17739-45-6

Basic information

• Product Name: 2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN
• Synonyms: 2H-Pyran,2-(2-broMoethoxy)tetrahydro-;2-(2-BroMoethoxy)tetrahydro-2H-pyran 96%;2-(2-BROMO-ETHOXY)-TETRAHYDRO-PYRAN;2-BROMO-O-TETRAHYDROPYRANYL-ETHANOL;2-[(2-Bromoethyl)oxy]tetrahaydro-2H-pyran;2-(2-Bromoethoxy)oxane;2-(2-Bromoethoxy)tetrahydro-2H-pyran (stabilized with K2CO3)
• CAS NO: 17739-45-6
• Molecular Formula: C₇H₁₃BrO₂
• Molecular Weight: 209.08
• EINECS: 145-859-6
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrans;PyransHeterocyclic Building Blocks
• Mol File: 17739-45-6.mol
• Article Data: 72

Chemical Properties

• Boiling Point: 62-64 °C0.4 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: Clear pale yellow liquid
• Density: 1.384 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.482(lit.)
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN(17739-45-6)
• EPA Substance Registry System: 2-(2-BROMOETHOXY)TETRAHYDRO-2H-PYRAN(17739-45-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 17739-45-6(Hazardous Substances Data)

Usage

Chemical Properties

Clear pale yellow liquid

Uses

2-(2-Bromoethoxy)tetrahydro-2H-pyran may be used in the synthesis of:4-(2-chloroethoxy)benzenesulfonyl chloride estrogen ligands bearing carborane2-(2-(1,3-di((E)-2-(2-(2-(2-(5-(4-(tert-butoxycarbonyl(methyl)amino)styryl)pyridin-2-yloxy)ethoxy)ethoxy)ethoxy)ethoxy)propan-2-yloxy)ethoxy)-tetrahydro-2H-pyran

General Description

2-(2-Bromoethoxy)tetrahydro-2H-pyran is an organic building block. It has been synthesized by employing 2-bromoethanol as a starting reagent.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 540-51-2 2-bromoethanol 
• 144-55-8 sodium hydrogencarbonate 
• 141072-57-3 1-bromoethanol 
• 142-68-7 TETRAHYDROPYRANE 
• 627-18-9 1-bromo-3-propanol 
• 59134-92-8 4-trifluoroacetamidothiazole 

Downstream Products

• 230620-74-3 2-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-tetrahydro-pyran 
• 146395-78-0 5-(3,4-dichlorophenyl)-5-[2-(tetrahydropyran-2-yloxy) ethyl]piperidine-2-one 
• 155308-39-7 4-(3,4-dichloro-phenyl)-4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-pyrrolidine 
• 155308-38-6 4-(3,4-dichloro-phenyl)-4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-pyrrolidin-2-one 
• 146395-81-5 3-(3,4-dichlorophenyl)-3-[2-(tetrahydropyran-2-yloxy) ethyl]piperidine 
• 155308-37-5 3-cyano-3-(3,4-dichloro-phenyl)-5-(tetrahydro-pyran-2-yl-oxy)-pentanoic acid ethyl ester 
• 193755-82-7 1-Benzoyl-3-(3,4-dichlorophenyl)-3-(2-[tetrahydropyran-2-yloxy]ethyl)pyrrolidine 
• 193755-80-5 1-benzenesulfonyl-3-(3,4-dichloro-phenyl)-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-piperidine 
• 473924-52-6 5-({5-Ethyl-3-(1-hydroxyethyl)-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-pyrazol-4-yl}oxy)-isophthalonitrile 
• 955979-13-2 4-(2-hydroxy-ethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester 
• 131952-80-2 2-{2-[(Tetrahydro-2-pyranyl)oxy]ethyl}-1-oxophthalazine 
• 130210-27-4 3-phenyl-3-(4-pyridyl)-1-propanol 
• 110765-97-4 1-phenyl-3-[4-(2-tetrahydropyranyloxyethyl)-1-piperazinyl]-7H-pyrrolo[1,2-a]azepin-7-one 
• 72338-89-7 1-(1-carbobenzoxy-4-piperidyl)-3-[2-(2-tetrahydropyranyloxy)-ethyl]-imidazolidin-2-one 

Relevant articles and documents

Syntheses, characterizations, and biological activities of tetradeca-4,8-dien-1-yl acetates as sex attractants of leaf-mining moth of the genus Phyllonorycter (Lepidoptera: Gracillariidae)

The four possible isomers of tetradeca-4,8-dien-1-yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)- and (Z,Z)-isomers, and alkylation of terminal alkynes for the preparation of (E,E)- and (E,Z)-isomers as the key steps. Synthetic products were characterized by 13C- and 1H-NMR spectroscopy as well as mass-spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca-4,8-dien-1-ols was determined as (Z,Z) (2082.1), (Z,E) (2082.8), (E,E) (2083.1), and (E,Z) (2083.2) from unpolar SPB-1 column, and as (E,E) (2210.2), (Z,E) (2222.1), (E,Z) (2223.4), and (Z,Z) (2224.7) from polar DB-WAX column. The isomers of tetradeca-4,8-dien-1-yl acetates eluted in the order of (Z,Z) (2176.1), (Z,E) (2178.4), (E,Z) (2185.9), and (E,E) (2186.4) from SPB-1, and (Z,E) (2124.3), (E,E) (2157.7), (Z,Z) (2128.9), and (E,Z) (2135.9) from DB-WAX columns. Field-screening tests for attractiveness of tetradeca-4,8-dien-1-yl acetates revealed that (4Z,8E)-tetradeca-4,8-dien-1-yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4E,8E)-Tetradeca-4,8-dien-1-yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4E,8Z)-tetradeca-4,8-dien-1-yl acetate was attractive to Ph. cerasicolella males.

