Category: bromides-buliding-blocks

《A Bithiophene-Promoted ppm Levels of Palladium-Catalyzed Regioselective Hydrosilylation of Terminal Allenes》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to Chen, Jun-Jia; Zeng, Jia-Hao; Yang, Ying; Liu, Zhi-Kai; Jiang, Ya-Nan; Li, Miao-Ran; Chen, Li; Zhan, Zhuang-Ping. Computed Properties of C4H2Br2S The article mentions the following:

A bithiophene-alkyne-based compound was synthesized and 1st used as a ligand for the selective hydrosilylation of allenes with primary and secondary phenylsilanes. It shows high selectivity towards the production of branched allylsilanes with a wide range of allenes. It is worth mentioning that the catalytic loading of the Pd can be reduced to 500 ppm. This work opens a new front of using bidentate thiophene ligand as a reaction promoter in transition-metal-catalyzed organic reaction. The experimental process involved the reaction of 2,5-Dibromothiophene(cas: 3141-27-3Computed Properties of C4H2Br2S)

2,5-Dibromothiophene(cas: 3141-27-3) , is mainly used as pharmaceutical intermediate and synthesis intermediate. 2,5-Dibromothiophene may be used in the preparation of soluble α,ω-diformyl-a-oligothiophenes.Computed Properties of C4H2Br2S

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Visible- and UV-Light-Induced Decarboxylative Radical Reactions of Benzoic Acids Using Organic Photoredox Catalysts》 was published in Journal of Organic Chemistry in 2020. These research results belong to Kubosaki, Suzuka; Takeuchi, Haruka; Iwata, Yutaka; Tanaka, Yosuke; Osaka, Kazuyuki; Yamawaki, Mugen; Morita, Toshio; Yoshimi, Yasuharu. Application of 586-76-5 The article mentions the following:

Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, resp. The reaction is thought to involve single-electron transfer promoted the generation of aryl radicals via decarboxylation. A diverse range of benzoic acids were found to be suitable substrates for this photoreaction. Only two-mol. organic photoredox system can work well for the direct photoinduced decarboxylation of benzoic acids. In the experiment, the researchers used many compounds, for example, 4-Bromobenzoic acid(cas: 586-76-5Application of 586-76-5)

4-Bromobenzoic acid(cas: 586-76-5) has been used in bromine-specific detection of the metabolites of 2-,3-and 4-bromobenzoic acid in the urine and bile of rats by inductively coupled plasma mass spectrometry.Application of 586-76-5 It was used to study the metabolic fate of 2-,3-and 4-bromo benzoic acids in rat hepatocytes incubation using high temperature liquid chromatography.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Triarylborane catalysed N-alkylation of amines with aryl esters》 was published in Catalysis Science & Technology in 2020. These research results belong to Nori, Valeria; Dasgupta, Ayan; Babaahmadi, Rasool; Carlone, Armando; Ariafard, Alireza; Melen, Rebecca L.. Application of 6825-20-3 The article mentions the following:

Herein, the N-alkylation reactions of a wide variety of amine substrates such as di-Ph amine, N-Me aniline, indoline, 9H-carbazole, etc. with aryl esters 4-FC6H4C(O)OCH(R)R1 (R = Ph, 4-fluorophenyl, naphthalen-2-yl, etc.; R1 = Me, cyclohexyl, 2-phenylethynyl, etc.) using catalytic amounts of B(C6F5)3 were described. This mild reaction protocol gives access to N-alkylated products RCH(R1)N(4-R2C6H4)R3 (R2 = H, Me, t-Bu; R3 = Me, Ph, 4-methylphenyl, 4-tert-butylphenyl)/e.g., I in good to excellent yields (up to 95%). The construction of a C-N bond at the propargylic position has also been demonstrated to yield synthetically useful propargyl amines. On the other hand, unsubstituted 1H-indole and 1H-pyrrole at the C3/C2 positions afforded exclusively C-C coupled products R4CH(4-FC6H4)2 (R4 = 1H-indol-3-yl, 1H-pyrrol-2-yl). Extensive DFT studies have been employed to understand the mechanism for this transformation. In the experiment, the researchers used 3,6-Dibromo-9H-carbazole(cas: 6825-20-3Application of 6825-20-3)

3,6-Dibromo-9H-carbazole(cas: 6825-20-3) is used as a reagent in the synthesis of P7C3-A20 which is a potent neuroprotective agent. And it has been used in the preparation of N-(2-hydroxyethyl)-3,6-dibromocarbazole.Application of 6825-20-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Stepwise Mechanism for the Bromination of Arenes by a Hypervalent Iodine Reagent》 was published in Journal of Organic Chemistry in 2020. These research results belong to Granados, Albert; Shafir, Alexandr; Arrieta, Ana; Cossio, Fernando P.; Vallribera, Adelina. Product Details of 523-27-3 The article mentions the following:

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodol. using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. D. functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring. The results came from multiple reactions, including the reaction of 9,10-Dibromoanthracene(cas: 523-27-3Product Details of 523-27-3)

9,10-Dibromoanthracene(cas: 523-27-3) can be sublimated and oxidized to generate anthraquinone. Soluble in hot benzene and hot toluene, slightly soluble in alcohol, ether and cold benzene, insoluble in water.Product Details of 523-27-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Stereochemistry-Controlled Supramolecular Architectures of New Tetrahydroxy-Functionalized Amphiphilic Carbocyanine Dyes》 was published in Chemistry – A European Journal in 2020. These research results belong to Schade, Boris; Singh, Abhishek Kumar; Wycisk, Virginia; Cuellar-Camacho, Jose Luis; von Berlepsch, Hans; Haag, Rainer; Boettcher, Christoph. Computed Properties of C6H11BrO2 The article mentions the following:

The syntheses of novel amphiphilic 5,5′,6,6′-tetrachlorobenzimidacarbocyanine (TBC) dye derivatives with aminopropanediol head groups, which only differ in stereochem. (chiral enantiomers, meso form and conformer), are reported. For the achiral meso form, a new synthetic route towards asym. cyanine dyes was established. All compounds form J aggregates in water, the optical properties of which were characterized by means of spectroscopic methods. The supramol. structure of the aggregates is investigated by means of cryo-transmission electron microscopy, cryo-electron tomog. and AFM, revealing extended sheet-like aggregates for chiral enantiomers and nanotubes for the mesomer, resp., whereas the conformer forms predominately needle-like crystals. The experiments demonstrate that the aggregation behavior of compounds can be controlled solely by head group stereochem., which in the case of enantiomers enables the formation of extended hydrogen-bond chains by the hydroxyl functionalities. In case of the achiral meso form, however, such chains turned out to be sterically excluded. In the experiment, the researchers used Ethyl 4-bromobutyrate(cas: 2969-81-5Computed Properties of C6H11BrO2)

Ethyl 4-bromobutyrate(cas: 2969-81-5) belongs to bromides. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents.Computed Properties of C6H11BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Multi-spectroscopic measurements, molecular modeling and density functional theory calculations for interactions of 2,7-dibromocarbazole and 3,6-dibromocarbazole with serum albumin》 were Wang, Lijun; Wu, Xiaoqin; Yang, Yanan; Liu, Xina; Zhu, Meiqing; Fan, Shisuo; Wang, Zhen; Xue, Jiaying; Hua, Rimao; Wang, Yi; Li, Qing X.. And the article was published in Science of the Total Environment in 2019. Formula: C12H7Br2N The author mentioned the following in the article:

2,7-Dibromocarbazole (2,7-DBCB) and 3,6-dibromocarbazole (3,6-DBCB) are emerging environmental pollutants, being potentially high risks to human health. In this study, interactions of the two compounds with human serum albumin (HSA) and bovine serum albumin (BSA) were investigated by mol. modeling, d. functional theory calculations (DFT) and multispectral techniques. The static quenching interaction deduced in the fluorescence quenching experiment is confirmed by the time-resolved analyses. The interactions of the two compounds with HSA/BSA induce mol. microenvironment and conformation changes, as assessed by synchronous and 3D fluorescence spectra, together with a destruction of polypeptide carbonyl hydrogen bond network by CD and Fourier transform IR analyses. The thermodn. anal. indicated that the spontaneous interaction was hydrogen bonding and hydrophobic forces. The binding constant Ka at 298 K was 3.54 × 105 M-1 in HSA-2,7-DBCB, 6.63 × 105 M-1 in HSA-3,6-DBCB, 1.32 × 105 M-1 in BSA-2,7-DBCB and 2.17 × 105 M-1 in BSA-3,6-DBCB. These results indicates that 3,6-DBCB binds HSA/BSA more strongly than 2,7-DBCB, which was estimated with DFT calculations Site marker competition experiments coupled with mol. modeling studies confirmed that both compounds bind HSA/BSA at site I (subdomain IIA). The results suggest that interactions between 2,7-DBCB and 3,6-DBCB with HSA and BSA may affect the normal physiol. activities in human and animals. In the part of experimental materials, we found many familiar compounds, such as 3,6-Dibromo-9H-carbazole(cas: 6825-20-3Formula: C12H7Br2N)

