203000-53-7

Basic information

• Product Name: (S,S)-1,2-BIS(TERT-BUTYLMETHYLPHOSPHINO)ETHANE
• Synonyms: (S,S)-1,2-BIS(TERT-BUTYLMETHYLPHOSPHINO)ETHANE;(S,S)-BISP
• CAS NO: 203000-53-7
• Molecular Formula: C12H28P2
• Molecular Weight: 234.3
• Mol File: 203000-53-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 277.4±23.0 °C(Predicted)
• Appearance: /
• CAS DataBase Reference: (S,S)-1,2-BIS(TERT-BUTYLMETHYLPHOSPHINO)ETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-1,2-BIS(TERT-BUTYLMETHYLPHOSPHINO)ETHANE(203000-53-7)
• EPA Substance Registry System: (S,S)-1,2-BIS(TERT-BUTYLMETHYLPHOSPHINO)ETHANE(203000-53-7)

Safety Data

• Hazardous Substances Data: 203000-53-7(Hazardous Substances Data)

Usage

General Description

(S,S)-1,2-BIS(TERT-BUTYLMETHYLPHOSPHINO)ETHANE, also known as BISPHANE, is a chiral diphosphine ligand commonly used in organic and inorganic chemistry. (S,S)-1,2-BIS(TERT-BUTYLMETHYLPHOSPHINO)ETHANE is known for its ability to form stable and selective complexes with various metal ions, making it a valuable tool in catalysis and coordination chemistry. It is particularly useful in asymmetric synthesis and homogeneous catalysis due to its chiral nature, and it has been utilized in the development of several important chemical processes. BISPHANE is also known for its high stability and low toxicity, making it a preferred reagent in many research and industrial applications.

Downstream Products

• 203000-59-3 Rh(P(CH₃)(C(CH₃)3)CH₂)2(CH₂(CH)6)⁽¹⁺⁾*BF₄^(1-)=[Rh(P(CH₃)(C(CH₃)3)CH₂)2(CH₂(CH)6)][BF₄] 

Relevant articles and documents

Preparation of (s,s)-1,2-bis(tert-butylmethylphosphino)ethane ((S,S)-t-Bu-BISP*) as a rhodium complex: [Rhodium(1+), [(2,3,5,6-)-bicyclo[2.2.1]hepta-2,5-diene] (S,S)-1,2-bis(M, -butymethylphosphino)ethane, trafluoroborate(1-)]

-

Asymmetric Hydrogenation Catalyzed by (S,S)-R-BisP*-Rh and (R,R)-R-MiniPHOS Complexes: Scope, Limitations, and Mechanism

A new class of chiral C2-symmetric bis(trialkyl)phosphine ligands has been prepared and used in Rh(I)-catalyzed asymmetric hydrogenation reactions. The ligands, 1,2-bis(alkylmethylphosphino)ethanes 1 a-g (abbreviated as BisP*, alkyl = t-butyl, 1-adamantyl, 1-methylcyclohexyl, 1,1-diethylpropyl, cyclopentyl, cyclohexyl, isopropyl) and 1,2-bis(alkylmethylphosphino)methanes 2 a-d (abbreviated as MiniPHOS, alkyl = t-butyl, cyclohexyl, isopropyl, phenyl) are prepared by a simple synthetic approach based on the air-stable phosphine-boranes. These new ligands give the corresponding Rh(I) complexes, which are effective catalytic precursors for the asymmetric hydrogenation of a representative series of dehydroamino acids and itaconic acid derivatives. Enantioselectivities observed in these hydrogenations are universally high and in many cases exceed 99%. X-Ray characterization of four precatalysts, study of the pressure effects, deuteration experiments, and characterization of the wide series of intermediates in the catalytic cycle are used for the discussion of the possible correlation between the structure of the catalysts and the outcome of the catalytic asymmetric hydrogenation.

Synthesis of P-chirogenic diphosphine oxides and their use in catalytic asymmetric Diels-Alder reaction

New P-chirogenic phosphine oxides, (R,R)-1,2-bis(alkylmethylphosphinyl)ethanes (alkyl = 1-adamantyl, tert-butyl) and (S,S)-1, 1-bis(tert-butylmethylphosphinyl)methane have been synthesized from PCl3 via four steps. Their iron(III) complexes are