18643-86-2

Usage

Chemical Properties

white powder

InChI:InChI=1/C9H8BrF3O/c10-4-5-14-8-3-1-2-7(6-8)9(11,12)13/h1-3,6H,4-5H2

Upstream product

• 67-56-1 methanol 
• 586-35-6 2-bromo-1,4-benzenedicarboxylic acid 
• 13815-89-9 2-bromobenzene-1,4-dicarbonyl dichloride 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 553-94-6 4-bromo-m-xylene 
• 7697-26-9 3-bromo-4-methylbenzoic acid 
• 264272-63-1 2-bromo-1,4-benzenedicarboxylic acid,1-methyl ester 
• 149-73-5 trimethyl orthoformate 
• 87808-49-9 2-bromo-4-methyl-benzoic acid methyl ester 
• 7697-27-0 2-bromo-4-methylbenzoic acid 
• 74-88-4 methyl iodide 
• 10312-55-7 3-aminoterephthalic acid 

Downstream Products

• 264272-63-1 2-bromo-1,4-benzenedicarboxylic acid,1-methyl ester 
• 30240-01-8 Bromterephthalohydroxamsaeure 
• 893415-43-5 2-(2-Methoxy-phenoxy)-terephthalic acid dimethyl ester 
• 915303-58-1 methyl 3-butyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate 
• 566155-74-6 5-phenylamino-terephthalic acid dimethyl ester 
• 566155-75-7 2-(phenylamino)terephthalic acid 
• 89980-92-7 (2-bromo-1,4-phenylene) dimethyl carbinol 
• 14186-60-8 2-Methyl-1,4-benzoldicarbonsaeure dimethylester 
• 67801-53-0 Dimethyl-2-(4-toluyl)-terepthalate 
• 1028338-64-8 dimethyl 2-acetylterephthalate 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 871897-28-8 biphenyl-2,5,2',5'-tetracarboxylic acid tetramethyl ester 
• 1351791-42-8 (S)-2-(4-benzyl-2-oxooxazolidin-3-yl)terephthalic acid 
• 1351791-41-7 (S)-2-(4-isopropyl-2-oxooxazolidin-3-yl)terephthalic acid 

Relevant academic research and scientific papers

Gated Channels and Selectivity Tuning of CO2over N2Sorption by Post-Synthetic Modification of a UiO-66-Type Metal–Organic Framework

The highly porous and stable metal–organic framework (MOF) UiO-66 was altered using post-synthetic modifications (PSMs). Prefunctionalization allowed the introduction of carbon double bonds into the framework through a four-step synthesis from 2-bromo-1,4-benzenedicarboxylic acid; the organic linker 2-allyl-1,4-benzenedicarboxylic acid was obtained. The corresponding functionalized MOF (UiO-66-allyl) served as a platform for further PSMs. From UiO-66-allyl, epoxy, dibromide, thioether, diamine, and amino alcohol functionalities were synthesized. The abilities of these compounds to adsorb CO2and N2were compared, which revealed the structure–selectivity correlations. All synthesized MOFs showed profound thermal stability together with an increased ability for selective CO2uptake and molecular gate functionalities at low temperatures.

SUBSTITUTED TRICYCLIC COMPOUNDS

Disclosed are compounds of the general formula (I), its tautomeric form, its stereoisomer, its pharmaceutically acceptable salt, its polymorph, or solvate thereof, wherein, ring A, ring B, R1 to R4, and n are as defined herein, for use as SOS1 inhibitors in the treatment of proliferative, infectious and RASopathy diseases or disorders. Also disclosed are methods of synthesizing the compound of formula I, pharmaceutical compositions containing the compound of formula I, method of treatment of proliferative, infectious and RASopathy diseases or disorder, for example, a cancer, by administering the said compound and combinations of the compound of formula I with other active ingredients.

Nickel?alkyne?functionalized metal?organic frameworks: An efficient and reusable catalyst

Electron-donating groups in the robust MOF motif are able to provide an excellent catalytic platform, therefore obtaining site-isolated metal sites. In this study, the terminal alkyne is firstly introduced into UiO-66-type metal-organic frameworks (UiO-66-alkyne). Herein, to further study the application potential of this material, a covalently bonded nickel catalyst based on the alkynyl-tagged UiO-66-alkyne has been prepared and afforded us unprecedented highly dispersed and highly efficient catalytic active species. Meanwhile, this nickel-contained catalyst method for joining metals provided an alternative pathway regarding catalyst designing. With UiO-66-alkyne-Ni, the heterogeneous transformation of homogeneous catalysts is realized. Using benzaldehyde and malononitrile as starting materials, we were able to catalyze the Knoevenagel condensation within 45 min under room temperature with yield (> 99 %). Moreover, the recovery rate of the UiO-66-alkyne-Ni also outperformed previous MOFs in both small-scale and gram-level reactions, which shows UiO-66-alkyne-Ni is a potential contributor to the subsequent industrialization.

Excited-state conformation capture by supramolecular chains towards triplet-involved organic emitters

Nowadays, the development of triplet-involved materials becomes a hot research topic in solid-state luminescence fields. However, the mechanism of triplet-involved emission still remains some mysteries to conquer. Here, we proposed a new concept of excited-state conformation capture for the constructions of different types of triplet-involved materials. Firstly, excited-state conformation could be trapped by supramolecular chains in crystal and form a new optimum excited-state structure which is different from that in solution or simple rigid environment, leading to bright thermally activated delayed fluorescence (TADF) emission. Based on excited-state conformation capture methodology, next, we obtained room-temperature phosphorescence (RTP) by introducing Br atoms for the enhancement of intersystem crossing. It could be concluded from experimental results that TADF may originate from aggregate effect while RTP may derive from monomers. Finally, heavy-atom free RTP and ultra RTP were achieved by eliminating aggregate effect. This work could not only extend the design methodology of triplet-involved materials but also set clear evidences for the mechanism of triplet-involved emissions.

Synthesis of: O-carborane-functionalized metal-organic frameworks through ligand exchanges for aggregation-induced emission in the solid state

The carborane (CB)-functionalized ligand was installed in a variety of MOFs through postsynthetic ligand exchange processes. This methodology is a general method for preparing o-CB-functionalized MOFs with known frameworks. Furthermore, the photoluminescence (PL) spectra revealed intriguing aggregation-induced emission (AIE) features following the systematic incorporation of o-CB functionalities into framework-type materials.

Thiol-ene photopolymerization of vinyl-functionalized metal-organic frameworks towards mixed-matrix membranes

We developed a facile methodology for fabricating a free-standing mixed-matrix membrane (MMM) containing covalently incorporated metal-organic framework (MOF) particles up to 60 wt% by utilizing thiol-ene photopolymerization with the MOF consisting of vinyl functionality. Vinyl-functionalized UiO-66 (UiO-66-CH═CH2) was synthesized from 2-vinyl-1,4-dicarboxylic acid with ZrCl4, and a free-standing MMM was readily produced by irradiation of a polymerization mixture containing UiO-66-CH═CH2, poly(ethylene glycol) divinyl ether (PEO-250), pentaerythritol tetra(3-mercaptopropionate) (PETM), 2,2′-(ethylenedioxy)diethanethiol (EDDT), and 2,2-dimethoxy-2-phenylacetophenone (DMPA) as a photoradical initiator. Assorted analyses combining FTIR, thermogravimetric analysis, scanning electron microscopy, energy dispersive X-ray spectroscopy, and X-ray diffraction strongly supported the fact that the desired MMM containing well-dispersed UiO-66-CH═CH2 particles was successfully produced by C-S bond formation, which provided strong union of the MOF with the polymer matrix without interfacial voids. The produced MMM was highly flexible and showed improved mechanical properties as compared to the pristine polymeric membrane, indicating that the covalently immobilized UiO-66-CH═CH2 particles were homogeneously distributed in the polymer matrix. Gas permeability across the MMM was significantly enhanced compared with the pristine polymeric membrane as diffusion of the gas molecules was facilitated in the porous space in the MOF.

Development of Dihydrodibenzooxepine Peroxisome Proliferator-Activated Receptor (PPAR) Gamma Ligands of a Novel Binding Mode as Anticancer Agents: Effective Mimicry of Chiral Structures by Olefinic E/Z-Isomers

A novel class of PPARγ ligand 1 (EC50 = 197 nM) with a dibenzoazepin scaffold was identified through high-throughput screening campaign. To avoid the synthetically troublesome chiral center of 1, its conformational analysis using the MacroModel was conducted, focusing on conformational flip of the tricyclic ring and the conformational restriction by the methyl group at the chiral center. On the basis of this analysis, scaffold hopping of dibenzoazepine into dibenzo[b,e]oxepine by replacing the chiral structures with the corresponding olefinic E/Z isomers was performed. Consequently, dibenzo[b,e]oxepine scaffold 9 was developed showing extremely potent PPARγ reporter activity (EC50 = 2.4 nM, efficacy = 9.5%) as well as differentiation-inducing activity against a gastric cancer cell line MKN-45 that was more potent than any other well-known PPARγ agonists in vitro (94% at 30 nM). The X-ray crystal structure analysis of 9 complexed with PPARγ showed that it had a unique binding mode to PPARγ ligand-binding domain that differed from that of any other PPARγ agonists identified thus far.

PRMT5 INHIBITORS

A compound of formula (Ia), (Ib) or (Ic) wherein: n is 1 or 2; RN is H or Me; R1 is optionally one or more halo or methyl groups; R2a and R2b are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R2c and R2d (if present) are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R3a and R3b are independently selected from H and Me; R4a is selected from OH, -NH2, -C(=O)NH2, and -CH2OH; R4b is either H or Me; X is either N or CH; R7 is selected from H and C1-4 alkyl; (a) one of R8a, R8b, R8c and R8d is selected from H, halo, C1-4 alkyl, C1-4 alkoxy, NHC1-4 alkyl; (b) another of R8a, R8b, R8c and R8d is selected from H, C1-4 alkyl, C1-4 fluoroalkyl, C3-6 cycloalkyl, C5-6 heteroaryl, C5-6 heteroaryl methyl, C4-6 heterocyclyl, C4-6 heterocyclyl methyl, phenyl, benzyl, halo, amido, amidomethyl, acylamido, acylamidomethyl, C1-4 alkyl ester, C1-4 alkyl ester methyl, C1-4 alkyl carbamoyl, C1-4 alkyl carbamoyl methyl, C1-4 alkylacyl, C1-4 alkylacyl methyl, phenylcarbonyl, carboxy, carboxymethyl, ether, amino, amino methyl, sulfonamido, sulfonamino, sulfone, sulfoxide, nitrile and nitrilemethyl; (c) the others of R8a, R8b, R8c and R8d are H.

TETRAHYDROISOQUINOLINES AS PRMT5-INHIBITORS

A compound of formula (I) wherein: n is 1 or 2; p is 0 or 1; R1a, R1b, R1c and R1d are independently selected from H, halo, methyl and methoxy; R2a and R2b are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R2c and R2d are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R2e is H or Me; R3a and R3b are independently selected from H and Me; R4 is either H or Me; R6a and R6b are independently selected from H and Me; X is either N or CH; R7 is selected from H and C1-4 alkyl; (a) one of R8a, R8b, R8c and R8d is selected from H, halo, C1-4 alkyl, C1-4 alkoxy, NHC1-4 alkyl; (b) another of R8a, R8b, R8c and R8d is selected from H, C1-4 alkyl, C1-4 fluoroalkyl, C3-6 cycloalkyl, C5-6 heteroaryl, C5-6 heteroaryl methyl, C4-6 heterocyclyl, C4-6 heterocyclyl methyl, phenyl, benzyl, halo, amido, amidomethyl, acylamido, acylamidomethyl, C1-4 alkyl ester, C1-4 alkyl ester methyl, C1-4 alkyl carbamoyl, C1-4 alkyl carbamoyl methyl, C1-4 alkylacyl, C1-4 alkylacyl methyl, phenylcarbonyl, carboxy, carboxymethyl, ether, amino, amino methyl, sulfonamido, sulfonamino, sulfone, sulfoxide, nitrile and nitrilemethyl; (c) the others of R8a, R8b, R8c and R8d are H.

Method for preparing derivatives of spiroketal

Provided is a process for the preparation of a spiroketal derivative via a compound represented by general formula (II) [wherein each variable group and each variable number are as defined in the description].