Month: January 2023

Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group was written by Zhan, Yi-Zhou;Xiao, Nan;Shu, Wei. And the article was included in Nature Communications in 2021.Category: bromides-buliding-blocks This article mentions the following:

The nickel-catalyzed intermol. cross-dialkylation of alkynes devoid of directing or activating groups afforded multiple aliphatic substituted alkenes in a syn-selective fashion at room temp was reported. The combination of two-electron oxidative cyclometallation and single-electron cross-electrophile coupling of nickel enabled the syn-cross-dialkylation of alkynes at room temperature This reductive protocol enabled the sequential installation of two different alkyl substituents onto alkynes in a regio- and stereo-selective manner, circumvented the tedious preformation of sensitive organometallic reagents. The synthetic utility of this protocol was demonstrated by efficient synthesis of multi-substituted unfunctionalized alkenes and diverse transformations of the product. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Category: bromides-buliding-blocks).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism was written by Liu, Qianyi;Hong, Junting;Sun, Beiqi;Bai, Guangcan;Li, Feng;Liu, Guoquan;Yang, Yang;Mo, Fanyang. And the article was included in Organic Letters in 2019.Reference of 4457-67-4 This article mentions the following:

The authors describe an operationally simple transition-metal-free borylation of alkyl iodides. This method uses com. available diboron reagents as the B source and exhibits excellent functional group compatibility. Also, a diverse range of primary and secondary alkyl iodides could be effectively transformed to the corresponding alkylboronates in excellent yield. Mechanistic studies suggest that this borylation reaction proceeds through a single-electron transfer mechanism featuring the generation of an alkyl radical intermediate. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Reference of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. 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. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Reference of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mechanistic Understanding of a Robust and Scalable Synthesis of Per(6-deoxy-6-halo)cyclodextrins, Versatile Intermediates for Cyclodextrin Modification was written by Zultanski, Susan L.;Kuhl, Nadine;Zhong, Wendy;Cohen, Ryan D.;Reibarkh, Mikhail;Jurica, Jon;Kim, Jungchul;Weisel, Lauren;Ekkati, Anil R.;Klapars, Artis;Gauthier, Donald R. Jr.;McCabe Dunn, Jamie M.. And the article was included in Organic Process Research & Development in 2021.Electric Literature of C42H63Br7O28 This article mentions the following:

Cyclodextrin (CD) perfunctionalization reactions are challenging to study because they proceed through a number of regioisomeric intermediates, thus warranting creative approaches to understanding the reaction mechanism. Particularly useful perfunctionalization targets are per(6-deoxy-6-halo)cyclodextrins. Their standard synthesis entails selective S_N2 halogenation at their primary alcs. using a Vilsmeier reagent, but this requires a strongly basic quench to unmask the Vilsmeier-capped secondary alcs. Herein we present an alternative and simple acidic hydrolytic quench that utilizes existing HX in the end-of-reaction solution and requires only the addition of water. We performed a detailed mechanistic investigation of the new quench, and a central feature was the use of proton sponge to develop an ¹H NMR titration method for HX in organic solvent. This method was used to both quantify and remove HX in the prequenched reaction solution The HX-free prequenched solution enabled us to (1) identify sensitive intermediates during the quench, (2) quantify all of the reaction byproducts, and (3) determine that HX is critical for hydrolysis. We then studied the halogenation reaction, wherein the new acidic quench facilitated high-throughput experimentation, using mass spectrometry as well as Design of Experiments with automated reaction profiling. Through this, we were able to establish robustness and understand the complex effects of Vilsmeier equivalent and temperature on the reaction outcome. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Electric Literature of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Electric Literature of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of N-(4-Aminobutyl)-N’-(2-methoxyethyl)guanidine as the First Selective, Nonamino Acid, Catalytic Site Inhibitor of Human Dimethylarginine Dimethylaminohydrolase-1 (hDDAH-1) was written by Lunk, Ina;Litty, Felix-Alexander;Hennig, Sven;Vetter, Ingrid R.;Kotthaus, Juerke;Altmann, Karin S.;Ott, Gudrun;Havemeyer, Antje;Garcia, Carmen Carrillo;Clement, Bernd;Schade, Dennis. And the article was included in Journal of Medicinal Chemistry in 2020.SDS of cas: 4457-67-4 This article mentions the following:

