Month: February 2023

HF-Induced Intramolecular C-Arylation and C-Alkylation/Fluorination of 2-Aminoglycopyranoses was written by Probst, Nicolas;Martin, Amelie;Desire, Jerome;Mingot, Agnes;Marrot, Jerome;Bleriot, Yves;Thibaudeau, Sebastien. And the article was included in Organic Letters in 2017.Safety of 2-(Bromomethyl)-1,3-dimethylbenzene This article mentions the following:

Internal C-aryl and C-alkyl glycosides derived from 2-aminoglycopyranoses have been synthesized, exploiting a HF-mediated stereoselective intramol. glycosylation. These conditions are compatible with acetate protecting groups and allow introduction of aromatics with various electronic distributions at the anomeric position. This strategy also provides straightforward entry to original fluorinated sugar-azacycle hybrids via a tandem internal C-glycosylation/fluorination reaction starting from 2-N-allyl/propargyl glycopyranoses. All cyclizations proceed in a 1,2-cis stereocontrolled manner. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Safety of 2-(Bromomethyl)-1,3-dimethylbenzene).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Safety of 2-(Bromomethyl)-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The induction of chromosome aberrations in Vicia faba by halogenated butyl ethers was written by Michaelis, A.;Rieger, R.;Sieber, G.. And the article was included in Biologisches Zentralblatt in 1964.Electric Literature of C5H11BrO This article mentions the following:

Treatment with 10^-4 – 64 × 10^-4M Me 4-bromobutyl ether (I), 10^-4 – 60 × 10^-4M, Et 4-bromobutyl ether (II), 5 × 10^-5 – 10^-4 4,4′-dichlorodibutyl ether (III), and 5 × 10^-5 – 10^-4 4,4′ dibromodibutyl ether (IV) for 1-24 hrs. at pH 7, followed by 0.05% colchicine treatment provoked chromatid types of chromosome aberrations in V. faba roots, localized in the heterochromatic regions. The degree of mutagenic activity was IV > I > II > III. It is suggested that I-IV and N mustard have similar mechanism of mutagenic activity. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Electric Literature of C5H11BrO).

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.Electric Literature of C5H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

One-Pot Alkene Hydroboration/Palladium-Catalyzed Migratory Suzuki-Miyaura Cross-Coupling was written by Baumgartner, Yann;Baudoin, Olivier. And the article was included in ACS Catalysis in 2020.Application of 28322-40-9 This article mentions the following:

Chain-walking is a powerful approach toward the functionalization of C-H bonds remote to a functional group. Whereas various Pd-catalyzed migratory cross-couplings have been developed in the past years, the design of an efficient migratory version of the popular Suzuki-Miyaura cross-coupling has remained elusive. The current article reports a one-pot procedure consisting of alkene hydroboration and migratory Suzuki-Miyaura coupling of the resulting alkylboronic acid intermediate. A high regioselectivity for the benzylic position of the initial alkene was achieved by using P(t-Bu)₂Me as the ligand and an ortho-substituted aryl electrophile. Regioconvergence from alkene positional and geometrical isomers and long-range migration were demonstrated. Mechanistic investigations indicated that the migration occurs through a partially reversible, nondissociative mechanism. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Application of 28322-40-9).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Application of 28322-40-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Simplified Synthetic Approach to Tetrabrominated Spiro-Cyclopentadithiophene and the Following Derivation to A-D-A Type Acceptor Molecules for Use in Polymer Solar Cells was written by Liu, Xiaochen;Zhang, Yuanxun;Wu, Jianchang;Ma, Yuchao;Lau, Kim K. T.;Fang, Jin;Ma, Chang-Qi;Lin, Yi. And the article was included in Journal of Organic Chemistry in 2022.Quality Control of 1-Bromopyrrolidine-2,5-dione This article mentions the following:

4,4â€?Spiro-bis[cyclopenta[2,1-b;3,4-b′]dithiophene] (SCT) is a versatile building block for constructing three-dimensional (3D) π-conjugated mols. for use in organic electronics. In this paper, we report a more convenient synthetic route to SCT and its derivatives, where a structurally sym. 3,3â€?dibromo-5,5â€?bis(trimethylsilyl)-2,2â€?bithiophene (2) serves as the precursor for both the synthesis of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one (4) and 4-(5,5â€?bis(trimethylsilyl)-2,2â€?bithiophen-3-yl)-2,6-bis(trimethylsilyl)-4-hydroxy-cyclopenta[2,1-b;3,4-b′]dithiophene (5). The later one is the key intermediate for the final brominated SCT building block. Such a “two birds with one stone” strategy simplifies the synthetic approach to the SCT core. Functionalization on the SCT core with different terminal electron-deficient groups, including 1H-indene-1,3(2H)-dione (ID), 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (IC), and 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (FIC), was carried out, yielding three spiro-conjugated A-D-A type mols., SCT-(TID)₄, SCT-(TIC)₄, SCT-(TFIC)₄, resp. The optical spectroscopy and electrochem. properties of these three compounds were investigated and compared to the corresponding linear oligomers. Results revealed that the IC and TFIC terminated compounds showed low-lying HOMO/LUMO energy levels with reduced optical bandgap, making them more suitable for use in polymer solar cells. A power conversion efficiency of 3.73% was achieved for the SCT-(TFIC)₄ based cell, demonstrating the application perspective of 3D mols. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Quality Control of 1-Bromopyrrolidine-2,5-dione).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Quality Control of 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Direct Construction of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Conjugated Diynes was written by Naoe, Saori;Saito, Tatsuo;Uchiyama, Masanobu;Oishi, Shinya;Fujii, Nobutaka;Ohno, Hiroaki. And the article was included in Organic Letters in 2015.Name: Methyl 3-bromo-4-fluorobenzoate This article mentions the following:

A gold-catalyzed cascade cyclization of aniline derivatives bearing a conjugated diyne moiety was developed. Following the 5-endo-dig indole formation, subsequent 7-endo-dig cyclization predominated over 6-exo-dig cyclization to give the indole fused with a seven-membered ring in good yields. E.g., in presence of IPrAuCl and AgOTf in DCE at 50 °C, cascade cyclization of diyne (I) gave 86% II and III (88:12). In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6Name: Methyl 3-bromo-4-fluorobenzoate).

Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6) 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. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Name: Methyl 3-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and structure of new potential electrochemically active boronic acid-based glucose sensors was written by Norrild, Jens Chr.;Sotofte, Inger. And the article was included in Journal of the Chemical Society, Perkin Transactions 2 in 2002.HPLC of Formula: 166821-88-1 This article mentions the following:

In the authors’ studies on new boronic acid based carbohydrate sensors three new boronic acids (2-FcCH₂NMeCH₂C₆H₄B(OH)₂ (3), 1,2-(2-(HO)₂BC₆H₄CH₂NMeCH₂)₂ferrocene (7) and 1,1′-(2-(HO)₂BC₆H₄CH₂NMeCH₂)₂ferrocene (11)) containing a ferrocene moiety were synthesized. Their design includes an intramol. B-N bonding motif to facilitate binding at physiol. pH. The authors report the synthesis of the compounds and studies on glucose complexation as studied by ¹³C NMR spectroscopy. The crystal structure of 2,4,6-tris[2-(N-ferrocenylmethyl-N-methylaminomethyl)phenyl]boroxin (13) (boroxin of boronic acid 3) (boroxin = cyclotriboroxane) was obtained and compared with structures obtained of 2,4,6-tris[2-(N,N-dimethylaminomethyl)phenyl]boroxin (14) and 2-(2-(dimethylaminomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (15). The structure of 13 shows the existence of intramol. B-N bonds in the solid phase. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1HPLC of Formula: 166821-88-1).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) 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. 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.HPLC of Formula: 166821-88-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sc(OTf)₃-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction was written by Jimenez-Aberasturi, Xabier;Palacios, Francisco;de los Santos, Jesus M.. And the article was included in Journal of Organic Chemistry in 2022.Name: 1-Bromopyrrolidine-2,5-dione This article mentions the following:

The first accomplishment of the azo-Povarov reaction involving Sc(OTf)₃-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offer a rapid access to an array of cinnoline derivatives in moderate to good yields for substrates over a wide scope. The synthetic potential of the protocol was achieved by the gram-scale reaction and further derivatization of the obtained polycyclic product. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Name: 1-Bromopyrrolidine-2,5-dione).

