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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

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

683175-500MG:4548173287331
683175-BULK:
683175-2G:4548173287348
683175-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ4592
MKCP0923
MKCK8146
MKCD6822
MKCC0973

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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)
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)

Articles

Umicore Precatalysts

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