N-(4-Aminobutyl)-N’-(2-methoxyethyl)guanidine (8a) is a potent inhibitor targeting the hDDAH-1 active site (K_i = 18μM) and derived from a series of guanidine- and amidine-based inhibitors. Its nonamino acid nature leads to high selectivities toward other enzymes of the nitric oxide-modulating system. Crystallog. data of 8a-bound hDDAH-1 illuminated a unique binding mode. Together with its developed N-hydroxyguanidine prodrug 11, 8a will serve as a most widely applicable, pharmacol. tool to target DDAH-1-associated diseases. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4SDS of cas: 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.SDS of cas: 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Thiophane compounds. II was written by Karrer, P.;Schmid, H.. And the article was included in Helvetica Chimica Acta in 1944.Application of 4457-67-4 This article mentions the following:

The methyl-3-thiophanone described in the preceding abstract could have had the Me group in position 2 or 4. To elucidate this point, 2-methyl-3-thiophanone was synthesized by condensing HSCH₂CH₂CO₂Et (I) and MeCHBrCO₂Et (II), followed by cyclization and ketone cleavage. HSCH₂CH₂CO₂H (17.7 g.) was esterified with 200 cc. absolute alc. containing 1 cc. H₂SO₄, in a CO₂ atm., giving 17.7 g. I, b₂₀ 77.5°. To an ice-cold solution of 2.57 g. Na in 50 cc. absolute alc., 15 g. I was added, under N; the mixture was cooled to -15° and 20.3 g. II added dropwise with shaking. This mixture was shaken for 1 hr. at 15°, then heated to boiling for 1.5 hrs., then the alc. removed in vacuo, and the residue acidified with HCl. This was extracted with ether, washed with NaHCO₃, dried with Na₂SO₄ and the ether evaporated The resulting EtO₂CCH₂CH₂SCHMeCO₂Et (III) b_10.5 149-53°, was obtained in 82.5% yield. To 6.4 g. pulverized NaNH₂ in 70 cc. absolute ether was added about 1/4 of a solution of 19 g. III in 40 cc. absolute ether, with stirring, and the bath heated to 40-50° to initiate the reaction. The rest of the III was then added and stirring and refluxing continued for 3 hrs. This mixture was then allowed to stand overnight, decomposed with ice and 11 cc. AcOH, saturated with NaCl and extracted with ether. The ether solution was washed with NaHCO₃, dried, the ether evaporated and distilled The 2-methyl-4-carbethoxy-3-thiophanone (IV) so obtained in 48.5% yield, b₁₁ 123-30°, and in aqueous alc. solution gave a red-violet color with FeCl₃. Ketone cleavage of IV with 10% H₂SO₄ gave 2-methyl-3-thiophanone (81%), b₁₁, 90-100° (semicarbazone, m. 183-4°, gave a definite m.-p. lowering when mixed with the semicarbazone of the compound designated VII in the preceding abstract); hence the substance VII of the preceding abstract must be 4-methyl-3-thiophanone. The phenylhydrazone of the keto ester designated VI in the preceding abstract was fractionated into 2 fractions, A, m. 141.5-2.5°, and B, m. 167°, demonstrating that VI was a mixture in which the CO₂Et group was at positions 2 and 4. A was much more abundant than B. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Application of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Application of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and structure-activity relationship of naphtho[1,2-b]furan-2-carboxamide derivatives as melanin concentrating hormone receptor 1 antagonists was written by Lim, Chae Jo;Choi, Jun Young;Lee, Byung Ho;Oh, Kwang-Seok;Yi, Kyu Yang. And the article was included in Chemical & Pharmaceutical Bulletin in 2013.Category: bromides-buliding-blocks This article mentions the following:

Synthesis and structure-activity relationship of naphtho[1,2-b]furan-2-carboxamides I (n = 2-5; R = H, Br, Ph, 4-MeC₆H₄, 3-ClC₆H₄, 2-pyridyl, 3-furyl, 3-thienyl, etc.) containing linked piperidinylphenylacetamide groups as melanin concentrating hormone receptor 1 (MCH-R1) antagonists are described. The structure activity relationship (SAR) study, probing members of this family that contain a variety of aryl and heteroaryl groups at C-5 of I skeleton and having different chain linker lengths, led to the identification of the 5-(4-pyridinyl)-substituted analog I (n = 2; R = pyridin-4-yl) as a highly potent MCH-R1 antagonist with an IC₅₀ value of 3nM. This compound also displayed excellent metabolic stability and did not significantly inhibit cytochrome P 450 (CYP450) enzymes. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Category: bromides-buliding-blocks).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans was written by Zheng, Hong-Xing;Shan, Xiang-Huan;Qu, Jian-Ping;Kang, Yan-Biao. And the article was included in Organic Letters in 2018.Recommanded Product: 2-Bromo-4-fluorobenzylbromide This article mentions the following:

An intermol. addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermol. alkyl radical addition to a carbonyl group followed by an intramol. alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR anal. The mechanism is investigated by KIE experiments and control experiments This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0Recommanded Product: 2-Bromo-4-fluorobenzylbromide).

2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Recommanded Product: 2-Bromo-4-fluorobenzylbromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Thiophene-Perylenediimide Bridged Dimeric Porphyrin Donors Based on the Donor-Acceptor-Donor Structure for Organic Photovoltaics was written by Piradi, Venkatesh;Gao, Yaxin;Yan, Feng;Imran, Muhammad;Zhao, Jianzhang;Zhu, Xunjin;So, Shu Kong. And the article was included in ACS Applied Energy Materials in 2022.COA of Formula: C4H4BrNO2 This article mentions the following:

Two D-A-D (D = donor, A = acceptor)-based small-mol. donors, TPDI-2P and F-TPDI-2P, are designed and synthesized for organic solar cells (OSCs), with two strong donor porphyrin units bridged by either an electron-deficient diethynyl-substituted thiophene-perylenediimide (TPDI) linker for the former or a diethynyl-fused TPDI linker for the latter; 3-ethylrhodanine units were then flanked sym. by phenylenethynylene π-linkers. Both compounds show strong absorption profiles from 400 to 800 nm, with a valley at 600 nm, attributed to the Soret and Q-bands of porphyrin units. Compared to TPDI-2P, F-TPDI-2P with a fused TPDI backbone exhibits high red shifted absorptions and low-lying energy levels due to increased coplanarity of the dimeric porphyrin units. As a result, the optimized photovoltaic device based on F-TPDI-2P/PC₇₁BM has a decent power conversion efficiency (PCE) of 8.21%, whereas the device TPDI-2P/PC₇₁BM has a slightly lower PCE (6.90%). The higher efficiency of F-TPDI-2P/PC₇₁BM is mainly due to better photocurrent generation and smoother surface morphol. with elevated charge carrier mobilities. The success of this mol. design strategy could be beneficial in the development of more efficient porphyrin-based donors for high-performance OSCs. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5COA of Formula: C4H4BrNO2).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. COA of Formula: C4H4BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Highly Stereoselective Synthesis of Fused Tetrahydropyrans via Lewis-Acid-Promoted Double C(sp³)-H Bond Functionalization was written by Yokoo, Kazuma;Sakai, Dan;Mori, Keiji. And the article was included in Organic Letters in 2020.Name: 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

We have achieved a sequential hydride-shift-triggered double C(sp³)-H bond functionalization at a position adjacent to an oxygen atom and a benzylic/aliphatic position through the employment of substrates with a dialkyl group in the alkyl chain, which enabled the highly diastereoselective synthesis of fused tetrahydropyrans. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Name: 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Name: 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Development of novel Gemini-cholesterol analogues for retinoid-related orphan receptors was written by Gomez-Bouzo, Uxia;Fall, Alioune;Osz, Judit;Fall, Yagamare;Rochel, Natacha;Santalla, Hugo. And the article was included in Organic Chemistry Frontiers in 2022.Related Products of 28322-40-9 This article mentions the following:

Retinoic-acid-related Orphan Receptors (RORs) regulate the maintenance of the circadian rhythm and immune response among others and are involved in increasing numbers of pathologies including autoimmune diseases, cancer and neurol. disorders leading to huge interest in the development of ROR ligands. Here, the synthesis of six novel Gemini cholesterol analogs such as I and the binding mode of I to RORγ was described. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Related Products of 28322-40-9).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Related Products of 28322-40-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary