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[(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene, also known as DPMOF, is a chiral chemical compound featuring a ferrocene core connected to a 2-oxazoline ring with a phenylmethyl substituent. This molecule possesses a 4S configuration, offering unique structural and electronic properties. The ferrocene core endows it with stability and redox characteristics, while the chiral 2-oxazoline ring facilitates selective interactions, making it a promising candidate for applications in asymmetric catalysis and as a chiral ligand in organometallic chemistry.

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  • 162157-05-3 Structure
  • Basic information

    1. Product Name: [(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene
    2. Synonyms: [(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene;[(4S)-4,5-Dihydro-4-phenylmethyl-2-oxazolyl]ferrocene,99%e.e.
    3. CAS NO:162157-05-3
    4. Molecular Formula: C20H10FeNO
    5. Molecular Weight: 336.15
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 162157-05-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: [(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene(CAS DataBase Reference)
    10. NIST Chemistry Reference: [(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene(162157-05-3)
    11. EPA Substance Registry System: [(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene(162157-05-3)
  • 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: 162157-05-3(Hazardous Substances Data)

162157-05-3 Usage

Uses

Used in Asymmetric Catalysis:
[(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene is utilized as a chiral ligand in asymmetric catalysis for its ability to induce enantioselectivity in various chemical reactions. Its unique structure allows for selective interactions with other molecules or catalysts, enhancing the efficiency and selectivity of enantioselective reactions.
Used in Organometallic Chemistry:
In organometallic chemistry, [(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene serves as a chiral ligand, contributing to the development of novel organometallic complexes with potential applications in catalysis and material science. Its redox properties and chiral nature enable the design of new catalysts with improved performance and selectivity.
Used in Enantioselective Reactions:
[(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene is employed as a chiral auxiliary or ligand in enantioselective reactions to achieve high levels of enantiomeric excess. Its unique structural features enable the control of stereochemistry during the reaction process, leading to the formation of enantiomerically pure products.
Used in Pharmaceutical Industry:
[(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene is used as a chiral building block in the synthesis of pharmaceutical compounds, particularly those requiring enantioselective synthesis. Its unique properties allow for the development of novel drugs with improved efficacy and selectivity, contributing to advancements in drug discovery and development.
Used in Material Science:
In the field of material science, [(4S)-4,5-dihydro-4-(phenylMethyl)-2-oxazolyl]-Ferrocene is utilized in the design and synthesis of new materials with specific properties, such as chiral polymers, catalysts, and sensors. Its redox characteristics and chiral nature enable the development of materials with tailored properties for various applications, including optoelectronics, sensors, and catalysis.

Check Digit Verification of cas no

The CAS Registry Mumber 162157-05-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,2,1,5 and 7 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 162157-05:
(8*1)+(7*6)+(6*2)+(5*1)+(4*5)+(3*7)+(2*0)+(1*5)=113
113 % 10 = 3
So 162157-05-3 is a valid CAS Registry Number.

162157-05-3Downstream Products

162157-05-3Relevant articles and documents

Bis(perfluoroalkyl) phosphino-oxazoline: A modular, stable, strongly π-accepting ligand for asymmetric catalysis

Hu, Zongjian,Li, Yuguang,Liu, Kai,Shen, Qilong

, p. 7957 - 7967 (2013/01/15)

A new class of stable, strongly π-accepting and modular bis-(perfluoroalkyl)-phosphine-oxazoline ligands (FOX) as CO mimics was prepared. It was demonstrated that these ligands, when coordinated to palladium catalysts, promote the asymmetric alkylation of monosubstituted allyl substrates with excellent regio- and enantioselectivity. Solid and solution structure analysis of the FOX-ligated Pd-allyl intermediate reveals that the combination of relative steric and strong trans influences presented by the P(CF 3)2 moiety gave rise to the excellent selectivity.

Synthesis and structure of novel chiral oxazolinylferrocenes and oxazolinylferrocenylphosphines, and their rhodium(I) -complexes

Nishibayashi, Yoshiaki,Segawa, Kyohei,Arikawa, Yasuyoshi,Ohe, Kouichi,Hidai, Masanobu,Uemura, Sakae

, p. 381 - 398 (2007/10/03)

A variety of chiral oxazolinylferrocenes are prepared from either ferrocenecarboxylic acid or cyanoferrocene and chiral β-amino alcohols. Highly diastereoselective ortho-lithiation (84 ~ 99% de) of the oxazolinylferrocenes is accomplished with sec-butyllithium and the treatment of the lithiated compounds with an electrophile such as MeI, Ph2PCI or (PhSe)2 gives the corresponding ortho-substituted oxazolinylferrocenes. The molecular structure of (S,S)-[2-(4′-isopropyloxazolin-2′-yl)ferrocenyl]diphenylphosphine (10), (S,S)-2-phenylseleno-1-(4′-isopropyloxazolinyl)ferrocene (17), (S,R)-3-methyl-1-diphenylphosphino-2-(4′-isopropyloxazolinyl)ferrocene (18), and (S,S,S)-[2-(4′,5′-diphenyloxazolin-2′-yl)ferrocenyl]diphenylphosphine ((S,S,S)-DIPOF; 21) has been fully characterized by X-ray crystallography. In connection with their usefulness as chiral ligands for Rh(I)-catalyzed asymmetric hydrosilylation of ketones, the square planar transition metal complexes having oxazolinylferrocenylphosphines, such as [Rh(COD)(P-N)]BF4 and Rh(CO)(P-N)Cl (P-N = 10 or 21), are prepared by treatment of [Rh(COD)2]BF4 and [Rh(CO)2Cl]2 with 10 and 21, respectively, and all structures have been characterized spectroscopically and further confirmed by X-ray crystallography.

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