Month: January 2023

An improved procedure for the oxidation of 2,5- and 5,6-dihalo-3-methylpyridines was written by Setliff, F. L.;Huie, W. R.;Adams, R. L.. And the article was included in Organic Preparations and Procedures International in 1983.Name: 5-Bromo-2-fluoronicotinic acid This article mentions the following:

Nicotinic acids I (R = Br, Cl, F; R¹ = iodo, Br, Cl) were obtained from methylpyridines II and Bu₄N⁺ MnO₄^–. Similarly prepared were acids III (R² = Br, Cl). 5,6-Dibromo-3-methylpyridine in pyridine was oxidized by Bu₄N⁺ MnO₄^– at 75-80° to give III (R² = Br). In the experiment, the researchers used many compounds, for example, 5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5Name: 5-Bromo-2-fluoronicotinic acid).

5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5) 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. 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: 5-Bromo-2-fluoronicotinic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery and optimization of a novel CNS penetrant series of mGlu₄ PAMs based on a 1,4-thiazepane core with in vivo efficacy in a preclinical Parkinsonian model was written by Kent, Caitlin N.;Fulton, Mark G.;Stillwell, Kaylee J.;Dickerson, Jonathan W.;Loch, Matthew T.;Rodriguez, Alice L.;Blobaum, Anna L.;Boutaud, Olivier;Rook, Jerri L.;Niswender, Colleen M.;Conn, P. Jeffrey;Lindsley, Craig W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Safety of 3-Bromo-5-chlorophenylamine This article mentions the following:

A high throughput screen (HTS) identified a novel, but weak (EC₅₀ = 6.2μM, 97% Glu Max) mGlu₄ PAM chemotype based on a 1,4-thiazepane core, VU0544412. Reaction development and chem. optimization delivered a potent mGlu₄ PAM VU6022296 (EC₅₀ = 32.8 nM, 108% Glu Max) with good CNS penetration (K_p = 0.45, K_p,uu = 0.70) and enantiopreference. Finally, VU6022296 displayed robust, dose-dependent efficacy in reversing Haloperidol-Induced Catalepsy (HIC), a rodent preclin. Parkinson’s disease model. In the experiment, the researchers used many compounds, for example, 3-Bromo-5-chlorophenylamine (cas: 96558-78-0Safety of 3-Bromo-5-chlorophenylamine).

3-Bromo-5-chlorophenylamine (cas: 96558-78-0) 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 3-Bromo-5-chlorophenylamine

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rates and regioselectivities of the palladium-catalyzed ethynylation of substituted bromo- and dibromobenzenes was written by Singh, Rina;Just, George. And the article was included in Journal of Organic Chemistry in 1989.Category: bromides-buliding-blocks This article mentions the following:

The Pd(0)/Cu₂Br₂-catalyzed ethynylation of 1,2-dibromo-4-nitro- and 1,2-dibromo-3-nitrobenzenes provide rapidly the product in which the bromine para or ortho to the nitro group is displaced, whereas the corresponding dibromoacetamidobenzenes provide the product of meta displacement slowly. Investigation of the rates of a series of p-substituted bromobenzenes indicates that the reaction is zero-order with respect to the heptyne and bromobenzene concentration, with a Hammett ρ value of 2.8. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Category: bromides-buliding-blocks).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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

Molecular diodes with rectification ratios exceeding 10⁵ driven by electrostatic interactions was written by Chen, Xiaoping;Roemer, Max;Yuan, Li;Du, Wei;Thompson, Damien;del Barco, Enrique;Nijhuis, Christian A.. And the article was included in Nature Nanotechnology in 2017.Reference of 56523-59-2 This article mentions the following:

Mol. diodes operating in the tunnelling regime are intrinsically limited to a maximum rectification ratio R of ∼10³. To enhance this rectification ratio to values comparable to those of conventional diodes (R ≥ 10⁵) an alternative mechanism of rectification is therefore required. Here, the authors report a mol. diode with R = 6.3 × 10⁵ based on self-assembled monolayers with Fc-C≃C-Fc (Fc, ferrocenyl) termini. The number of mols. (n(V)) involved in the charge transport changes with the polarity of the applied bias. More specifically, n(V) increases at forward bias because of an attractive electrostatic force between the pos. charged Fc units and the neg. charged top electrode, but remains constant at reverse bias when the Fc units are neutral and interact weakly with the pos. charged electrode. The authors successfully model this mechanism using mol. dynamics calculations In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Reference of 56523-59-2).

15-Bromopentadecanoic acid (cas: 56523-59-2) 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. 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.Reference of 56523-59-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of arylpropylamines. I. From allyl chloride was written by Patrick, T. M. Jr.;McBee, E. T.;Hass, H. B.. And the article was included in Journal of the American Chemical Society in 1946.Quality Control of 2-(2-Bromophenyl)propan-2-amine This article mentions the following:

New compounds possessing potential pressor activity have been prepared PhCl (450 g.) and 32.4 g. anhydrous FeCl₃ at -21°, treated dropwise with 76.5 g. CH₂:CHCH₂Cl during 2 h. with stirring for an addnl. 3 h. (temperature rise to -16°), the mixture shaken with 1 kg. crushed ice and 100 mL. concentrated HCl, and the residue from the organic layer dried and distilled, give 21% of 2-chloro-1-(p-chlorophenyl)propane, b₁₀ 111-12°, d₂₀²⁰ 1.1678, n_D²⁰ 1.5360 (all d. and n at 20° in Na_D light), and 32% of the o-chlorophenyl isomer, b₁₀ 103°, d. 1.1706, n 1.1706; there also result 9 g. MeCHClCH₂Cl, 12 g. CH₂(CH₂Cl)₂, and 10-12% of bis(chlorophenyl)propanes. 1-(p-Bromophenyl)-2-chloropropane, b₁₀ 124-6°, d. 1.4100, n 1.5582, 13%; o-bromophenyl isomer, b₁₀ 115-17°, d. 1.4159, n 1.5568, 31%. 2-Chloro-1-(p-fluorophenyl)propane, b₁₀ 81°, d. 1.1186, n 1.4971, 24%. 2-Chloro-1-(p-methoxyphenyl)propane, b₅ 107°, d. 1.0891, n 1.5270, 14%. The method of Truffault (C.A. 33, 2886.6), in which 380 g. H₂SO₄ (10 % oleum) and 337.5 g. PhCl were treated with 153 g. CH₂:CHCH₂Cl during 2 h., gives 6% of p-ClC₆H₄CHMeCH₂Cl, b₅ 94°, and 7.5% of an isomer (?), b₅ 90.5-2°, d. 1.1801, n 1.5405; PhOMe and PhOEt do not react under these conditions. Ammonolysis was carried out in an autoclave at 125-160° for 4-9 h.; EtOH solutions give somewhat better yields and mixtures containing, fewer byproducts; the NH₃ solution contained 125 g./l.; the MeNH₂ solution, 204 g./l. 2-(p-Chlorophenyl)propylamine, b₅ 99-101°, d. 0.9639, n 1.5398, 40% (picrate, m. 205°). 2-(p-Chlorophenyl)isopropylamine, b₅ 93-4°, d. 1.0762, n 1.5343, 44% (HCl salt, m. 164-5°). 2-(p-Bromophenyl)isopropylamine, b₁₀ 123-4°, d. 1.3080, n 1.5569, 35% (HCl salt, m. 204-6°); o-bromophenyl isomer, b₁₀ 118°, d. 1.2984, n 1.5582, 26% (HCl salt, m. 200-1°). N-Methyl-2-phenylpropylamine, b₁₅, 95-6° d. 0.9178, n 1.5102, 62% (picrate, m. 155°). N-Methyl-2-(o-chlorophenyl)isopropylamine, b₁₀ 110°, d. 1.0536, n 1.5288, 24% (picrate, m. 156°); p-chlorophenyl isomer, b₁₀ 114-15°, d. 1.0442, n 1.5259, 35% (picrate, m. 103°). N-Methyl-2-(p-fluorophenyl)isopropylamine, b₁₀ 87-9°, d. 0.9984, n 1.4922, 41% (picrate, m. 125°). In the experiment, the researchers used many compounds, for example, 2-(2-Bromophenyl)propan-2-amine (cas: 173026-23-8Quality Control of 2-(2-Bromophenyl)propan-2-amine).

2-(2-Bromophenyl)propan-2-amine (cas: 173026-23-8) 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.Quality Control of 2-(2-Bromophenyl)propan-2-amine

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Visible-Light-Mediated (sp³)Cα-H Functionalization of Ethers Enabled by Electron Donor-Acceptor Complex was written by Roy, Sourav;Chatterjee, Indranil. And the article was included in ACS Organic & Inorganic Au in 2022.Recommanded Product: 128-08-5 This article mentions the following:

A synthetically beneficial visible-light-mediated protocol has been disclosed to achieve C-H amination of readily available feedstocks cyclic and acyclic ethers. A rarely identified N-bromosuccinamide-tetrahydrofuran electron donor-acceptor complex served as an initiator to functionalize both α-diazoketones and dialkyl azodicarboxylates. This developed methodol. gives an alternative and milder way to construct the C-N bond and can be explored for the formation of C-C bond to perform arylation and allylation reactions. 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 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. Recommanded Product: 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

8-Aminoquinolines as anticoccidials – I was written by Armer, Richard E.;Barlow, Jacqueline S.;Dutton, Christopher J.;Greenway, David H. J.;Greenwood, Sean D. W.;Lad, Nita;Tommasini, Ivan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1997.Name: N-(5-Bromopentyl)phthalimide This article mentions the following:

The proposed ring metabolites of the 8-aminoquinoline antimalarial, pentaquine, I, have been synthesized and their biol. activity as anticoccidial agents investigated in vivo. Several analogs in which this metabolic pathway had been blocked were also synthesized and their anticoccidial activity measured. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Name: N-(5-Bromopentyl)phthalimide).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Name: N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

An Efficient Synthesis of Substituted meta-Halophenols and Their Methyl Ethers: Insight into the Reaction Mechanism was written by Khan, Faiz Ahmed;Choudhury, Sumit. And the article was included in European Journal of Organic Chemistry in 2010.Computed Properties of C8H7BrO3 This article mentions the following:

An expeditious synthetic methodol. leading to substituted meta-halophenols and their corresponding Me ether derivatives through acid-mediated fragmentation of suitably substituted dihalonorbornyl ketones has been devised. The reaction sequence consists of TBTH-mediated (TBTH is tri-n-butyltin hydride) selective bridgehead halogen reduction of easily accessible Diels-Alder adducts derived from 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene and β-substituted vinyl acetates, with subsequent conversion into the requisite bicyclic ketones by a two-step hydrolysis/oxidation approach. An extensive mechanistic investigation based on isotope labeling and cross experiments has been carried out and plausible mechanistic pathways based on these results have been proposed. The absence of halogen atoms at the bridgehead positions steers the reaction through a novel pathway involving the incorporation of proton (or deuterium) followed by elimination of HX (or DX), so the described methodol. also provides a reliable route to ortho-para dideuteratedphenolic derivatives In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-hydroxybenzoate (cas: 192810-12-1Computed Properties of C8H7BrO3).

Methyl 3-bromo-5-hydroxybenzoate (cas: 192810-12-1) 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). 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.Computed Properties of C8H7BrO3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of symmetrical bromo-1,3,5-triphenylbenzenes was written by Cheng, Ge;Gan, Qiu;Wang, Yuechuan;Xie, Minggui. And the article was included in Huaxue Shijie in 2000.Recommanded Product: 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl This article mentions the following:

1,3,5-Tri(3-bromophenyl)benzene and 1,3,5-tri(3,5-dibromophenyl)benzene were synthesized from m-bromoacetophenone and 3,5-dibromoacetophenone, resp., in the presence of SiCl₄ in ethanol. The yield of 1,3,5-tri(3-bromophenyl)benzene was 74%, and that of 1,3,5-tri(3,5-dibromophenyl)benzene was 40%. The products were identified by UV, MS, IR, and ¹H NMR. The yields can be improved by increasing the amount of SiCl₄ or decreasing that of ethanol. In the experiment, the researchers used many compounds, for example, 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl (cas: 96761-85-2Recommanded Product: 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. 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. 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.Recommanded Product: 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A Concise and Scalable Strategy for the Total Synthesis of Dictyodendrin B Based on Sequential C-H Functionalization was written by Pitts, Andrew K.;O’Hara, Fionn;Snell, Robert H.;Gaunt, Matthew J.. And the article was included in Angewandte Chemie, International Edition in 2015.Electric Literature of C9H11BrO This article mentions the following:

A sequential C-H functionalization strategy for the synthesis of the marine alkaloid dictyodendrin B (I.NH₃) is reported. Our synthesis begins from com. available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural product. 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. 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. 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