Tag: 200-300

Nonsolvent Application of Ionic Liquids: Organo-Catalysis by 1-Alkyl-3-methylimidazolium Cation Based Room-Temperature Ionic Liquids for Chemoselective N-tert-Butyloxycarbonylation of Amines and the Influence of the C-2 Hydrogen on Catalytic Efficiency was written by Sarkar, Anirban;Roy, Sudipta Raha;Parikh, Naisargee;Chakraborti, Asit K.. And the article was included in Journal of Organic Chemistry in 2011.Application of 18437-66-6 This article mentions the following:

Imidazolium ionic liquids such as [bmim]⁺·Tf₂N^– (I; bmim = 1-butyl-3-methylimidazolium) efficiently catalyze the chemoselective N-tert-butyloxycarbonylation of amines; the catalyst can be recycled by extraction of the product into ether followed by heating under vacuum. The ionic liquid catalyst activates di-tert-Bu dicarbonate electrophilically through formation of a bifurcated hydrogen bond with the C-2 hydrogen of the imidazolium cation; the role of the C2 proton in catalysis is supported by the change in the ¹H NMR shift of the imidazolium C-2 hydrogen of I from δ 8.39 to δ 8.66 in the presence of Boc₂O and by the significantly reduced activities of analogous 1-butyl-2,3-dimethylimidazolium ionic liquids lacking C-2 hydrogens. Alkylamines are tert-butoxycarbonylated more rapidly than aromatic amines, allowing the chemoselective protection of the benzylamine moiety of 4-aminobenzylamine; Boc protection of piperidine and 1-piperidineethanamine in the presence of I yields a 62:38 mixture of the Boc piperidine and tert-Bu piperidineethylcarbamate. The efficiencies of the Boc protection of 3-chloro-4-fluoroaniline in the presence of I and in the presence of Lewis acids (from literature references) are compared. In the experiment, the researchers used many compounds, for example, tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6Application of 18437-66-6).

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. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control.Application of 18437-66-6

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

Metabolism of SKLB-TB1001, a potent antituberculosis agent, in animals was written by Xiong, Lu;Gao, Chao;Shi, Yao-Jie;Tao, Xin;Peng, Cui-Ting;Rong, Juan;Liu, Kun-Lin;Lei, Qian;Zhang, Yi-Wen;Wang, Ning-Yu;Yu, Luo-Ting. And the article was included in Antimicrobial Agents and Chemotherapy in 2018.Name: 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid This article mentions the following:

Tuberculosis is a major global health problem, and the emergence of multidrug-resistant and extensively drug-resistant strains has increased the difficulty of treating this disease. Among the novel antituberculosis drugs in the pipeline, decaprenylphosphoryl-beta-D-ribose-2-epimerase (DprE1) inhibitors such as BTZ043 and pBTZ169 exhibited extraordinary antituberculosis potency. Here, the metabolites of the new DprE1 inhibitor SKLB-TB1001 in vivo and its inhibition of cytochrome P 450 isoforms and plasma protein binding (PPB) in vitro were studied. The results showed that rapid transformation and high PPB resulted in inadequate exposure in vivo and thus led to the moderate potency of SKLB-TB1001 in vivo. This study provided explanations for the discrepant potency of this scaffold in vivo and in vitro. Meanwhile, it also provides a rationale for lead optimization of this very promising scaffold of antituberculosis agents to prevent them from being metabolized, thus improving their exposure in vivo. In the experiment, the researchers used many compounds, for example, 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4Name: 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid).

2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4) 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.Name: 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid

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

Borylfuroxans: Synthesis and Applications was written by Xie, Weibin;Hayashi, Masahiko;Matsubara, Ryosuke. And the article was included in Organic Letters in 2021.COA of Formula: C19H15Cl This article mentions the following:

Herein the authors report the 1st synthesis of borylfuroxans via the reaction of sulfonylfuroxans with Lewis base-ligated boranes under radical conditions. As a synthetic application, the transformation of borylfuroxans to a range of 1,2-dioximes and their derivatives is demonstrated. In the experiment, the researchers used many compounds, for example, (Chloromethanetriyl)tribenzene (cas: 76-83-5COA of Formula: C19H15Cl).

(Chloromethanetriyl)tribenzene (cas: 76-83-5) 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. 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.COA of Formula: C19H15Cl

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

Kinetics of Oxidation of 4-Oxoacids by N-Chlorosaccharin in Aqueous Acetic Acid Medium was written by Farook, N. A. Mohamed. And the article was included in Journal of Solution Chemistry in 2007.Recommanded Product: 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide This article mentions the following:

The oxidation kinetics of substituted and unsubstituted 4-oxoacids (S) by N-chlorosaccharin (NCSA) have been studied in aqueous acetic acid media. The reaction follows first-order kinetics in each of the 4-oxoacids, NCSA and H⁺. The effect of changes in the electronic nature of the substrate reveals that pos. charge develops in the transition state. Based on the kinetic results and product anal., a suitable mechanism has been proposed for the reaction of NCSA with 4-oxoacids. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 14070-51-0Recommanded Product: 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide).

2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 14070-51-0) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Recommanded Product: 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide

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

Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides was written by Kanyiva, Kyalo Stephen;Uchida, Kanako;Shibata, Takanori. And the article was included in Bulletin of the Chemical Society of Japan in 2021.Category: chlorides-buliding-blocks This article mentions the following:

We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound The mechanism studies are conducted using radical scavengers and deuterated toluene. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)benzene-1-sulfonyl chloride (cas: 777-44-6Category: chlorides-buliding-blocks).

3-(Trifluoromethyl)benzene-1-sulfonyl chloride (cas: 777-44-6) 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. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Category: chlorides-buliding-blocks

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

T3P mediated intramolecular rearrangement of o-aminobenzamide to o-ureidobenzonitrile using isothiocyanates was written by Shamanth, Sadashivamurthy;Nagarakere, Sandhya C.;Sagar, Kunigal S.;Narayana, Yatheesh;Mamatha, Mahesha;Rangappa, Kanchugarakoppal S.;Kempegowda, Mantelingu. And the article was included in Synthetic Communications in 2021.COA of Formula: C7H3Cl2NS This article mentions the following:

Current work describes the environmentally benign approach for the synthesis of o-ureidobenzonitriles, from o-aminobenzamides and isothiocyanates using T3P. Here, the conversion of thiourea to urea and amide to nitrile take place simultaneously via unprecedented intramol. rearrangement. This protocol is operationally facile and offers wide variety of o-ureidobenzonitriles at room temperature in good to excellent yields. In the experiment, the researchers used many compounds, for example, 2,4-Dichlorophenylisothiocyanate (cas: 6590-96-1COA of Formula: C7H3Cl2NS).

2,4-Dichlorophenylisothiocyanate (cas: 6590-96-1) 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. 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.COA of Formula: C7H3Cl2NS

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

The potential transformation mechanisms of the marker components of Schizonepetae Spica and its charred product was written by Liu, Xindan;Zhang, Ying;Wu, Menghua;Ma, Zhiguo;Cao, Hui. And the article was included in Molecules in 2020.Category: chlorides-buliding-blocks This article mentions the following:

Schizonepetae Spica (SS) is commonly used for treating colds, fevers, bloody stool and metrorrhagia in China. To treat colds and fevers, traditional Chinese medicine doctors often use raw SS, while to treat bloody stool and metrorrhagia, they usually use Schizonepetae Spica Carbonisata (SSC; raw SS processed by stir-frying until carbonization). However, there have been limited investigations designed to uncover the mechanism of stir-fry processing. In the present study, a method combining gas chromatog.-mass spectrometry (GC-MS) and high-performance liquid chromatog. (HPLC) was developed for the comprehensive anal. of the chem. profiles of SS and SSC samples. Principal component anal. of the GC-MS data demonstrated that there were 16 significant differences in volatile compounds between the SS and SSC samples. The simultaneous quantification of six nonvolatile compounds was also established based on HPLC, and remarkable differences were found between the two products. These changes were probably responsible for the various pharmacol. effects of SS and SSC as well as the observed hepatotoxicity. Finally, the mechanisms could be rationalized by deducing possible reactions involved in the transformation of these marker components. This work reports a new strategy to reveal the chem. transformation of SS during stir-fry processing. In the experiment, the researchers used many compounds, for example, 1-Chlorooctadecane (cas: 3386-33-2Category: chlorides-buliding-blocks).

1-Chlorooctadecane (cas: 3386-33-2) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control.Category: chlorides-buliding-blocks

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

Discovery of a Potent and Highly Selective Dipeptidyl Peptidase IV and Carbonic Anhydrase Inhibitor as “Antidiabesity” Agents Based on Repurposing and Morphing of WB-4101 was written by Artasensi, Angelica;Angeli, Andrea;Lammi, Carmen;Bollati, Carlotta;Gervasoni, Silvia;Baron, Giovanna;Matucci, Rosanna;Supuran, Claudiu T.;Vistoli, Giulio;Fumagalli, Laura. And the article was included in Journal of Medicinal Chemistry in 2022.Electric Literature of C19H15Cl This article mentions the following:

The management of patients with type 2 diabetes mellitus (T2DM) is shifting from cardio-centric to weight-centric or, even better, adipose-centric treatments. Considering the downsides of multidrug therapies and the relevance of dipeptidyl peptidase IV (DPP IV) and carbonic anhydrases (CAs II and V) in T2DM and in the weight loss, we report a new class of multitarget ligands targeting the mentioned enzymes. We started from the known α₁-AR inhibitor WB-4101, which was progressively modified through a tailored morphing strategy to optimize the potency of DPP IV and CAs while losing the adrenergic activity. The obtained compound 12 (I) shows a satisfactory DPP IV inhibition with a good selectivity CA profile (DPP IV IC₅₀: 0.0490μM; CA II K_i 0.2615μM; CA VA K_i 0.0941μM; CA VB K_i 0.0428μM). Furthermore, its DPP IV inhibitory activity in Caco-2 and its acceptable pre-ADME/Tox profile indicate it as a lead compound in this novel class of multitarget ligands. In the experiment, the researchers used many compounds, for example, (Chloromethanetriyl)tribenzene (cas: 76-83-5Electric Literature of C19H15Cl).

(Chloromethanetriyl)tribenzene (cas: 76-83-5) 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. Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.Electric Literature of C19H15Cl

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

Nitration of 6-hydroxynicotinic acid and related compounds was written by Berrie, A. H.;Newbold, G. T.;Spring, F. S.. And the article was included in Journal of the Chemical Society in 1951.Related Products of 59237-53-5 This article mentions the following:

The following study is a part of a projected synthesis of lysergic acid. 6-Hydroxynicotinic acid (I) (50 g.) in 500 cc. HNO₃ (d. 1.52), kept 4 hrs. at 45-50°, gives 20 g. 5-nitro derivative (II), yellow, m. 278° (decomposition), absorption maximum at 2110 and 3600 A. (ε 19,200 and 7900); Me ester, pale yellow, m. 206°, 65%; Et ester, pale yellow, m. 165-7°. I (2 g.) in 20 cc. HNO₃ (d. 1.52), refluxed 30 hrs., gives 1 g. 3,5-dinitro-2(1H)-pyridone (III), yellow, m. 175°, absorption maximum at 2140 and 3260 A. (ε 13,400 and 11,400); 1 g. II and 10 cc. HNO₃, heated 30 hrs., give 0.5 g. III; 0.92 g. 2-amino-3,5-dinitropyridine and HNO₂ and later, NaOH, give 0.8 g. III; 1 g. 3-nitro-2(1H)-pyridone, refluxed 2 hrs. with HNO₃, gives 0.3 g. III; 5-nitro-2(1H)-pyridone yields 38% III. 1,6-Dihydro-6-oxo-1-methylnicotinic acid (IV) (3.06 g.) and 30.6 cc. HNO₃ (d. 1.52), heated 5 hrs. at 50-5°, evaporated to dryness, and crystallized from H₂O, gave 2.0 g. 1-methyl-3,5-dinitro-2(1H)-pyridone (V), pale yellow, m. 178°, absorption maximum at 2080, 2180, and 3100 A. (ε 20,600, 19,100, and 12,700); acidification of the filtrate (concentrated HCl) gives 15.8% of the 5-NO₂ derivative (VI) of IV, yellow, m. 217-22°, absorption maximum at 2180 and 3640 A. (ε 18,100 and 6600); Me ester, yellow, m. 147-9°; Et ester, pale yellow, m. 124°. IV (3.06 g.) and 30.6 g. HNO₃ (d. 1.52), refluxed 5 hrs., give 2 g. V; 0.25 g. VI and HNO₃, refluxed 4 hrs., give 0.2 g. V. 1-Methyl-3-nitro-2(1H)-pyridone (0.7 g.) and HNO₃, refluxed 2 hrs., give 0.3 g. V; 0.7 g. of the 5-NO₂ isomer yields 0.3 g. V; 0.92 g. III and 0.28 g. KOH in 10 cc. H₂O, evaporated to dryness and heated 3 hrs. at 120° with MeI in MeOH, give 0.5 g. V. II (1.84 g.), heated 20 hrs. at 100° with 10 cc. PBr₃ and 6.4 g. Br and the bromide decomposed with 20 cc. MeOH, gives 1.6 g. Me 6-bromo-5-nitronicotinate (VII), pale yellow, m. 98°; Et ester, pale yellow, m. 85°. II (0.92 g.), heated 2 hrs. at 100° with PCl₅, and POCl₃, gives 0.92 g. of the 6-Cl analog of VII, pale yellow, m. 76°; Et ester, m. 61°, 44%. III(0.92 g.),1.5 g. PCl₅, and 2 cc. POCl₃, heated 2 hrs. at 120°, give 0.5 g. 2-chloro-3,5-dinitropyridine, m. 64.5°. 2-Amino-5-chloro-3-nitropyridine (1.25 g.) in 4 cc. H₂SO₄ (d. 1.84) and 2.5 cc. H₂O, treated with I g. NaNO₂ (below 10°), stirred 1 hr., diluted with 25 cc. H₂O, and kept overnight at 0°, gives 1.18 g. 5-chloro-3-nitro-2(1H)-pyridone (VIII), yellow, m. 235°; 1.75 g. VIII in 10 cc. 6% aqueous KOH, evaporated to dryness and heated 2 hrs. with 4 g. MeI in 10 cc. EtOH, gives 0.5 g. of the 1-Me derivative of VIII, pale yellow, m. 126°. 2-Amino-5-nitropyridine (1.39 g.) in 100 cc. EtOH, treated (ice cooling) with 0.71 g. Cl, gives 0.85 g. 2-amino-3-chloro-5-nitropyridine (IX), pale yellow, m. 211-13°. IX (0.35 g.) through the diazo reaction in H₂SO₄ gives 0.2 g. 3-chloro-5-nitro-2(1H)pyridone (X), pale yellow, m. 198°. V (1 g.), 3 g. PCl₅, and 2 cc. POCl₃, heated 4 hrs. at 150°, give 0.5 g. unchanged V and 0.2 g. 3-chloro-1-methyl-5-nitro-2(1H)-pyridone (XI), pale yellow, m. 115°; 0.99 g. V and 5 cc. SOCl₂, heated 5 hrs. at 140-50°, give 0.25 g. unchanged V and 0.4 g. XI; the K compound from 1.75 g. X, MeI, and EtOH, boiled 2 hrs., give 1.5 g. XI. 3-Nitro-2(1H)-pyridone (1.4 g.) in 10 cc. hot 5% NaOH gives 0.9 g. Na 3-nitro-2-pyridyl oxide (XII), with I mol. H₂O, yellow, m. 340°, absorption maximum at 2580 and 3600 A. (ε 2400 and 6600). Na 5-nitro-2-pyridyl oxide, with 3 mols. H₂O, yellow, m. 303° (decomposition), absorption maximum at 2060 and 3020 A. (ε 9100 and 10,500); Na 3,5-dinitro-2-pyridyl oxide (XIII), with 2 mols. H₂O, m. 298° (decomposition), absorption maximum at 2100 and 3260 A. (ε 13,600 and 10,100); these 3 Na salts decompose violently when heated. Nitration of 2(1H)-pyridone by the method of Chichibabin and Shapiro (C.A. 18, 2394) gives a compound m. 286° (decomposition), believed to be a mixture of XII and XIII; further nitration gives a good yield of III. In the experiment, the researchers used many compounds, for example, Methyl 6-chloro-5-nitronicotinate (cas: 59237-53-5Related Products of 59237-53-5).

Methyl 6-chloro-5-nitronicotinate (cas: 59237-53-5) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Alkyl chlorides are versatile building blocks in organic chemistry. While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available.Related Products of 59237-53-5

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

Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane was written by Cortez, Norma A.;Aguirre, Gerardo;Parra-Hake, Miguel;Somanathan, Ratnasamy. And the article was included in Tetrahedron: Asymmetry in 2008.Quality Control of 4-Butoxybenzene-1-sulfonyl chloride This article mentions the following:

A series of aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane were synthesized with electron withdrawing and donating groups. These were complexed with Rh(Cp^*) or Ru(arene) and their catalytic efficiencies were compared in the ATH of acetophenone using sodium formate/water or isopropanol/KOH as the hydrogen source. Results suggest that substituents on the benzene ring of the sulfonamide have very little electronic impact on the enantioselectivity and mechanism of the reaction. In the experiment, the researchers used many compounds, for example, 4-Butoxybenzene-1-sulfonyl chloride (cas: 1138-56-3Quality Control of 4-Butoxybenzene-1-sulfonyl chloride).

4-Butoxybenzene-1-sulfonyl chloride (cas: 1138-56-3) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators.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.Quality Control of 4-Butoxybenzene-1-sulfonyl chloride

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