Month: January 2023

Cobalt carbonyl catalyzed selective mono-carbonylation of halobenzyl halides. I. was written by Shim, Sang Chul;Doh, Chil Hoon;Yoon, Young Zoo;Cho, Chan Sik;Woo, Byung Won. And the article was included in Taehan Hwahakhoe Chi in 1990.Product Details of 2178-24-7 This article mentions the following:

A method for regioselective mono-carbonylation of halobenzyl halides is described. Alkyl halophenylacetate is easily prepared by carbonylating a halobenzyl halide in the presence of a catalytic amount of cobalt carbonyl, a base, and an alc. under atm. pressure of carbon monoxide. The base plays a decisive role in the selectivity of product, and NEt₃ is the best one among bases used. In the experiment, the researchers used many compounds, for example, Ethyl (2-bromophenyl)acetate (cas: 2178-24-7Product Details of 2178-24-7).

Ethyl (2-bromophenyl)acetate (cas: 2178-24-7) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Product Details of 2178-24-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of the pyrrolo[2,3-c]carbazole core of the dictyodendrins was written by Ayats, Carles;Soley, Roger;Albericio, Fernando;Alvarez, Mercedes. And the article was included in Organic & Biomolecular Chemistry in 2009.Safety of 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

The pyrrolo[2,3-c]carbazole I, the common core of the marine alkaloids known as the dictyodendrins, has been synthesized. The sequence is based on a Suzuki cross-coupling reaction between a pyrrole fragment and an indole fragment, followed by tandem photochem. 6π-electrocyclization/aromatization. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Safety of 1-(2-Bromoethyl)-4-methoxybenzene).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. 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.Safety of 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

An amine template strategy to construct successive C-C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade was written by McFadden, Timothy Patrick;Nwachukwu, Chideraa Iheanyi;Roberts, Andrew George. And the article was included in Organic & Biomolecular Chemistry in 2022.Safety of 2-Bromo-4-fluorobenzylbromide This article mentions the following:

A convergent strategy to build, cyclize and excise nitrogen from tertiary amines for the synthesis of polyheterocyclic aromatics was developed. Biaryl-linked azepine intermediates underwent a deaminative ring contraction cascade reaction, excising nitrogen with the formation of an aromatic core. This strategy and deaminative ring contraction reaction was useful for the synthesis of benzo[h]quinolines. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0Safety of 2-Bromo-4-fluorobenzylbromide).

2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0) 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.Safety of 2-Bromo-4-fluorobenzylbromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Forward and Reverse (Retro) Iron(III) or Gallium(III) Desferrioxamine E and Ring-Expanded Analogues Prepared Using Metal-Templated Synthesis from endo-Hydroxamic Acid Monomers was written by Lifa, Tulip;Tieu, William;Hocking, Rosalie K.;Codd, Rachel. And the article was included in Inorganic Chemistry in 2015.Category: bromides-buliding-blocks This article mentions the following:

