Month: February 2023

Condensed isoquinolines. Part 9. Alkylation of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones was written by Kisel, V. M.;Potikha, L. M.;Kovtunenko, V. A.. And the article was included in Chemistry of Heterocyclic Compounds (New York)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) in 2000.Safety of 3-(Bromomethyl)benzoic acid This article mentions the following:

The alkylation of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one proceeds at N(6) or C(7) depending on the type of alkylating agent and reaction conditions. C(7)-alkylation occurs in the presence of base. The secondary alkylation of the 7-alkyl derivatives occurs at the same position under these conditions. Depending on the conditions, the reaction with ortho-xylylene dibromide leads to spiro[5H-isoquino-[2,3-a]quinazolin-7(12H),2′-indane]-5-one or 11-oxo-4b,5,10,16-tetrahydro-11H-10a-azonia-15b-azadibenzo[a,e]pleiadene bromide. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Safety of 3-(Bromomethyl)benzoic acid).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. 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.Safety of 3-(Bromomethyl)benzoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design of Potent and Proteolytically Stable Biaryl-Stapled GLP-1R/GIPR Peptide Dual Agonists was written by Yang, Yifang;Lee, Candy;Reddy, Reddy Rajasekhar;Huang, David J.;Zhong, Weixia;Nguyen-Tran, Van T. B.;Shen, Weijun;Lin, Qing. And the article was included in ACS Chemical Biology in 2022.Application In Synthesis of 1-Bromopyrrolidine-2,5-dione This article mentions the following:

Recent clin. trials have revealed that the chimeric peptide hormones simultaneously activating glucagon-like peptide-1 receptor (GLP-1R) and glucose-dependent insulinotropic polypeptide receptor (GIPR) demonstrate superior efficacy in glycemic control and body weight reduction, better than those activating the GLP-1R alone. However, the linear peptide-based GLP-1R/GIPR dual agonists are susceptible to proteolytic cleavage by common digestive enzymes present in the gastrointestinal tract and thus not suitable for oral administration. Here, we report the design and synthesis of biaryl-stapled peptides, with and without fatty diacid attachment, that showed potent GLP-1R/GIPR dual agonist activities. Compared to a linear peptide dual agonist and semaglutide, the biaryl-stapled peptides displayed drastically improved proteolytic stability against the common digestive enzymes. Furthermore, two stapled peptides showed excellent efficacy in an oral glucose tolerance test in mice, owing to their potent receptor activity in vitro and good pharmacokinetics exposure upon s.c. injection. By exploring a more comprehensive set of biaryl staplers, we expect that this stapling method could facilitate the design of the stapled peptide-based dual agonists suitable for oral administration. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Application In Synthesis of 1-Bromopyrrolidine-2,5-dione).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application In Synthesis of 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis was written by Yan, Xiao-Biao;Li, Chun-Ling;Jin, Wen-Jie;Guo, Peng;Shu, Xing-Zhong. And the article was included in Chemical Science in 2018.Application In Synthesis of 1-Bromo-4-methoxybutane This article mentions the following:

Coupling reactions involving non-sulfonated C-O electrophiles provide a promising method for forming C-C bonds, but the incorporation of functionalized or secondary alkyl groups remains a challenge due to the requirement for well-defined alkylmetal species. In this study, a reductive nickel-catalyzed cross-coupling of benzyl oxalates with alkyl bromides, using oxalate as a new leaving group is reported. A broad range of highly functionalized alkyl units (such as functional groups: alkyl chloride, alc., aldehyde, amine, amide, boronate ester, ether, ester, heterocycle, phosphonate, strained ring) were efficiently incorporated at the benzylic position. The utility of this synthetic method was further demonstrated by late-stage modification of complex bioactive compounds Preliminary mechanistic experiments revealed that a radical process might be involved in the reaction. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Application In Synthesis of 1-Bromo-4-methoxybutane).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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鑱砨romine bond is electrophilic in nature. 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.Application In Synthesis of 1-Bromo-4-methoxybutane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Development of C₂-Symmetric Chiral Spirocyclic Phase-Transfer Catalysts: Synthesis and Application to Asymmetric Alkylation of Glycinate Schiff Base was written by Xu, Changming;Qi, Yinsheng;Yang, Xinshuang;Li, Xiangfan;Li, Zhenpeng;Bai, Lei. And the article was included in Organic Letters in 2021.Quality Control of 2-(Bromomethyl)-1,3-dimethylbenzene This article mentions the following:

