Tag: 100-200

Design and Performance Validation of a Conductively Heated Sealed-Vessel Reactor for Organic Synthesis was written by Obermayer, David;Znidar, Desiree;Glotz, Gabriel;Stadler, Alexander;Dallinger, Doris;Kappe, C. Oliver. And the article was included in Journal of Organic Chemistry in 2016.SDS of cas: 3438-16-2 This article mentions the following:

A newly designed robust and safe laboratory scale reactor for syntheses under sealed-vessel conditions at 250° maximum temperature and 20 bar maximum pressure is presented. The reactor uses conductive heating of a sealed glass vessel via a stainless steel heating jacket and implements both online temperature and pressure monitoring in addition to magnetic stirring. Reactions are performed in 10 mL borosilicate vials that are sealed with a silicone cap and Teflon septum and allow syntheses to be performed on a 2-6 mL scale. This conductively heated reactor is compared to a standard single-mode sealed-vessel microwave instrument with respect to heating and cooling performance, stirring efficiency, and temperature and pressure control. Importantly, comparison of the reaction outcome for a number of different synthetic transformations performed side by side in the new device and a standard microwave reactor suggest that results obtained using microwave conditions can be readily mimicked in the operationally much simpler and smaller conventionally heated device. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2SDS of cas: 3438-16-2).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) 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. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).SDS of cas: 3438-16-2

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

Scandium triflate-catalyzed transesterification of carboxylic esters was written by Remme, Nicole;Koschek, Katharina;Schneider, Christoph. And the article was included in Synlett in 2007.Safety of Methyl 2-chloro-2-phenylacetate This article mentions the following:

The direct transesterification of carboxylic esters is efficiently catalyzed with Sc(OTf)₃ (10 mol%) in boiling alc. solvent. Me, Et, iso-Pr, and allyl esters were prepared from a broad range of different substrates in high yields. The application of microwave irradiation led to significantly reduced reaction times. In the experiment, the researchers used many compounds, for example, Methyl 2-chloro-2-phenylacetate (cas: 7476-66-6Safety of Methyl 2-chloro-2-phenylacetate).

Methyl 2-chloro-2-phenylacetate (cas: 7476-66-6) 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. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Safety of Methyl 2-chloro-2-phenylacetate

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

Electrophilic fluorination of N,N-dimethylaniline, N,N-dimethylnaphthalen-1-amine and 1,8-bis(dimethylamino)naphthalene with N-F reagents was written by Sorokin, Vladimir I.;Pozharskii, Alexander F.;Ozeryanskii, Valery A.. And the article was included in Journal of Fluorine Chemistry in 2013.Safety of 2-Chloro-N,N-dimethylaniline This article mentions the following:

Reaction of N,N-dimethylaniline, N,N-dimethylnaphthalen-1-amine and 1,8-bis(dimethylamino)naphthalene (proton sponge) with 1-chloromethyl-4-fluorodiazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) and N-fluorobenzenesulfonimide (NFSI) has been studied under various conditions. Unlike the proton sponge, which is fluorinated rather selectively at the ortho-position to NMe₂ group, producing 2-fluoro derivatives in moderate yield, two other amines react with Selectfluor and NFSI with strong tarring and the formation of complex mixtures of the corresponding biaryls, biarylmethanes and N-demethylated products. 2-Fluoro and 4-fluoro derivatives are also formed in minor quantities with the former isomer being predominant. Using the NFSI-ZrCl₄ system results in competitive chlorination of the aromatic ring. In the experiment, the researchers used many compounds, for example, 2-Chloro-N,N-dimethylaniline (cas: 698-01-1Safety of 2-Chloro-N,N-dimethylaniline).

2-Chloro-N,N-dimethylaniline (cas: 698-01-1) 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. 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.Safety of 2-Chloro-N,N-dimethylaniline

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

Synthesis and antitumor activity of novel 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives was written by Liu, Fang;Huai, Ziyou;Xia, Guotai;Song, Liuping;Li, Sha;Xu, Yulan;Hong, Kangjun;Yao, Mingyue;Liu, Gang;Huang, Yinjiu. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2018.Category: chlorides-buliding-blocks This article mentions the following:

A series of 6,7,8-trimethoxy-N-aryl-substituted-4-aminoquinazoline derivatives, e.g., I, were synthesized as epidermal growth factor receptor (EGFR) inhibitors, and their antitumor activities were assessed in the gastric cancer cell line SGC7901 using MTT assay. All compounds were found to inhibit SGC7901 cell proliferation, and compound I (IC₅₀ = 0.434 μM) was found to be slightly more effective against SGC7901 cells than epirubicin (IC₅₀ = 5.16 μM). This suggests that compound I can be used as a new substitution structure to develop more efficacious antitumor agents. Western blot anal. showed that treatment with I (40 μM for 30 min) resulted in near complete inhibition of EGF-induced ERK1/2 phosphorylation, indicating that its anti-proliferative effect is largely associated with inhibition of ERK1/2 activation. These data imply that I is a potential anticancer agent capable of inhibiting cell proliferation. In the experiment, the researchers used many compounds, for example, 3-Chloro-2,4-difluoroaniline (cas: 2613-34-5Category: chlorides-buliding-blocks).

3-Chloro-2,4-difluoroaniline (cas: 2613-34-5) 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. 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.Category: chlorides-buliding-blocks

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

Cyclopropanation via the Michael addition was written by Nishiyama, Kazuyoshi;Oda, Junichi;Inouye, Yuzo. And the article was included in Bulletin of the Institute for Chemical Research, Kyoto University in 1974.Application of 7476-66-6 This article mentions the following:

RCH2R1 (R = Ph, R1 = CN) and CH2:C[OP(O)(OMe)2]CO2Me (I) in DMF containing NaH gave cis- and trans-II (R = Ph, R1 = CN) via the RC-R1CH2CH[OP(O)(OMe)2]CO2Me (R = Ph, R1 = CN) intermediate which was formed from the initial Michael adduct, RCHR1CH2C-[OP(O)(OMe)2]CO2Me. The reaction of PhCH2CO2Me with I to give II (R = Ph, R1 = CO2Me) proceeded by the same mechanism. In the experiment, the researchers used many compounds, for example, Methyl 2-chloro-2-phenylacetate (cas: 7476-66-6Application of 7476-66-6).

Methyl 2-chloro-2-phenylacetate (cas: 7476-66-6) 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. 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.Application of 7476-66-6

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

Alkyne Linchpin Strategy for Drug:Pharmacophore Conjugation: Experimental and Computational Realization of a Meta-Selective Inverse Sonogashira Coupling was written by Porey, Sandip;Zhang, Xinglong;Bhowmick, Suman;Kumar Singh, Vikas;Guin, Srimanta;Paton, Robert S.;Maiti, Debabrata. And the article was included in Journal of the American Chemical Society in 2020.Product Details of 620-19-9 This article mentions the following:

The late-stage functionalization (LSF) of pharmaceutical and agrochem. compounds by the site-selective activation of C-H bonds provides access to diverse structural analogs and expands synthetically-accessible chem. space. We report a C-H functionalization LSF strategy that hinges on the use of an alkyne linchpin to assemble conjugates of sp²-rich marketed pharmaceuticals and agrochems. with sp³-rich 3D fragments and natural products. This is accomplished through a template-assisted inverse Sonogashira reaction that displays high levels of selectivity for the meta position. This protocol is also amenable to distal structural modifications of α-amino acids. The transformation of alkyne functionality to other functional groups further highlights the applicative potential. Computational and exptl. mechanistic studies shed light on the detailed mechanism. Turnover-limiting 1,2-migratory insertion of the bromoalkyne coupling partner occurs after relatively fast C-H activation. While this insertion occurs unselectively, regioconvergence results from one of the adducts undergoing a 1,2-trialkylsilyl migration to form the alkynylated product. A heterobimetallic Pd-Ag transition structure is essential for product formation in the β-bromide elimination step. In the experiment, the researchers used many compounds, for example, 1-(Chloromethyl)-3-methylbenzene (cas: 620-19-9Product Details of 620-19-9).

1-(Chloromethyl)-3-methylbenzene (cas: 620-19-9) 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. 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 620-19-9

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

Development of aqueous oxidative Ugi-type reactions by copper-catalyzed surfactant-promoted C(sp³)-H direct functionalization in water was written by Xie, Chunsong;Han, Laihong. And the article was included in Tetrahedron Letters in 2014.Synthetic Route of C8H10ClN This article mentions the following:

Direct assembly of α-amino amides from N-alkyl amines and isocyanides through oxidative Ugi-type reactions in aqueous conditions, has been achieved in a Cu(I)-TBHP-surfactant catalysis system. Various N-alkyl amines and isocyanides could be tolerated in this reaction and furnish α-amino amides in moderate yields. In the experiment, the researchers used many compounds, for example, 2-Chloro-N,N-dimethylaniline (cas: 698-01-1Synthetic Route of C8H10ClN).

2-Chloro-N,N-dimethylaniline (cas: 698-01-1) 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.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.Synthetic Route of C8H10ClN

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

Transition-metal-free persulfuration to construct unsymmetrical disulfides and mechanistic study of the sulfur redox process was written by Xiao, Xiao;Feng, Minghao;Jiang, Xuefeng. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Quality Control of 2-(Chloromethyl)-1,3-difluorobenzene This article mentions the following:

A sulfur redox process has been developed between sulfinate and thiosulfate, which efficiently affords diverse unsym. disulfides and provides a new method to modify pharmaceuticals and natural products without requiring an extra oxidant or reductant. A gram-scale investigation further demonstrates the practicality and application potential of this process. Isolated key intermediates and a series of control experiments afford an unusual process, which reveals the mechanism of comproportionation (i.e., redox reaction) and a transition-metal-free sulfur redox process. The synthesis of the target compounds was achieved using sodium thiosulfate pentahydrate (Na₂S₂O₃.5H₂O) [i.e., thiosulfuric acid (H₂S₂O₃), sodium salt, hydrate] as a starting material in addition to benzenesulfinic acid sodium salt derivatives, 4-chlorobutanenitrile, 1-chlorbutane, (chloromethyl)benzene derivatives (benzyl chloride). Other starting materials included 4-(trifluoromethyl)benzenesulfonic acid sodium salt, 2-naphthalenesulfinic acid sodium salt (naphthalene derivative), 2,5-dichloro-3-thiophenesulfinc acid sodium salt (thiophene derivative), (1S,4R)-7,7-dimethyl-2-(oxo)bicyclo[2.2.1]heptane-1-methanesulfinic acid sodium salt (camphor derivative), 17-(oxo)estra-1,3,5(10)-triene-3-sulfinic acid sodium salt (estrone derivative, estrogen). In the experiment, the researchers used many compounds, for example, 2-(Chloromethyl)-1,3-difluorobenzene (cas: 697-73-4Quality Control of 2-(Chloromethyl)-1,3-difluorobenzene).

2-(Chloromethyl)-1,3-difluorobenzene (cas: 697-73-4) 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. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Quality Control of 2-(Chloromethyl)-1,3-difluorobenzene

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

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