Author: Jessica.F

Some interconversion reactions of organolithium compounds was written by Gilman, Henry;Langham, Wright;Moore, Fred W.. And the article was included in Journal of the American Chemical Society in 1940.Product Details of 3438-16-2 This article mentions the following:

Details are given of 28 reactions of halo derivatives of C₆H₆, PhMe and PhOMe with BuLi in ether or petr. ether (I) with carbonation by pouring upon solid CO₂ to give acids. PhBr in ether (0.25-0.5 h.) gives 46-51% of BzOH; reaction of 0.05 mol. mixture for 1, 5, 20 and 24 h. gives 36, 15, trace and 3.4% BzOH; in I (24 h.) the yield of BzOH is 44.8%. PhI (0.25 h.) gives 49-51% BzOH; after 0.5 and 1 h. the yields are 41 and 27%; in 5 and 20 h. the yields are 13% and a trace. m-ClC₆H₄I gives 41.5% of m-ClC₆H₄CO₂H. p-ClC₆H₄Br gives 90% of p-ClC₆H₄CO₂H. p-C₆H₄B₂ in ether gives 54% p-BrC₆H₄CO₂H; in I (24 h.), 88.7% of p-C₆H₄(CO₂H)₂; in ether (5.5 h.) there was formed 67% of p-BrC₆H₄CO₂H and 33% of p-C₆H₄(CO₂H)₂. 1,3,5-C₆H₃Br₃ gives 71% of 3,5-Br₂C₆H₃CO₂H. o-BrC₆H₄Me in ether (0.25 h.) gives 83.8% and in I (20 h.) 41.7% o-MeC₆H₄CO₂H. m-BrC₆H₄Me in ether (0.25 h.) gives 65.4% and in I (20 h.) 46.1% of m-MeC₆H₄CO₂H. p-BrC₆H₄Me in ether gives 51% and in I 86.2% of p-MeC₆H₄CO₂H. p-IC₆H₄Me in ether yields 72% p-MeC₆H₄CO₂H. o- and p-BrC₆H₄OMe give 72.3 and 52% of o- and p-MeOC₆H₄CO₂H; p-IC₆H₄OMe gives 78% of p-MeOC₆H₄CO₂H. 2,5-Br₂C₆H₃Me (II) and BuLi (0.025 mol each) (15 min.) give 63% of a mixture containing 29% of 3,4-MeBrC₆H₃CO₂H (III), 20.5% of the 2,4-isomer (?) (IV) and 19% of II; with 0.025 mol of II and 0.03 mol BuLi (2 min.) there results 36.1% III and 22.3% IV; in I 0.015 mol II and 0.033 mol BuLi after 20 h. give 12.4% of III and 51.8% of 3-MeC₆H₃-(CO₂H)₂-1,4 (V); 0.01 mol II and 0.04 mol BuLi give 64.4% of V. 3-Bromoacenaphthene gives 55-62% of 3-acenaphthoic acid. (4-BrC₆H₄)₂ in 1 experiment gave 65% p-BrC₆H₄C₆H₄CO₂H (VI); in a 2nd experiment there was formed 67% of VI and 30% of (p-HO₂CC₆H₄)₂ (VII); in I the yield is 13% VI and 60.6% VII; in an experiment in which the I was distilled off during 10 h. the yield of VII was 91%. PhCH:CHBr and BuLi, heated in I for 20 h., give 23% of trans-PhCH:CHCO₂H; after 1 h., the yield is 19%; in ether there is formed 42.5% of PhCCCO₂H. p-ClC₆H₄OMe in ether gives 56% of 5,2-Cl(MeO)C₆H₃CO₂H, m. 97.5° (previously reported 80-2°); after 24 h. at 18-20° the yield was 74%. p-FC₆H₄OMe gives 10-13% of 5,2-F(MeO)C₆H₃CO₂H. 2,4,6-Br₃C₆H₂OMe in ether gives 16-19% of 3,5,2-Br₂(MeO)C₆H₂CO₂H; in I there results 75-88% of 5,2,1,3-Br(MeO)C₆H₂(CO₂H)₂. p-BrC₆H₄OPh gives 70% of p-PhOC₆H₄CO₂H. (4-BrC₆H₄)₂O yields 56.3% of 4-(4-BrC₆H₄O)C₆H₄CO₂H. Procedures are given for the conversion of small blocks of Li to the generally more effective smaller particles. An apparatus is illustrated for filtration of organolithium solutions Advantages of the use of I as a solvent in this type of reaction are listed. The following generalizations are drawn from this work: Metalation of aryl ethers involves H or hydrogens on C ortho to the ether linkage. All types of aryl bromides and iodides undergo the halogen-metal interconversion reaction. Iodides react more readily than the bromides, and chlorides and fluorides are essentially not affected. There are 2 chief competitive reactions: halogen-metal interconversions (RX + R’Li → RLi + R’X) and couplings (RX + R’Li → RLi + R’X → RR’ + LiX). The coupling reaction is not only the slower reaction but often also follows the interconversion reaction. As the reaction time is extended, the coupling reaction predominates and eventuates in the essential disappearance of RLi compound In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Product Details of 3438-16-2).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Organic chlorides can cause corrosion in pipelines, valves and condensers, and cause catalyst poisoning. The hydrocarbon processing industry (HPI) and others are affected by damage caused by these substances. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Product Details of 3438-16-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Intermolecular Reductive Heck Reaction of Unactivated Aliphatic Alkenes with Organohalides was written by Zheng, Kewang;Xiao, Guanlin;Guo, Tao;Ding, Yalan;Wang, Chengdong;Loh, Teck-Peng;Wu, Xiaojin. And the article was included in Organic Letters in 2020.Application In Synthesis of 5-Bromo-2-chloro-m-xylene This article mentions the following:

A general intermol. reductive Heck reaction of organohalides with both terminal and internal unactivated aliphatic alkenes has been first realized in high yield with complete anti-Markovnikov selectivity. The challenging vinyl bromides, aryl chlorides, and polysubstituted internal alkenes were first applied. More than 100 remote carbofunctionalized alkyl carboxylic acid derivatives were rapidly synthesized from easily accessible starting materials. The synthesis of drug mols. has further demonstrated the wide synthetic utility of this scalable strategy. Preliminary mechanistic studies are consistent with the proposed catalytic cycle. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-chloro-m-xylene (cas: 206559-40-2Application In Synthesis of 5-Bromo-2-chloro-m-xylene).

5-Bromo-2-chloro-m-xylene (cas: 206559-40-2) belongs to organic chlorides. Organochlorines stimulate the central nervous system and cause convulsions, tremor, nausea, and mental confusion. Examples are dichlorodiphenyltrichloroethane (DDT), chlordane, lindane, endosulfan, and dieldrin.While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Application In Synthesis of 5-Bromo-2-chloro-m-xylene

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthesis and SAR of 5-, 6-, 7- and 8-Aza Analogues of 3-Aryl-4-hydroxyquinolin-2(1H)-one as NMDA/Glycine Site Antagonists was written by Zhou, Z.-L.;Navratil, J. M.;Cai, S. X.;Whittemore, E. R.;Espitia, S. A.;Hawkinson, J. E.;Tran, M.;Woodward, R. M.;Weber, E.;Keana, J. F. W.. And the article was included in Bioorganic & Medicinal Chemistry in 2001.COA of Formula: C9H9ClO2 This article mentions the following:

A series of 5-, 6-, 7- and 8-aza analogs of 3-aryl-4-hydroxyquinolin-2(1H)-one was synthesized and assayed as NMDA/glycine receptor antagonists. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [³H]5,7-dichlorokynurenic acid ([³H]DCKA) in rat brain cortical membranes. Selected compounds were also tested for functional antagonism using electrophysiol. assays in Xenopus oocytes expressing cloned NMDA receptor (NR) 1A/2C subunits. Among the 5-, 6-, 7-, and 8-aza-3-aryl-4-hydroxyquinoline-2(1H)-ones investigated, 5-aza-7-chloro-4-hydroxy-3-(3-phenoxyphenyl)quinolin-2-(1H)-one (I) is the most potent antagonist, having an IC₅₀ value of 110 nM in [³H]DCKA binding and a K_b of 11 nM in the electrophysiol. assay. Compound I is also an active anticonvulsant when administered systemically in the mouse maximum electroshock-induced seizure test (ED₅₀=2.3 mg/kg, IP). In the experiment, the researchers used many compounds, for example, 2-(3-Methoxyphenyl)acetyl chloride (cas: 6834-42-0COA of Formula: C9H9ClO2).

2-(3-Methoxyphenyl)acetyl chloride (cas: 6834-42-0) belongs to organic chlorides. Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.COA of Formula: C9H9ClO2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Facile synthesis of CdO-ZnO heterojunction photocatalyst for rapid removal of organic contaminants from water using visible light was written by Warshagha, Murad Z. A.;Muneer, Mohammad. And the article was included in Environmental Nanotechnology, Monitoring and Management in 2022.Related Products of 61-73-4 This article mentions the following:

The synthesis of an efficient photocatalyst for removing organic contaminants in the water is of major importance for researchers working in heterogeneous photocatalysis. To do this, we provide the co-precipitation approach for synthesizing heterojunction nanocomposite (CdO-ZnO). Standard anal. techniques were used to characterize the synthesized components. According to the XRD and DRS results, a composite of ZnO and CdO was effectively synthesized with a shift of λ^max towards the higher wavelength. SEM pictures reveal well-decorated oval-shaped CdO nanoparticles with hexagonal ZnO particle morphol. Under visible light irradiation, the as-prepared CdO-ZnO nanocomposite demonstrated very efficient photocatalytic performance as measured by the decomposition of RhB, MB, paracetamol, and ciprofloxacin in an aqueous solution The photo-mineralization of MB and RhB over the most active CZ-3 catalyst was also assessed by measuring the decrease in TOC (total organic carbon) content over time when exposed to visible light. The breakdown of paracetamol produces no hazardous byproducts, according to high-performance liquid chromatog. (HPLC) study. The photocatalytic process appears to be dominated by ^·OH and h⁺, according to the radical scavenger tests. In the experiment, the researchers used many compounds, for example, 3,7-Bis(dimethylamino)phenothiazin-5-ium chloride (cas: 61-73-4Related Products of 61-73-4).

3,7-Bis(dimethylamino)phenothiazin-5-ium chloride (cas: 61-73-4) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Related Products of 61-73-4

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Design and bio-evaluation of indole derivatives as potent Kv1.5 inhibitors was written by Guo, Xiaoke;Yang, Qian;Xu, Jing;Zhang, Li;Chu, Hongxi;Yu, Peng;Zhu, Yingying;Wei, Jinglian;Chen, Weilin;Zhang, Yaozhong;Zhang, Xiaojin;Sun, Haopeng;Tang, Yiqun;You, Qidong. And the article was included in Bioorganic & Medicinal Chemistry in 2013.COA of Formula: C10H13ClO3S This article mentions the following:

Atrial fibrillation (AF) is one of the common arrhythmias that threaten human health. Kv1.5 potassium channel is reported as an efficacious and safe target for the treatment of AF. In this paper, we designed and synthesized three series of compounds through modifying the lead compound RH01617 that was screened out by the pharmacophore model we reported earlier. All of the compounds were evaluated by the whole-patch lamp technol. and most of them possessed potent inhibitory activities against Kv1.5. Two of the compounds were evaluated for the target selectivity as well as the pharmacodynamic effects in an isolated rat model. Due to the promising pharmacol. behavior, one compound deserves further pharmacodynamic and pharmacokinetic evaluations. In the experiment, the researchers used many compounds, for example, 4-Butoxybenzene-1-sulfonyl chloride (cas: 1138-56-3COA of Formula: C10H13ClO3S).

4-Butoxybenzene-1-sulfonyl chloride (cas: 1138-56-3) belongs to organic chlorides. Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.COA of Formula: C10H13ClO3S

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Rh(III)-catalyzed oxidative C-H activation/domino annulation of anilines with 1,3-diynes: a rapid access to blue-emitting tricyclic N,O-heteroaromatics was written by Qian, Shengyou;Pu, Xingwen;Chang, Guanjun;Huang, Ying;Yang, Yudong. And the article was included in Organic Letters in 2020.Safety of tert-Butyl (4-chlorophenyl)carbamate This article mentions the following:

Disclosed herein is a rhodium-catalyzed oxidative C-H activation/domino annulation of N-Boc-anilines with 1,3-diynes for the construction of tricyclic N,O-heteroaromatics This reaction features easily available substrates, mild reaction conditions, high regioselectivity, mono/diannulation selectivity, and intra/intermol. annulation selectivity. Moreover, this synthetic protocol enables the rapid assembly of a library of blue-emitting mols. with high quantum yields, among of which two fluorophores with pure blue-emission in toluene are discovered. In the experiment, the researchers used many compounds, for example, tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6Safety of tert-Butyl (4-chlorophenyl)carbamate).

tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Safety of tert-Butyl (4-chlorophenyl)carbamate

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Metal-free directed C-H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines was written by Wu, Gaorong;Xu, Xiaobo;Wang, Shuai;Chen, Lu;Pang, Binghan;Ma, Tao;Ji, Yafei. And the article was included in Chinese Chemical Letters in 2022.Reference of 620-19-9 This article mentions the following:

A novel method for metal-free C-H pyridine-directed borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines with BBr₃ has been reported, affording complexes R¹C₆H₃(Bpin)-2-XR²-5-FC₅H₄N-2 (X = N, CH; R¹ = H, alkyl, halo; R² = H, Me). The 5-fluoropyridine directed borylation reaction exhibited high efficiency and site exclusivity. The useful protocol could be executed on a gram-scale easily and the borylated products showed good derivatization applications. Moreover, the practicality of the strategy was expanded by the fact that the directing group could be removed in an acceptable yield. In the experiment, the researchers used many compounds, for example, 1-(Chloromethyl)-3-methylbenzene (cas: 620-19-9Reference of 620-19-9).

1-(Chloromethyl)-3-methylbenzene (cas: 620-19-9) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications.While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Reference of 620-19-9

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Design, synthesis and biological evaluation of novel pyrrolidone-based derivatives as potent p53-MDM2 inhibitors was written by Si, Dongjuan;Luo, Huijuan;Zhang, Xiaomeng;Yang, Kundi;Wen, Hongmei;Li, Wei;Liu, Jian. And the article was included in Bioorganic Chemistry in 2021.Application In Synthesis of 2,5-Difluorophenylacetyl chloride This article mentions the following:

Inhibition of the interactions of the tumor suppressor protein p53 with its neg. regulators MDM2 in vitro and in vivo, representing a valuable therapeutic strategy for cancer treatment. The natural product chalcone exhibited moderate inhibitory activity against MDM2, thus based on the binding mode between chalcone and MDM2, a hit unsaturated pyrrolidone scaffold was obtained through virtual screening. Several unsaturated pyrrolidone derivatives were synthesized and biol. evaluated. As a result, because the three critical hydrophobic pockets of MDM2 were occupied by the substituted-Ph linked at the pyrrolidone fragment, compound I demonstrated good binding affinity with the MDM2. Addnl., compound I also showed excellent antitumor activity and selectivity, and no cytotoxicity against normal cells in vitro. The further antitumor mechanism studies were indicated that compound I could successfully induce the activation of p53 and corresponding downstream p21 proteins, thus successfully causing HCT116 cell cycle arrest in the G1/M phase and apoptosis. Thus, the novel unsaturated pyrrolidone p53-MDM2 inhibitors could be developed as novel antitumor agents. In the experiment, the researchers used many compounds, for example, 2,5-Difluorophenylacetyl chloride (cas: 157033-23-3Application In Synthesis of 2,5-Difluorophenylacetyl chloride).

2,5-Difluorophenylacetyl chloride (cas: 157033-23-3) belongs to organic chlorides. Organochlorines are organic compounds having multiple chlorine atoms. They were the first synthetic pesticides that were used in agriculture. They are resistant to most microbial and chemical degradations. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control.Application In Synthesis of 2,5-Difluorophenylacetyl chloride

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Discovery and optimization of efficacious neutral 4-amino-6-biphenyl-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5-one diacylglycerol acyl transferase-1 (DGAT1) inhibitors was written by Goldberg, Frederick W.;Birch, Alan M.;Leach, Andrew G.;Groombridge, Sam D.;Snelson, Wendy L.;Gutierrez, Pablo Morentin;Hammond, Clare D.;Birtles, Susan;Buckett, Linda K.. And the article was included in MedChemComm in 2013.Computed Properties of C9H9ClO3 This article mentions the following:

A series of neutral DGAT1 inhibitors with good potency and pharmacokinetics (PK) has been designed by modification of an acidic startpoint. This was achieved by selecting the acid with the highest ligand lipophilicity efficiency (LLE) and replacing the acid with neutral isosteres. PK properties (F_abs) were then improved by removing the sidechain to reduce mol. weight and polar surface area (PSA). Compound 13 has shown good cross-species PK, with pre-clin. efficacy and PK/PD relationships comparable to those previously described for acidic inhibitors. In the experiment, the researchers used many compounds, for example, Methyl 3-chloro-4-hydroxyphenylacetate (cas: 57017-95-5Computed Properties of C9H9ClO3).

Methyl 3-chloro-4-hydroxyphenylacetate (cas: 57017-95-5) belongs to organic chlorides. Organic chlorides can cause corrosion in pipelines, valves and condensers, and cause catalyst poisoning. The hydrocarbon processing industry (HPI) and others are affected by damage caused by these substances. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control.Computed Properties of C9H9ClO3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Palladium-Catalyzed Oxidative Carbonylation of Aromatic C-H Bonds of N-Alkylanilines with CO and Alcohols for the Synthesis of o-Aminobenzoates was written by Chen, Ming;Ren, Zhi-Hui;Wang, Yao-Yu;Guan, Zheng-Hui. And the article was included in Journal of Organic Chemistry in 2015.Reference of 18437-66-6 This article mentions the following:

A Pd(II)-catalyzed C-H monocarbonylation of N-alkylanilines for the synthesis of o-aminobenzoates has been developed. Various aliphatic alcs. and phenol were tolerated in the reaction to afford the corresponding o-aminobenzoates in good yields under mild balloon pressure of CO. In the experiment, the researchers used many compounds, for example, tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6Reference of 18437-66-6).

tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6) belongs to organic chlorides. Organochlorines are organic compounds having multiple chlorine atoms. They were the first synthetic pesticides that were used in agriculture. They are resistant to most microbial and chemical degradations. Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.Reference of 18437-66-6

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics