129098-54-0

Basic information

• Product Name: (R)-2-((3-CHLOROPHENOXY)METHYL)OXIRANE
• Synonyms: (R)-2-((3-CHLOROPHENOXY)METHYL)OXIRANE;(2R)-2-[(3-chlorophenoxy)methyl]oxirane;Oxirane, [(3-chlorophenoxy)Methyl]-, (R)-
• CAS NO: 129098-54-0
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.61956
• Mol File: 129098-54-0.mol

Chemical Properties

• Boiling Point: 273.574°C at 760 mmHg
• Flash Point: 117°C
• Appearance: /
• Density: 1.267g/cm³
• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: (R)-2-((3-CHLOROPHENOXY)METHYL)OXIRANE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-((3-CHLOROPHENOXY)METHYL)OXIRANE(129098-54-0)
• EPA Substance Registry System: (R)-2-((3-CHLOROPHENOXY)METHYL)OXIRANE(129098-54-0)

Safety Data

• Hazardous Substances Data: 129098-54-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
(R)-2-((3-CHLOROPHENOXY)METHYL)OXIRANE is used as a key component in the production of epoxy resins for various applications, such as coatings, adhesives, and electrical insulation materials. Its high reactivity allows for the formation of strong cross-linked polymers, providing excellent mechanical, chemical, and thermal properties to the final products.
Used in Solvent Applications:
(R)-2-((3-CHLOROPHENOXY)METHYL)OXIRANE is used as a solvent in certain chemical processes due to its ability to dissolve a wide range of substances. Its solubility properties make it suitable for use in various industrial applications, including the manufacturing of pharmaceuticals, agrochemicals, and other specialty chemicals.
However, it is important to note that the use of (R)-2-((3-CHLOROPHENOXY)METHYL)OXIRANE is regulated by environmental and safety standards due to its toxic properties. Strict safety precautions, including proper handling, storage, and disposal methods, must be followed to minimize the risk of exposure and potential health hazards.

InChI:InChI=1/C9H9ClO2/c10-7-2-1-3-8(4-7)11-5-9-6-12-9/h1-4,9H,5-6H2/t9-/m0/s1

Upstream product

• 2211-95-2 1-(3-chlorophenoxy)-2,3,epoxypropane 
• 124-38-9 carbon dioxide 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 108-43-0 3-monochlorophenol 
• 106-89-8 epichlorohydrin 
• 60456-23-7 (S)-oxiranemethanol 
• 1972-28-7 diethylazodicarboxylate 
• 24824-86-0 1-(allyloxy)-3-chlorobenzene 

Downstream Products

• 129098-53-9 (S)-2-(3-chlorophenoxymethyl)oxirane 
• 39735-81-4 1-chloro-3-(3-chloro-phenoxy)-propan-2-ol 
• 4427-92-3 (4S)-4-phenyl[1,3]dioxolan-2-one 
• 90971-11-2 (R)-1-phenyl-1,2-ethanediol carbonate 
• 83195-08-8 3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylamino]-propionic acid ethyl ester; hydrochloride 

Relevant articles and documents

Concise, scalable and enantioselective total synthesis of prostaglandins

Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]

Substituted diaryl compound and preparation method and application thereof

The invention relates to the field of medicinal chemistry, in particular to a substituted diaryl compound (I). The preparation method comprises the following steps: medicine preparation and medical application thereof. Test results show that the substituted diaryl compound has a good inhibition effect on human lung cancer (A549), human ovarian cancer (SKOV3), human melanoma (A375) and human colon cancer (LOVO) cells. Formula (I):

Chemoselective Epoxidation of Allyloxybenzene by Hydrogen Peroxide Over MFI-Type Titanosilicate

The chemoselective synthesis of 2-(phenoxymethyl)oxirane from allyloxybenzene is achieved with over 90 % yield in a sustainable reaction system using titanium-substituted silicalite-1 (TS-1) as a catalyst, hydrogen peroxide (H2O2) as an oxidant, and a mixture of MeOH/MeCN as a solvent at 40 °C. No acid-catalyzed side reactions prompted by the Lewis acidity of the Ti active site in TS-1 are observed. The TS-1 catalyst can also promote the formation of oxiranes from various p-substituted allyloxybenzenes in good yields. The reaction mechanism is investigated through the reaction with other allyloxy compounds. The results, which are supported by DFT calculations, indicate that an active species of Ti peroxides formed from the reaction of TS-1 with H2O2 selectively oxidizes the allyloxybenzene to 2-(phenoxymethyl)oxirane.

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.

Structure-guided design, synthesis and evaluation of oxazolidinone-based inhibitors of norovirus 3CL protease

Acute nonbacterial gastroenteritis caused by noroviruses constitutes a global public health concern and a significant economic burden. There are currently no small molecule therapeutics or vaccines for the treatment of norovirus infections. A structure-gu

Directed evolution of an enantioselective epoxide hydrolase: Uncovering the source of enantioselectivity at each evolutionary stage

Directed evolution of enzymes as enantioselective catalysts in organic chemistry is an alternative to traditional asymmetric catalysis using chiral transition-metal complexes or organocatalysts, the different approaches often being complementary. Moreover, directed evolution studies allow us to learn more about how enzymes perform mechanistically. The present study concerns a previously evolved highly enantioselective mutant of the epoxide hydrolase from Aspergillus niger in the hydrolytic kinetic resolution of racemic glycidyl phenyl ether. Kinetic data, molecular dynamics calculations, molecular modeling, inhibition experiments, and X-raystructural work for the wild-type (WT) enzyme and the best mutant revea l the basis of the large increase in enantioselectivity (E = 4.6 versus E = 115). The overall structures of the WT and the mutant are essentially identical, but dramatic differences are observed in the active site asrevealed by the X-ray structures. All of the experimental and computati onal results support a model in which productive positioning of the preferred (S)-glycidyl phenyl ether, but not the (R)-enantiomer, forms the basis of enhanced enantioselectivity. Predictions regarding substrate scope and enantioselectivity of the best mutant are shown to be possible.

Hydrolytic kinetic resolution of terminal epoxides catalyzed by novel bimetallic chiral Co (salen) complexes

Novel bimetallic chiral Co (salen) complexes bearing transition-metal salts have been synthesized. The easily prepared complexes exhibited very high catalytic reactivity and enantioselectivity in hydrolytic kinetic resolution (HKR) of racemic terminal epoxides and consequently provided enantiomerically enriched epoxides (up to 99% ee). Copyright Taylor & Francis Group, LLC.

A new dinuclear chiral salen complexes for asymmetric ring opening and closing reactions: Synthesis of valuable chiral intermediates

A new dinuclear chiral Co(salen) complexes bearing group 13 metals have been synthesized and characterized. The easily prepared complexes exhibited very high catalytic reactivity and enantioselectivity for the asymmetric ring opening of epoxides with H2O, chloride ions and carboxylic acids and consequently provide enantiomerically enriched terminal epoxides (>99% ee). It also catalyzes the asymmetric cyclization of ring opened product, to prepare optically pure terminal epoxides in one step. The homogeneous dinuclear chiral Co(salen) have been covalently immobilized on MCM-41. The potential benefits of heterogenization include facilitation of catalyst separation and recyclability requiring very simple techniques. The system described is very efficient.

SUBSTITUTED HETEROCYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF CARDIOVASCULAR DISEASES

wherein: a.o. T is oxygen, sulfur, or NR11 , in which R11 is hydrogen or lower alkyl; V is -N1 is hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl; X2 is optionally substituted aryl or optionally substituted heteroaryl; Y is optionally substituted dihydroheteroarcyl; and Z1 and Z2 are independently optionally substituted alkylene of 1-4 carbon atoms, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal’s (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

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.