2212-06-8

Basic information

• Product Name: 2-[(4-BROMOPHENOXY)METHYL]OXIRANE
• Synonyms: 2-[(4-BROMOPHENOXY)METHYL]OXIRANE;BROMOPHENYL GLYCIDYL ETHER;((4-bromophenoxy)methyl)-oxiran;((4-bromophenoxy)methyl)oxirane;1-(p-bromophenoxy)-2,3-epoxy-propan;1-(p-Bromophenoxy)-2,3-epoxypropane;4-Bromophenyl glycidyl ether;4-bromophenylglycidylether
• CAS NO: 2212-06-8
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.07
• EINECS: 218-656-3
• Mol File: 2212-06-8.mol

Chemical Properties

• Melting Point: 51-52 °C
• Boiling Point: 296°Cat760mmHg
• Flash Point: 138.1°C
• Appearance: /
• Density: 1.527g/cm³
• Vapor Pressure: 0.00259mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: 2-[(4-BROMOPHENOXY)METHYL]OXIRANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-BROMOPHENOXY)METHYL]OXIRANE(2212-06-8)
• EPA Substance Registry System: 2-[(4-BROMOPHENOXY)METHYL]OXIRANE(2212-06-8)

Safety Data

• Hazardous Substances Data: 2212-06-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
2-[(4-Bromophenoxy)methyl]oxirane is used as a research compound for its unique reactivity with a wide range of substances. Its ability to form new chemical bonds and participate in various reactions makes it a valuable tool in the development of new chemical processes and products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-[(4-Bromophenoxy)methyl]oxirane is used as an intermediate in the synthesis of various drugs. Its high reactivity allows for the creation of new molecular structures that can be used to develop innovative medications with potential therapeutic applications.
Used in Material Science:
2-[(4-Bromophenoxy)methyl]oxirane is used as a building block in the development of new materials with specific properties. Its reactivity enables the formation of novel polymers and composites that can be tailored for various applications, such as in electronics, coatings, or adhesives.
Used in Environmental Applications:
2-[(4-Bromophenoxy)methyl]oxirane is used as a component in the development of environmentally friendly products, such as biodegradable plastics and green chemicals. Its reactivity can be harnessed to create new compounds that are less harmful to the environment and more sustainable in their use.

InChI:InChI=1/C9H9BrO2/c10-7-1-3-8(4-2-7)11-5-9-6-12-9/h1-4,9H,5-6H2

Upstream product

• 25244-30-8 4-(allyloxy)bromobenzene 
• 106-41-2 4-bromo-phenol 
• 70303-33-2 C₉H₉BrO₄S 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 106-89-8 epichlorohydrin 
• 122-60-1 Phenyl glycidyl ether 
• 96-23-1 1,3-Dichloro-2-propanol 
• 108-95-2 phenol 

Downstream Products

• 106-41-2 4-bromo-phenol 
• 32017-84-8 1-methoxy-3-phenoxy-propan-2-ol 
• 122-60-1 Phenyl glycidyl ether 
• 95681-94-0 1-(4-bromophenoxy)-3-methoxypropan-2-ol 
• 108-95-2 phenol 
• 227089-38-5 1-(4-bromo-phenoxymethyl)-3-pyridin-4-yl-propylamine 
• 642070-07-3 [1-(4-bromo-phenoxymethyl)-3-pyridin-4-yl-propyl]-methyl-amine 
• 642070-06-2 2-[1-(4-bromo-phenoxymethyl)-3-pyridin-4-yl-propyl]-isoindole-1,3-dione 
• 227088-94-0 AZ11645373 
• 227089-27-2 1-(4-Bromophenoxy)-4-(pyridin-4-yl) butan-2-ol 
• 5610-10-6 1-(4-bromophenoxy)-3-morpholin-4-yl-propan-2-ol 

Relevant articles and documents

Design, Synthesis, and Structural Analysis of Cladosporin-Based Inhibitors of Malaria Parasites

Here we have described a systematic structure activity relationship (SAR) of a set of compounds inspired from cladosporin, a tool compound that targets parasite (Plasmodium falciparum) lysyl tRNA synthetase (KRS). Four sets of analogues, synthesized based on point changes in the chemical scaffold of cladosporin and other logical modifications and hybridizations, were assessed using high throughput enzymatic and parasitic assays along with in vitro pharmacokinetics. Co-crystallization of the most potent compound in our series (CL-2) with PfKRS revealed its structural basis of enzymatic binding and potency. Further, we report that CL-2 has performed better than cladosporin in terms of metabolic stability. It thus represents a new lead for further optimization toward the development of antimalarial drugs. Collectively, along with a lead compound, the series offers insights on how even the slightest chemical modification might play an important role in enhancing or decreasing the potency of a chemical scaffold.

Switchable Chemoselectivity of Reactive Intermediates Formation and Their Direct Use in A Flow Microreactor

A chemoselectivity switchable microflow reaction was developed to generate reactive and unstable intermediates. The switchable chemoselectivity of this reaction enables a selection for one of two different intermediates, an aryllithium or a benzyl lithium, at will from the same starting material. Starting from bromo-substituted styrenes, the aryllithium intermediates were converted to the substituted styrenes, whereas the benzyl lithium intermediates were engaged in an anionic polymerization. These chemoselectivity-switchable reactions can be integrated to produce polymers that cannot be formed during typical polymerization reactions.

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.

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b] [1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes

(2,3-Dihydrobenzo[b][1,4]oxathiin-3-yl)methanols were synthesized via reactions of aryloxymethylthiiranes and N-bromosuccinimide (NBS) in DMSO under microwave irradiation. The reaction mechanism was proposed as an intramolecular aromatic electrophilic substitution of 1-bromo-2-(aryloxymethyl)thiiran-1-iums, generated from aryloxymethylthiiranes and NBS, and the subsequent DMSO nucleophilic ring opening reaction of thiiran-1-iums followed by the water displacement. The current method provides a direct and simple strategy in the efficient preparation of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from readily available aryloxymethylthiiranes.

LSD1 Inhibitors

The present invention relates to compounds that inhibit LSD1 activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention.

Synthesis of 2-(phenoxymethyl)oxirane derivatives through unexpected rearrangement of oxiran-2-ylmethyl benzenesulfonates

The synthesis of 2-(phenoxymethyl)oxirane derivatives from oxiran-2-ylmethyl benzenesulfonates was developed through a base promoted rearrangement. A new C-O bond was formed along with the unexpected cleavage of C-S bond via this process. This unusual reaction was characterized with mild reaction conditions, high efficiency, and excellent functional group tolerance. A plausible reaction mechanism was proposed on the basis of experimental results and control experiments.

Synthesis and evaluation of 4-(2-hydroxypropyl)piperazin-1-yl) derivatives as Hsp90 inhibitors

We previously reported 4-(3-((6-bromonaphthalen-2-yl)oxy)-2-hydroxypropyl)-N,N-dimethylpiperazine-1-sulfonamide (1) as a novel heat shock protein 90 inhibitor with moderate activity. In our ongoing efforts for the discovery of Hsp90 modulators we undertake structural investigations on 1. Series of the titled compound were designed, synthesized and evaluated. We have found that compounds with a hydroxyl group at C-4 of the aryl ring on the piperazine moiety possess Hsp90 inhibition properties. Compound 6f with improved activity could be further developed and optimized as Hsp90 inhibitor.

A new synthesis of sultams from amino alcohols

The base-mediated cyclization of N,O-dimesylate derivatives of cyclic and acyclic amino alcohols provides a simple access to five- and six-member sultams: isothiazolidine-1,1-dioxides and thiazinane-1,1-dioxides respectively.