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Merck
CN

704628

R-(tert-Butylmethylphosphino-di-tert-butylphosphinomethane)-η4-(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate

96%

Synonym(s):

(R)-TCFP-Rh, TCFP, R-[Rh cod TCFP]BF4

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About This Item

Empirical Formula (Hill Notation):
C22H44P2Rh
Molecular Weight:
473.44
NACRES:
NA.22
PubChem Substance ID:
329762467
UNSPSC Code:
12352002
MDL number:
MFCD11973806

Key Documents

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Product Name

R-(tert-Butylmethylphosphino-di-tert-butylphosphinomethane)-η4-(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, 96%

InChI

1S/C14H32P2.C8H12.BF4.Rh/c1-12(2,3)15(10)11-16(13(4,5)6)14(7,8)9;1-2-4-6-8-7-5-3-1;2-1(3,4)5;/h11H2,1-10H3;1-2,7-8H,3-6H2;;/q;;-1;+1/b;2-1-,8-7-;;/t15-;;;/m1.../s1

SMILES string

[Rh+].F[B-](F)(F)F.C1CC=CCCC=C1.CP(CP(C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI key

CQCAQRWECWCUBU-JMJDVLNDSA-N

assay

96%

form

solid

mp

171-177 °C

functional group

phosphine

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

R-(tert-Butylmethylphosphino-di-tert-butylphosphinomethane)-η4-(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate can be used:
  • In the asymmetric reduction of amines, ketones and unsaturated acids.
  • As a hydrogenation catalyst in the preparation of diastereomers of trifluorovaline.
  • As a catalyst in the olefin asymmetric hydrogenation.

Legal Information

Sold in collaboration with Johnson Matthey for research purposes only.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
67697LJ

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Johann Moschner et al.
Chemical reviews, 119(18), 10718-10801 (2019-08-23)
Fluorine does not belong to the pool of chemical elements that nature uses to build organic matter. However, chemists have exploited the unique properties of fluorine and produced countless fluoro-organic compounds without which our everyday lives would be unimaginable. The
Ilya D Gridnev et al.
Journal of the American Chemical Society, 130(8), 2560-2572 (2008-02-02)
The rhodium complex of (R)-(tert-butylmethylphosphino)(di-tert-butylphosphino)methane used in Rh-catalyzed asymmetric hydrogenation of representative substrates 3-14 demonstrated high catalytic activity coupled with wide scope and nearly perfect enantioselectivity. Mechanistic studies (NMR and DFT computations) were carried out in order to investigate the
Garrett Hoge et al.
Journal of the American Chemical Society, 126(19), 5966-5967 (2004-05-13)
A concise synthesis of both enantiomers of ligand 2 and rhodium complex 5 is presented. The crux of the synthesis is a chiral HPLC separation of the enantiomers of 4. Rhodium complex 5 possesses three hindered quadrants in the steric
Stefan Kraft et al.
Journal of the American Chemical Society, 139(34), 11630-11641 (2017-08-12)
The asymmetric hydrogenation of tetrasubstituted olefins provides direct access to very useful biological molecules and intermediates. The development of the technology has been slow, due in part to the synthetic challenges involved in developing chiral catalysts for a successful asymmetric
He-Ping Wu et al.
Organic letters, 6(20), 3645-3647 (2004-09-25)
[reaction: see text] A previously reported three-hindered quadrant chiral ligand and its corresponding rhodium complex provide high enantioselectivity for the asymmetric hydrogenation of beta-acetamido dehydroamino acid substrates. Both (E)- and (Z)-substrates are hydrogenated with high enantioselectivity in all of the

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