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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Name: 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Screening of a virtual mirror-image library of natural products was written by Noguchi, Taro;Oishi, Shinya;Honda, Kaori;Kondoh, Yasumitsu;Saito, Tamio;Ohno, Hiroaki;Osada, Hiroyuki;Fujii, Nobutaka. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2016.Application In Synthesis of Isopentyltriphenylphosphonium bromide This article mentions the following:

We established a facile access to an unexplored mirror-image library of chiral natural product derivatives using D-protein technol. In this process, two chem. syntheses of mirror-image substances including a target protein and hit compound(s) allow the lead discovery from a virtual mirror-image library without the synthesis of numerous mirror-image compounds In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Application In Synthesis of Isopentyltriphenylphosphonium bromide).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. 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 In Synthesis of Isopentyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis, properties and antimicrobial activity of 5-trifluoromethyl-2-formylphenylboronic acid was written by Adamczyk-Wozniak, Agnieszka;Gozdalik, Jan T.;Wieczorek, Dorota;Madura, Izabela D.;Kaczorowska, Ewa;Brzezinska, Ewa;Sporzynski, Andrzej;Lipok, Jacek. And the article was included in Molecules in 2020.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde This article mentions the following:

2-Formylphenylboronic acids display many interesting features, not only from synthetic but also from an application as well as structural points of view. 5-Trifluoromethyl-2-formyl phenylboronic acid has been synthesized and characterized in terms of its structure and properties. The presence of an electron-withdrawing substituent results in a considerable rise in the acidity in comparison with its analogs. Taking into account the probable mechanism of antifungal action of benzoxaboroles, which blocks the cytoplasmic leucyl-tRNA synthetase (LeuRS) of the microorganism, docking studies with the active site of the enzymes have been carried out. It showed possible binding of the cyclic isomer into the binding pocket of Candida albicans LeuRS, similar to that of the recently approved benzoxaborole antifungal drug (AN2690, Tavaborole, Kerydin). In case of Escherichia coli LeuRS, the opened isomer displays a much higher inhibition constant in comparison with the cyclic one. The antimicrobial activity of the title compound was also investigated in vitro, showing moderate action against Candida albicans. The compound reveals higher activity against Aspergillus niger as well as bacteria such as Escherichia coli and Bacillus cereus. In case of Bacillus cereus, the determined Min. Inhibitory Concentration (MIC) value is lower than that of AN2690 (Tavaborole). The results confirm potential of 2-formylphenylboronic acids as antibacterial agents and give a hint of their possible mechanism of action. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

S_N2 Substitution Reactions at the Amide Nitrogen in the Anomeric Mutagens, N-Acyloxy-N-alkoxyamides was written by Cavanagh, Katie L.;Glover, Stephen A.;Price, Helen L.;Schumacher, Rhiannon R.. And the article was included in Australian Journal of Chemistry in 2009.Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene This article mentions the following:

N-Acyloxy-N-alkoxyamides 1a are unusual anomeric amides that are pyramidal at the nitrogen because of bis oxyl substitution. Through this configuration, they lose most of their amide character and resemble α-haloketones in reactivity. They are susceptible to S_N2 reactions at nitrogen, a process that is responsible for their mutagenic behavior. Kinetic studies have been carried out with the nucleophile N-methylaniline that show that, like S_N2 reactions at carbon centers, the rate constant for S_N2 displacement of carboxylate is lowered by branching β to the nitrogen center, or bulky groups on the alkoxyl side chain. Branching or bulky groups on the carboxylate leaving group, however, do not impact on the rate of substitution, which is mostly controlled by the pK_A of the departing carboxylate group. These results are in line with computed properties for the model reaction of ammonia with N-acetoxy-N-methoxyacetamide but are in contrast to the role of steric effects on their mutagenicity. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) 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 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.Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary