Category: bromides-buliding-blocks

An improved preparation of (S)-N-(Boc)-cyclohexylalaninal. The Moffat-Swern oxidation of α-amino alcohols was written by Krysan, D. J.;Haight, A. R.;Lallaman, J. E.;Langridge, D. C.;Menzia, J. A.;Narayanan, B. A.;Pariza, R. J.;Reno, D. S.;Rockway, T. W.. And the article was included in Organic Preparations and Procedures International in 1993.Formula: C23H26BrP This article mentions the following:

Moffat-Swern oxidation of protected alc. (S)-BocNHCH(CH₂R)CH₂OH (I; Boc = Me₃CO₂C; R = cyclohexyl) with DMSO/(COCl)₂/EtN(CHMe₂)₂ or DMSO/pyridine-SO₃/Et₃N gave the title compound (S)-BocNHCH(CH₂R)CHO (II) in >95% enantiomeric excess. The chem. efficiency of this oxidation os demonstrated in the 2-step conversion of I to (S,Z)-BocNHCH(CH₂R)CH:CHCH₂CHMe₂ in 60% yield via subsequent olefination of intermediate II with Ph₂P⁺CH₂CH₂CHMe₂ Br^–. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Formula: C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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 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.Formula: C23H26BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Condensation of tertiary aliphatic alcohols with aromatic compounds in the presence of aluminum chloride. IV. Tertiary dimethylamylcarbinols with phenol was written by Huston, R. C.;Guile, R. L.. And the article was included in Journal of the American Chemical Society in 1939.SDS of cas: 35065-86-2 This article mentions the following:

The Grignard reagent from 2-methyl-3-bromobutane with AcCl gives 9.3% of 3,4-dimethylpentan-2-one, b₇₄₄ 135-40°; with MeI this yields 58% of 2,3,4-trimethylpentan-2-ol, b₇₅₂ 155-7°, n_D¹³ 1.4400, d₂₀²⁰ 0.8095, γ²⁰ 27.48 dynes. Condensations were carried out by adding dropwise (2 h.) 32 g. of the alc. and 28 g. PhOH in 100 cc. petr. ether to 17 g. AlCl₃ in petr. ether at 25-30° and after standing overnight decomposing with dilute HCl. The following compounds were thus prepared: 2-methyl-2-p-hydroxyphenylheptane (I), b₂ 114-17°, b₇₄₁ 293.5°, d₂₀²⁰ 0.95053, n_D¹⁶ 1.5102, γ²⁸ 32.31, 69.5% yield; 2,3-dimethyl-2-p-hydroxyphenylhexane (II), b₂ 111-14°, b₇₄₁ 293°, d. 0.96836, n 1.5191, γ 33.74, 35.5%; 2,4-di-Me isomer (III), b₂ 113-16°, b₇₄₁ 290.5°, d. 0.95427, n 1.5121, γ 32.00, 58.5%; 2,5-di-Me isomer (IV), b₂ 105-7°, b₇₄₁ 288°, d. 0.95183, n 1.5110, γ 31.69, 64.6%; 2-methyl-3-ethyl-2-p-hydroxyphenylpentane (V), b₂ 109-11°, b₇₄₁ 293°, d. 0.96845, n 1.5190, γ 33.80, 28.3%; 2,4,4-tri-Me isomer (VI), b₇₄₁ 289°, m. 83°, 64.6%; 2,3,4-tri-Me isomer (VII), m. 74°, 23.1% yield; 2,3,3-tri-Me isomer, b₇₄₁ 325° (decomposition), m. 160°, 2.1%. Bz esters; I m. 27-23° (?), II m. 54.2-5.2°, III m. 37-8°, IV m. 46-7°, V m. 69-70°, VI m. 73-4°, VII m. 47-8°. α-Naphthylurethanes: I m. 120-1°, II m. 105-5.5°, III m. 119.5-20.5°, IV m. 132.5-33.5°, V m. 109.5-10.5°, VI m. 102-3°, VII m. 114.5-15.5°. p-Nitro- and p-amino-tert-octylbenzenes were prepared in establishing the structures of I-VI; 2-methyl-2-p-nitrophenylheptane, b₂ 148-50°; p-NH₂ derivative, b₂ 108-11°; 2,3-dimethyl-2-p-nitrophenylhexane, b₂ 133-5°; 2,4-di-Me isomer, b₂ 135-7°; 2,5-di-Me isomer, b₂ 129-31°; the corresponding p-NH₂ derivatives b₄ 115-19°, b₂ 99-101° and b₂ 99-102°; 2-methyl-3-ethyl-2-p-nitrophenylpentane, b₄ 127-30°; 2,4,-4-tri-Me isomer, b₄ 108-10°; the corresponding p-NH₂ derivatives b₂ 103-6° and b₅ 112-15°. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2SDS of cas: 35065-86-2).

3-Bromophenyl acetate (cas: 35065-86-2) 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.SDS of cas: 35065-86-2

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Bromide – Wikipedia,
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Substituted caffeic and ferulic acid phenethyl esters: synthesis, leukotrienes biosynthesis inhibition and cytotoxic activity was written by Morin, Pier Jr.;St-Coeur, Patrick-Denis;Doiron, Jeremie A.;Cormier, Marc;Poitras, Julie J.;Surette, Marc E.;Touaibia, Mohamed. And the article was included in Molecules in 2017.Electric Literature of C9H11BrO This article mentions the following:

A series of caffeic and ferulic acid esters bearing addnl. oxygens moieties (OH or OCH₃) were designed and synthesized. Polyphenolic compounds, including caffeic acid phenethyl ester (CAPE) was investigated for their anticancer properties in several types of cancer while ferulic acid phenethyl ester (FAPE) displayed substantial cytotoxicity against two glioma cell lines. Some selected compounds derived from both (CAPE) and (FAPE) also displayed cytotoxicity. All CAPE-derived compounds were able to significantly inhibit 5-lipoxygenase (5-LO), however FAPE-derived compounds were largely ineffective 5-LO inhibitors. Mol. docking revealed new hydrogen bonds and π-π interactions between the enzyme and some of the investigated compounds Overall, this work highlighted the relevance of exploring polyphenolic compounds in cancer models and provides addnl. led in the development of novel therapeutic strategies in gliomas. 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. 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.Electric Literature of C9H11BrO

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Bromide – Wikipedia,
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Design, synthesis and structure-activity relationships of novel biarylamine-based Met kinase inhibitors was written by Williams, David K.;Chen, Xiao-Tao;Tarby, Christine;Kaltenbach, Robert;Cai, Zhen-Wei;Tokarski, John S.;An, Yongmi;Sack, John S.;Wautlet, Barri;Gullo-Brown, Johnni;Henley, Benjamin J.;Jeyaseelan, Robert;Kellar, Kristen;Manne, Veeraswamy;Trainor, George L.;Lombardo, Louis J.;Fargnoli, Joseph;Borzilleri, Robert M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Reference of 29241-66-5 This article mentions the following:

Aminopyridinyloxy- or azaindolyloxy phenylamino heteroarylcarboxamides such as I are prepared and tested for their inhibition of Met kinase and for their inhibition of a human gastric cancer cell line. X-ray crystallog. of an aminopyridinyloxyphenylamino pyridinecarboxamide bound to Met kinase reveals that these compounds adopt a bioactive conformation, in the kinase domain, consistent with that seen for a 2-pyridone-based Met kinase inhibitor. I demonstrated potent in vivo antitumor activity in the GTL-16 human tumor xenograft model; its selectivity against various kinases is determined In the experiment, the researchers used many compounds, for example, 5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5Reference of 29241-66-5).

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

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Bromide – Wikipedia,
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Multicomponent synthesis of furopyridopyrimidines – heterocyclic analogs of podophyllotoxin was written by author. And the article was included in Izvestiya Timiryazevskoi Sel’skokhozyaistvennoi Akademii in 2012.SDS of cas: 108940-96-1 This article mentions the following:

Proposed a convenient method for the synthesis of furopyridopyrimidines I [R¹ = HO, H₂N; R² = 4-HOC₆H₄, 3,4,5-(MeO)₃C₆H₂, 3-Br-4,5-(MeO)₂C₆H₂, etc.] by multicomponent reaction of 2-methylthiopyrimidine-4,6-diamine, tetronic acid and aromatic aldehydes R²CHO. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1SDS of cas: 108940-96-1).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sequential Assembly of Morita-Baylis-Hillman Carbonates and Activated ortho-Vinylbenzaldehydes To Construct Chiral Methanobenzo[7]annulenone Frameworks was written by Jiang, Bo;Xiao, Ben-Xian;Ouyang, Qin;Liang, Hua-Ping;Du, Wei;Chen, Ying-Chun. And the article was included in Organic Letters in 2019.Reference of 85118-24-7 This article mentions the following:

The α-regioselective asym. [3 + 2] annulation reaction of Morita-Baylis-Hillman carbonates from isatins and activated ortho-vinylbenzaldehyses was developed by the catalysis of a chiral tertiary amine. The sequential N-heterocyclic carbene-mediated intramol. Stetter reaction was conducted to finally furnish the bridged 5,8-methanobenzo[7]annulen-9-one architectures incorporating a spirooxindole motif with excellent stereoselectivity. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Reference of 85118-24-7).

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. 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 85118-24-7

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Bromide – Wikipedia,
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Iron-catalyzed C(sp²)-H alkylation of carboxamides with primary electrophiles was written by Monks, Brendan M.;Fruchey, Erin R.;Cook, Silas P.. And the article was included in Angewandte Chemie, International Edition in 2014.Safety of 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

A robust iron-catalyzed ortho alkylation of aryl amides was carried out. The reaction generally proceeds in high yields with exceptional regioselectivity. The reaction is complete in less than 10 min and can be performed in bio-derived 2-methyltetrahydrofuran as solvent on gram scale. The reactivity and selectivity provides a reaction profile unique among the reported C-H functionalization reactions, thereby complementing current strategies. The low cost and toxicity of the reagents should simplify the large-scale implementation of this C-H functionalization. Moreover, mechanistic experiments indicate that substrate coordination is irreversible and occurs prior to C-H cleavage. Further efforts will be directed toward mechanistic understanding and expanding the scope of this interesting transformation. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 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. 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. Safety of 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Condensation of 2-methylindole with acetophenones: An unexpected formation of 2-arylanilines was written by Noland, Wayland E.;Novikov, Alexei V.;Brown, Christopher D.. And the article was included in Synthetic Communications in 2019.Computed Properties of C24H15Br3 This article mentions the following:

2-Methylindole condenses with acetophenones under acidic conditions to produce 2-arylanilines in moderate to good yields. The reaction proceeds well with a range of 3′- and 4′- substituted acetophenones (fluoro-, chloro-, bromo-, iodo-, Me, methoxy), and select 2′- substituted ones (fluoro-, methoxy-). No products were obtained with nitro- substitution in any position. In the experiment, the researchers used many compounds, for example, 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl (cas: 96761-85-2Computed Properties of C24H15Br3).

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). In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Computed Properties of C24H15Br3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Internal lewis acid assisted benzoic acid catalysis was written by Auvil, Tyler J.;Mattson, Anita E.. And the article was included in Synthesis in 2012.Category: bromides-buliding-blocks This article mentions the following:

Internal Lewis acid assisted benzoic acid derivatives are introduced as new low-mol.-weight single-hydrogen-bond donor catalysts for the activation of nitroalkenes. Selected 2-borylbenzoic acid derivatives gave good yields of products in the addition of indoles to nitroalkenes. Control experiments suggest that both the internal Lewis acid coordination and the carboxylic acid functionalities are critical to the optimal performance of these catalysts. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Category: bromides-buliding-blocks).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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.Category: bromides-buliding-blocks

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Bromide – Wikipedia,
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Separation of stereoisomers by column fractional precipitation was written by Schulz, Wolfgang W.;Purdy, William C.. And the article was included in Anal. Chem. in 1963.SDS of cas: 96761-85-2 This article mentions the following:

Column fractional precipitation is extended to the separation of 1,3,5-tris(3-bromophenyl)benzene from 1,3,5-tris(4-bromophenyl)benzene, with p-dioxane-water. The 3 fractions of greatest overlap were analyzed from the absorbances at 260.2 and 253.0 mμ by using simultaneous equations. o,p-Quaterphenyl was separated from m,p-quaterphenyl and the overlapping fractions were analyzed by the absorbance ratios at 265 and 248 mμ. In the experiment, the researchers used many compounds, for example, 3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl (cas: 96761-85-2SDS of cas: 96761-85-2).

3,3”-Dibromo-5′-(3-bromophenyl)-1,1′:3′,1”-terphenyl (cas: 96761-85-2) 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. 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.SDS of cas: 96761-85-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary