Month: January 2023

A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent was written by Zheng, Bo;Wang, Hui;Han, Yong;Liu, Changlu;Peng, Yungui. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2013.Reference of 14425-64-0 This article mentions the following:

α-Substituted-γ-nitropentanals I [R = Me₂CH, Me(CH₂)_n, Ph; R¹ = Ph, 4-MeOC₆H₄, 2-ClC₆H₄, 3-ClC₆H₄, 2-BrC₆H₄, H, TBDMSO; n = 1-7; TBDMS = tert-butyldimethylsilyl] [or ent-I (R = EtCH₂; R¹ = TBDMSO)] were prepared in 56-86% yields, in 79:21-99:1 dr, and in 70-98% ee by addition of aldehydes RCH₂CHO to α-substituted nitroalkenes R¹CH₂C(NO₂):CH₂ in the presence of a nonracemic N-siloxypyrrolidinylmethyl triflimide II (TBDPS = tert-butyldiphenylsilyl; Tf = F₃CSO₂) and 4-nitrobenzoic acid in DMF. Reduction of the nitro groups of I (R = Me₂CH, EtCH₂, PhCH₂; R¹ = Ph, TBDMS) followed by intramol. reductive amination yielded the nonracemic pyrrolidines III (R = Me₂CH, EtCH₂, PhCH₂; R² = Ph, HO) in 46-70% yields and in 70-96% ee. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Reference of 14425-64-0).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Regiocontrolled and Stereoselective Syntheses of Tetrahydrophthalazine Derivatives using Radical Cyclizations was written by Zhang, Wei;Mo, Jia Yi;He, Weiying;Kennepohl, Pierre;Sammis, Glenn M.. And the article was included in Chemistry – A European Journal in 2019.Related Products of 61150-57-0 This article mentions the following:

Tetrahydrophthalazine derivatives found important applications in pharmaceutical research, but existing synthetic methods are unable to access them regio- and stereoselectively. Here, a new approach is presented that addresses these challenges by using a 6-endo-trig radical cyclization in the key step. The desired tetrahydrophthalazines can be accessed in high yields (55-98 %) and high diastereoselectivities for the trans-product (>95:5) starting either from readily accessible hydrazones, or from the corresponding aldehydes and substituted Boc-hydrazides in a one-pot process. The synthetic versatility of the tetrahydrophthalazine core was demonstrated by its straightforward conversion to dihydro-phthalazines, phthalazines, or pyrazolo dione derivatives Furthermore, the N-N bond was reduced to afford a new route to 1,4-diamines. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0Related Products of 61150-57-0).

2-Bromo-4-fluorobenzylbromide (cas: 61150-57-0) 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). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Related Products of 61150-57-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

On-Water Synthesis of Biaryl Sulfonyl Fluorides was written by Chinthakindi, Praveen K.;Kruger, Hendrik G.;Govender, Thavendran;Naicker, Tricia;Arvidsson, Per I.. And the article was included in Journal of Organic Chemistry in 2016.Recommanded Product: 3-Bromobenzene-1-sulfonyl fluoride This article mentions the following:

Herein, we report an efficient, ligand-free, and additive-free Suzuki-Miyaura coupling that is compatible with the aromatic sulfonyl fluoride functional group. The protocol proceeds at room temperature, on water, and offers facile access to a wide range of biaryl sulfonyl fluorides as bioorthogonal “click” reagents. In the experiment, the researchers used many compounds, for example, 3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9Recommanded Product: 3-Bromobenzene-1-sulfonyl fluoride).

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. 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.Recommanded Product: 3-Bromobenzene-1-sulfonyl fluoride

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Preparation and Evaluation of ^99mTc(CO)₃-Labeled Pentadecanoic Acid Derivative and Its Suspension in Lipiodol was written by Satpati, Drishty;Pandey, Usha;Sarma, H. D.;Venkatesh, Meera;Banerjee, Sharmila. And the article was included in Cancer Biotherapy and Radiopharmaceuticals in 2009.Electric Literature of C15H29BrO2 This article mentions the following:

Transarterial embolization by the intra-arterial administration of ¹³¹I-lipiodol is a modality used in the treatment of liver cancer. Long-chain fatty acids, being highly lipophilic, are also known to localize in the liver, thus constituting favorable vectors for this modality of treatment. Toward this, we envisaged the derivatization of 15-bromopentadecanoic acid, rendering it suitable for incorporation of a tridentate chelating moiety, for radiolabeling with the [^99mTc(CO)₃(H₂O)₃]⁺ precursor. The complex prepared, being lipophilic, was expected to behave as a lipiodol surrogate. The radiolabeled complex could be obtained in >95% radiochem. yield, as characterized by high-performance liquid chromatog. The i.v. injection of the radiolabeled complex in mice resulted in 23.5% ± 4.3% uptake of injected dose (ID) organ in the liver at 3 h postinjection. However, the uptake of the lipiodol suspension of the complex at 3 h postinjection in the liver was found to be 43.8 ± 13.4% ID/organ, when injected via the portal vein. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Electric Literature of C15H29BrO2).

15-Bromopentadecanoic acid (cas: 56523-59-2) 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. 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.Electric Literature of C15H29BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Effect of structural factors and solvent nature in bromination of anilines was written by Bagmanov, B. T.. And the article was included in Russian Journal of Applied Chemistry in 2009.Category: bromides-buliding-blocks This article mentions the following:

Electrophilic bromination of anilines containing various ortho-, meta-, and para-substituents in the aromatic ring was studied. The optimal conditions for the synthesis of mono-, di-, tri-, and tetrabrominated anilines and brominated analog of Aniline Black were found. In the experiment, the researchers used many compounds, for example, 4-Amino-3-bromophenol (cas: 74440-80-5Category: bromides-buliding-blocks).

4-Amino-3-bromophenol (cas: 74440-80-5) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Molecular Engineering of Robust Starburst-Based Organic Photosensitizers for Highly Efficient Photocatalytic Hydrogen Generation from Water was written by Kwok, Yan-Yi;Ho, Po-Yu;Wei, Ying;Zheng, Zhong;Yiu, Sze-Chun;Ho, Cheuk-Lam;Huang, Shuping. And the article was included in Chemistry of Materials in 2022.Formula: C4H4BrNO2 This article mentions the following:

Six donor-donor-π-acceptor (D-D-π-A) triphenylamine-based starburst organic dyes with different electron-donating moieties and thiophene-based π-linkers were synthesized and characterized. Their photophys. and electrochem. properties, together with their photocatalytic hydrogen evolution performance as photosensitizers (PSs), were investigated. Distinctive and prolonged hydrogen evolution performances of these PSs under visible-light irradiation from water in their platinized TiO₂ composites were demonstrated: a turnover number (TON) of up to 24 900 (252 h) with 1560 μmol (37.6 mL) hydrogen produced, an initial turnover frequency (TOF_i) of 1130 h^-1, initial activity (Activity_i) of 705 mmol g^-1 h^-1, and initial apparent quantum yield (AQY_i) of 12.1%. To the best of our knowledge, according to the TOF and TON values, the designed PS system is one of the most efficient and robust photocatalytic H₂ generation systems adopting a TiO₂-anchoring mol. PS in the literature. The results showed that the starburst triarylamine donor moiety with phenothiazine functionality and the alkyl chain on the thiophene π-linker could boost the performance and longevity of the photocatalytic system, providing a powerful strategy for the development of starburst-based highly efficient and robust D-D-π-A organic photosensitizers in the future. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Formula: C4H4BrNO2).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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. 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: C4H4BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Polarographic behavior of disubstituted derivatives of benzene or heterocycles. I. Substituted bromothiophenes was written by Person, Maurice;Mora, Raymond. And the article was included in Bulletin de la Societe Chimique de France in 1973.Category: bromides-buliding-blocks This article mentions the following:

The polarog. of the title compounds was studied at pH 2-15 in aqueous and anhydrous EtOH. In the group of 3- and 5-bromo-2-formyl-, 2-bromo-3-formyl-, and 3-bromo-2-acetylthiophenes, the wave for the splitting of the C-Br bond precedes that for the carbonyl group. Their oximes and thiosemicarbazones behave similarly. In the group of 4-bromo-2-formyl-, 2- and 5-bromo-3-formylthiophenes, the corresponding wave positions were reversed from the 1st group. The 5-bromothiophenes, substituted in the 2-position by CO2H, CO2Me, and CONH2, give C-Br scission waves which are identical in ethanolic and aqueous solutions depending on the pH. The effects of structure and the influence of substituents on the lability of the C-Br bond is discussed. In the experiment, the researchers used many compounds, for example, 5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2Category: bromides-buliding-blocks).

5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2) 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Polar tagging in the synthesis of monodisperse oligo(p-phenyleneethynylene)s and an update on the synthesis of oligoPPEs was written by Sahoo, Dhananjaya;Thiele, Susanne;Schulte, Miriam;Ramezanian, Navid;Godt, Adelheid. And the article was included in Beilstein Journal of Organic Chemistry in 2010.Related Products of 50592-87-5 This article mentions the following:

One important access to monodisperse (functionalized) oligoPPEs is based on the orthogonality of the alkyne protecting groups triisopropylsilyl and hydroxymethyl (HOM) and on the polar tagging with the hydroxymethyl moiety for an easy chromatog. separation of the products. This paper provides an update of this synthetic route. For the deprotection of HOM protected alkynes, γ-MnO₂ proved to be better than (highly) activated MnO₂. The use of HOM as an alkyne protecting group is accompanied by carbometalation as a side reaction in the alkynyl-aryl coupling. The extent of carbometalation can be distinctly reduced through substitution of HOM for 1-hydroxyethyl. The strategy of polar tagging is extended by embedding ether linkages 2 within the solubilizing side chains. With building blocks such as 1,4-diiodo-2,5-bis(6-methoxyhexyl) less steps are needed to assemble oligoPPEs with functional end groups and the isolation of pure compounds becomes simple. For the preparation of 1,4-dialkyl-2,5-diiodobenzene a better procedure is presented together with the finding that 1,4-dialkyl-2,3-diiodobenzene, a constitutional isomer of 1,4-dialkyl-2,5-diiodobenzene, is one of the byproducts. In the experiment, the researchers used many compounds, for example, 1-Bromo-6-methoxyhexane (cas: 50592-87-5Related Products of 50592-87-5).

1-Bromo-6-methoxyhexane (cas: 50592-87-5) 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. 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.Related Products of 50592-87-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

New syntheses of 1α,25-dihydroxycholesterol was written by Fuerst, Andor;Labler, Ludvik;Meier, Werner. And the article was included in Helvetica Chimica Acta in 1982.Computed Properties of C23H26BrP This article mentions the following:

1α,25-Dihydroxycholesterol was prepared via 5 convergent syntheses by combining C₂₁– or C₂₂-steroids with C₄– or C₅-side-chain building blocks. Thus, pregnene I (R = tetrahydro-2-pyranyl, R¹ = CH₂O₃SC₆H₄Me-H) was combined with the dioxolane II, PhSO₂CH₂CH₂CMe₂OR² (R² = tetrahydro-2-pyranyl) and HCCCMe₂OR² and I (R = Ac, R¹ = CHO) was combined with Ph₃P:CHCH₂CMe₂OH. Also, pregnenone III was condensed with phosphorane IV. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Computed Properties of C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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.Computed Properties of C23H26BrP

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Stereoselective synthesis and fungicidal activities of (E)-α-(methoxyimino)-benzeneacetate derivatives containing 1,3,4-oxadiazole ring was written by Li, Yan;Liu, Jie;Zhang, Hongquan;Yang, Xiangping;Liu, Zhaojie. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Safety of Ethyl 4-bromo-2-fluorobenzoate This article mentions the following:

Fifteen novel (E)-α-(methoxyimino)benzeneacetate derivatives, the analogs of strobilurins, which contain two pharmacophoric substructures of (E)-Me methoxyiminoacetate moiety and 1,3,4-oxadiazole ring were stereoselectively synthesized. It was first found that the coupling reaction could give stereoselectively the key intermediate (E)- and (Z)-Me 2-(hydroxyimino)-2-o-tolylacetate with a ratio of 14:1. The preliminary bioassays indicated that all the compounds I (R = H, 4-MeO, 2,3-Cl₂, 2-I, etc.) showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola and Bipolaris mayclis, and all of the tested compounds had more potent fungicidal activities against R. solani than Kresoxim-Me. In the experiment, the researchers used many compounds, for example, Ethyl 4-bromo-2-fluorobenzoate (cas: 474709-71-2Safety of Ethyl 4-bromo-2-fluorobenzoate).

Ethyl 4-bromo-2-fluorobenzoate (cas: 474709-71-2) 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. 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.Safety of Ethyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary