Category: chlorides-buliding-blocks

The author of 《Antimalarials. 9. Methylthio- and methylsulfonyl-substituted 9-phenanthrenemethanols》 were Markovac, A.; LaMontagne, M. P.. And the article was published in Journal of Medicinal Chemistry in 1976. Synthetic Route of C7H3Cl2NO3 The author mentioned the following in the article:

Nine di- and trisubstituted 9-phenanthrenemethanols bearing methylthio and methylsulfonyl substituents in the 2 and/or 6 positions of the phenanthrene nucleus were prepared and screened for antimalarial activity against Plasmodium berghei in mice. Six of the nine compounds were curative at or below 160 mg/kg. The most active structures contained a methylthio substituent in combination with two chlorine atoms. The most effective compound was 2,4-dichloro-α-dibutylaminomethyl-6-methylthio-9-phenanthrenemethanol-HCl (I) [59215-48-4]. The results came from multiple reactions, including the reaction of 3,5-Dichloro-2-nitrobenzaldehyde(cas: 59178-12-0Synthetic Route of C7H3Cl2NO3)

3,5-Dichloro-2-nitrobenzaldehyde(cas: 59178-12-0) belongs to organochlorine compounds. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.Synthetic Route of C7H3Cl2NO3

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

Ohtsuka, Yuhki; Uraguchi, Daisuke; Yamamoto, Kyoko; Tokuhisa, Kenji; Yamakawa, Tetsu published an article on January 31 ,2016. The article was titled 《Fenton reagent-catalyzed trifluoromethylation of enamines of 3-oxocarboxylates with CF3I》, and you may find the article in Journal of Fluorine Chemistry.Safety of Ethyl 3-(4-chlorophenyl)propanoate The information in the text is summarized as follows:

The trifluoromethylation of enamines of Et 3-oxocarboxylates catalyzed by Fenton reagent with CF3I was investigated. Trifluoromethylation followed by acid hydrolysis provided 3-oxo-2-(trifluoromethyl)carboxylates in 64-94% yields, which were greater than those obtained by the trifluoromethylation of 3-oxocarboxylates as reported previously. Enamines trifluoromethylated at the 2-position were isolated as intermediates. Hydrolysis and successive decarboxylation of the obtained 3-oxo-2-(trifluoromethyl)carboxylates under acidic conditions provided (2,2,2-trifluoroethyl)ketones in satisfactory yields. The synthesis of the target compounds was achieved using sulfuric acid iron(2+) salt (i.e., iron sulfate) and hydrogen peroxide (H2O2) as Fenton reagent. Starting materials included (iodo)trifluoromethane and enamines, such as 3-amino-2-butenoic acid ester, 3-amino-4-methyl-2-pentenoic acid ester, 3-amino-2-heptenoic acid ester, 3-amino-3-phenyl-2-propenoic acid ester. The title compounds thus formed included 3-oxo-2-(trifluoromethyl)butanoic acid ester, 4-methyl-3-oxo-2-(trifluoromethyl)pentanoic acid ester, β-oxo-α-(trifluoromethyl)benzenepropanoic acid ester. Hydrolysis products included trifluoromethyl ketones, such as 4,4,4-trifluoro-2-butanone, 1,1,1-trifluoro-4-methyl-3-pentanone, 1,1,1-trifluoro-3-heptanone, 3,3,3-trifluoro-1-phenyl-1-propanone. In the part of experimental materials, we found many familiar compounds, such as Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1Safety of Ethyl 3-(4-chlorophenyl)propanoate)

Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1) belongs to organochlorine compounds. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties.Safety of Ethyl 3-(4-chlorophenyl)propanoate Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.

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

The author of 《Facile one-pot synthesis of diarylacetylenes from arylaldehydes via an addition-double elimination process》 were Chen, Jianyang; Zhang, Xuan; Wu, Jiajun; Wang, Rui; Lei, Chunlin; An, Yanan. And the article was published in Organic & Biomolecular Chemistry in 2021. Application of 620-20-2 The author mentioned the following in the article:

A practical one-pot protocol has been developed to synthesize diarylacetylenes ArCCAr1 (Ar = Ph, naphthalen-1-yl, furan-2-yl, etc.; Ar1 = Ph, 4-chlorophenyl, naphthalen-2-yl, etc.) from arylaldehydes ArCHO by treatment with 1-(arylmethyl)benzotriazoles I and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of diarylacetylene (Ar = 4-bromophenyl, Ar1 = Ph) has been demonstrated. The experimental process involved the reaction of 3-Chlorobenzylchloride(cas: 620-20-2Application of 620-20-2)

3-Chlorobenzylchloride(cas: 620-20-2) has been used in the reaction of 3-methoxybenzyl chloride and ethyl 4-bromobenzoate in pure water, using zinc dust and a Pd catalyst.Application of 620-20-2

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

Elwaie, Tamer A.; Abbas, Safinaz E.; Aly, Enayat I.; George, Riham F.; Ali, Hamdy; Kraiouchkine, Nikolai; Abdelwahed, Khaldoun S.; Fandy, Tamer E.; El Sayed, Khalid A.; Abd Elmageed, Zakaria Y.; Ali, Hamed I. published their research in Journal of Medicinal Chemistry on December 24 ,2020. The article was titled 《HER2 Kinase-Targeted Breast Cancer Therapy: Design, Synthesis, and In Vitro and In Vivo Evaluation of Novel Lapatinib Congeners as Selective and Potent HER2 Inhibitors with Favorable Metabolic Stability》.Product Details of 350-30-1 The article contains the following contents:

HER2 kinase as a well-established target for breast cancer (BC) therapy is associated with aggressive clin. outcomes; thus, herein we present structural optimization for HER2-selective targeting. HER2 profiling of the developed derivatives demonstrated potent and selective inhibitions (IC50: 5.4-12 nM) compared to lapatinib (IC50: 95.5 nM). Favorably, 17d exhibited min. off-target kinase activation. NCI-5-dose screening revealed broad-spectrum activities (GI50: 1.43-2.09μM) and 17d had a remarkable selectivity toward BC. Our compounds revealed significant selective and potent antiproliferative activities (~20-fold) against HER2+ (AU565, BT474) compared to HER2(-) cells. At 0.1 IC50, 15i, 17d, and 25b inhibited pERK1/2 and pAkt by immunoblotting. Furthermore, 17d demonstrated potent in vivo tumor regression against the BT474 xenograft model. Notably, a metastasis case was observed in the vehicle but not in the test mice groups. CD-1 mice metabolic stability assay revealed high stability and low intrinsic clearance of 17d (T1/2 > 145 min and CLint(mic) < 9.6 mL/min/kg). The experimental process involved the reaction of 3-Chloro-4-fluoronitrobenzene(cas: 350-30-1Product Details of 350-30-1)

3-Chloro-4-fluoronitrobenzene(cas: 350-30-1) belongs to organochlorine compounds. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties.Product Details of 350-30-1 Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

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

Chandrashekhar, Vishwas G.; Senthamarai, Thirusangumurugan; Kadam, Ravishankar G.; Malina, Ondrej; Kaslik, Josef; Zboril, Radek; Gawande, Manoj B.; Jagadeesh, Rajenahally V.; Beller, Matthias published an article on January 31 ,2022. The article was titled 《Silica-supported Fe/Fe-O nanoparticles for the catalytic hydrogenation of nitriles to amines in the presence of aluminium additives》, and you may find the article in Nature Catalysis.Reference of (2-chloro-3-methylphenyl)methanamine hydrochloride The information in the text is summarized as follows:

The hydrogenation of nitriles to amines represents an important and frequently used industrial process due to the broad applicability of the resulting products in chem. and life sciences. Despite the existing portfolio of catalysts reported for the hydrogenation of nitriles, the development of iron-based heterogeneous catalysts for this process is still a challenge. Here, we show that the impregnation and pyrolysis of iron(II) acetate on com. silica produces a reusable Fe/Fe-O@SiO2 catalyst with a well-defined structure comprising the fayalite phase at the Si-Fe interface and α-Fe nanoparticles, covered by an ultrathin amorphous iron(III) oxide layer, growing from the silica matrix. These Fe/Fe-O core-shell nanoparticles, in the presence of catalytic amounts of aluminum additives, promote the hydrogenation of all kinds of nitriles, including structurally challenging and functionally diverse aromatic, heterocyclic, aliphatic and fatty nitriles, to produce primary amines under scalable and industrially viable conditions. In the experimental materials used by the author, we found (2-chloro-3-methylphenyl)methanamine hydrochloride(cas: 2055841-68-2Reference of (2-chloro-3-methylphenyl)methanamine hydrochloride)

(2-chloro-3-methylphenyl)methanamine hydrochloride(cas: 2055841-68-2) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Reference of (2-chloro-3-methylphenyl)methanamine hydrochloride

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

COA of Formula: C11H13ClO2On May 31, 1988, Uscumlic, G. S.; Krstic, V. V.; Muskatirovic, M. D. published an article in Journal of Molecular Structure. The article was 《Correlation of ultraviolet absorption frequences of cis- and trans-substituted cinnamic acids with Hammett substituent constants》. The article mentions the following:

The UV absorption spectra of cis- and trans-3- and 4-substituted cinnamic acids have been determined Examination of the spectra shows that there is a fair linear relation between the positions of the absorption bands for the electronic transitions of the carbonyl group and the Hammett substituent constants The plot of the λmax values of the cinnamic acids vs. the rate constants for the corresponding acids with diazodiphenylmethane (DDM) in ethanol gave a fair correlations. This relation was discussed in view of the proportionality of the energy of activation for the reaction of these acids with DDM in ethanol and the energy for the electronic transitions in the carbonyl group under the influence of UV radiation. In the experiment, the researchers used many compounds, for example, Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1COA of Formula: C11H13ClO2)

Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1) belongs to organochlorine compounds. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.COA of Formula: C11H13ClO2

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

Formula: C8H6Cl2O3On May 23, 1997, Khanna, Ish K.; Weier, Richard M.; Yu, Yi; Xu, Xiang D.; Koszyk, Francis J.; Collins, Paul W.; Koboldt, Carol M.; Veenhuizen, Amy W.; Perkins, William E.; Casler, Jacquelen J.; Masferrer, Jaime L.; Zhang, Yan. Y.; Gregory, Susan A.; Seibert, Karen; Isakson, Peter C. published an article in Journal of Medicinal Chemistry. The article was 《1,2-Diarylimidazoles as potent, cyclooxygenase-2 selective and orally active antiinflammatory agents》. The article mentions the following:

Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole were modified to establish SAR. Systematic variations of the substituents in the aryl ring has yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mpk for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mpk) and hyperalgesia (ED50 = 11-40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk. In the experiment, the researchers used 3,5-Dichloro-4-methoxybenzoic acid(cas: 37908-97-7Formula: C8H6Cl2O3)

3,5-Dichloro-4-methoxybenzoic acid(cas: 37908-97-7) belongs to organochlorine compounds. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.Formula: C8H6Cl2O3

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

《A Strategy for the Targeting of Photosensitizers. Synthesis, Characterization, and Photobiological Property of Porphyrins Bearing Glycodendrimeric Moieties》 was written by Ballut, Severine; Naud-Martin, Delphine; Loock, Bernard; Maillard, Philippe. Application of 14258-40-3 And the article was included in Journal of Organic Chemistry on April 1 ,2011. The article conveys some information:

This paper describes the conception, synthesis, and characterization of new tetrapyrrolic chromophores bearing glycodendrimeric moieties inducing a potential increase of tumor targeting by a cluster effect. Two families of monoglycodendrimeric photosensitizers bearing three glycosyl units were designed, prepared with an acceptable overall efficiency and characterized by NMR, UV-visible, and fluorescence spectroscopies. The polarity and log P were evaluated by HPLC and the stir-flask method, resp. The in vitro photoefficiency against two human tumor cell lines was assessed. The presence of the glycodendrimeric group does not appear to increase the tumor in vitro targeting. In the experiment, the researchers used 2-(2-Chloroethoxy)ethyl acetate(cas: 14258-40-3Application of 14258-40-3)

2-(2-Chloroethoxy)ethyl acetate(cas: 14258-40-3) belongs to aliphatic hydrocarbons. Aliphatic hydrocarbons belong to the most abundant fraction in crude oil. Aliphatics molecules are linear or branched open-chain structures such as n-alkanes, isoalkanes, cycloalkanes (naphthenes), terpenes and steranes.Application of 14258-40-3

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

Application In Synthesis of 4-Chlorobenzenesulfonyl chlorideIn 2021 ,《Synthesis of Symmetrical Thiosulfonates via Cu(OTf)2-Catalyzed Reductive Homocoupling of Arenesulfonyl Chlorides》 was published in European Journal of Organic Chemistry. The article was written by Liu, Lixia; Luo, Bo; Wang, Chengming. The article contains the following contents:

A variety of sym. thiosulfonates ArSO2SAr [Ar = 4-MeC6H4, 4-ClC6H4, 2-thienyl, etc.] were synthesized via Cu-catalyzed reductive homocoupling of aryl sulfonyl chlorides. This protocol used organic amine acting as a mild reductant and low-cost copper as an effective catalyst. Such a reductive coupling process featured a broad substrate scope and good functional group tolerance. Related thiosulfonate products could also be converted into diverse functional mols.4-Chlorobenzenesulfonyl chloride(cas: 98-60-2Application In Synthesis of 4-Chlorobenzenesulfonyl chloride) was used in this study.

4-Chlorobenzenesulfonyl chloride(cas: 98-60-2) belongs to organochlorine compounds. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. Application In Synthesis of 4-Chlorobenzenesulfonyl chloride However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.

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

SDS of cas: 16629-19-9In 2021 ,《tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines》 was published in Advanced Synthesis & Catalysis. The article was written by Zhou, Nengneng; Kuang, Kaimo; Wu, Meixia; Wu, Sixin; Xu, Qiankun; Xia, Ziqin; Zhang, Man. The article contains the following contents:

A tert-Bu hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes I (R = H, F, Cl, Br, t-Bu; R1 = H; R2 = C6H5, 4-BrC6H4, 2-thienyl, etc.; R3 = H, Me; R4 = H, Me, OMe, Br; R5 = H, t-Bu; RR1 = -CH=CHCH=CH-; X = O, NTs) with sulfinic acids R6S(O)OH (R6 = 4-CH3C6H4, 1-naphthyl, 2-thienyl, etc.) for the construction of sulfonated benzoxepines II (R7 = C6H5, 4-BrC6H4, 2-thienyl, etc.; R8 = H, Me) is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodol. features mild reaction conditions, a broad substrate scope and good functional group tolerance. After reading the article, we found that the author used Thiophene-2-sulfonyl chloride(cas: 16629-19-9SDS of cas: 16629-19-9)

Thiophene-2-sulfonyl chloride(cas: 16629-19-9) is a member of sulfonyl chlorides. Sulfonyl chlorides are reactive sulfonic acid derivatives similar in properties and reactivity to acid chlorides of carboxylates. The sulfonic acid group, however, is a highly hindered molecule, containing a tetrahedral configuration of substituents. SDS of cas: 16629-19-9

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