Category: bromides-buliding-blocks

Arylation of aryllithiums with S-arylphenothiazinium ions for biaryl synthesis was written by Morofuji, Tatsuya;Yoshida, Tatsuki;Tsutsumi, Ryosuke;Yamanaka, Masahiro;Kano, Naokazu. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.SDS of cas: 162258-89-1 This article mentions the following:

Herein, arylation of aryllithiums ArLi (Ar = Ph, 4-MeOC₆H₄, 1-naphthyl, etc.) with S-arylphenothiazinium ions I (R¹ = H, 4-Br, 4-t-Bu, etc.) through selective ligand coupling of intermediary sulfuranes is reported. Various unsym. biaryls II (R¹ = H, 4-Br, 4-SMe, etc.; R² = H, 4-Cl, 4-I, etc.) could be obtained without transition-metal catalysis. In the experiment, the researchers used many compounds, for example, 4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1SDS of cas: 162258-89-1).

4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.SDS of cas: 162258-89-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Metal free synthesis of 1,3-diynes through C_sp-C_sp homo- and hetero-coupling reaction of terminal alkynes was written by Tamuli, Kashyap J.;Bordoloi, Manobjyoti. And the article was included in Sustainable Chemistry and Pharmacy in 2022.Recommanded Product: 128-08-5 This article mentions the following:

Recent methodologies aimed at utilization of eco-friendly pathways and sustainable chem. has turned out to be a convergent point in chem. research. With an objective to derive an economical, greener approach, herein, authors report a mild and straightforward synthetic strategy to synthesize a series of substituted sym. and unsym. 1,3-diyne derivatives This metal free synthetic route catalyzed by N-Bromosuccinimide with tBuOK and KF as fluorine source at room temperature affords excellent yields up to 95% within 2 h. Such type of a greener and sustainable process was adopted for the development of organic building blocks or compounds with minimal waste afford to define the most of the green chem. principles. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Recommanded Product: 128-08-5).

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. 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: 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

N-alkoxy-N-acylnitrenium ions in intramolecular aromatic addition reactions was written by Glover, Stephen A.;Goosen, Andre;McCleland, Cedric W.;Schoonraad, Johan L.. And the article was included in Tetrahedron in 1987.Electric Literature of C10H13BrO This article mentions the following:

N-Alkoxy-N-acylnitrenium ions are generated by treating N-alkoxy-N-chloroamides with Ag⁺ ions in ethereal solvents. These intermediates readily cyclize onto aromatic nuclei on alkoxy side chains to give benzoxazines and benzoxazepines and on acyl side chains to give γ-, δ-, and ε-benzolactams. E.g., treating Ph(CH₂)₃ONClBz in Et₂O with AgBF₄ gave 50% benzoxazepine I. Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side chain aromatic rings. The yields and regioselectivities of these reactions are ascribed to different transition structures for cyclization onto the acyl and alkoxy side chains, which involve an exo- and endocyclic N⁺-O π-bond, resp. Evidence for this exceptionally high π-bond character is obtained from MNDO calculations, which predict a π-bond order of 0.9 and a rotational barrier of 29.7 kcal mol^-1. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Electric Literature of C10H13BrO).

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. 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.Electric Literature of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Preparation of aromatic sulfonyl halides was written by Jenkins, F. E.;Hambly, A. N.. And the article was included in Australian Journal of Chemistry in 1953.Recommanded Product: 454-65-9 This article mentions the following:

The following RC₆H₄SO₂Cl are prepared by chlorination of the RSO₂H, which are obtained by the modified Gattermann procedure (addition of the diazonium sulfate of the appropriate amine to a suspension of Cu powder in dilute H₂SO₄ saturated with SO₂) (R, % yield given): m-Me, 50, b_0.3 77-8° (sulfonamide, m. 108.5-9.5°); ο-MeO, 51; m-Cl, 50; m-Br, 54. Refluxing the RC₆H₄SO₂Cl with excess of a saturated aqueous solution of KF gave RC₆H₄SO₂F: m-Me, 85, b_1.4 78.5-79°, n²⁵_D 1.4909; ο-MeO, 42, m. 39-40°; p-AcNH (I), 47, m. 176°; m-Cl, 63, b_0.8 69-70°, n²⁵_D 1.5114; m-Br, 63, b_1.0 90°, n²⁵_D 1.5358; p-O₂N (II), 65, m. 77.5-8.5°. I is best prepared in aqueous dioxane. Reduction of II with Sn and HCl gives p-H₂NC₆H₄SO₂F (45%), m. 72-3°, converted into I by Ac₂O in AcOH. In the experiment, the researchers used many compounds, for example, 3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9Recommanded Product: 454-65-9).

3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9) 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. 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.Recommanded Product: 454-65-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Preparation of N-methyl-1,2,3-triazoles was written by Pedersen, Christian. And the article was included in Acta Chemica Scandinavica in 1959.Synthetic Route of C3H4BrN3 This article mentions the following:

The reaction of CH₂N₂ (I) and excess BrCN (II) gave 4-bromo-1,2,3-triazole; excess I with II gave 2-methyl-4-bromo-1,2,3-triazole (III), b. 161-2°, m. 22°. With I overnight at 0° 1,2,3-triazole (IV), b. 205-6°, gave a mixture of 42% 1-methyl-1,2,3-triazole, b. 223-5°, and 46% 2-methyl-1,2,3-triazole, b. 102-3°. Distillation of the product of the reaction of I and II gave 3 fractions-the largest and lowest boiling one being a mixture of BrCH₂CN (V) and 21% III. With NH₃ V gave BrH₃NCH₂CN, m. 165-7° (decomposition) (absolute EtOH). The other 2 fractions were 6% 1-methyl-5-bromo-1,2,3-triazole (VI), m. 41-2° (petr. ether), and 5.5% 1-methyl-4-bromo-1,2,3-triazole (VII), m.98-9° (C₆H₆-petr. ether), prepared from 1-methyl-4-amino-1,2,3-triazole, m. 97-9° (CHCl₃-petr. ether), in 41% yield by the Gattermann reaction. VI heated 6 h. with PhNH₂ gave 45% 1-methyl-5-anilino-1,2,3-triazole, m. 169-71° (C₆H₆-petr. ether). VI was more reactive than III or VII and gave 22% 1-methyl-5-amino-1,2,3-triazole [HCl salt m. 181-2° (absolute EtOH)] with 5% alc. NH₃ solution in a sealed tube 10 h. at 100°, whereas III and VII did not react. IV was prepared in 93% yield by decarboxylating (at 220°) 4-carboxy-1,2,3-triazole, m. 222-4° (H₂O), prepared in good (71%) yield by refluxing HCCCO₂H (VIII) 15 h. with HN₃ in boiling C₆H₆. Similarly, VIII and MeN₃ (from NaN₃ and Me₂SO₄) gave 57% 1-methyl-4-carboxy-1,2,3-triazole (IX), m. 218-19° (H₂O), free from 1-methyl-5-carboxy-1,2,3-triazole. IX via the chloride gave 93% of the azide, m. 152-4° (decomposition) (isocyanate, m. 215-17°), which on boiling 36 h. in EtOH gave 74% 1-methyl-4-carbethoxyamino-1,2,3-triazole, m. 123-4° (EtOH) (urethane m. 114-18°), which on boiling 4 h. with dilute NaOH gave 64% 1-methyl-4-amino-1,2,3-triazole, m. 88-9° (C₆H₆-petr. ether) [HCl salt m. 182-5° (absolute EtOH)]. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methyl-1H-1,2,3-triazole (cas: 13273-53-5Synthetic Route of C3H4BrN3).

4-Bromo-1-methyl-1H-1,2,3-triazole (cas: 13273-53-5) 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. 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.Synthetic Route of C3H4BrN3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Enantioselective Vinylogous Mannich-Type Reactions to Construct CF₃S-Containing Stereocenters Catalysed by Chiral Quaternary Phosphonium Salts was written by Xu, Lijun;Yu, Longhui;Liu, Jun;Wang, Hongyu;Zheng, Changwu;Zhao, Gang. And the article was included in Advanced Synthesis & Catalysis in 2020.Name: 1-(Bromomethyl)-4-fluoro-2-nitrobenzene This article mentions the following:

A series of benzyl trifluoromethyl sulfides bearing a nitro group was utilized as CF₃S-containing building blocks R-2-O₂NC₆H₃CH₂SCF₂X (R = H, 4-F, 5-Cl, 4-Br; X = F, CF₃) to construct chiral CF₃S-containing mols. I (R¹ = naphthalen-1-yl, thiophen-2-yl, 4-methylphenyl, etc.) via enantioselective vinylogous Mannich-type reactions. In such reactions, high yields and enantioselectivities were obtained using chiral quaternary phosphonium salts II (R² = Ph, 3-nitrophenyl) derived from amino acids. Moreover, a chiral cyclic urea bearing the CF₃S moiety III was obtained from further transformation of the product I (R = H; R¹ = Ph; X = F). In the experiment, the researchers used many compounds, for example, 1-(Bromomethyl)-4-fluoro-2-nitrobenzene (cas: 76437-44-0Name: 1-(Bromomethyl)-4-fluoro-2-nitrobenzene).

1-(Bromomethyl)-4-fluoro-2-nitrobenzene (cas: 76437-44-0) 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.Name: 1-(Bromomethyl)-4-fluoro-2-nitrobenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Heterocyclic systems containing bridgehead nitrogen atom: Part XXXIX. Reaction of 2-mercapto-4-bromo-6-methylbenzimidazole with chloroacetic acid and 1,2-dibromoethane was written by Jain, K. K.;Pujari, H. K.. And the article was included in Indian Journal of Chemistry in 1981.Quality Control of 2-Bromo-4-methyl-6-nitroaniline This article mentions the following:

The thiazolobenzimidazoles I (X = O, S) were synthesized from 2-mercapto-4-bromo-6-methylbenzimidazole (II), which was prepared by the reaction of 3-bromo-5-methyl-1,2-diaminobenzene with CS₂; II on condensation with ClCH₂CO₂H followed by cyclization with Ac₂O gave I (X = O) and not the linear isomer. Reaction of II with 1,2-dibromoethane gave I (X = H₂) and not the linear isomer. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-methyl-6-nitroaniline (cas: 827-24-7Quality Control of 2-Bromo-4-methyl-6-nitroaniline).

2-Bromo-4-methyl-6-nitroaniline (cas: 827-24-7) 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. 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 2-Bromo-4-methyl-6-nitroaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction was written by Kumar, Gadde Sathish;Peshkov, Anatoly;Brzozowska, Aleksandra;Nikolaienko, Pavlo;Zhu, Chen;Rueping, Magnus. And the article was included in Angewandte Chemie, International Edition in 2020.Formula: C9H11BrO This article mentions the following:

The first electrochem. approach for nickel-catalyzed cross-electrophile coupling was developed. This method provides a novel route to 1,1-diarylalkane derivatives from simple and readily available alkyl and aryl halides in good yields and excellent regioselectivity under mild conditions. The procedure shows good tolerance for a broad variety of functional groups and both primary and secondary alkyl halides can be used. Furthermore, the reaction was successfully scaled up to the multigram scale, thus indicating potential for industrial application. Mechanistic study suggested the formation of a nickel hydride in the electroreductive chain-walking arylation, which led to the development of a new nickel-catalyzed hydroarylation of styrenes to provide a series of 1,1-diaryl alkanes in good yields under mild reaction conditions. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Formula: C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Formula: C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chiral Ammonium Salt Catalyzed Asymmetric Alkylation of Unactivated Amides was written by Xu, Changming;Yang, Xinshuang. And the article was included in Synlett in 2022.Product Details of 83902-02-7 This article mentions the following:

A chiral spirocyclic quaternary ammonium salt catalyzed asym. alkylation of unactivated amides under homogeneous conditions has been developed, giving the target products with up to 60% ee. This novel methodol. provides a general and concise protocol for asym. α-functionalization of unactivated amides. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Product Details of 83902-02-7).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) 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. 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.Product Details of 83902-02-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nickel-Catalyzed Electro-Reductive Cross-Coupling of Aliphatic N-Acyl Imides with Alkyl Halides as a Strategy for Dialkyl Ketone Synthesis: Scope and Mechanistic Investigations was written by Kerackian, Taline;Bouyssi, Didier;Pilet, Guillaume;Medebielle, Maurice;Monteiro, Nuno;Vantourout, Julien C.;Amgoune, Abderrahmane. And the article was included in ACS Catalysis in 2022.Electric Literature of C9H11BrO This article mentions the following:

The development and in-depth study of a cross-electrophile coupling of alkyl N-acyl imides with alkyl halides relying on the combination of nickel catalysis and electrochem. are described. This methodol. takes advantages of the stability and simple access of N-acyl imides as coupling partners for the selective synthesis of dissym. dialkyl ketones. Noteworthy, the developed electrochem. protocol affords selective access to linear alkyl ketones when using primary alkyl bromides featuring different chain lengths. Mechanistic studies including cyclic voltammetry, stoichiometric reactions, and isolation of catalytic intermediates provide a set of fundamental insights into monovalent (bpy)nickel-mediated activation of alkyl halides and alkyl N-acyl imides. Alkyl bromides react with electrogenerated (bpy)Ni(I) species via single-electron oxidation to give alkyl radicals. N-Acyl imides are shown to undergo spontaneous C-N bond oxidative addition at both (bpy)Ni(0) and (bpy)Ni(I) species, leading to Ni(II) acyl intermediates. A stable nickel(II) acyl complex has also been isolated and fully characterized, and its catalytic competency is demonstrated. Finally, electrogenerated (bpy)Ni(I)-acyl species are shown to react with both alkyl bromide and alkyl N-acyl imides. Overall, these investigations allowed for a comprehensive mechanistic picture of this selective cross-electrophile coupling to be assembled. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Electric Literature of C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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 C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary