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Usage

Uses

Used in Organic Synthesis:
(R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE is used as a key intermediate in organic synthesis for the creation of various chemical compounds. Its unique structure allows for versatile reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used as a Starting Material:
In the chemical industry, (R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE is utilized as a starting material for the production of other chemical compounds. Its epoxide functionality and the presence of a chlorine atom on the phenyl group provide opportunities for further chemical modifications, leading to the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
(R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE is used as a building block in the pharmaceutical industry for the development of new drugs. Its unique structure can be exploited to create molecules with specific biological activities, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE is employed as a precursor for the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties can be tailored to create compounds with targeted effects on pests and weeds, contributing to more effective and sustainable agricultural practices.
Used in Specialty Chemicals:
(R)-2-((4-CHLOROPHENOXY)METHYL)OXIRANE is also used in the production of specialty chemicals, which are high-value compounds with specific applications in various industries. Its unique structure and reactivity make it suitable for the development of advanced materials, such as polymers, coatings, and adhesives.

Upstream product

• 2212-05-7 4-chlorophenyl 2,3-epoxypropyl ether 
• 124-38-9 carbon dioxide 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 106-48-9 4-chloro-phenol 
• 67843-74-7 (S)-epichlorohydrin 
• 70987-78-9 (S)-Glycidyl tosylate 

Downstream Products

• 1166991-18-9 1-((S)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol 
• 1311146-79-8 (R)-1-(((1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-chlorophenoxy)propan-2-ol 
• 1394906-80-9 (R)-1-(tert-butylamino)-3-(4-chlorophenoxy)propan-2-ol 
• 1383939-95-4 C₂₀H₂₅ClN₂O₃ 
• 1383939-96-5 C₂₀H₂₅ClN₂O₃ 
• 1383939-98-7 C₂₀H₂₄Cl₂N₂O₂ 
• 1383939-99-8 C₂₀H₂₄Cl₂N₂O₂ 
• 1383940-00-8 C₂₀H₂₃Cl₃N₂O₂ 
• 1383940-01-9 C₂₀H₂₃Cl₂FN₂O₂ 
• 1383940-03-1 C₂₀H₂₄ClFN₂O₂ 
• 1383939-92-1 C₁₉H₂₂ClFN₂O₂ 
• 1383939-91-0 C₁₉H₂₂ClFN₂O₂ 
• 511255-41-7 (R)-1-(4-chlorophenoxy)-3-methylaminopropan-2-ol 

Relevant academic research and scientific papers

Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide

Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO2. Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.

Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide

Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of epoxides. A catalytic cycle proposed was supported by DFT calculations.

Synthesis and biological evaluation of 1-(2-hydroxy-3-phenyloxypropyl) piperazine derivatives as T-type calcium channel blockers

To obtain selective and potent inhibitor for T-type calcium channel by ligand based drug design, 2-hydroxy-3-phenoxypropyl piperazine derivatives were synthesized and evaluated for in vitro activities. Compound 6m and 6q showed high selectivity over hERG

Enantioselective α-hydroxylation of β-keto esters catalyzed by chiral S-timolol derivatives

A screen of aryloxy aminopropanol organocatalysts derived from the β-blocker inhibitor S-timolol determined the most active catalyst of asymmetric α-hydroxylation of β-keto esters. (R)-1-(tert-butylamino)- 3-(3,4,5-trimethoxyphenoxy) propan-2-ol (3k) was the most effective derivative, enantioselectively catalyzing α-hydroxylation of β-keto esters using tert-butyl hydroperoxide as the oxidant in hexane to afford the corresponding products in excellent yield and with good enantioselectivity (up to 96% yield, 88% ee).

Development of β-amino alcohol derivatives that inhibit toll-like receptor 4 mediated inflammatory response as potential antiseptics

Toll-like receptor 4 (TLR4) induced proinflammatory signaling has been directly implicated in severe sepsis and represents an attractive therapeutic target. Herein, we report our investigations into the structure-activity relationship and preliminary drug metabolism/pharmacokinetics study of β-amino alcohol derivatives that inhibit the TLR4 signaling pathway. Lead compounds were identified from in vitro cellular examination with micromolar potency for their inhibitory effects on TLR4 signaling and subsequently assessed for their ability to suppress the TLR4-induced inflammatory response in an ex vivo whole blood model. In addition, the toxicology, specificity, solubility, brain-blood barrier permeability, and drug metabolism of several compounds were evaluated. Although further optimizations are needed, our findings lay the groundwork for the future drug development of this class of small molecule agents for the treatment of severe sepsis.

An unusual (R)-selective epoxide hydrolase with high activity for facile preparation of enantiopure glycidyl ethers

A novel epoxide hydrolase (BMEH) with unusual (R)-enantioselectivity and very high activity was cloned from Bacillus megaterium ECU1001. Highest enantioselectivities (E>200) were achieved in the bioresolution of ortho-substituted phenyl glycidyl ethers and para-nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)-enantiopreference was unexpectedly observed for the ortho-nitrophenyl glycidyl ether. As a proof-of-concept, five enantiopure epoxides (>99% ee) were obtained in high yields, and a gram-scale preparation of (S)-ortho-methylphenyl glycidyl ether was then successfully performed within a few hours, indicating that BMEH is an attractive biocatalyst for the efficient preparation of optically active epoxides. Copyright

Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity

Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 mem

Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes

The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2- dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2- diols was proposed.

Analogs of the dopamine D4 receptor ligand FAUC 113 with planar- and central-chirality

By employing yeast enzymes, natural amino acids and the Jacobsen's catalyst as sources of chirality, we have synthesized pyrazolo[1,5-a]pyridine derivatives with central- and planar-chirality as analogs of the dopamine D4 receptor ligand FAUC 113. In vitro binding experiments displayed enhanced D2 and D3 affinity for both enantiomers of the [2.2]paracyclophane 3. The C-methylpiperazine (R)-4a revealed excellent D4 selectivity.

CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers

The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1,2-epoxyalkanes. These reactions provide convenient access to enantiopure β-blockers.