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341134

Sigma-Aldrich

[1,4-Bis(diphenylphosphino)butane](1,5-cyclooctadiene)rhodium(I) tetrafluoroborate

98%

Synonym(s):

[Rh(dppb)(COD)]BF4

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About This Item

Empirical Formula (Hill Notation):
C36H40BF4P2Rh
CAS Number:
79255-71-3
Molecular Weight:
724.36
MDL number:
MFCD00075219
UNSPSC Code:
12161600
PubChem Substance ID:
24860907
NACRES:
NA.22

Quality Level

100

Assay

98%

reaction suitability

core: rhodium
reagent type: catalyst

mp

205 °C (dec.) (lit.)

SMILES string

[Rh+].F[B-](F)(F)F.C1CC=CCCC=C1.C(CCP(c2ccccc2)c3ccccc3)CP(c4ccccc4)c5ccccc5

InChI

1S/C28H28P2.C8H12.BF4.Rh/c1-5-15-25(16-6-1)29(26-17-7-2-8-18-26)23-13-14-24-30(27-19-9-3-10-20-27)28-21-11-4-12-22-28;1-2-4-6-8-7-5-3-1;2-1(3,4)5;/h1-12,15-22H,13-14,23-24H2;1-2,7-8H,3-6H2;;/q;;-1;+1/b;2-1-,8-7-;;

InChI key

YESRLRPURJQQBI-ONEVTFJLSA-N

Related Categories

General description

[1,4-Bis(diphenylphosphino)butane](1,5-cyclooctadiene)rhodium(I) tetrafluoroborate is a rhodium-based catalyst used for regioselective hydrogenation and enantioselective reductive amination reactions.

Application

[1,4-Bis(diphenylphosphino)butane](1,5-cyclooctadiene)rhodium(I)tetrafluoroborate can be used as a catalyst for the:
  • Regioselective hydrogenation of thebaine to synthesize tetrahydrothebaine.
  • Enantioselective reductive amination of α-ketoacids with benzylamines to synthesize α-N-benzylamino acids.
  • Stereoselective hydrogenation of α-(hydroxymethyl)-acrylate derivatives to synthesize 3-hydroxy-2-methylpropanoates.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - 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

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

341134-100MG:4548173137650
341134-BULK:
341134-VAR:
341134-500MG:4548173137667

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV4812
MKCT1340
MKCP6361
MKCG3650
MKBQ1621V

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Christopher J Lata et al.
Journal of the American Chemical Society, 132(1), 131-137 (2009-12-09)
The addition of Lewis acids such as trispentafluoroboron as cocatalysts has been found to have a dramatic effect on the Rh-catalyzed hydroboration of olefins with pinacol borane. For example, aliphatic olefins do not react at all in noncoordinating solvents, but
Akihiro Takemiya et al.
Journal of the American Chemical Society, 128(18), 6042-6043 (2006-05-04)
The intramolecular anti-Markovnikov hydroamination of 1-(3-aminopropyl)vinylarenes in the presence of a readily available rhodium catalyst to form 3-arylpiperidines is reported. In contrast to intermolecular hydroamination of vinylarenes, which occurred in high yields in the presence of rhodium catalysts containing DPEphos
Dariusz Gołowicz et al.
ChemistryOpen, 8(2), 196-200 (2019-03-01)
Low-field benchtop nuclear magnetic resonance (BT-NMR) spectrometers with Halbach magnets are being increasingly used in science and industry as cost-efficient tools for the monitoring of chemical reactions, including hydrogenation. However, their use of low-field magnets limits both resolution and sensitivity.
Andrey N Pravdivtsev et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 21(7), 667-672 (2020-01-04)
Nuclear Magnetic Resonance (NMR) is an intriguing quantum-mechanical effect that is used for routine medical diagnostics and chemical analysis alike. Numerous advancements have contributed to the success of the technique, including hyperpolarized contrast agents that enable real-time imaging of metabolism

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