A metal-templated synthesis (MTS) approach was used to preorganize the forward endo-hydroxamic acid monomer 4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoic acid (for-PBH) about iron(III) in a 1:3 metal/ligand ratio to furnish the iron(III) siderophore for-[Fe(DFOE)] (ferrioxamine E) following peptide coupling. Substitution of for-PBH with the reverse (retro) hydroxamic acid analog 3-(6-amino-N-hydroxyhexanamido)propanoic acid (ret-PBH) furnished ret-[Fe(DFOE)] (ret-ferrioxamine E). As isomers, for-[Fe(DFOE)] and ret-[Fe(DFOE)] gave identical mass spectrometry signals ([M + H⁺]⁺, m/z_calc 654.3, m/z_obs 654.3), yet for-[Fe(DFOE)] eluted in a more polar window (t_R = 23.44 min) than ret-[Fe(DFOE)] (t_R = 28.13 min) on a C18 reverse-phase HPLC (RP-HPLC) column. for-[Ga(DFOE)] (t_R = 22.99 min) and ret-[Ga(DFOE)] (t_R = 28.11 min) were prepared using gallium(III) as the metal-ion template and showed the same trend for the retention time. Ring-expanded analogs of for-[Fe(DFOE)] and ret-[Fe(DFOE)] were prepared from endo-hydroxamic acid monomers with one addnl. methylene unit in the amine-containing region, 4-[(6-aminohexyl)(hydroxy)amino]-4-oxobutanoic acid (for-HBH) or 3-(7-amino-N-hydroxyheptanamido)propanoic acid (ret-HBH), to give the corresponding tris(homoferrioxamine E) macrocycles, for-[Fe(HHDFOE)] or ret-[Fe(HHDFOE)] ([M + H⁺]⁺, m/z_calc 696.3, m/z_obs 696.4). The MTS reaction using a constitutional isomer of for-HBH that transposed the methylene unit to the carboxylic acid containing region, 5-[(5-aminopentyl)(hydroxy)amino]-5-oxopentanoic acid (for-PPH), gave the macrocycle for-[Fe(HPDFOE)] in a yield significantly less than that for for-[Fe(HHDFOE)], with the gallium(III) analog for-[Ga(HPDFOE)] unable to be detected. The work demonstrates the utility and limits of MTS for the assembly of macrocyclic siderophores from endo-hydroxamic acid monomers. Indirect measures (RP-HPLC order of elution, c log P values, mol. mechanics, and d. functional theory calculations) of the relative water solubility of the ligands, the iron(III) macrocycles, and the apomacrocycles were consistent in identifying for-DFOE as the most water-soluble macrocycle from for-DFOE, ret-DFOE, for-HHDFOE, ret-HHDFOE, and for-HPDFOE. From this group, only for-DFOE is known in nature, which could suggest that water solubility is an important trait in its natural selection. 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Screening of bromotyramine analogues as antifouling compounds against marine bacteria was written by Andjouh, Sofyane;Blache, Yves. And the article was included in Biofouling in 2016.Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

Rapid and efficient synthesis of 23 analogs inspired by bromotyramine derivatives, marine natural products, by means of CuSO₄-catalyzed [3+2] alkyne-azide cycloaddition is described. The final target was then assayed for anti-biofilm activity against three Gram-neg. marine bacteria, Pseudoalteromonas ulvae (TC14), Pseudoalteromonas lipolytica (TC8) and Paracoccus sp. (4M6). Most of the synthesized bromotyramine/triazole derivatives are more active than the parent natural products Moloka’iamine () and 3,5-dibromo-4-methoxy-β-phenethylamine () against biofilm formation by the three bacterial strains. Some of these compounds were shown to act as non-toxic inhibitors of biofilm development with EC₅₀ < 200 μM without any effect on bacterial growth even at high concentrations (200 μM). In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Novel saccharide-photoinduced electron transfer sensors based on the interaction of boronic acid and amine was written by James, Tony D.;Sandanayake, K. R. A. Samankumara;Iguchi, Ritsuko;Shinkai, Seiji. And the article was included in Journal of the American Chemical Society in 1995.Recommanded Product: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane This article mentions the following:

Two boronic acid systems, monoboronic acid 3 and diboronic acid 8, were synthesized. When saccharides form cyclic boronate esters with these boronic acids, the Lewis acid-base interaction between the boronic acid moiety and tertiary amine is strengthened; when saccharides form cyclic boronate esters with boronic acids the acidity of the boronic acid is enhanced. The strength of this acid-base interaction modulates the photoinduced electron transfer (PET) from the amine to anthracene. Both of these compounds show increased fluorescence at pH 7.77 through suppression of the photoinduced electron transfer from nitrogen to anthracene on saccharide binding, a direct result of the stronger boron-nitrogen bond. Compound 3 shows the typical selectivity of monoboronic acids towards saccharides. Compound 8 which has a cleftlike structure is particularly selective and sensitive for glucose due to the formation of an intramol. 1:1 complex between the two boronic acids and the 1,2- and 4,6-hydroxyls of glucose. This is the first example in which ditopic recognition of monosaccharides is achieved in a PET sensor system. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Recommanded Product: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) 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). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Recommanded Product: 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Transition-Metal-Free Reverse Reactivity of (2-Alkynyl)-Arylaldimines: Assembly of Functionalized Amino-Indenones was written by Saini, Kapil Mohan;Saunthwal, Rakesh K.;Sushmita;Verma, Akhilesh K.. And the article was included in Chemistry – A European Journal in 2020.Related Products of 85118-24-7 This article mentions the following:

Transition-metal-free regioselective synthesis of functionalized amino-indenones by the reaction of ortho-alkynylaldehydes with a broad range of primary amines by intramol. cyclization was described. The designed reaction proceeded through KOH-mediated Prins-type cyclization and DMSO-promoted oxidation of the cyclopent-2-en-1-one system. The proposed mechanism and role of solvent were well supported by control experiments For the first time, the reverse reactivity of (2-alkynyl)-arylaldimines in a super basic system was reported. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Related Products of 85118-24-7).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) 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. Related Products of 85118-24-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: facile synthesis of PARP14 inhibitors was written by Wang, Pingyuan;Li, Jian;Jiang, Xue;Liu, Zhiqing;Ye, Na;Xu, Youjun;Yang, Guangfu;Xu, Yechun;Zhang, Ao. And the article was included in Tetrahedron in 2014.Formula: C8H6BrFO2 This article mentions the following:

We have developed a palladium-catalyzed N-arylation of the biol. interesting, but synthetically rather challenging 2-arylaminobenzothiazoles bearing multiple functionalities. This protocol was successfully used to readily synthesize our initial PARP14 inhibitor followed by a limited structural optimization. A more potent PARP14 inhibitor with an IC₅₀ value of 1.69 μM was identified, and the interaction was ascertained by the X-ray co-crystal structure of the catalytic domain of PARP14 in complex with compound I. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Formula: C8H6BrFO2).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Formula: C8H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Highly Regioselective Isoquinoline Synthesis via Nickel-Catalyzed Iminoannulation of Alkynes at Room Temperature was written by Sun, Jian-Guo;Zhang, Xiao-Yu;Yang, Hua;Li, Ping;Zhang, Bo. And the article was included in European Journal of Organic Chemistry in 2018.Category: bromides-buliding-blocks This article mentions the following:

A simple and cost-efficient nickel catalytic system for the annulation of 2-haloaldimines with alkynes to synthesize 3,4-disubstituted and 3-substituted isoquinolines at room temperature has been developed. The air-stable and inexpensive Ni(dppe)Cl₂ was employed as a precatalyst, and Et₃N was found to be an essential additive for obtaining high yields. By using this nickel catalytic system one-pot three-component direct synthesis of isoquinolines starting with simple 2-halobenzaldehydes, tert-butylamine, and alkynes were also achieved. These reactions occur in moderate to excellent yields with complete regioselectivity. Moreover, these reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Category: bromides-buliding-blocks).

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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

GC-Targeted C8-Linked Pyrrolobenzodiazepine-Biaryl Conjugates with Femtomolar in Vitro Cytotoxicity and in Vivo Antitumor Activity in Mouse Models was written by Rahman, Khondaker M.;Jackson, Paul J. M.;James, Colin H.;Basu, B. Piku;Hartley, John A.;de la Fuente, Maria;Schatzlein, Andreas;Robson, Mathew;Pedley, R. Barbara;Pepper, Chris;Fox, Keith R.;Howard, Philip W.;Thurston, David E.. And the article was included in Journal of Medicinal Chemistry in 2013.Category: bromides-buliding-blocks This article mentions the following:

DNA binding 4-(1-methyl-1H-pyrrol-3-yl)benzenamine (MPB) building blocks have been developed that span two DNA base pairs with a strong preference for GC-rich DNA. They have been conjugated to a pyrrolo[2,1-c][1,4]benzodiazepine (PBD) mol. to produce C8-linked PBD-MPB hybrids that can stabilize GC-rich DNA by up to 13-fold compared to AT-rich DNA. Some have subpicomolar IC₅₀ values in human tumor cell lines and in primary chronic lymphocytic leukemia cells, while being up to 6 orders less cytotoxic in the non-tumor cell line WI38, suggesting that key DNA sequences may be relevant targets in these ultrasensitive cancer cell lines. One conjugate, I (KMR-28-39), which has femtomolar activity in the breast cancer cell line MDA-MB-231, has significant dose-dependent antitumor activity in MDA-MB-231 (breast) and MIA PaCa-2 (pancreatic) human tumor xenograft mouse models with insignificant toxicity at therapeutic doses. Preliminary studies suggest that I may sterically inhibit interaction of the transcription factor NF-κB with its cognate DNA binding sequence. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3Category: bromides-buliding-blocks).

Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary