20697-04-5

Usage

Uses

Used in Organic Synthesis:
2-(3-chloro-phenyl)-oxirane is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for a range of chemical reactions, facilitating the creation of diverse molecules with potential applications across different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-(3-chloro-phenyl)-oxirane is utilized as a building block for the development of new drugs. Its chemical properties enable the formation of complex molecular structures that can target specific biological pathways, potentially leading to the discovery of novel therapeutic agents.
Used in Agricultural Industry:
2-(3-chloro-phenyl)-oxirane may also find applications in the agricultural industry, potentially serving as a precursor for the development of new agrochemicals. Its reactivity and structural features can be harnessed to create compounds with pesticidal or herbicidal properties, contributing to more effective crop protection strategies.
Safety and Regulatory Compliance:
Given the reactivity of 2-(3-chloro-phenyl)-oxirane, it is crucial to adhere to proper handling and storage procedures to ensure the safety of personnel and compliance with environmental regulations. This includes the use of appropriate containment and protective equipment during its synthesis, storage, and application processes.

InChI:InChI=1/C8H7ClO/c9-7-3-1-2-6(4-7)8-5-10-8/h1-4,8H,5H2/t8-/m0/s1

Upstream product

• 100-42-5 styrene 
• 2039-85-2 3-Chlorostyrene 
• 100-13-0 4-nitrostyrene 
• 6814-64-8 methylenedimethyl sulfurane 
• 587-04-2 m-Chlorobenzaldehyde 
• 2181-42-2 trimethylsulphonium iodide 
• 117538-45-1 2-bromo-1-(3-chlorophenyl)ethanol 
• 2181-44-4 trimethylsulfonium methylsulfate 
• 106262-93-5 (R)-1-(3-chlorophenyl)-2-chloro-1-hydroxyethane 
• 106262-93-5 (+)-2-chloro-1-(3-chlorophenyl)ethanol 
• 21886-56-6 3-chlorophenacyl chloride 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 75-15-0 carbon disulfide 
• 53631-02-0 2-(3-chlorophenyl)-2,3,5,6-tetrahydroimidazo-[2,1-b]thiazole 

Downstream Products

• 106262-93-5 (+)-2-chloro-1-(3-chlorophenyl)ethanol 
• 20697-04-5 (R)-meta-chlorostyrene oxide 
• 152008-72-5 (S)-(+)-1-(3-chlorophenyl)-1,2-ethanediol 
• 80051-04-3 (R)-(-)-1-(3-chlorophenyl)-1,2-ethanediol 
• 115648-90-3 (S)-3-chlorostyrene oxide 

Relevant academic research and scientific papers

Synthesis, characterization and crystal structure of a novel tetranuclear oxidovanadium(V) complex derived from N’-(2-hydroxy-3-methoxybenzylidene)isonicotinohydrazide with catalytic property

A novel tetranuclear oxidovanadium(V) complex, [V4O4(OEt)4L4], where L is the dianionic form of N’-(2-hydroxy-3-methoxybenzylidene)isonicotinohydrazide (H2L), has been prepared and characterized by physico-chemical methods and single crystal X-ray diffraction. The V atom in the complex is coordinated by the phenolate oxygen, imino nitrogen and enolate oxygen of one aroylhydrazone ligand, one pyridine nitrogen of another aroylhydrazone ligand, one deprotonated ethanol oxygen, and one oxo group, forming an octahedral coordination. The oxidation of olefins with the complex as the catalyst was evaluated, which indicated that the complex has effective catalytic efficiency in the oxidation of several aliphatic and aromatic substrates by using tert-butyl hydrogen peroxide as oxidant.

A new clade of styrene monooxygenases for (R)-selective epoxidation

Styrene monooxygenases (SMOs) are excellent enzymes for the production of (S)-enantiopure epoxides, but so far, only one (R)-selective SMO has been identified with a narrow substrate spectrum. Mining the NCBI non-redundant protein sequences returned a new distinct clade of (R)-selective SMOs. Among them,SeStyA fromStreptomyces exfoliatus,AaStyA fromAmycolatopsis albispora, andPbStyA fromPseudonocardiaceaewere carefully characterized and found to convert a spectrum of styrene analogues into the corresponding (R)-epoxides with up to >99% ee. Moreover, site 46 (AaStyA numbering) was identified as a critical residue that affects the enantioselectivity of SMOs. Phenylalanine at site 46 was required for the (R)-selective SMO to endow excellent enantioselectivity. The identification of new (R)-selective SMOs would add a valuable green alternative to the synthetic tool box for the synthesis of enantiopure (R)-epoxides.

Aerobic epoxidation of styrene over Zr-based metal-organic framework encapsulated transition metal substituted phosphomolybdic acid

Catalytic epoxidation of styrene with molecular oxygen is regarded as an eco-friendly alternative to producing industrially important chemical of styrene oxide (STO). Recent efforts have been focused on developing highly active and stable heterogeneous catalysts with high STO selectivity for the aerobic epoxidation of styrene. Herein, a series of transition metal monosubstituted heteropolyacid compounds (TM-HPAs), such as Fe, Co, Ni or Cu-monosubstituted HPA, were encapsulated in UiO-66 frameworks (denoted as TM-HPA@UiO-66) by direct solvothermal method, and their catalytic properties were investigated for the aerobic epoxidation of styrene with aldehydes as co-reductants. Among them, Co-HPA@UiO-66 showed relatively high catalytic activity, stability and epoxidation selectivity at very mild conditions (313 K, ambient pressure), that can achieve 82 % selectivity to STO under a styrene conversion of 96 % with air as oxidant and pivalaldehyde (PIA) as co-reductant. In addition, the hybrid composite catalyst can also efficiently catalyze the aerobic epoxidation of a variety of styrene derivatives. The monosubstituted Co atoms in Co-HPA@UiO-66 are the main active sites for the aerobic epoxidation of styrene with O2/PIA, which can efficiently converting styrene to the corresponding epoxide through the activation of the in-situ generated acylperoxy radical intermediate.

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Enantiomer Separation of Nitriles and Epoxides by Crystallization with Chiral Organic Salts: Chirality Switching Modulated by Achiral Acids

Enantiomer separation of nitriles and epoxides by inclusion crystal formation with organic-salt type chiral hosts was achieved. The stereochemistry of the preferentially included nitrile could be switched only by changing the achiral carboxylic acid component. Crystallographic analysis of the inclusion crystals reveals that the hydrogen-bonding networks are controlled by the acidity of the phenol group of the acids, which results in chirality switching.

Oxidovanadium(V) and dioxidomolybdenum(VI) Complexes of N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-fluorobenzohydrazide: Synthesis, characterization, crystal structures and catalytic property

N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-fluorobenzohydrazide (H2L) was used to prepare oxidovanadium(V) complex [VOL(OEt)(MeOH)] (1) and dioxidomolybdenum(VI) complex [MoO2L(OH2)]·[MoO2L(EtOH)] (2). The complexes were characterized by IR, UV-Vis, NMR spectroscopy, and single crystal X-ray diffraction. X-ray analysis indicates that the complexes are mononuclear species with the metal atoms in octahedral coordination. The complexes were studied for catalytic oxidation property on some olefins with tert-butyl hydroperoxide as oxidant.

Reprogramming Epoxide Hydrolase to Improve Enantioconvergence in Hydrolysis of Styrene Oxide Scaffolds

Enantioconvergent hydrolysis by epoxide hydrolase is a promising method for the synthesis of important vicinal diols. However, the poor regioselectivity of the naturally occurring enzymes results in low enantioconvergence in the enzymatic hydrolysis of styrene oxides. Herein, modulated residue No. 263 was redesigned based on structural information and a smart variant library was constructed by site-directed modification using an “optimized amino acid alphabet” to improve the regioselectivity of epoxide hydrolase from Vigna radiata (VrEH2). The regioselectivity coefficient (r) of variant M263Q for the R-isomer of meta-substituted styrene oxides was improved 40–63-fold, and variant M263V also exhibited higher regioselectivity towards the R-isomer of para-substituted styrene oxides compared with the wild type, which resulted in improved enantioconvergence in hydrolysis of styrene oxide scaffolds. Structural insight showed the crucial role of residue No. 263 in modulating the substrate binding conformation by altering the binding surroundings. Furthermore, increased differences in the attacking distance between nucleophilic residue Asp101 and the two carbon atoms of the epoxide ring provided evidence for improved regioselectivity. Several high-value vicinal diols were readily synthesized (>88% yield, 90%–98% ee) by enantioconvergent hydrolysis using the reprogrammed variants. These findings provide a successful strategy for enhancing the enantioconvergence of native epoxide hydrolases through key single-site mutation and more powerful enzyme tools for the enantioconvergent hydrolysis of styrene oxide scaffolds into single (R)-enantiomers of chiral vicinal diols. (Figure presented.).

