Category: 189518-78-3

The author of 《(R)-3,3′-Bis(9-phenanthryl)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate》 were Hu, Wenhao; Zhou, Jing; Xu, Xinfang; Liu, Weijun; Gong, Liuzhu. And the article was published in Organic Syntheses in 2011. Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene The author mentioned the following in the article:

Enantiomerically pure (R)-3,3′-bis(9-phenanthryl)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate (I) is prepared in four steps from (R)-(+)-2,2′-bis(methoxymethoxy)-1,1′-binaphthyl (II). Thus, regioselective ortho-iodination of II with I2 and BuLi in THF gives 40% of the corresponding diiodo compound, which then undergoes Suzuki coupling with 9-phenanthreneboronic acid in 91% yield. Next, the OMOM ethers are cleaved with HCl to give 99% of the corresponding diol, followed by treatment with POCl3 to give 91% I. The preparative information is followed by a short review of the use of I and related enantiomerically pure binaphthalene hydrogen phosphates as chiral Bronsted acids for multicomponent reactions. In addition to this study using (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene, there are many other studies that have used (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene) was used in this study.

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. 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.Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene

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

The author of 《Dramatic enantioselectivity reversal in the propargylation of aldehyde with alkynyllithium catalyzed by dilithium binaphtholate derivatives》 were Nakajima, Makoto; Watanabe, Rika; Osakama, Kazuki; Sakamoto, Midori; Takemoto, Daijiro; Kukita, Kenji. And the article was published in Heterocycles in 2018. Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene The author mentioned the following in the article:

A slight structural modification of a chiral catalyst (R)-I (R = C6H5, 2-CH3OC6H4, 2,3-dihydro-1-benzofuran-7-yl, etc.) caused a dramatic enantioselectivity reversal in the propargylation of aldehydes R1CHO (R1 = C6H5, (CH2)2C6H5, 2-naphthyl, etc.) with alkynyllithium. The experimental process involved the reaction of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Quality Control of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.

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

Wu, T. Robert; Shen, Lixin; Chong, J. Michael published their research in Organic Letters on August 5 ,2004. The article was titled 《Asymmetric Allylboration of Aldehydes and Ketones Using 3,3′-Disubstituted Binaphthol-Modified Boronates》.Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene The article contains the following contents:

Allylboronates derived from 3,3′-disubstituted 2,2′-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness. The results came from multiple reactions, including the reaction of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine.Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene

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

HPLC of Formula: 189518-78-3On September 16, 2011 ,《Enantioselective Conjugate Addition of Alkenylboronic Acids to Indole-Appended Enones》 was published in Organic Letters. The article was written by Lundy, Brian J.; Jansone-Popova, Santa; May, Jeremy A.. The article contains the following contents:

An enantioselective addition of alkenylboronic acids and alkynylboronic esters to unprotected indole-appended enones is reported. This transformation proceeds with high enantioselectivity and high product yields via the use of catalytic amounts of 3,3′-bis(pentafluorophenyl)-BINOL and Mg(Ot-Bu)2. A range of α-branched indole derivatives, e.g., I, are available from the transformation.(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3HPLC of Formula: 189518-78-3) was used in this study.

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine.HPLC of Formula: 189518-78-3

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

SDS of cas: 189518-78-3On March 20, 2020, Osakabe, Hiroto; Saito, Shota; Miyagawa, Masamichi; Suga, Takuya; Uchikura, Tatsuhiro; Akiyama, Takahiko published an article in Organic Letters. The article was 《Enantioselective Dehydroxyhydrogenation of 3-Indolylmethanols by the Combined Use of Benzothiazoline and Chiral Phosphoric Acid: Construction of a Tertiary Carbon Center》. The article mentions the following:

An enantioselective hydrogen transfer reaction of indolylmethanol, I (R = H, Me, Bn; R1 = Me, i-Pr, Ph, t-Bu; Ar = C6H5, 4-ClC6H4, CCC6H5, etc.; X = H, Me, OMe, Br) which is characterized by the combined use of 2,3-dihydro-2-(2-naphthalenyl)benzothiazole and a newly synthesized chiral phosphoric acid II (Y = 4-Ph-2,6-(i-Pr)2C6H2) has been described. The reaction furnished indoles (R)-III bearing a chiral tertiary carbon center at the 3-position in high to excellent yields and with excellent enantioselectivities, most of which are greater than 95% ee. The chiral indole (R)-III (R = Me; R1 = t-Bu; Ar = 4-BrC6H4; X = H) was converted into an inhibitor of leukotriene production while retaining excellent ee.(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3SDS of cas: 189518-78-3) was used in this study.

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.SDS of cas: 189518-78-3

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

In 2017,Polymer Chemistry included an article by Meng, Fandian; Li, Yunzhi; Zhang, Wenjie; Li, Shuhua; Quan, Yiwu; Cheng, Yixiang. Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene. The article was titled 《Circularly polarized luminescence based chirality transfer of the chiral BINOL moiety via rigid π-conjugation chain backbone structures》. The information in the text is summarized as follows:

Three kinds of chiral BINOL-based polymers could be synthesized by polymerization in a Pd-catalyzed cross-coupling reaction. The resulting chiral polymers can exhibit strong mirror image Cotton effects. Interestingly, only P2 and P3 can emit circularly polarized luminescence (CPL) signals, which can be attributed to the chirality transfer of the BINOL moiety via the rigid π-conjugation chain backbone structure system. This work can develop a new strategy for the design of novel CPL materials. The results came from multiple reactions, including the reaction of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.

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

In 2020,Chemical Science included an article by Akporji, Nnamdi; Thakore, Ruchita R.; Cortes-Clerget, Margery; Andersen, Joel; Landstrom, Evan; Aue, Donald H.; Gallou, Fabrice; Lipshutz, Bruce H.. Synthetic Route of C24H20I2O4. The article was titled 《N2Phos – an easily made, highly effective ligand designed for ppm level Pd-catalyzed Suzuki-Miyaura cross couplings in water》. The information in the text is summarized as follows:

A new biaryl phosphine-containing ligand from an active palladium catalyst for ppm level Suzuki-Miyaura couplings to afford biaryls, was enabled by an aqueous micellar reaction medium. A wide array of functionalized substrates including aryl/heteroaryl bromides were amenable, as were, notably, chlorides. The catalytic system was both general and highly effective at low palladium loadings (1000-2500 ppm or 0.10-0.25 mol%). D. functional theory calculations suggested that greater steric congestion in N2Phos induced increased steric crowding around the Pd center, helping to destabilize the 2 : 1 ligand-Pd(0) complex more for N2Phos than for EvanPhos (and less bulky ligands), and thereby favoring formation of the 1 : 1 ligand-Pdo complex that is more reactive in oxidative addition to aryl chlorides. After reading the article, we found that the author used (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Synthetic Route of C24H20I2O4)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. 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.Synthetic Route of C24H20I2O4

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

Kang, Seongbum; Cha, Inhwan; Han, Jeon Geon; Song, Changsik published an article in Materials Express. The title of the article was 《Electroactive polymer sensors for chiral amines based on optically active 1,1′-binaphthyls》.Synthetic Route of C24H20I2O4 The author mentioned the following in the article:

Mol. chirality is vital in biol. functions and discriminating such chirality is important in organic synthesis, bio-synthesis, medicinal chem., and drug development. The authors developed electroactive chiral sensors by incorporating binaphthol moieties into the polymer main chains. The binaphthyl scaffold of the binaphthol moiety recognizes one form of chirality from the other, and its phenol groups play a vital role in the charge transporting mechanism. Aiming for chiral amine sensors, the authors synthesized binaphthol-containing electropolymerizable monomers and polymerized to produce proton-dopable chiral polymers, which were characterized by cyclic voltammetry, potentiometry, and in situ conductivity measurements. Chiral discriminating ability of the resulting polymers was tested and their sensing mechanism is proposed. In the experiment, the researchers used many compounds, for example, (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Synthetic Route of C24H20I2O4)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. Organic iodides are used in veterinary products (Organic Iodide Powder) as a nutritional source 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.Synthetic Route of C24H20I2O4

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

《Self-Assembly and Catalytic Reactivity of BINOL-Bridged Bis(phenanthroline) Metallocages》 was written by Cheng, Kai-Yu; Wang, Shi-Cheng; Chen, Yu-Sheng; Chan, Yi-Tsu. COA of Formula: C24H20I2O4 And the article was included in Inorganic Chemistry on April 2 ,2018. The article conveys some information:

Upon treatment with ZnII ions, a series of BINOL-bridged bis(phenanthroline) ligands was self-assembled into [M2L3] metallocages, which were carefully characterized by NMR spectroscopy and ESI-MS spectrometry. Among them, a racemic mixture of the BINOL-bridged bis(phenanthrolines) underwent chiral self-sorting to afford two homochiral metallocages. The narcissistic self-sorting process of the metallocages was observed in the complexation reaction of the constitutionally isomeric bis(phenanthrolines) with varying connection positions. Moreover, the endo hydroxyl-functionalized metallocage [Zn2{(S)-L2OH}3] exhibited catalytic activity and substrate selectivity for the Knoevenagel condensation reactions of aromatic tricarbaldehydes with malononitrile. The results came from multiple reactions, including the reaction of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3COA of Formula: C24H20I2O4)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.COA of Formula: C24H20I2O4Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.

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

Category: iodides-buliding-blocksOn November 11, 1998 ,《Molecular recognition of pyranosides by a family of trimeric, 1,1′-binaphthalene-derived cyclophane receptors》 appeared in Helvetica Chimica Acta. The author of the article were Baehr, Anja; Droz, Anne Sophie; Puentener, Martin; Neidlein, Ulf; Anderson, Sally; Seiler, Paul; Diederich, Francois. The article conveys some information:

The synthesis and carbohydrate-recognition properties of optically active cyclophane receptors I [R = PhCH2O, R1 = H; R, R1 = H; R = H, R1 = Ph(CH2)2], in which 3 1,1′-binaphthalene-2,2′-diol spacers are interconnected by 3 1,3-butadiyne-1,4-diyl linkers, are described. The macrocycles all contain highly preorganized cavities lined with 6 convergent OH groups for H-bonding and complementary in size and shape to monosaccharides. The preparation of the more planar, D3-sym. receptors (R,R,R)-I (R = PhCH2O, R1 = H) and (S,S,S)-I [R = PhCH2O, R1 = H; R, R1 = H; R = H, R1 = Ph(CH2)2] involved as key step the Glaser-Hay cyclotrimerization of the corresponding OH-protected 3,3′-diethynyl-1,1′-binaphthalene-2,2′-diol precursors, which yielded tetrameric and pentameric macrocycles in addition to the desired trimeric compounds The synthesis of the less planar, C2-sym. receptors (R,R,S)-I (R, R1 = H) and (S,S,R)-I [R = H, R1 = Ph(CH2)2] proceeded via 2 Glaser-Hay coupling steps. The flat D3-sym. receptors (R,R,R)- and (S,S,S)-I (R = PhCH2O, R1 = H) formed 1:1 cavity inclusion complexes with octyl 1-O-pyranosides in CDCl3 (300 K) with moderate stability (ΔG0 ≈ -3 kcal mol-1) as well as moderate diastereo- [Δ(ΔG0) ≤ 0.7 kcal mol-1] and enantioselectivity [Δ(ΔG0) = 0.4 kcal mol-1]. Stoichiometric 1:1 complexation by (S,S,S)-I [R, R1 = H; R = H, R1 = Ph(CH2)2] could not be investigated by 1H-NMR binding titrations, due to very strong signal broadening. This broadening of the 1H-NMR resonances is presumably indicative of higher-order associations, in which the planar macrocycles sandwich the carbohydrate guests. The less planar C2-sym. receptor (S,S,R)-I [R = H, R1 = Ph(CH2)2] formed stable 1:1 complexes with binding free-enthalpies of up to ΔG0 = -5.0 kcal mol-1. With diastereoselectivities up to Δ(ΔG0) = 1.3 kcal mol-1 and enantioselectivities of Δ(ΔG0) = 0.9 kcal mol-1, (S,S,R)-I [R = H, R1 = Ph(CH2)2] is among the most selective artificial carbohydrate receptors known. In the experimental materials used by the author, we found (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Category: iodides-buliding-blocks)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Category: iodides-buliding-blocks Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.

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