57602-02-5

Usage

Uses

Used in Chemical Synthesis:
1,14-DIBROMO-3,6,9,12-TETRAOXATETRADECANE is used as a cross-linking reagent for its ability to facilitate nucleophilic substitution reactions, allowing for the formation of covalent bonds between molecules.
Used in Pharmaceutical Industry:
1,14-DIBROMO-3,6,9,12-TETRAOXATETRADECANE is used as a reagent for the synthesis of bioconjugates and drug delivery systems, taking advantage of its solubility and reactivity to create stable and functional pharmaceutical compounds.
Used in Material Science:
In the field of material science, 1,14-DIBROMO-3,6,9,12-TETRAOXATETRADECANE is used as a cross-linking agent to improve the mechanical properties and stability of polymers and other materials.
Used in Research and Development:
1,14-DIBROMO-3,6,9,12-TETRAOXATETRADECANE is utilized as a key component in the development of new chemical entities, bioconjugates, and materials, thanks to its reactivity and solubility-enhancing properties.
Overall, 1,14-DIBROMO-3,6,9,12-TETRAOXATETRADECANE is a valuable compound with a wide range of applications in various industries, from chemical synthesis to pharmaceutical development and material science, due to its unique chemical properties and reactivity.

InChI:InChI=1/C10H20Br2O4/c11-1-3-13-5-7-15-9-10-16-8-6-14-4-2-12/h1-10H2

Upstream product

• 112-60-7 Tetraethylene glycol 
• 55400-73-2 ((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) dimethanesulfonate 
• 5197-65-9 1,14-dichloro-3,6,9,12-tetraoxatetradecane 
• 4792-15-8 Pentaethylene glycol 
• 109789-39-1 pentaethylene glycol dimesylate 

Downstream Products

• 120363-90-8 hexa-P-phenyl-P,P'-(3,6,9,12-tetraoxa-tetradecanediyl)-di-phosphonium; dibromide 
• 130740-01-1 1,16-bis-1,4,7,10,13,16-hexaoxahexadecane 
• 87338-16-7 18,20-benzo-1,16-bis(4-tolylsulfonyl)-1,16-diaza-4,7,10,13-tetraoxacyclouncosane 
• 152898-20-9 17-benzyloxy-19-methylbenzo-1,4,7,10,13,16-hexaoxacyclooctadecane 
• 77963-46-3 o-hydroxyphenyl 3,6,9,12,15-pentaoxa-17-bromoheptadecyl ether 
• 866572-92-1 1,14-bis-(2,4,6-trimethylphenoxyl)-3,6,9,12-tetraoxatetradecane 
• 1253809-80-1 1,5-bis[2,2'-(1,3-phenylenedimethylenedithio)-5-benzoylimino-1,3,4-thiadiazolin-4-yl]-3,6,9,12-tetraoxatetradecane 
• 212262-00-5 14-bromo-3,6,9,12-tetraoxatetradecyl methanethiosulfonate 
• 212262-08-3 3,6,9,12-tetraoxatetradecane-1,14-diyl-bis-methanethiosulfonate 
• 500297-38-1 C₂₈H₃₈Br₄O₆ 
• 592544-68-8 1,14-bis-(2,4,6-trimethyl-3,5-dibromomethylphenoxyl)-3,6,9,12-tetraoxatetradecane 
• 88631-15-6 5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-dihydroxycalix[4]arene-crown-6 
• 524728-94-7 C₆₆H₉₀O₁₀ 
• 500297-36-9 (2-{2-[2-(2-{2-[2-(2,6-bis-hydroxymethyl-4-methyl-phenoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-3-hydroxymethyl-5-methyl-phenyl)-methanol 

Relevant academic research and scientific papers

Intraannular functionalization of the 1,3-phenylene-19-crown-6 system via bromine-lithium exchange

In contrast to the behavior of its lower homologue 1,3-phenylene-16-crown-5 (1), the direct lithiation of 1,3-phenylene-19-crown-6 (2) with n-BuLi at the intruannular position-2 was found to be slow and not quantitative. Therefore, (2-bromo-1,3-phenylene)-19-crown-6 (8) was synthesized by the reaction of the dicesium salt of 2-bromo-resorcinol (7) with pentaethylene glycol dibromide. The crystal structure of 8 revealed the existence of three chemically identical residues in the unit cell; in all cases, the bromine atom sticks out of the crown ether ring. The bromine-lithium exchange reaction of 8 with n-BuLi to furnish the desired (2-lithio-1,3-phenylene)-19-crown-6 (4) was quantitative after 2 h at -65°C in THF. Derivatization of 4 with deuterium oxide, dimethyl disulfide, iodine, carbon dioxide, mercuric bromide (1 or 0.5 molar equivalents), and magnesium bromide yielded (2-deuterio-1,3-phenylene)-19-crown-6 (2a), (2methylthio-1,3-phenylene)-19-crown-6 (10), (2-iodo-1,3-phenylene)-19-crown-6 (11), (2-carboxy-1,3-phenylene)-19-crown-6 (12), (2-bromomercurio-1,3-phenylene)-19-crown-6 (13), bis[(1,3-phenylene-19-crown-6)-2-yl]mercury (14), and (2-bromomagnesio-1,3-phenylene)-19-crown-6 (15), respectively. The synthesis of the Grignard reagent 15 was also carried out by the direct reaction of 8 with magnesium; contrary to the corresponding 1,3-xylylene crown ethers, cleavage of the crown ether ring during the formation of 15 was not observed. At room temperature, the solution of crude 4 (prepared from 8) gave rise to ether cleavage and to the formation of (2-n-butyl-1,3-phenylene)-19-crown 6 (16).

Dithia-crown-annelated tetrathiafulvalene disulfides: Synthesis, electrochemistry, self-assembled films, and metal ion recognition

The synthesis and electrochemistry of a series of tetrathiafulvalene (TTF) and dithia-crown-TTF derivatives attached with one or two disulfide group(s) 7a-f are reported. The self-assembled monolayers (SAMs) of these TTF disulfides on gold were prepared and characterized by reflection - absorption infrared spectroscopy. The SAMs are extremely stable under a wide variety of conditions and over extended periods of time and show remarkable electrochemical stability upon repeated potential scans. SAMs of the crown-TTF disulfides 7c,d,f can recognize alkali metal ions, and the process can be monitored following the electrochemical potential shift of the surface-confined TTF group.

Crown-ether-modified cyclic dipeptides as supramolecular chiral catalysts

With the objective to develop supramolecular catalysts for useful chemical transformations, we report here a rapid and efficient solid-phase synthesis of novel cyclic dipeptides (crown-CDPs) with a diversity of L-DOPA derived crown ether substituents and

LOW MOLECULAR WEIGHT POLYETHYLENE GLYCOL DRUG CONJUGATES HAVING IMPROVED DRUG BIOLOGICAL ACTIVITY

Provided are polyethylene glycol drug conjugates of general formula (I), (II) or (III) and pharmaceutical compositions and a use thereof. The conjugates are formed by combining low molecular weight polyethylene glycol with 2-4 drug molecules. The conjugates can interact with receptor dimers or polymers, thereby improving the in vivo distribution of the drug, changing the oil and water distribution coefficient, enhancing the pharmacological activity, reducing the blood-brain barrier permeability of the drug, and improving the bioavailability of the drug.

Bifunctional thiosialosides inhibit influenza virus

We have synthesized a panel of bivalent S-sialoside analogues, with modifications at the 4 position, as inhibitors of influenza virus. These first generation compounds show IC50 values ranging from low micromolar to high nanomolar in enzyme inhibition and plaque reduction assays with two intact viruses, Influenza H1N1 (A/California/07/2009) and H3N2 (A/Hongkong/8/68).

Synthesis of unique 17β-estradiol homo-dimers, estrogen receptors binding affinity evaluation and cytocidal activity on breast, intestinal and skin cancer cell lines

A rapid and efficient synthesis of a series of C2-symmetric 17β-estradiol homo-dimers is described. The new molecules are linked at position 17α of the steroid nucleus with either an alkyl chain or a polyethylene glycol chain. They are made from estrone in only five chemical steps with an overall yield exceeding 30%. The biological activity of these compounds was evaluated in vitro on estrogen dependent and independent (ER+ and ER-) human breast tumor cell lines: MCF-7 and MDA-MB-231. Some of the dimers present selective cytotoxic activity against the ER+ cell line. However, they are not very cytotoxic when compared to the antiestrogen tamoxifen. Unfortunately, they show only weak affinity for the estrogen receptor alpha (ERα) and no affinity for the estrogen receptor beta (ERβ). The new compounds were also tested on human intestinal (HT-29) cancer and on murine skin cancer (B16-F10) cell lines for further biological assessment. Interestingly, the dimers were found to be cytotoxic to the murine skin cancer cell line but were inactive towards the intestinal cancer cell line.

Design, synthesis, and characterization of peptide nanostructures having ion channel activity

We report the synthesis and the functional studies of multiple crown α-helical peptides designed to form artificial ion channels. The approach combines the versatility of solid phase peptide synthesis, the conformational predictability of peptidic molecul

Estrogen-linked platinum (II) complexes as anticancer agents

wherein n may be 1, 2, 3, 4 or 5 when X is O, wherein n may be 2/3, 1, 4/3, 5/3, 2, 7/3, 8/3, 3, or 10/3 when X is C, wherein o may be 1, 2 or 3, wherein Y may be O or 17β-OH, wherein R1 may be selected from the group consisting of H, a straight alkyl group of 1 to 5 carbon atoms, a branched alkyl group of 3 to 5 carbon atoms, wherein R2 may be selected for the group consisting of H, a straight alkyl group of 1 to 4 carbon atoms, a branched alkyl group of 3 or 4 carbon atoms, F, Cl, Br, I, —CF3, —NO2, —OR1, —COR1 and —CH2OH. These compounds possess anticancer activity against hormono-dependent breast, uterus as well as ovarian cancer.

A facile synthesis of C2-symmetric 17β-estradiol dimers

A rapid and efficient synthesis of a series of C2-symmetric 17β-estradiol dimers is described. The new molecules are linked at position 17α of the steroid nucleus with either an alkyl chain or a polyethylene glycol chain. They are made from estrone in five chemical steps with an overall yield exceeding 30%. The biological activity of these compounds was evaluated in vitro on estrogen dependent and independent (ER+ and ER-) human breast tumor cell lines: MCF-7 and MDA-MB-231. Some of the dimers present selective cytotoxic activity against the ER+ cell line.