Category: 653-92-9

Synthetic and Structure/Activity Studies on Acid-Substituted 2-Arylphenols: Discovery of 2-[2-Propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]- propoxy]phenoxy]benzoic Acid, a High-Affinity Leukotriene B₄ Receptor Antagonist was written by Sawyer, J. Scott;Bach, Nicholas J.;Baker, S. Richard;Baldwin, Ronald F.;Borromeo, Peter S.;Cockerham, Sandra L.;Fleisch, Jerome H.;Floreancig, Paul;Froelich, Larry L.. And the article was included in Journal of Medicinal Chemistry in 1995.Category: bromides-buliding-blocks This article mentions the following:

Structural derivatives of LY255283 have been studied as receptor antagonists of leukotriene B₄. Substitution of the 2-hydroxyacetophenone subunit of 1-[5-Ethyl-2-hydroxy-4-[[6-methyl-6-(1H-tetrazol-5-yl)heptyl]oxy]phenyl]ethanone (LY255283) with a 2-arylphenol group provided entry into several new series that feature various mono- and diacidic core functionality. These new analogs, the subject of a broad structure-activity investigation, displayed significantly increased in vitro and in vivo activity as receptor antagonists of LTB₄. A series of diaryl ether carboxylic acids demonstrated especially interesting activity and led to the discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenoxy]benzoic acid (LY293111), a 2-arylphenol-substituted diaryl ether carboxylic acid which displayed potent binding to human neutrophils (IC₅₀ = 17 闁?4.6 nM) and guinea pig lung membranes (IC₅₀ = 6.6 闁?0.71 nM), inhibition of LTB₄-induced expression of the CD11b/CD18 receptor on human neutrophils (IC₅₀ = 3.3 闁?0.81 nM), and inhibition of LTB₄-induced contraction of guinea pig lung parenchyma (pK_B = 8.7 闁?0.16). 801Vivo, LY293111 demonstrated potent activity in inhibiting LTB₄-induced airway obstruction in the guinea pig when dosed by the oral (ED₅₀ = 0.40 mg/kg) or i.v. (ED₅₀ = 0.014 mg/kg) routes. A specific LTB₄ receptor antagonist, LY293111 had little effect on inhibiting contractions of guinea pig lung parenchyma induced by leukotriene D₄ (LTD₄), histamine, carbachol, or U46619. LY293111 was chosen as a clin. candidate and is currently in phase I studies for a variety of inflammatory diseases. 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Efficient Access to Methyl-1-hydroxy-2-naphthoates and Heterocyclic Analogues was written by Podeschwa, Michael A. L.;Rossen, Kai. And the article was included in Organic Process Research & Development in 2015.Quality Control of Methyl 2-bromo-4-fluorobenzoate This article mentions the following:

We report the synthesis of Me 1-hydroxy-2-naphthoate derivatives and heterocyclic analogs using a two-step approach. This short route employs a Heck coupling of a 2-halobenzoate with Me 3-butenoate followed by a Dieckmann cyclization, yielding the 1-hydroxynaphthalene-2-carboxylic acid derivatives in the multigram scale. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Quality Control of Methyl 2-bromo-4-fluorobenzoate).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Quality Control of Methyl 2-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

First Structure-Activity Relationship Study of Potent BLT2 Agonists as Potential Wound-Healing Promoters was written by Hernandez-Olmos, Victor;Heering, Jan;Planz, Viktoria;Liu, Ting;Kaps, Alexander;Rajkumar, Rinusha;Gramzow, Matthias;Kaiser, Astrid;Schubert-Zsilavecz, Manfred;Parnham, Michael J.;Windbergs, Maike;Steinhilber, Dieter;Proschak, Ewgenij. And the article was included in Journal of Medicinal Chemistry in 2020.Product Details of 653-92-9 This article mentions the following:

The first potent leukotriene B4 (LTB4) receptor type 2 (BLT2) agonists, endogenous 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid (12-HHT), and synthetic CAY10583 (CAY) have been recently described to accelerate wound healing by enhanced keratinocyte migration and indirect stimulation of fibroblast activity in diabetic rats. CAY represents a very valuable starting point for the development of novel wound-healing promoters. In this work, the first structure-activity relationship study for CAY scaffold-based BLT2 agonists is presented. The newly prepared derivatives showed promising in vitro wound-healing activity. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Product Details of 653-92-9).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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). 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.Product Details of 653-92-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

