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142494-67-5

(2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE, also known as the Sharphos ligand, is a chiral bisphosphine that is commonly used in organic synthesis and catalysis. It consists of a hexane backbone with two diphenylphosphino groups attached at the 2nd and 5th positions. The chiral nature of the molecule allows for the formation of enantioselective products, making it an important tool in the production of pharmaceuticals, agrochemicals, and other high-value organic compounds.

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  • 142494-67-5 Structure

  • Basic information

    1. Product Name: (2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE
    2. Synonyms: (2S,5S)-(-)-BIS(DIPHENYLPHOSPHINO)HEXANE;(2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE
    3. CAS NO:142494-67-5
    4. Molecular Formula:
    5. Molecular Weight: 454.532
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 142494-67-5.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE(CAS DataBase Reference)
    10. NIST Chemistry Reference: (2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE(142494-67-5)
    11. EPA Substance Registry System: (2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE(142494-67-5)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 142494-67-5(Hazardous Substances Data)

142494-67-5 Usage

Uses

Used in Pharmaceutical Industry:
(2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE is used as a ligand for transition metal catalysts in the production of pharmaceuticals. Its chiral nature allows for the formation of enantioselective products, which is crucial for the synthesis of chiral drugs with desired biological activity.
Used in Agrochemical Industry:
(2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE is used as a ligand for transition metal catalysts in the production of agrochemicals. Its ability to form enantioselective products helps in the synthesis of chiral pesticides and other agrochemicals with improved efficacy and selectivity.
Used in Organic Synthesis:
(2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE is used as a ligand for transition metal catalysts in various organic synthesis applications. Its high efficiency and versatility make it a valuable compound for the synthesis of a wide range of high-value organic compounds.
Used in Asymmetric Hydrogenation Reactions:
(2R,5R)-(+)-BIS(DIPHENYLPHOSPHINO)HEXANE is used as a ligand for transition metal catalysts in asymmetric hydrogenation reactions. Its chiral nature allows for the selective reduction of prochiral compounds, leading to the formation of enantiomerically pure products. This is particularly important in the synthesis of chiral compounds with specific biological activities.

Check Digit Verification of cas no

The CAS Registry Mumber 142494-67-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,2,4,9 and 4 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 142494-67:
(8*1)+(7*4)+(6*2)+(5*4)+(4*9)+(3*4)+(2*6)+(1*7)=135
135 % 10 = 5
So 142494-67-5 is a valid CAS Registry Number.

142494-67-5Downstream Products

142494-67-5Relevant articles and documents

An Efficient Procedure for the Synthesis of Electron Rich Biphosphines Containing Homochiral Backbones.

McKinstry, Lydia,Livinghouse, Tom

, p. 9319 - 9322 (1994)

An eminently practical method for the synthesis of homochiral biphosphines is described.This procedure entails the sequential reaction of homochiral ditosylate with the appropriate dialkylphosphine-borane anion followed by BH3 decomplexation mediated by HBF4*OMe2.

Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids

Saito, Susumu,Wen, Ke,Yoshioka, Shota

supporting information, p. 1510 - 1524 (2021/06/18)

Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.

Ligand substituent effects on asymmetric induction. Effect of structural variations of the DIOP ligand on the Rh-catalyzed asymmetric hydrogenation of enamides

Yan, Yuan-Yong,RajanBabu

, p. 4137 - 4140 (2007/10/03)

(equation presented) Substituent changes in the ligand (L*) backbone and the chelating phosphorus atoms of the classical DIOP ligand result in dramatic changes in the enantioselectivity of Rh+L*-catalyzed enamide hydrogenations.

Synthesis, determination of enantiomeric purity and structural characterisation of enantiopure (2R,5R)-(+)-2,5-bis-(diphenylphosphino)-hexane, a chiral DPPB analogue

Wiesauer, Christian,Kratky, Christoph,Weissensteiner, Walter

, p. 397 - 398 (2007/10/03)

Enantiopure (2R,5R)-(+)-2,5-bis-(diphenylphosphino)hexane, 3, a chiral analogue of 1,4-bis-(diphenylphosphino)butane was synthesized in two steps from enantiomerically pure (2S,5S)-(+)-hexanediol. The molecular structure of (2R,5R)-3 was determined by X-ray structure analysis of its nickel-(II)-complex showing a rare dimeric species; NMR analysis of the reaction product of 3 with (+)-di-μ-chloro-bis-{2-[1-(dimethylamino)ethyl]phenyl-C,N}-dipallad ium allowed to deduce the enantiomeric purity.

An Efficient Procedure for the Synthesis of C-Chiral Bisphosphines.

McKinstry, Lydia,Livinghouse, Tom

, p. 7655 - 7666 (2007/10/02)

A practical method for the synthesis of bisphosphines containing homochiral carbon backbones is described.This procedure entails sequential reaction of a homochiral ditosylate with the appropriate dialkyl- or diarylphosphine-borane anion followed by BH3 decomplexation mediated by HBF4*OMe2.

Ruthenium phosphine complex

-

, (2008/06/13)

A ruthenium phosphine complex having catalytic, hydrogenation activity is disclosed. The catalyst as the formula STR1 wherein R and R' are the same or different and are C1 to C6 linear or branched alkyl; R" is hydrogen or C1/su

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