A class of C₂-sym. chiral spirocyclic phase-transfer catalysts based on the tetramethyl-1,1′-spirobiindane scaffold such as I璺疊r^– was synthesized from com. available bisphenol A in 12 steps in 22-25% total yields; the scaffold features a more rigid and stable backbone and smaller dihedral angles and can be easily modified. These catalysts show high catalytic performance in the asym. alkylation of tert-Bu glycinate Schiff base Ph₂C:NCH₂CO₂t-Bu at only 2 mol % catalyst loading, giving nonracemic protected 浼?amino acid esters such as (R)-Ph₂C:NCH(CH₂Ph)CO₂t-Bu in up to 92% yield and 98% ee. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Quality Control of 2-(Bromomethyl)-1,3-dimethylbenzene).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Quality Control of 2-(Bromomethyl)-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Theoretical study of a few 2D polymer networks and MOFs formed by chiral mTBPB molecules was written by Xiang, Zhihao;Kang, Shuangyu;Feng, Xuyang;Mu, Huijing;Cai, Yingxiang. And the article was included in Materials Chemistry and Physics in 2020.Name: 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl This article mentions the following:

Two-dimensional (2D) materials have become the most popular research targets due to their unique structural characteristics, novel phys. properties and potential applications such as photovoltaics, semiconductors, electrodes and water purification In this study, a few 2D polymer networks and their corresponding metal organic frameworks (MOFs) formed by the debromination (also including dehydrogenation) of mTBPB mols. were investigated based on first-principles calculations It was found that L-C₄₈H₃₀, LR-C₄₈H₃₀ and achiral-C₁₂H₆ were direct-bandgap semiconductors but L-C₄₈H₃₀Cr₃, LR-C₄₈H₃₀Cr₃ and achiral-C₄₈H₂₄Cr₆ 2D MOFs were ferromagnetic semiconductors. The origin of ferromagnetism in three 2D MOFs was mainly attributed to the contribution of Cr-d and C-p_z orbitals. Furthermore, anisotropic carrier effective masses were determined and the reaction energy barriers to form these 2D polymer networks and MOFs were evaluated. In the experiment, the researchers used many compounds, for example, 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl (cas: 96761-85-2Name: 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl).

3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl (cas: 96761-85-2) 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). Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Name: 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of 1-aryl-tetralins and 4-aryl-benzopyrans by sulfoxide-mediated benzylic carbocation cyclizations was written by Volonterio, Alessandro;Zanda, Matteo. And the article was included in Tetrahedron Letters in 2005.Safety of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

An alkylation/cyclization sequence, with both steps mediated by the ortho-N-methylformamido-phenylsulfinyl function, provided two new C-C bonds and an efficient entry to 1-aryltetralins and 4-arylbenzopyrans. Scope and limits of the process were studied in detail. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Safety of 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Safety of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Catalytically active supramolecular porphyrin boxes: acceleration of the methanolysis of phosphate triesters via a combination of increased local nucleophilicity and reactant encapsulation was written by Kang, Byungman;Kurutz, Josh W.;Youm, Kyoung-Tae;Totten, Ryan K.;Hupp, Joseph T.;Nguyen, Son Binh T.. And the article was included in Chemical Science in 2012.Reference of 100189-84-2 This article mentions the following:

Box-like tetrakis(metalloporphyrin) supramol. assemblies possessing Zn and Al metal sites can catalyze the methanolysis of phosphate triesters with a high rate enhancement, up to 430 times faster than the uncatalyzed reaction. Mechanistic studies suggest that the observed rate enhancement can be attributed to a high local concentration of methoxide ion that operates in concert with a solvophobically driven encapsulation of substrates by the porphyrinic assembly. In the experiment, the researchers used many compounds, for example, 2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2Reference of 100189-84-2).

2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2) 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. 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.Reference of 100189-84-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nickel-catalyzed intramolecular desymmetrization addition of aryl halides to 1,3-diketones was written by Zhou, Pan;Xu, Tao. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Synthetic Route of C7H5Br2F This article mentions the following:

A nickel-catalyzed intramol. addition of aryl halides to 1,3-diketones was first developed. This desymmetrization reaction afforded polycyclic products I [R = Me, i-Bu, Bn, etc.; R¹ = H; R² = H, Cl, OMe, etc.; R³ = H, Me; R⁴ = H, Me; R¹R² = OCH₂O] bearing two tetrasubstituted centers with excellent diastereoselectivities and high yields. Moderate enantioselectivities were achieved in the presence of a chiral ligand. This transformation had great potential for the synthesis of polycyclic compounds including spiro[4,4,3,0] compounds In the experiment, the researchers used many compounds, for example, 2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0Synthetic Route of C7H5Br2F).

2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0) 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.Synthetic Route of C7H5Br2F

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Pyridine-2(1H)-thiones: Versatile Precursors for Novel Pyrazolo[3,4-b]pyridine, Thieno[2,3-b]pyridines, and Their Fused Azines was written by Sanad, Sherif M. H.;Abdel-Fattah, Azza M.;Attaby, Fawzy A.;Elneairy, Mohamed A. A.. And the article was included in Journal of Heterocyclic Chemistry in 2019.Computed Properties of C8H6Br2O2 This article mentions the following:

Pyridine-2(1H)-thiones were prepared and reacted with several active halogenated reagents to afford novel thieno[2,3-b]pyridines in excellent yields. Thieno[2,3-b]pyridine-2-carbohydrazide derivative was prepared by the reaction of either Et 2-((3-cyanopyridin-2-yl)thio)acetate derivative or thieno[2,3-b]pyridine-2-carboxylate derivative with hydrazine hydrate. On the other hand, the reaction of either pyridine-2(1H)-thione or Et 2-((pyridin-2-yl)thio)acetate derivative with hydrazine hydrate afforded the corresponding 1H-pyrazolo[3,4-b]pyridine derivative Thieno[2,3-b]pyridine derivatives reacted with several reagents to afford the corresponding pyrimidine-4(3H)-ones and [1,2,3]triazin-4-(3H)-one. Moreover, 2-carbohydrazide derivative reacted with 灏?dicarbonyl reagents to give 2-((3-methyl-1H-pyrazol-1-yl)carbonyl)thienopyridines. The structure of the target mols. is elucidated using elemental analyses and spectral data. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Computed Properties of C8H6Br2O2).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) 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. 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.Computed Properties of C8H6Br2O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Isomeric change in the phenol series. (Third notice.) was written by Ling, Arthur R.. And the article was included in Journal of the Chemical Society, Transactions in 1889.Recommanded Product: 4-Bromo-2-chloro-6-nitrophenol This article mentions the following:

An interesting and at a first sight rather complicated case of isomeric change takes place, when orthochloroparabromophenol is nitrated by warming it in an acetic acid solution with a slight excess of nitric acid, namely, together with the normal products, ortho-chloroparabromorthonitrophenol and orthochlororthoparadinitrophenol, which are formed in the largest quantity, a not inconsiderable amount of diorthochlorobromoparanitrophenol is also produced. The production of orthochlororthoparadinitrophenol, and the consequent elimination of bromine renders this case, however, equivalent to the action of bromine renders this case, however, equivalent to the action of bromine on orthochloroparabromoorthonitrophenol, the latter being without doubt the initial product of the reaction. The isomeric change of parachlororthobromorthonitrophenol into orthochloroparabromoorthonitrophenol does not take place at all, and that a mistake which must have arisen in working with impure materials is explained. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-chloro-6-nitrophenol (cas: 58349-01-2Recommanded Product: 4-Bromo-2-chloro-6-nitrophenol).

4-Bromo-2-chloro-6-nitrophenol (cas: 58349-01-2) 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.Recommanded Product: 4-Bromo-2-chloro-6-nitrophenol

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary