Month: October 2022

The author of 《A Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist》 were Douglas, James J.; Albright, Haley; Sevrin, Martin J.; Cole, Kevin P.; Stephenson, Corey R. J.. And the article was published in Angewandte Chemie, International Edition in 2015. Safety of Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate The author mentioned the following in the article:

In the presence of Ru(bpy)3Cl2 (bpy = 2,2′-bipyridine), 2-bromo-2,2-difluoroethyl arylsulfonates (and a styrenesulfonate) such as bromodifluoroethoxysulfonylthiophenecarboxylate I underwent chemoselective photochem. Smiles rearrangements mediated by Bu3 and HCO2H in DMSO to yield β-aryl-β,β-difluoroethanols such as II in 24-94% yields; a pyridinesulfonate and a chloropyrazolesulfonate were ineffective substrates in the photochem. Smiles rearrangement. Using the method, I was converted to the ORL-1 receptor antagonist III•HCl in five steps; the photochem. step could be conducted on 15 g scale using 0.01 mol% of the ruthenium catalyst, and the overall route compares favorably to the current synthetic sequence for III. The bromodifluoroethyl esters were prepared in two steps from Et bromodifluoroacetate via reduction to 2-bromo-2,2-difluoroethanol which was prepared on 40 g scale. 2-Bromo-2,2-difluoroethanol is volatile and a lachrymator and should be handled in a hood, and the photochem. Smiles rearrangements generate toxic SO2 gas as a byproduct. In the experiment, the researchers used Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate(cas: 306936-53-8Safety of Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate)

Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate(cas: 306936-53-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Safety of Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate

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

The author of 《Bio-potent sulfonamides》 were Dineshkumar, Selvakumar; Thirunarayanan, Ganesamoorthy. And the article was published in Journal of the Chilean Chemical Society in 2019. Name: 4-Chlorobenzenesulfonyl chloride The author mentioned the following in the article:

Some 4-(substituted phenylsulfonamido)benzoic acids have been synthesized by fly-ash:H3PO3 nano catalyst catalyzed condensation of substituted benzenesulfonyl chlorides and 4-aminobenzoic acid in ultrasound irradiation conditions. The yields of the sulfonamides are more than 90%. The synthesized 4-(substituted phenylsulfonamido) benzoic acid derivatives were characterized by their phys. constants, anal. and spectroscopic data. Antimicrobial activities of all sulfonamides were measured by Bauer-Kirby disk diffusion method. After reading the article, we found that the author used 4-Chlorobenzenesulfonyl chloride(cas: 98-60-2Name: 4-Chlorobenzenesulfonyl chloride)

4-Chlorobenzenesulfonyl chloride(cas: 98-60-2) belongs to organochlorine compounds. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.Name: 4-Chlorobenzenesulfonyl chloride

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

SDS of cas: 5781-53-3In 2022 ,《Chiral phosphoric acid-catalyzed enantioselective synthesis of pyrazole-based unnatural α-amino acid derivatives》 appeared in Advanced Synthesis & Catalysis. The author of the article were Woldegiorgis, Alemayehu Gashaw; Han, Zhao; Lin, Xufeng. The article conveys some information:

An enantioselective synthesis of unnatural pyrazole-based α-chiral amino acid derivatives from the asym. reaction of N-aryl-5-aminopyrazoles with β,γ-alkynyl-α-imino esters using a chiral spirocyclic phosphoric acid catalyst was developed. Using the established methodol., various pyrazole-based α-amino acid derivatives with tetrasubstituted carbon stereocenters were obtained in 67-98% yields and with 73-99% enantioselectivities. The NH2 functionality in the corresponding products enables further transformations to a chiral thiourea and a lactam.Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3SDS of cas: 5781-53-3) was used in this study.

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1.SDS of cas: 5781-53-3

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

SDS of cas: 172222-30-9In 2022 ,《Four Stereoisomeric Norbornadiene Dimers Containing a Cyclopropane Ring: ROMP, Polymer Properties, and Post-Polymerization Modification》 was published in Macromolecules (Washington, DC, United States). The article was written by Hase, Kazuki; Matsuoka, Shin-ichi; Suzuki, Masato. The article contains the following contents:

The efficient and selective introduction of functional groups to hydrocarbon polymers enables facile access to new polymer materials with various phys. properties. In the present study, we have focused on cyclopropane-containing norbornadiene dimers (NBDDs) as bifunctional monomers and post-polymerization modification (PPM) for the synthesis of functionalized cyclic olefin polymers (COPs). The ring-opening metathesis polymerization (ROMP) of the four NBDD stereoisomers (exo-exo, exo-endo, endo-exo, and endo-endo) and the subsequent hydrogenation proceeded selectively to give the corresponding COPs (H-poly(NBDD)s) with reactive cyclopropane moieties. There are distinct differences between the four isomers in terms of polymerization rate and the phys. properties of the resultant polymers. The endo-exo- and endo-endo-NBDDs show lower ROMP reactivities than the exo-exo- and exo-endo-NBDDs due to steric hindrance. All of the polymers before and after hydrogenation are amorphous, regardless of annealing (with the exception for the unannealed H-poly(exo-endo-NBDD)). Compared with the polymers of the exo-norbornenyl isomers, their endo-counterparts show lower solubilities, higher glass transition temperatures, sharper X-ray diffraction peaks, and larger d-spacings. The highly soluble H-poly(exo-exo-NBDD) was employed for the PPM via protic acid-catalyzed cyclopropane ring-opening to produce six new COPs bearing acyloxy, alkoxy, or aryl groups. Although rearrangements occur during ring-opening presumably through nonclassical carbocations, the polymer structures were determined with reference to the reactions of their corresponding monomeric model compounds The PPM with m-xylene, for example, proceeds regioselectively while maintaining a narrow mol. weight distribution to produce a xylyl-substituted COP with good solubility and high thermal stability. After reading the article, we found that the author used Benzylidenebis(tricyclohexylphosphine)dichlororuthenium(cas: 172222-30-9SDS of cas: 172222-30-9)

Benzylidenebis(tricyclohexylphosphine)dichlororuthenium(cas: 172222-30-9) is the first metathesis catalyst to be widely used in organic synthesis. It is useful for acyclic diene metathesis polymerization (ADMET), Ring-Opening Metathesis Polymerization (ROMP) of strained cyclic olefins, ring opening metathesis (ROM), and so on.SDS of cas: 172222-30-9

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

《Microwave-assisted organic acid-base-co-catalyzed tandem Meinwald rearrangement and annulation of styrylepoxides》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Shi, Yi; Li, Siqi; Lu, Yang; Zhao, Zizhen; Li, Pingfan; Xu, Jiaxi. HPLC of Formula: 139502-80-0 The article mentions the following:

A novel organic acid-base-co-catalyzed conversion of styrylepoxides I [R = Ph, 2,3-dichlorophenyl, 3-(trifluoromethyl)phenyl, etc.; R1 = H, Me] into [1,1′-biaryl]-3-carbaldehydes 3-RC6H4CHO was realized under microwave irradiation Styrylepoxides I first underwent an acid-catalyzed Meinwald rearrangement followed by a tandem base-catalyzed Michael addition, aldol addition, and aromatization sequence to generate [1,1′-biaryl]-3-carbaldehydes. The experimental process involved the reaction of 4′-Chloro-[1,1′-biphenyl]-3-carbaldehyde(cas: 139502-80-0HPLC of Formula: 139502-80-0)

4′-Chloro-[1,1′-biphenyl]-3-carbaldehyde(cas: 139502-80-0) 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.HPLC of Formula: 139502-80-0

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

《Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis》 was published in Chemical Communications (Cambridge, United Kingdom) in 2021. These research results belong to Zhao, Xian; Zhu, Shengqing; Qing, Feng-Ling; Chu, Lingling. Quality Control of 3-Chlorobenzylchloride The article mentions the following:

A photoredox/nickel dual catalyzed reductive hydrobenzylation of alkynes and benzyl chlorides by employing alkyl amines as a stoichiometric reductant is described. This synergistic protocol proceeds via Markovnikov-selective migratory insertion of an alkyne into nickel hydride, followed by cross-coupling with benzyl chloride, providing facile access to important 1,1-disubstituted olefins. This reaction enables the generation of nickel hydride by utilizing readily available alkyl amines as the hydrogen source. The mild conditions are compatible with a wide range of aryl and alkyl alkynes as well as chlorides.3-Chlorobenzylchloride(cas: 620-20-2Quality Control of 3-Chlorobenzylchloride) was used in this study.

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.Quality Control of 3-Chlorobenzylchloride

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

Computed Properties of C8H6Cl2O3On March 31, 2002, Kousaka, Takeshi; Mori, Kenji published an article in Bioscience, Biotechnology, and Biochemistry. The article was 《Synthesis of (1R,2S)-1-(3′-Chloro-4′-methoxyphenyl)-1,2-propanediol (Trametol) and (1R,2S)-1-(3′,5′-dichloro-4′-methoxyphenyl)-1,2-propanediol, chlorinated fungal metabolites in the natural environment》. The article mentions the following:

(1R,2S)-1-(3′-Chloro-4′-methoxyphenyl)-1,2-propanediol (trametol), a metabolite of the fungus Trametes sp. IVP-F640 and Bjerkandera sp. BOS55, was synthesized by employing Sharpless asym. dihydroxylation as the key step. Similarly, the (1R,2S)-isomer of 1-(3′,5′-dichloro-4′-methoxyphenyl)-1,2-propanediol, another metabolite of Bjerkandera sp. BOS55, was synthesized by asym. dihydroxylation. The experimental process involved the reaction of 3,5-Dichloro-4-methoxybenzoic acid(cas: 37908-97-7Computed Properties of C8H6Cl2O3)

3,5-Dichloro-4-methoxybenzoic acid(cas: 37908-97-7) belongs to organochlorine compounds. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. 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.Computed Properties of C8H6Cl2O3

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

Quality Control of Ethyl 3-(4-chlorophenyl)propanoateOn November 4, 1998 ,《Ni(II)-Catalyzed Cross-Coupling between Polyfunctional Arylzinc Derivatives and Primary Alkyl Iodides》 appeared in Journal of the American Chemical Society. The author of the article were Giovannini, Riccardo; Knochel, Paul. The article conveys some information:

A novel nickel-catalyzed coupling reaction of arylzinc bromides ArZnBr (Ar = Ph, 4-ClC6H4, 4-MeOC6H4, 4-NCC6H4, 3-EtO2CC6H4, 2-EtO2CC6H4), generated from the aryl iodides, and functionalized primary alkyl iodides R(CH2)nI (n = 2,3,5; R = Me3CCOO, 2-methyl-1,3-dithiolanyl, EtO2C, BuCO, PhS, (CH2)5NCO) to give aralkyl derivative Ar(CH2)nR in 71-80% yield. Arylzinc bromides are generated from aryl iodides by either treatment of the iodide with Me2CHMgBr in THF followed by addition of ZnBr2 to the Grignard reagent, or by treatment of the aryl iodide with BuLi and addition of ZnBr2. E.g., 4-cyanophenylzinc bromide is formed by transmetalation of 4-NCC6H4I at -90° with BuLi in THF and addition of ZnBr2; the arylzinc bromide was then concentrated and added to a THF solution containing 10 mol% Ni(acac)2, 1 equivalent 4-F3CC6H4CH:CH2, and 1 equivalent Me(SCH2CH2S)CH2CH2I to give I in 80% yield. The absence of 4-F3CC6H4CH:CH2 leads to formation of products formed form homocoupling and zinc-iodine transmetalation of the alkyl iodides. The coupling tolerates ketone, amide, ester, and nitrile functionality and allows coupling of sp2-aryl and sp3-alkyl groups fro which few coupling methods exist. After reading the article, we found that the author used Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1Quality Control of Ethyl 3-(4-chlorophenyl)propanoate)

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. Quality Control of Ethyl 3-(4-chlorophenyl)propanoate 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.

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

In 2022,International Journal of Molecular Sciences included an article by Pla-Lopez, Alberto; Castillo, Raquel; Cejudo-Marin, Rocio; Garcia-Pedrero, Olaya; Bakir-Laso, Mariam; Falomir, Eva; Carda, Miguel. Safety of 3-Chlorobenzylchloride. The article was titled 《Synthesis and Biological Evaluation of Small Molecules as Potential Anticancer Multitarget Agents》. The information in the text is summarized as follows:

Twenty-six triazole-based derivatives were designed for targeting both PD-L1 (programmed death receptor ligand 1) and VEGFR-2 (vascular endothelial growth factor receptor 2). These compounds were synthesized and biol. evaluated as multitarget inhibitors of VEGFR-2, PD-L1 and c-Myc proteins. The antiproliferative activity of these mols. on several tumor cell lines (HT-29, A-549, and MCF-7) and on the non-tumor cell line HEK-293 was determined The effects on the abovementioned biol. targets were evaluated for some selected compounds Compound I, bearing a p-chlorophenyl group, showed better results than sorafenib in regard to the downregulation of VEGFR-2 and a similar effect to BMS-8 on both PD-L1 and c-Myc proteins. The antiangiogenic and antivascular activities of chloro derivatives were also established by endothelial microtube formation assay on Matrigel. After reading the article, we found that the author used 3-Chlorobenzylchloride(cas: 620-20-2Safety of 3-Chlorobenzylchloride)

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.Safety of 3-Chlorobenzylchloride

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

Iwanowicz, Edwin J.; Watterson, Scott H.; Guo, Junqing; Pitts, William J.; Murali Dhar, T. G.; Shen, Zhongqi; Chen, Ping; Gu, Henry H.; Fleener, Catherine A.; Rouleau, Katherine A.; Cheney, Daniel L.; Townsend, Robert M.; Hollenbaugh, Diane L. published an article in Bioorganic & Medicinal Chemistry Letters. The title of the article was 《Inhibitors of inosine monophosphate dehydrogenase: SARs about the N-[3-Methoxy-4-(5-oxazolyl)phenyl] moiety》.Recommanded Product: 39183-20-5 The author mentioned the following in the article:

The first reported structure-activity relationships (SARs) about the N-[3-methoxy-4-(5-oxazolyl)phenyl] moiety for a series of recently disclosed inosine monophosphate dehydrogenase (IMPDH) inhibitors are described. The syntheses and in vitro inhibitory values for IMPDH II, and T-cell proliferation (for select analogs) are given. The results came from multiple reactions, including the reaction of 2-Methyl-5-nitro-6-chlorophenol(cas: 39183-20-5Recommanded Product: 39183-20-5)

2-Methyl-5-nitro-6-chlorophenol(cas: 39183-20-5) 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.Recommanded Product: 39183-20-5

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