Synthesis, Characterization and Crystal Structures of Oxidovanadium(V) and Dioxidomolybdenum(VI) Complexes Derived from 2-bromo-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide with Catalytic Property

Abstract: A hydrazone compound 2-bromo-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (H2L) was prepared and characterized by IR, UV-Vis and NMR spectra. Based on the hydrazone compound, a new oxidovanadium(V) and a new dioxidomolybdenum(VI) complexes, [VO(L)(OEt)(EtOH)] (I) and [MoO2(L)(OH2)] (II), were prepared and characterized by IR, UV-Vis, NMR spectra, and single crystal X-ray diffraction (CIF files nos. 1866755 (I) and 1866756 (II)). Complex I crystallizes as the monoclinic space group P21/c with unit cell dimensions a = 12.8733(12), b = 13.5088(13), c = 11.9262(11) ?, β = 91.765(2)°, V = 2073.0(3) ?3, Z = 4, R1 = 0.0524, wR2 = 0.1329, GOOF = 1.245. Complex II crystallizes as the monoclinic space group P21/c with unit cell dimensions a = 8.1140(9), b = 16.2975(19), c = 13.4318(15) ?, β = 106.456(2)°, V = 1703.4(3) ?3, Z = 4, R1 = 0.0296, wR2 = 0.0728, GOOF = 1.046. X-ray analysis indicates that the complexes are mononuclear species with the metal atoms in octahedral coordination. The complexes were studied for catalytic oxidation property on some olefins with tert-butyl hydrogen peroxide as oxidant.

Highly selective and efficient olefin epoxidation with pure inorganic-ligand supported iron catalysts

Over the past two decades, there have been major developments in the transition iron-catalyzed selective oxidation of alkenes to epoxides; a common structure found in drug, isolated natural products, and fine chemicals. Many of these approaches have enabled highly efficient and selective epoxidation of alkenes via the design of specialized ligands, which facilitates to control the activity and selectivity of the reactions catalyzed by iron atom. Herein, we report the development of the olefin epoxidation with inorganic-ligand supported iron-catalysts using 30% H2O2 as an oxidant, and the mechanism is similar to iron-porphyrin type. With the catalyst 1, (NH4)3[FeMo6O18(OH)6], various aromatic and aliphatic alkenes were successfully transformed into the corresponding epoxides with excellent yields as well as chemo- and stereo-selectivity. This catalytic system possesses the advantages of being able to avoid the use of expensive, toxic, air/moisture sensitive and commercially unavailable organic ligands. The generality of this methodology is simple to operate and exhibits high catalytic activity as well as excellent stability, which gives it the potential to be used on an industrial scale, and maybe opens a way for the catalytic oxidation reaction via inorganic-ligand coordinated iron catalysis.

Unified Mechanism of Oxygen Atom Transfer and Hydrogen Atom Transfer Reactions with a Triflic Acid-Bound Nonheme Manganese(IV)-Oxo Complex via Outer-Sphere Electron Transfer

Outer-sphere electron transfer from styrene, thioanisole, and toluene derivatives to a triflic acid (HOTf)-bound nonheme Mn(IV)-oxo complex, [(N4Py)MnIV(O)]2+-(HOTf)2 (N4Py = N,N-bis(2-pyridylmethyl)-N-bis(2-pyridyl)methylamine), has been shown to be the rate-determining step of different types of redox reactions such as epoxidation, sulfoxidation, and hydroxylation of styrene, thioanisole, and toluene derivatives, respectively, by [(N4Py)MnIV(O)]2+-(HOTf)2. The rate constants of HOTf-promoted epoxidation of all styrene derivatives with [(N4Py)MnIV(O)]2+ and electron transfer from electron donors to [(N4Py)MnV(O)]2+ exhibit a remarkably unified correlation with the driving force of outer-sphere electron transfer in light of the Marcus theory of electron transfer. The same electron-transfer driving force dependence is observed in the oxygen atom transfer from [(N4Py)MnIV(O)]2+-(HOTf)2 to thioanisole derivatives as well as in the hydrogen atom transfer from toluene derivatives to [(N4Py)MnIV(O)]2+-(HOTf)2. Thus, mechanisms of oxygen atom transfer (epoxidation and sulfoxidation) reactions of styrene and thioanisole derivatives and hydrogen atom transfer (hydroxylation) reactions of toluene derivatives by [(N4Py)MnIV(O)]2+-(HOTf)2 have been unified for the first time as the same reaction pathway via outer-sphere electron transfer, followed by the fast bond-forming step, which exhibits the singly unified electron-transfer driving force dependence of the rate constants as outer-sphere electron-transfer reactions. In the case of the epoxidation of cis-stilbene by [(N4Py)MnIV(O)]2+-(HOTf)2, the isomerization of cis-stilbene radical cation to trans-stilbene radical cation occurs after outer-sphere electron transfer from cis-stilbene to [(N4Py)MnIV(O)]2+-(HOTf)2 to yield trans-stilbene oxide selectively, which is also taken as evidence for the occurrence of electron transfer in the acid-catalyzed epoxidation.