C-H Bond Functionalization via Hydride Transfer: Formation of 浼?Arylated Piperidines and 1,2,3,4-Tetrahydroisoquinolines via Stereoselective Intramolecular Amination of Benzylic C-H Bonds was written by Vadola, Paul A.;Carrera, Ignacio;Sames, Dalibor. And the article was included in Journal of Organic Chemistry in 2012.Safety of Methyl 2-bromo-4-fluorobenzoate This article mentions the following:

We here report a study of the intramol. amination of sp³ C-H bonds via the hydride transfer cyclization of N-tosylimines (HT-amination). In this transformation, 5-aryl aldehydes are subjected to N-toluenesulfonamide in the presence of BF₃璺疧Et₂ to effect imine formation and HT-cyclization, leading to 2-arylpiperidines and 3-aryl-1,2,3,4-tetrahydroisoquinolines in a one-pot procedure. We examined the reactivity of a range of aldehyde substrates as a function of their conformational flexibility. Substrates of higher conformational rigidity were more reactive, giving higher yields of the desired products. However, a single substituent on the alkyl chain linking the N-tosylimine and the benzylic sp³ C-H bonds was sufficient for HT-cyclization to occur. In addition, an examination of various arenes revealed that the electronic character of the hydridic C-H bonds dramatically affects the efficiency of the reaction. We also found that this transformation is highly stereoselective; 2-substituted aldehydes yield cis-2,5-disubstituted piperidines, while 3-substituted aldehydes afford trans-2,4-disubstituted piperidines. The stereoselectivity is a consequence of thermodn. control. The pseudoallylic strain between the arene and tosyl group on the piperidine ring is proposed to rationalize the greater stability of the isomer with the aryl ring in the axial position. This preferential placement of the arene is proposed to affect the observed stereoselectivity. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Safety of Methyl 2-bromo-4-fluorobenzoate).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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). 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.Safety of Methyl 2-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Regio- and stereo-selective olefinic C-H functionalization of aryl alkenes in ethanol was written by Shen, Cong;Zhu, Yuhang;Jin, Shuqi;Xu, Kejie;Luo, Shuxin;Xu, Lixia;Zhong, Guofu;Zhong, Liangjun;Zhang, Jian. And the article was included in Organic Chemistry Frontiers in 2022.Synthetic Route of C8H6BrFO2 This article mentions the following:

N,N-bidentate-chelation-assisted 浼? and 灏?olefinic C-H alkenylation of aryl alkenes in ethanol to afford aryl dienes/trienes with excellent regio- and stereo-selectivities was reported. The reaction of 2-alkenyl benzylamine and benzoic acid derived substrates proceeded through six-membered exo-cyclometallation and seven-membered endo-cyclometallation. The aerobic protocols feature wide functionality tolerance, high selectivities and yields, mild conditions and scalable preparation, and the directing group can be easily removed to afford Boc-protected amine by simple reduction In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Synthetic Route of C8H6BrFO2).

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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Synthetic Route of C8H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

One-Pot Preparation of (NH)-Phenanthridinones and Amide-Functionalized [7]Helicene-like Molecules from Biaryl Dicarboxylic Acids was written by Murai, Takuya;Xing, Yongning;Kurokawa, Mayu;Kuribayashi, Toshifumi;Nikaido, Masanori;Elboray, Elghareeb E.;Hamada, Shohei;Kobayashi, Yusuke;Sasamori, Takahiro;Kawabata, Takeo;Furuta, Takumi. And the article was included in Journal of Organic Chemistry in 2022.Electric Literature of C8H6BrFO2 This article mentions the following:

A one-pot transformation of biaryl dicarboxylic acids to (NH)-phenanthridinone derivatives based on a Curtius rearrangement and subsequent basic hydrolysis was developed. This method is also applicable for the preparation of optically active amide-functionalized [7]helicene-like mols. Furthermore, aza[5]helicene derivatives with a phosphate moiety were isolated as a product of the Curtius rearrangement step in the case of substrates that bear chalcogen atoms. The stereostructures of these products, revealed by X-ray diffraction anal., suggested that chalcogen-bonding and pnictogen-bonding interactions might contribute to their stabilization. The configurational stability of the helicene-like mols. and their chiroptical properties were further investigated. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Electric Literature of C8H6BrFO2).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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.Electric Literature of C8H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Dynamic Kinetic Resolution of Biaryl Atropisomers via Peptide-Catalyzed Asymmetric Bromination was written by Gustafson, Jeffrey L.;Lim, Daniel;Miller, Scott J.. And the article was included in Science (Washington, DC, United States) in 2010.Safety of Methyl 2-bromo-4-fluorobenzoate This article mentions the following:

Despite the widespread use of axially chiral, or atropisomeric, biaryl ligands in modern synthesis and the occurrence of numerous natural products exhibiting axial chirality, few catalytic methods have emerged for the direct asym. preparation of this compound class. Here, the authors present a tripeptide-derived small-mol. catalyst for the dynamic kinetic resolution of racemic biaryl substrates. The reaction proceeds via an atropisomer-selective electrophilic aromatic substitution reaction using simple bromination reagents. The result is an enantioselective synthesis that delivers chiral nonracemic biaryl compounds with excellent optical purity and good isolated chem. yields (in most cases a >95:5 enantiomer ratio and isolated yields of 65 to 87%). A mechanistic model is advanced that accounts for the basis of selectivity observed In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Safety of Methyl 2-bromo-4-fluorobenzoate).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine 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.Safety of Methyl 2-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones was written by Jia, Feng-Cheng;Xu, Cheng;Cai, Qun;Wu, An-Xin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2014.SDS of cas: 653-92-9 This article mentions the following:

A highly efficient three-component domino protocol has been developed for the synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones from simple and readily available o-halogenated benzohydrazides, aldehydes and nitriles. This domino process involves sequential selective condensation, copper-catalyzed intermol. C-arylation and bicyclization. Notably, the use of ligands and anaerobic conditions can be avoided in this reaction. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9SDS of cas: 653-92-9).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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. SDS of cas: 653-92-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic and Structure/Activity Studies on Acid-Substituted 2-Arylphenols: Discovery of 2-[2-Propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]- propoxy]phenoxy]benzoic Acid, a High-Affinity Leukotriene B₄ Receptor Antagonist was written by Sawyer, J. Scott;Bach, Nicholas J.;Baker, S. Richard;Baldwin, Ronald F.;Borromeo, Peter S.;Cockerham, Sandra L.;Fleisch, Jerome H.;Floreancig, Paul;Froelich, Larry L.. And the article was included in Journal of Medicinal Chemistry in 1995.Category: bromides-buliding-blocks This article mentions the following:

Structural derivatives of LY255283 have been studied as receptor antagonists of leukotriene B₄. Substitution of the 2-hydroxyacetophenone subunit of 1-[5-Ethyl-2-hydroxy-4-[[6-methyl-6-(1H-tetrazol-5-yl)heptyl]oxy]phenyl]ethanone (LY255283) with a 2-arylphenol group provided entry into several new series that feature various mono- and diacidic core functionality. These new analogs, the subject of a broad structure-activity investigation, displayed significantly increased in vitro and in vivo activity as receptor antagonists of LTB₄. A series of diaryl ether carboxylic acids demonstrated especially interesting activity and led to the discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenoxy]benzoic acid (LY293111), a 2-arylphenol-substituted diaryl ether carboxylic acid which displayed potent binding to human neutrophils (IC₅₀ = 17 鍗?4.6 nM) and guinea pig lung membranes (IC₅₀ = 6.6 鍗?0.71 nM), inhibition of LTB₄-induced expression of the CD11b/CD18 receptor on human neutrophils (IC₅₀ = 3.3 鍗?0.81 nM), and inhibition of LTB₄-induced contraction of guinea pig lung parenchyma (pK_B = 8.7 鍗?0.16). 801Vivo, LY293111 demonstrated potent activity in inhibiting LTB₄-induced airway obstruction in the guinea pig when dosed by the oral (ED₅₀ = 0.40 mg/kg) or i.v. (ED₅₀ = 0.014 mg/kg) routes. A specific LTB₄ receptor antagonist, LY293111 had little effect on inhibiting contractions of guinea pig lung parenchyma induced by leukotriene D₄ (LTD₄), histamine, carbachol, or U46619. LY293111 was chosen as a clin. candidate and is currently in phase I studies for a variety of inflammatory diseases. 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. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Efficient Access to Methyl-1-hydroxy-2-naphthoates and Heterocyclic Analogues was written by Podeschwa, Michael A. L.;Rossen, Kai. And the article was included in Organic Process Research & Development in 2015.Quality Control of Methyl 2-bromo-4-fluorobenzoate This article mentions the following:

We report the synthesis of Me 1-hydroxy-2-naphthoate derivatives and heterocyclic analogs using a two-step approach. This short route employs a Heck coupling of a 2-halobenzoate with Me 3-butenoate followed by a Dieckmann cyclization, yielding the 1-hydroxynaphthalene-2-carboxylic acid derivatives in the multigram scale. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Quality Control of Methyl 2-bromo-4-fluorobenzoate).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Quality Control of Methyl 2-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary