Tag: 200-300

Pd-Catalyzed Asymmetric Intramolecular Aryl C-O Bond Formation with SDP(O) Ligand: Enantioselective Synthesis of (2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methanols was written by Shi, Jialing;Wang, Ting;Huang, Yusha;Zhang, Xinhao;Wu, Yun-Dong;Cai, Qian. And the article was included in Organic Letters in 2015.Recommanded Product: 207115-22-8 This article mentions the following:

Employing a chiral spirodiphosphine monoxide ligand with 1,1′-spirobiindane backbone I [Ar = 3,5-di(t-Bu)C₆H₃], a desymmetrization strategy of Pd-catalyzed intramol. asym. aryl C-O coupling of 2-(2-halophenoxy)propane-1,3-diols, was developed. The ligand I shows much better results than its SDP counterpart. The protocol provides an efficient and highly enantioselective method for the synthesis of 2-hydroxymethyl-1,4-benzodioxanes, e.g. II. D. functional theory studies provide a model that accounts for the origin of the enantioselectivity. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Recommanded Product: 207115-22-8).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons鑱砈mith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Recommanded Product: 207115-22-8

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Bromination, iodination, and phenylation of thianaphthenes was written by Gaertner, Russell. And the article was included in Journal of the American Chemical Society in 1952.Product Details of 36748-88-6 This article mentions the following:

2-Bromo-3-methylthianaphthene (12.4 g.), 9.7 g. N-bromosuccinimide, and 0.4 g. (BzO)₂ in 130 cc. CCl₄ refluxed 90 min., cooled, filtered, and the CCl₄ replaced by petr. ether (70-90鎺? yielded 14.4 g. 2-bromo-3-(bromomethyl)thianaphthene (I), m. 97.6-8.6, b_0.5 148-51鎺?(decomposition). I (19.3 g.) converted in the cyclic reactor, treated with ClCO₂Et, and the product hydrolyzed (alkali) yielded a polymer, m. 200-40鎺?(decomposition); the neutral material yielded 1.2 g. 1,2-bis(2-bromo-3-thianaphthenyl)ethane, m. 195-6鎺? Conversion of 21.3 g. I and treatment with HCHO yielded a taffylike polymer. Thianaphthene (II) (44.4 g.) in 70 cc. C₆H₆ at 55-65鎺?treated during 1 hr. with 54 g. yellow HgO and 76 g. iodine, the mixture filtered, and the C₆H₆ removed in vacuo gave 15.7 g. II and 39.6 g. liquid which on chromatography on C and Al₂O₃ yielded 3-iodothianaphthene (III), b_1.6 120-1鎺? d₂₀ 1.898, n²⁰_D > 1.7. Attempted chloromethylation of III at 90 in the presence of ZnCl₂ gave III and a trace of higher-boiling material. III reacted normally with Mg. Carbonation yielded 7.4 g. 3-thianaphthenecarboxylic acid, m. 176-7.5鎺? and 1.4 g. crude material, m. 150-65鎺? II (67 g.) was converted to the Li derivative, the solution added dropwise to 252 g. iodine and 100 cc. Et₂O in an ice-salt bath, the mixture let warm to room temperature, diluted with water, the excess iodine removed, and 48.2 g. crude II recovered, leaving 37.4 g. 2-iodothianaphthene (IV), b_1.6 119-20鎺? m. 59-62鎺? Attempted chloromethylation failed. Conversion of 13 g. IV to the Grignard reagent and carbonation yielded 1.02 g. 2-thianaphthenecarboxylic acid, m. 242-3鎺? AcN(NO)Ph (25 g.) dissolved in 25 g. molten II at 32鎺?(the mixture reacted violently and about half was lost through foaming) and the unchanged II removed by distillation in vacuo yielded 10.5 g. liquid, b_0.3 150-5鎺? which on recrystallization gave 1.63 g. 2-phenylthianaphthene (V), m. 174.2-5.2鎺? V (1.00 g.) and 12 g. Raney Ni in 70 cc. EtOH heated 3 hrs. yielded 0.81 g. bibenzyl, m. 49-51鎺? The mother liquors yielded 2.5 g. of the picrate of II. Attempted preparation of the 1,1-dioxide yielded a gummy polymer. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Product Details of 36748-88-6).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Product Details of 36748-88-6

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Pd-Catalyzed Alkyne Insertion/C-H Activation/[4 + 2] Carboannulation of Alkenes to the Synthesis of Polycyclics was written by Guo, Songjin;Li, Panpan;Guan, Zhe;Cai, Libo;Chen, Siwei;Lin, Aijun;Yao, Hequan. And the article was included in Organic Letters in 2019.Recommanded Product: 289039-26-5 This article mentions the following:

An unprecedented Pd-catalyzed alkyne insertion/C-H activation/intramol. [4 + 2] carboannulation of alkenes has been reported. In this transformation, the C-H activation was triggered by an in situ generated alkenylpalladium species via the Pd-catalyzed cross-coupling reaction of aryl iodides and alkynes. Subsequently, the resulting five-membered C, C-palladacycle intermediates were added across the alkenes, providing a unique approach to access diversified polycyclics in good efficiency. Two new rings and three C-C bonds were formed in one pot. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-iodophenol (cas: 289039-26-5Recommanded Product: 289039-26-5).

2-Chloro-5-iodophenol (cas: 289039-26-5) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C閳ユ彂 bond is the weakest of the carbon閳ユ従alogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Recommanded Product: 289039-26-5

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A Putative Single-Photon Emission CT Imaging Tracer for Erythropoietin-Producing Hepatocellular A2 Receptor was written by Furukawa, Takenori;Kimura, Hiroyuki;Torimoto, Hanae;Yagi, Yusuke;Kawashima, Hidekazu;Arimitsu, Kenji;Yasui, Hiroyuki. And the article was included in ACS Medicinal Chemistry Letters in 2021.Synthetic Route of C6H4INO2 This article mentions the following:

Erythropoietin-producing hepatocellular (Eph) receptors are receptor tyrosine kinases involved in cell-cell contact. The EphA2 receptor is associated with cancer proliferation and migration. Therefore, EphA2 receptor imaging has the potential for cancer diagnosis. Here, we synthesized N-(5-((4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)carbamoyl)-2-methylphenyl)-5-[¹²³I]iodonicotinamide ([¹²³I]ETB) and evaluated it as an imaging tracer for single-photon emission computed tomog. (SPECT) imaging of the EphA2 receptor. [¹²³I]ETB was designed on the basis of ALW-II-41-27, an inhibitor of EphA2 receptor kinase. Nonradioactive ETB was also synthesized and has been shown to efficiently inhibit EphA2 receptor kinase activity in vitro (IC₅₀: ETB, 90.2 鍗?18.9 nM). A cell-binding assay demonstrated that [¹²⁵I]ETB binds specifically to the EphA2 receptor. The ex vivo biodistribution study of [¹²⁵I]ETB in U87MG tumor-bearing mice also revealed tumor uptake (2.2% ID/g at 240 min). In addition, [¹²³I]ETB uptake in tumors was visualized via SPECT/CT imaging. On the basis of the above, [¹²³I]ETB can be considered a potential SPECT imaging tracer for the EphA2 receptor. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Synthetic Route of C6H4INO2).

5-Iodonicotinic acid (cas: 15366-65-1) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C閳ユ彂 bond. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Synthetic Route of C6H4INO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Photoredox relay-catalyzed gem-difluoroallylation of alkyl iodides was written by Guo, Yuanqiang;Cao, Yunpeng;Song, Hongjian;Liu, Yuxiu;Wang, Qingmin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.SDS of cas: 10297-05-9 This article mentions the following:

Herein, a new example of relay catalysis, using a combination of Mn₂(CO)₁₀ and an iridium-based photocatalyst, is reported. In this relay catalytic reaction, the Mn catalyst and iridium-based photocatalyst catalyze the reaction at different stages in the desired sequence under the same reaction conditions, and do not inhibit each other. This convenient method transforms a broad scope of alkyl iodides RI (R = iso-Pr, cyclopentyl, 4-methoxyphenethyl, morpholino, etc.) into the corresponding gem-difluoroalkenes R¹C(=CF₂)CH₂R (R¹ = Ph, 2-naphthyl, pyridin-3-yl, etc.) via C(sp³)-C(sp³) bond construction. The protocol has good functional group tolerance and is suitable for the late-stage modification of multifunctional complex mols. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9SDS of cas: 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.SDS of cas: 10297-05-9

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Convergent syntheses of 2,3-dihydrobenzofurans via a Catellani strategy was written by Wu, Chenggui;Cheng, Hong-Gang;Chen, Ruiming;Chen, Han;Liu, Ze-Shui;Zhang, Jingyang;Zhang, Yuming;Zhu, Yuxin;Geng, Zhi;Zhou, Qianghui. And the article was included in Organic Chemistry Frontiers in 2018.Formula: C8H7IO2 This article mentions the following:

A cooperative catalytic system comprising a Pd/XPhos complex and a potassium salt of 5-norbornene-2-carboxylic acid to promote the annulation between aryl iodides and epoxides was developed, thereby providing highly convergent access to valuable 2,3-dihydrobenzofuran (DHBF) scaffolds. The unique potassium salt of the inexpensive 5-norbornene-2-carboxylic acid serves as a highly efficient catalytic mediator (10 mol%), which leads to fewer side reactions. The salient features of the reaction include its broad substrate scope (with respect to both aryl iodides and epoxides), its high atom economy and good chemo-selectivity. Furthermore, no extra base is needed for the process. In the experiment, the researchers used many compounds, for example, 3-Iodo-2-methylbenzoic acid (cas: 133232-56-1Formula: C8H7IO2).

3-Iodo-2-methylbenzoic acid (cas: 133232-56-1) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Formula: C8H7IO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Mn-Mediated Coupling of Alkyl Iodides and Chiral N-Acylhydrazones: Optimization, Scope, and Evidence for a Radical Mechanism was written by Friestad, Gregory K.;Marie, Jean-Charles;Suh, YoungSung;Qin, Jun. And the article was included in Journal of Organic Chemistry in 2006.Product Details of 10297-05-9 This article mentions the following:

Stereoselective radical additions have excellent potential as mild, nonbasic carbon-carbon bond constructions for direct asym. amine synthesis. Efficient intermol. radical addition to C:N bonds with acyclic stereocontrol has previously been limited mainly to secondary and tertiary radicals, a serious limitation from the perspective of synthetic applications. Here, we provide full details of the use of photolysis with manganese carbonyl to mediate stereoselective intermol. radical addition to N-acylhydrazones. Photolysis (300 nm) of alkyl halides and hydrazones in the presence of Mn₂(CO)₁₀ and InCl₃ as a Lewis acid led to reductive radical addition; diastereomer ratios ranged from 93:7 to 98:2 at ca. 35 鎺矯. The reaction tolerates addnl. functionality in either reactant, enabling subsequent transformations as shown in an efficient asym. synthesis of coniine. A series of hydrazones bearing different substituents on the oxazolidinone auxiliary were compared; consistently high diastereoselectivity revealed that the identity of the substituent had little practical effect on the diastereoselectivity. Further mechanistic control experiments confirmed the intermediacy of radicals and showed that independently prepared alkyl- or acyl manganese pentacarbonyl compounds do not undergo efficient addition to the N-acylhydrazones under thermal or photolytic (300 nm) conditions. These Mn-mediated conditions avoid toxic tin reagents and enable stereoselective intermol. radical additions to C:N bonds with the broadest range of alkyl halides yet reported, including previously ineffective primary alkyl halides. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Product Details of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Product Details of 10297-05-9

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A practical iodination of aromatic compounds by using iodine and iodic acid was written by Shinde, Avinash T.;Zangade, Sainath B.;Chavan, Shivaji B.;Vibhute, Archana Y.;Nalwar, Yogesh S.;Vibhute, Yeshwant B.. And the article was included in Synthetic Communications in 2010.Application In Synthesis of 4-Bromo-2-iodophenol This article mentions the following:

This article described simple and efficient method for the iodination of different aromatic amines, hydroxy aromatic aldehydes, hydroxy acetophenones and phenols using iodine and iodic acid in ethanol as a solvent. Notable advantages include mild reaction condition, no need of catalyst, short reaction time, simple practical procedure, giving excellent yield of the product. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Application In Synthesis of 4-Bromo-2-iodophenol).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C閳ユ彂 bond is the weakest of the carbon閳ユ従alogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Application In Synthesis of 4-Bromo-2-iodophenol

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Diamine derivatives containing imidazolidinylidenepropanedinitrile as a new class of histamine H₃ receptor antagonists. Part I was written by Sasho, Setsuya;Seishi, Takashi;Kawamura, Mariko;Hirose, Ryo;Toki, Shinichiro;Shimada, Jun-ich. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Safety of 1-Chloro-4-iodobutane This article mentions the following:

Title compounds (I) were synthesized and evaluated for histamine H₃ receptor-binding affinities. I [R = piperidino, n = 4; R = 2-methylpyrroldiino (Q), (S)-Q, n = 3] showed potent H₃ receptor antagonism and excellent selectivity over human H₁, H₂ and H₄ receptors. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Safety of 1-Chloro-4-iodobutane).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons鑱砈mith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Safety of 1-Chloro-4-iodobutane

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Iodothyronine Deiodinase Mimics. Deiodination of o,o’-Diiodophenols by Selenium and Tellurium Reagents was written by Vasil’ev, Andrei A.;Engman, Lars. And the article was included in Journal of Organic Chemistry in 1998.SDS of cas: 207115-22-8 This article mentions the following:

To better understand, and in the extension mimic, the action of the three selenium-containing iodothyronine deiodinases, o,o’-diiodophenols were reacted under acidic conditions with sodium hydrogen telluride, benzenetellurol, sodium hydrogen selenide, or benzeneselenol and under basic conditions with the corresponding deprotonated reagents. Sodium hydrogen telluride was found to selectively remove one iodine from a variety of 4-substituted o,o’-diiodophenols, including a protected form of thyroxine. Thus, it mimics the D1 variety of the iodothyronine deiodinases. Sodium telluride was a more reactive deiodinating agent toward o,o’-diiodophenols, often causing removal of both halogens. Benzenetellurol and sodium benzenetellurolate sometimes showed useful selectivity for monodeiodination. However, the products were often contaminated by small amounts of organotellurium compounds Sodium hydrogen selenide, sodium selenide, benzeneselenol, and sodium benzeneselenolate were essentially unreactive toward o,o’-diiodophenols. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8SDS of cas: 207115-22-8).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C閳ユ彂 bond is the weakest of the carbon閳ユ従alogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.SDS of cas: 207115-22-8

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com