Fluorene-containing polyhedral oligomericsilsesquioxanes modified hyperbranched polymer for white light-emitting diodes with ultra-high color rendering index of 96

In this work, a series of hyperbranched white-emitting conjugated polymers were synthesized with polyfluorene (PF) as the branches and three-dimensional-structured spiro[3.3]heptane-2,6-dispirofluorene (SDF) as the conjugated branching point by one-pot Suzuki polycondensation, where 4,7-dithienyl-2,1,3-benzothiadiazole (DBT) as orange-light emitting unit and fluorene-containing polyhedral oligomericsilsesquioxanes (POSSs) as conjugated linking monomer were introduced into the backbones to obtain white-light emission. The influence mechanism of POSSs for hyperbranched white-emitting polymers was explored by adjusting the feeding ratios of fluorene-containing POSSs (from 1 to 20 ?mol%). The results indicated that the synthesized polymers still maintained the high thermal stabilities, and exhibited the improved amorphous film morphology and hydrophobicity, which were beneficial for obtaining optimized interface between the aqueous hole transport layer Poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate) (PEDOT: PSS) layer and polymer light-emitting layer in device fabrication. As a consequence, all of the fabricated devices with the hyperbranched polymers as light-emitting layers realized white light-emission, and the optimized device exhibite good electroluminescent (EL) performance with Commission Internationale de l'Eclairage (CIE) coordinates at (0.32, 0.33) and maximum color rendering index (CRI) of 96. The fluorene-containing POSSs modified hyperbranched copolymers with broad full width at half maximum (>284 ?nm) are attractive candidates for sunlight-style white polymer light-emitting diodes.

An efficient synthesis of ω-(2,2′-bipyridyl)alkyl alcohols and their acrylates

ω-(2,2′-Bipyridyl)alkyl alcohols were synthesized by treatment of methyl-2,2′-bipyridine with LDA at -78°C followed by the addition of ω-bromoalkyl THP ether and hydrolysis of the resulting THP ether. Furthermore, ω-2,2′-bipyridylalkyl acrylates were obtained by the reaction of the corresponding ω-(2,2′-bipyridyl)alkyl alcohols with acryloyl chloride in good yields.

Synthesis and mesomorphic properties of some anthraquinone derivatives: New difunctionalised discotic monomers

Some new 9,10-anthraquinone (rufigallol) derivatives have been prepared and their mesomorphic properties have been studied. The unsymmetrically substituted tetrahydropyranyloxy-ethers (THP-ethers), exhibited columnar mesomorphism at fairly low temperatures and the xray studies carried out for one of the homologues confirmed the hexagonal nature of the mesophase. The deprotected derivatives of these THP-ethers, also form columnar mesophases. All these derivatives are very good candidates for polymerisation studies.

Development of high-affinity fluorinated ligands for cannabinoid subtype 2 receptor, and in vitro evaluation of a radioactive tracer for imaging

The development of neurodegenerative diseases is associated with cerebral inflammation, which activates resident immune cells of the central nervous system (CNS), namely microglial cells that show an up-regulation of the cannabinoid subtype 2 receptor (CB2R) expression. Therefore our work aimed to design and synthesize a radiotracer for the detection of CB2R expression by positron emission tomography (PET) allowing an early diagnosis of neurodegenerative diseases. For the development of such a PET tracer, N-alkyl-substituted indole-3-yl-tetramethylcyclopropylketones served as lead structures due to their high CB2R potency and selectivity, allowing radiolabeling on the N-alkyl chain. To this end, eight novel fluorinated N-alkyl-indole-3-yl-tetramethylcyclopropylketones were synthesized, investigated in radioligand binding studies, and structure-activity relationships were evaluated. The most promising candidate was (1-(4-fluoropropyl)-1H-indole-3-yl)(2,2,3,3-tetramethyl-cyclopropyl)methanone (Ki: 7.88 nM at the CB2R, 3430 nM at cannabinoid subtype 1 receptor (CB1R)). A precursor was synthesized, radiofluorinated with no-carrier-added [18F]F? by nucleophilic substitution of a tosyl group, and the resulting PET ligand was purified, all being performed on a fully automated synthesis module. The tracer was produced in 34 ± 6% radiochemical yield within 2 h and with molar activities of up to 1500 GBq/μmol. A first preclinical evaluation was carried out including determination of logP, metabolic stability by liver microsomes, and autoradiography. The novel PET tracer for imaging CB2R showed promising results warranting subsequent clinical evaluation.

PIKFYVE KINASE INHIBITORS

The present invention relates to compounds useful as inhibitors of phosphatidylinositol-3-phosphate 5-kinase (PIKfyve) as well as their use for treating diseases and disorders associated with PIKfyve.