Tag: 100-200

Discovery of practical production processes for arylsulfur pentafluorides and their higher homologs, bis- and tris-(sulfur pentafluorides): beginning of a new era of super-trifluoromethyl arene chemistry and its industry was written by Umemoto, Teruo;Garrick, Lloyd M.;Saito, Norimichi. And the article was included in Beilstein Journal of Organic Chemistry in 2012.Application of 29364-29-2 This article mentions the following:

Various arylsulfur pentafluorides, ArSF₅, have long been desired in both academic and industrial areas and ArSF₅ compounds have attracted considerable interest in many areas such as medicine, agrochems., and other new materials, since the highly stable SF₅ group is considered a super-trifluoromethyl group due to its significantly higher electronegativity and lipophilicity. This article describes the first practical method for the production of various arylsulfur pentafluorides and their higher homologs, bis- and tris-(sulfur pentafluorides), from the corresponding diaryl disulfides or aryl thiols. The method consists of two steps: (step 1) treatment of a diaryl disulfide or an aryl thiol with chlorine in the presence of an alkali metal fluoride and (step 2) treatment of the resulting arylsulfur chlorotetrafluoride with a fluoride source, such as zinc fluoride (ZnF₂), hydrofluoric acid (HF) and antimony fluorides, Sb(III/V) fluorides. The intermediate arylsulfur chlorotetrafluoride derivatives were isolated by distillation or recrystallization and characterized. The aspects of these new reactions are revealed and reaction mechanisms are discussed. As the method offers considerable improvement over previous methods in cost, yield, practicality, applicability and large-scale production, the new processes described here can be employed as the first practical method for the economical production of various arylsulfur pentafluorides and their higher homologs, which could then open up a new era of super-trifluoromethyl arene chem. and its applications in many areas. A reaction (chlorine/potassium fluoride) of bis(2,3,6-trifluorophenyl)disulfide (I) gave trans-chlorotetrafluoro(2,3,6-trifluorophenyl)sulfur (II) and cis-chlorotetrafluoro(2,3,6-trifluorophenyl)sulfur (III). The synthesis of the target compound was achieve by the treatment of II, III with fluorination agents, to provide, e.g., pentafluoro(2,3,6-trifluorophenyl)sulfur (IV). In the experiment, the researchers used many compounds, for example, Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2Application of 29364-29-2).

Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Application of 29364-29-2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of lathyrane diterpenoid nitrogen-containing heterocyclic derivatives and evaluation of their anti-inflammatory activities was written by Wang, Wang;Xiong, Liangliang;Li, Yutong;Song, Zhuorui;Sun, Dejuan;Li, Hua;Chen, Lixia. And the article was included in Bioorganic & Medicinal Chemistry in 2022.Reference of 111-46-6 This article mentions the following:

As our ongoing work on lathyrane diterpenoid derivatization, three series of lathyrane diterpenoid derivatives were designed and synthesized based combination principles, including pyrazole, thiazole and furoxan moieties I [R = Et, phenyl; R¹ = Me, Cl, F, etc], II [R² = Me, Ph, cyclohexyl, etc.] and III [R³ = Bu, butyne, 1,4-dimethylbenzene, etc.] . Biol. evaluation indicated that compound III [R³ = ethoxyethane] exhibited excellently inhibitory activity on LPS-induced NO production in RAW264.7 cells (IC₅₀ = 0.38 卤 0.18 渭M). The preliminary structure-activity relationships (SARs) suggested that phenylsulfonyl substituted furoxan moiety had the strongest ability to improve anti-inflammatory activity of lathyrane diterpenoids. Furthermore, compound III [R³ = ethoxyethane] significantly reduced the level of ROS. Its mol. mechanism was related to inhibiting the transcriptional activation of Nrf₂/HO-1 pathway. Based on these considerations, III [R³ = ethoxyethane] might be a promising anti-inflammatory agent, which is noteworthy for further exploration. In the experiment, the researchers used many compounds, for example, 2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6Reference of 111-46-6).

2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Reference of 111-46-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electrochemistry of transition metal hydride diphosphine complexes trans-MH(X)(PP)₂ and trans-[MH(L)(PP)₂]⁺, M = Fe, Ru, Os; PP = chelating phosphine ligand was written by Drouin, Samantha D.;Maltby, Patricia A.;Rennie, Benjamin E.;Schweitzer, Caroline T.;Golombek, Adina;Cappellani, E. Paul;Morris, Robert H.. And the article was included in Inorganica Chimica Acta in 2021.Formula: C4H9NaS This article mentions the following:

A series of over 30 iron, ruthenium, and osmium hydride phosphine complexes are reported, along with their M^III/II redox potentials. The complexes are of the type MH(PP)_n(X) or [MH(PP)_n(L)]⁺, where PP is one of the following bidentate phosphine ligands: dppe, dtpe, depe, and dtfpe, with n = 2; or the tetradentate phosphine ligand meso-tet-1, with n = 1. The electrochem. data of these complexes and those from the literature are used to determine the Lever E_L parameter of -0.65 V for the hydride ligand for iron and ruthenium. For osmium, however, the E_L value for the hydride ligand is found to be more pos. at only -0.37 V, an increase which is attributed to Os-H 蟽 bond strengthening due to relativistic effects. The correlation holds for irreversible oxidations as well as reversible ones. These E_L values can now be used along with Lever’s equations to predict redox potentials of other iron-group hydride complexes. In the experiment, the researchers used many compounds, for example, Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2Formula: C4H9NaS).

Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Formula: C4H9NaS

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

CuO-Fe(III)-Zeolite-Y as efficient catalyst for oxidative alcohol-amine coupling reactions was written by Gogoi, Gautam;Baruah, Manash J.;Biswas, Subir;Hoque, Nazimul;Lee, Seonghwan;Park, Young-Bin;Saikia, Lakshi;Bania, Kusum K.. And the article was included in Molecular Catalysis in 2022.Application In Synthesis of (2,4-Dichlorophenyl)methanol This article mentions the following:

CuO nanocatalyst with layered structure was supported over Fe-exchanged zeolite-Y (CuO-Fe(III)-Y) for selective synthesis of amides by oxidative coupling of aromatic primary alcs. and amines. The CuO-Fe(III)-Y catalyst was characterized by different physicochem. and spectroscopic techniques. The amide bond formation reaction was found to occur in absence of any external base and reagents. The temperature-programmed desorption (TPD) study predicted the development of strong basic sites in the CuO-Fe(III)-Y catalyst that boosted the dehydrogenative coupling process. The activity of the material in such coupling reaction was found to be comparable to those of other costly metal catalysts under different reaction conditions. The product yield of the reaction was found to be substrate-dependent giving moderate to maximum yield of 85%. The anomalies in the reaction appeared in case of 5-nitro-2-chloro-benzylalc. that undergoes a C-N coupling product through C-Cl bond activation. The mechanism of the reaction was believed to proceed through FeIV=O species that helped in the activation of the benzylic C-H bond . In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8Application In Synthesis of (2,4-Dichlorophenyl)methanol).

(2,4-Dichlorophenyl)methanol (cas: 1777-82-8) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Application In Synthesis of (2,4-Dichlorophenyl)methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Facile Cu(OTf)₂-Catalyzed Preparation of Per-O-acetylated Hexopyranoses with Stoichiometric Acetic Anhydride and Sequential One-Pot Anomeric Substitution to Thioglycosides under Solvent-Free Conditions was written by Tai, Cheng-An;Kulkarni, Suvarn S.;Hung, Shang-Cheng. And the article was included in Journal of Organic Chemistry in 2003.Formula: C6H14O6 This article mentions the following:

Solvent-free per-O-acetylation of hexoses with a stoichiometric amount of acetic anhydride employing 0.03 mol % Cu(OTf)₂ proceeded in high yields (90-99%) at room temperature to give exclusively pyranosyl products as an anomeric mixture, the 伪/尾 ratio of which was dependent on the temperature and amount of catalyst used. Sequential anomeric substitution with p-thiocresol in the presence of BF₃路etherate gave the thioglycosides, isolated exclusively or predominantly as one anomer in 66-75% yields. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal hydrate (cas: 10030-85-0Formula: C6H14O6).

(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal hydrate (cas: 10030-85-0) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Formula: C6H14O6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Base-induced Sommelet-Hauser rearrangement of N-(pyridinylmethyl) tetraalkylammonium salts was written by Tayama, Eiji;Shimizu, Goshu;Nakao, Ryo. And the article was included in Tetrahedron in 2022.Formula: C7H9NO This article mentions the following:

The base-induced Sommelet-Hauser (S-H) rearrangement of various types of N-(pyridinylmethyl) tetraalkylammonium salts to produce N,N-dialkyl-伪-pyridinylamino acid esters were investigated. For example, a treatment of N-(2-pyridinylmethyl) glycine tert-Bu ester-derived tetraalkylammonium salt with 1.2 equiv of potassium tert-butoxide in THF at -40掳C gave the corresponding S-H product, I [R = Obut; R¹ = R² = Me; R³= H] in 93% yield. Method was an efficient C-H functionalization of pyridines under simple and mild conditions. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Formula: C7H9NO).

6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Formula: C7H9NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege was written by Passera, Alessandro;Mezzetti, Antonio. And the article was included in Angewandte Chemie, International Edition in 2020.SDS of cas: 120121-01-9 This article mentions the following:

The bis(carbonyl) manganese(I) complex [Mn(CO)₂(ligand)]Br with a chiral (NH)₂P₂ macrocyclic ligand catalyzes the asym. transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcs. in high yields (up to >99%) and with excellent enantioselectivities (90-99% ee). A stereochem. model based on attractive CH-蟺 interactions is proposed. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9SDS of cas: 120121-01-9).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.SDS of cas: 120121-01-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Cutting root treatment combined with low-temperature storage regimes on non-volatile and volatile compounds of Oudemansiella raphanipes was written by Xia, Rongrong;Wang, Zicheng;Xu, Heran;Hou, Zhenshan;Li, Yunting;Wang, Yafei;Feng, Yao;Zhang, Xiang;Xin, Guang. And the article was included in LWT–Food Science and Technology in 2022.Reference of 3391-86-4 This article mentions the following:

Oudemansiella raphanipes (O. raphanipes) has recently been gaining popularity due to its active and flavor compounds In this study, the profiles of phenolics, flavonoids, non-volatile and volatile compounds of fresh O. raphanipes were subjected to cutting root (CR) and pulling root (PR) harvesting methods during different storage temperatures (5掳C and 20掳C) were investigated. The results showed that CR treatment effectively increased phenolic and flavonoid contents, maintained the sensory scores and the umami value based on e-tongue, increased more C8 volatile contents, and inhibited off-flavor acids production during 5掳C storage. The EUC values of the fresh O. raphanipes ranged from 4.72 to 23.66 g monosodium glutamate (MSG) 100 g-1, which TAVs were at a relatively high level in CR treatment than in PR treatment. A two-way anal. of variance (ANOVA) and principal component anal. (PCA) revealed statistically significant differences in different harvesting methods that affected the mushroom flavor. Eleven components were screened as taste characteristics contributors by partial least squares regression model (PLS-R) anal., including Glu, umami nucleotides, and 1-octene-3-ol and 3-octanone. Thus, the cutting root treatment is a promising method for obtaining the high flavor quality of fresh O. raphanipes during cooling storage. In the experiment, the researchers used many compounds, for example, Oct-1-en-3-ol (cas: 3391-86-4Reference of 3391-86-4).

Oct-1-en-3-ol (cas: 3391-86-4) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Reference of 3391-86-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Novel oxovanadium and dioxomolybdenum complexes of tridentate ONO-donor Schiff base ligand: Synthesis, characterization, crystal structures, Hirshfeld surface analysis, DFT computational studies and catalytic activity for the selective oxidation of benzylic alcohols was written by Kargar, Hadi;Forootan, Pooran;Fallah-Mehrjardi, Mehdi;Behjatmanesh-Ardakani, Reza;Amiri Rudbari, Hadi;Shahzad Munawar, Khurram;Ashfaq, Muhammad;Nawaz Tahir, Muhammad. And the article was included in Inorganica Chimica Acta in 2021.Synthetic Route of C7H6Cl2O This article mentions the following:

Two new oxovanadium and dioxomolybdenum Schiff base complexes, [V^VO(L)(OCH₃)(CH₃OH)] and [Mo^VIO₂(L)(CH₂CH₃OH)], were synthesized by treating an ONO-donor type Schiff base ligand (H₂L) derived by condensation of 5-nitrosalicylaldehyde and nicotinic hydrazide with oxo and dioxo acetylacetonate salts of vanadium and molybdenum, [VO(acac)₂ and MoO₂(acac)₂], resp. The synthesized ligand and complexes were characterized by various spectroscopic techniques like FT-IR, multinuclear (¹H, ¹³C) NMR, elemental anal. and the most authentic single crystal X-ray diffraction anal. In both complexes the geometry around the central metal ions was distorted octahedral as revealed by the data collected from diffraction studies. Theor. calculation of the synthesized compounds were carried out by DFT as well as TD-DFT using B3LYP method by employing the Def2-TZVP basis set. The findings of theor. data indicated that the calculated results are in accordance with the exptl. findings. Moreover, the catalytic efficiencies of both complexes were investigated by oxidizing the benzylic alcs. in the presence of urea hydrogen peroxide (UHP) in acetonitrile. In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8Synthetic Route of C7H6Cl2O).

(2,4-Dichlorophenyl)methanol (cas: 1777-82-8) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Synthetic Route of C7H6Cl2O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety was written by Xie, Jin;Yang, Fengzhi;Zhang, Man;Lam, Celine;Qiao, Yixue;Xiao, Jia;Zhang, Dongdong;Ge, Yuxuan;Fu, Lei;Xie, Dongsheng. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Quality Control of 2-(Trifluoromethyl)phenethyl alcohol This article mentions the following:

A series of caffeic acid phenylethyl ester (CAPE) derivatives with mono-substituted phenylethanols moiety were synthesized and evaluated by MTT assay on growth of 4 human cancer cell lines (Hela, DU-145, MCF-7 and ECA-109). The substituent effects on the antiproliferative activity were systematically investigated for the first time. It was found that electron-donating and hydrophobic substituents at 2′-position of phenylethanol moiety could significantly enhance CAPE’s antiproliferative activity. 2′-Propoxyl derivative, as a novel caffeic acid ester, exhibited exquisite potency (IC₅₀ = 0.4 卤 0.02 & 0.6 卤 0.03 渭M against Hela and DU-145 resp.). In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethyl)phenethyl alcohol (cas: 94022-96-5Quality Control of 2-(Trifluoromethyl)phenethyl alcohol).

2-(Trifluoromethyl)phenethyl alcohol (cas: 94022-96-5) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Quality Control of 2-(Trifluoromethyl)phenethyl alcohol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts