substance ID:
329760802
NACRES:
NA.22

form

solid

reaction suitability

core: rhodium
reagent type: catalyst

mp

136.9-139.9 °C

SMILES string

[Rh+].F[B-](F)(F)F.C1C2C=CC1C=C2.C3C4C=CC3C=C4

InChI

1S/2C7H8.BF4.Rh/c2*1-2-7-4-3-6(1)5-7;2-1(3,4)5;/h2*1-4,6-7H,5H2;;/q;;-1;+1/t2*6-,7+;;

InChI key

HAYDJWBQWOEERB-JAGGYEKFSA-N

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Application

Umicore Precatalysts for Asymmetric and Cross-Coupling Catalysis
Bis(norbornadiene)rhodium(I) tetrafluoroborate can be used as a catalyst for the synthesis of:
  • Lactones via the 1,4-addition of arylboronic acids to butenolide.
  • Chiral β-aryl-substituted ketones and esters.
  • β-aryloxycarboxylic esters from β-aryloxy-α,γ-unsaturated esters.

Legal Information

Product of Umicore

Additional information available at www.pmc.umicore.com

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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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Enantioselective Synthesis of ?-Aryloxycarboxylic Esters via Asymmetric Hydrogenation of ?-Aryloxy-?, ?-Unsaturated Esters
Stewart GW, et al.
Organic Letters, 14(21), 5440-5443 (2012)
Practical method for asymmetric addition of arylboronic acids to ?, ?-unsaturated carbonyl compounds utilizing an in situ prepared rhodium catalyst
Lukin K, et al.
The Journal of Organic Chemistry, 74(2), 929-931 (2008)
Determination of the absolute configuration of two ?v?6 integrin inhibitors for the treatment of idiopathic pulmonary fibrosis and investigations on the asymmetric 1, 4-addition of arylboronic acids to crotonate esters bearing a C4-oxygen substituent
Procopiou PA, et al.
Tetrahedron Asymmetry, 28(10), 1384-1393 (2017)

Articles

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