3,6-Dibromo-9H-carbazole(cas: 6825-20-3) is used as a pharmaceutical intermediate, and also an important intermediate of synthesizing optoelectronic materials. It has been used as a reagent in the synthesis of P7C3-A20 which is a potent neuroprotective agent.Formula: C12H7Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Driving Quick and Large Amplitude Contraction of Viologen-Incorporated Poly-L-Lysine-Based Hydrogel by Reduction》 was written by Wang, Bo; Tahara, Hironobu; Sagara, Takamasa. Related Products of 17696-11-6This research focused onviologen functionalized polylysine hydrogel reduction induced contraction; actuation; contraction and re-expansion; hydrogel; redox; viologen. The article conveys some information:

A glutaraldehyde-crosslinked poly-L-lysine-based hydrogel with pendant viologens was synthesized with various [viologen unit]/[Lys unit] ratios. The hydrogel with the ratio of 25% had (i) a water content of 95.8%, (ii) unbound viologen unit was absent, and (iii) lyophilized gel showing porous structure was rewettable. The hydrogel in contact with a gold, glassy carbon, pyrolytic graphite, or ITO electrode was electroactive, showing voltammetric responses involving diffusion process. Occurrence of electron transfer between viologen sites was verified by ESR measurements. The electroreflectance spectrum indicated significant dimerization of one-electron-reduced forms, viologen radical cations. Reduction of the hydrogel by dithionite showed a 93% volume decrease, being near to the water content, at 100 s and finally 97% contraction at 380 s. The initial rate of contraction was 0.02 s-1, and the swelling weight ratio was > 17. The contraction rate was much faster than that observed when adding of redox-inactive salts in the outer medium. Recovery by reoxidation was relatively sluggish even when O2-saturated water was used. The quick and large-amplitude contraction with removal of water from the gel body should be the consequence of permeability of reductant, interchain π-stacking of one-electron-reduced forms (viologen monoradical monocation), desolvation of viologen upon reduction, electron hopping between viologen units and its acceleration with contraction, and effective osmotic pressure difference. The experimental process involved the reaction of 8-Bromooctanoic acid(cas: 17696-11-6Related Products of 17696-11-6)

8-Bromooctanoic acid(cas: 17696-11-6) acid is used in the synthesis of 8-(N-Methyl-4,4′-bipyridinyl)- octanoic acid. 8-Mercaptooctanoic acid was prepared from 8-bromooctanoic acid.Related Products of 17696-11-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of C9H9BrO2In 2020 ,《Discovery of Thieno[2,3-d]pyrimidine-Based Hydroxamic Acid Derivatives as Bromodomain-Containing Protein 4/Histone Deacetylase Dual Inhibitors Induce Autophagic Cell Death in Colorectal Carcinoma Cells》 was published in Journal of Medicinal Chemistry. The article was written by Pan, Zhaoping; Li, Xiang; Wang, Yujia; Jiang, Qinglin; Jiang, Li; Zhang, Min; Zhang, Nan; Wu, Fengbo; Liu, Bo; He, Gu. The article contains the following contents:

Bromodomain-containing protein 4 (BRD4) and histone deacetylases (HDAC) are both attractive epigenetic targets in cancer and other chronic diseases. Based on the integrated fragment-based drug design, synthesis, and in vitro and in vivo evaluations, a series of novel thieno[2,3-d]pyrimidine-based hydroxamic acid derivatives are discovered as selective BRD4-HDAC dual inhibitors. Compound 17c is the most potent inhibitor for BRD4 and HDAC with IC50 values at nanomolar levels, as well as the expression level of c-Myc, and increases the acetylation of histone H3. Moreover, 17c presents inhibitory effects on the proliferation of colorectal carcinoma (CRC) cells via inducing autophagic cell death. It also has a good pharmacokinetic profile in rats and oral bioavailability of 40.5%. In the HCT-116 xenograft in vivo models, 17c displays potent inhibitory efficiency on tumor growth by inducing autophagic cell death and suppressing IL6-JAK-STAT signaling pathways. Our results suggest that the BRD4-HDAC dual inhibition might be an attractive therapeutic strategy for CRC. The results came from multiple reactions, including the reaction of Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8Synthetic Route of C9H9BrO2)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals.Synthetic Route of C9H9BrO2 The most pervasive is the naturally produced bromomethane.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Recommanded Product: 3141-27-3In 2022 ,《Synthesis, molecular docking, and biological evaluation of 5-alkyl(aryl)-2-isobutylthiazole derivatives as α-amylase, α-glucosidase, and protein kinase inhibitors》 was published in Applied Organometallic Chemistry. The article was written by Khan, Siraj; Bugday, Nesrin; Rehman, Asim Ur; Haq, Ihsan Ul; Yasar, Sedat; Ozdemir, Ismail. The article contains the following contents:

A series of 18 biol. active C5-arylated-2-isobutylthiazoles (aryl = Ph, 4-MeCOC6H4, 4-methyl-1-naphthyl, 5-formyl-2-furyl, etc.) was synthesized from 2-isobutylthiazole and the corresponding aryl bromides via C-H bond activation using Pd-NHC complexes [Pd(μ-Cl)Cl(NHC)]2 [NHC = 1,3-bis(2,6-dimethylphenyl)imidazolylidene] and [LCl2Pd-NHC] (L = PPh3, pyridine, 3-formylpyridine). All Pd-NHC complexes were prepared and characterized by 1H NMR, 13C NMR and FTIR spectroscopy, quadrupole-time of flight-liquid chromatog./mass spectroscopy (Q-TOF-LC/MS), gas chromatog.-mass spectrometry (GCMS), and m.p. techniques. The physicochem. properties, pharmacokinetics and drug-likeness of the thiazole products were calculated by SwissADME. PkCSM database was used to calculated the toxicity profile. Almost all the compounds showed no to low toxicity. All the products were addnl. assessed in vitro for their antidiabetic potential using α-amylase and α-glucosidase inhibitory activities. Except for 7 compounds, the prepared thiazoles showed good α-glucosidase inhibitory potential (IC50 7.17 ± 0.201 to 74.08 ± 0.244μg/mL) when compared with acarbose standard (IC50 16.59 ± 0.135μg/mL). All compounds had moderate to good inhibitory potential against the α-amylase enzyme, with IC50 values ranging from 12.00 ± 0.289 to 76.15 ± 0.477μg/mL. The protein kinase inhibition potential was determined for the first time, and 7 compounds showed activity with the zone of inhibition in the range of 9 ± 1.3 to 19 ± 1.5 mm. The ligands and active site binding interactions of α-glucosidase, α-amylase, and protein kinase enzymes were also studied using mol. modeling. In the experiment, the researchers used many compounds, for example, 2,5-Dibromothiophene(cas: 3141-27-3Recommanded Product: 3141-27-3)

2,5-Dibromothiophene(cas: 3141-27-3) , is mainly used as pharmaceutical intermediate and synthesis intermediate. 2,5-Dibromothiophene polymerizes by debromination with magnesium catalyzed by nickel compounds to form poly(2,5- thienylene) .Recommanded Product: 3141-27-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Recommanded Product: 4-Bromobutanoic acidIn 2019 ,《Synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E from a common synthetic intermediate》 was published in Organic & Biomolecular Chemistry. The article was written by Yalla, Raju; Raghavan, Sadagopan. The article contains the following contents:

The stereoselective synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E, from a common synthetic intermediate, is disclosed. The propargylic sulfide stereo-center is created stereoselectively via carbon-carbon bond formation in the reaction of α-chloro sulfides with alkynyl zinc reagents via 1,2-asym. induction by a β-siloxy group. The characteristic 1,4-diol motif of the natural products is introduced by a [2,3] sigmatropic rearrangement of an allylic sulfoxide or by the Mislow-Evans-Braverman rearrangement of a propargylic sulfoxide followed by stereoselective reduction of the ensuing α,β-unsaturated ketone. Unlike earlier reports, the C11/C9 carbinol center is created with excellent stereocontrol and derivatives of natural products differing at C14/C12 can be readily obtained. In the experiment, the researchers used 4-Bromobutanoic acid(cas: 2623-87-2Recommanded Product: 4-Bromobutanoic acid)

4-Bromobutanoic acid(cas: 2623-87-2) belongs to carboxylic acids. The chief chemical characteristic of the carboxylic acids is their acidity. They are generally more acidic than other organic compounds containing hydroxyl groups but are generally weaker than the familiar mineral acids (e.g., hydrochloric acid, HCl, sulfuric acid, H2SO4, etc.).Recommanded Product: 4-Bromobutanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary