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683175

Sigma-Aldrich

Chiralyst P374

Umicore

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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
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

Quality Level

100

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

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)

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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)

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