Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

704628

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

Quality Level

100

Assay

96%

form

solid

mp

171-177 °C

storage temp.

2-8°C

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

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

InChI key

CQCAQRWECWCUBU-JMJDVLNDSA-N

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 Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
67697LJ

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service