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692573

Sigma-Aldrich

Bis(1,5-cyclooctadiene)rhodium(I) tetrakis[bis(3,5-trifluoromethyl)phenyl]borate

Synonym(s):

Bis(1,5-cyclooctadiene)rhodium BARF, Bis(1,5-cyclooctadiene)rhodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

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About This Item

Empirical Formula (Hill Notation):
C48H36BF24Rh
CAS Number:
404573-66-6
Molecular Weight:
1182.48
UNSPSC Code:
12161600
PubChem Substance ID:
329761509
NACRES:
NA.22

form

solid

reaction suitability

core: rhodium
reagent type: catalyst

mp

155-156 °C (D)

storage temp.

−20°C

SMILES string

[Rh+].C1CC=CCCC=C1.C2CC=CCCC=C2.FC(F)(F)c3cc(cc(c3)C(F)(F)F)[B-](c4cc(cc(c4)C(F)(F)F)C(F)(F)F)(c5cc(cc(c5)C(F)(F)F)C(F)(F)F)c6cc(cc(c6)C(F)(F)F)C(F)(F)F

InChI

1S/C32H12BF24.2C8H12.Rh/c34-25(35,36)13-1-14(26(37,38)39)6-21(5-13)33(22-7-15(27(40,41)42)2-16(8-22)28(43,44)45,23-9-17(29(46,47)48)3-18(10-23)30(49,50)51)24-11-19(31(52,53)54)4-20(12-24)32(55,56)57;2*1-2-4-6-8-7-5-3-1;/h1-12H;2*1-2,7-8H,3-6H2;/q-1;;;+1/b;2*2-1-,8-7-;

InChI key

HQQAEXNVAYMZON-AUUWQFPRSA-N

Application

Bis(1,5-cyclooctadiene)rhodium(I) tetrakis[bis(3,5-trifluoromethyl)phenyl]borate can be used as a catalyst for various transformations, including hydrogenation, intramolecular C-H alkenylation, cycloaddition of enynes, and reductive coupling reactions.

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

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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Intramolecular C- H Alkenylation of N-Alkynylindoles: Exo and Endo Selective Cyclization According to the Choice of Metal Catalyst
Shibata, T, et al.
advanced synthesis and catalysis, 359(11), 1849-1853 (2017)
Proline-Based P, O Ligand/Iridium Complexes as Highly Selective Catalysts: Asymmetric Hydrogenation of Trisubstituted Alkenes
Rageot D, et al.
Angewandte Chemie (International Edition in English), 123(41), 9772-9775 (2011)
Intramolecular C- H Alkenylation of N-Alkynylindoles: Exo and Endo Selective Cyclization According to the Choice of Metal Catalyst
Shibata, T, et al.
Advanced Synthesis & Catalysis, 359(11), 1849-1853 (2017)
Highly diastereo-and enantioselective construction of both central and axial chiralities by Rh-catalyzed [2+ 2+ 2] cycloaddition
Shibata T, et al.
Organic & Biomolecular Chemistry, 6(23), 4296-4298 (2008)
Venukrishnan Komanduri et al.
Journal of the American Chemical Society, 130(38), 12592-12593 (2008-09-02)
Hydrogenation of 2-vinyl azines 1a-1e in the presence of N-arylsulfonyl imines 2a-2l at ambient temperature and pressure employing cationic rhodium catalysts ligated by tri-2-furylphosphine results in regioselective reductive coupling to furnish branched products of imine addition 3a-3v, which embody modest

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