Tag: M.W=250-300

D’Auria, Maurizio; Mauriello, Giacomo published the artcile< Reevaluation of benzyltrimethylammonium dichloroiodide, previously reported to be a selective iodinating agent>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is benzyltrimethylammonium dichloroiodate chlorination agent; thiophenecarboxylate chloro.

Benzyltrimethylammonium dichloroiodate [N,N,N-trimethylbenzenemethanaminium dichloroiodate(1-)], previously reported as an iodinating agent of thiophenes, appears to be a selective chlorinating agent of both thienyl and furyl derivatives containing a carbonyl group. Treatment of Me 2-thiophenecarboxylate with benzyltrimethylammonium dichloroiodate/ZnCl2/AcOH gave Me 5-iodo-2-thiophenecarboxylate, Me 4,5-diiodo-2-thiophenecarboxylate, and Me 5-chloro-2-thiophenecarboxylate.

Synthesis published new progress about Chlorination. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

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

Gronowitz, Salo; Vilks, Vija published the artcile< Iodo thiophenes and bithienyls>, Product Details of C6H5IO2S, the main research area is .

Iodo thiophenes could be prepared by the reaction of thiophene with iodine and HIO3 to give 2,3,5-triiodothiophene (I), from which other iodothiophenes were obtained. I, m. 82-5° (EtOH), was prepared in 77% yield by refluxing for 100 hrs. a mixture of 1.25 moles thiophene, 800 ml. HOAc, 369 ml. H2O,300 ml. CCl4, 21 ml. concentrated H2SO4, 1.5 moles iodine, and 0.77 moles HIO3, adding H2O and CCl4, extracting, washing, drying, and removing CCl4. A solution of 0.1 mole I in 300 ml. anhydrous Et2O was added to 100 ml. 1.03N BuLi at -70° to give a 63% yield of 2,4-diiodothiophene (II), b10 142-4.5°, which, when added then to an equivalent amount of BuLi at -70° and the resulting solution poured onto CO2 and hydrolyzed, gave 53% 4-iodo-2-thiophene-carboxylic acid (III), m. 115-17°; Me ester m. 41.5-3°. The reaction of 2 moles BuLi with 1 mole II gave 80% 2,4-thiophenedicarboxylic acid, m. 299-301°. Addition of 0.238 moles I continuously to a boiling mixture of 100 ml. H2O, 70 g. Zn powder, and 40 ml. HOAc with immediate distillation of the product gave 25.5 g. (52%) 3-iodothiophene (IV), b9 66-8°, n20D 1.6584, and 10 g. thiophene. The reaction of IV with iodine-HIO3 gave 73% 2,3-diiodothiophene (V), b10 133-5°, and 0.5% II, whereas the reaction of IV in C6H6 with HgO and iodine gave a mixture b14 14650°, which was shown by infrared analysis to contain 93% V and 7% II. Iodination of Me 2-thiophenecarboxylate with iodine and HIO3 gave 45% Me 5-iodo-2-thiophenecarboxylate (VI), m. 88-9° (ligroine), containing 3% Me 4-iodo-2-thiophenecarboxylate. Refluxing VI 10 hrs. with methanolic KOH gave 80% 5-iodo-2-thiophenecarboxylic acid, m. 132-4° (EtOH). To 33 g. 5,5′-dicarboxy-2,2′-bithienyl, prepared by refluxing BuLi and 2,2′-bithienyl and pouring the mixture onto CO2, was added dropwise 60 g. SOCl2, the mixture refluxed 60 hrs., excess SOCl2 removed, 150 ml. anhydrous MeOH added dropwise, and the mixture refluxed 21 hrs. to give 31 g. (85%) 5,5′-dicarbomethoxy-2,2′-bi-thienyl (VII), m. 208-10°. Addition of 26 g. iodine to a mixture of 28 g. VII and 32 g. Hg(OAc)2 in HOAc at 95° followed by stirring at 100° for 72 hrs. and continuously extracting with Et2O for 72 hrs. gave 26.6 g. (65%) 3-iodo-5,5′-dicarbomethoxy-2,2′-bithienyl, m. 127.5-9° (ligroine). To BuLi at -70° was added 2,3-di-iodothiophene in Et2O, then CuCl2, and the mixture worked up to give 25% 3,3′-diiodo-2,2′-bithienyl (VIII), m. 149.5-51° (ligroine). Prepared similarly from I was 3,3′,5,5′-tetraiodo-2,2′-bi-thienyl, m. 190.5-2° (ligroine).

Arkiv foer Kemi published new progress about IR spectra. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Product Details of C6H5IO2S.

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

Ting, Chi P.; Tschanen, Esther; Jang, Esther; Maimone, Thomas J. published the artcile< Total synthesis of podophyllotoxin and select analog designs via C-H activation>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is podophyllotoxin analog synthesis arylation.

An account of our previously disclosed total synthesis of the aryltetralin lignan natural product podophyllotoxin, a building block used in the synthesis of the FDA-approved anticancer drug etoposide, is disclosed. A C-H activation disconnection was viewed as being amenable to the preparation of E-ring modified analogs but proved challenging to execute. Various insights into palladium-catalyzed C-H arylation reactions on complex scaffolds are reported ultimately leading to the implementation of this strategy and the synthesis of compounds inaccessible by semisynthetic means.

Tetrahedron published new progress about Arylation. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

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

Brea, Oriana; Szabo, Kalman J.; Himo, Fahmi published the artcile< Mechanisms of Formation and Rearrangement of Benziodoxole-Based CF3 and SCF3 Transfer Reagents>, SDS of cas: 1391728-13-4, the main research area is benziodoxole based trifluoromethyl trifluoromethylthio group transfer reagent formation rearrangement.

Togni’s benziodoxole-based reagents are widely used in trifluoromethylation reactions. It has been established that the kinetically stable hypervalent iodine form (I-CF3) of the reagents is thermodynamically less stable than its acyclic ether isomer (O-CF3). On the other hand, the trifluoromethylthio analog exists in the thermodynamically stable thioperoxide form (O-SCF3), and the hypervalent form (I-SCF3) has been elusive. Despite the importance of these reagents, very little is known about the reaction mechanisms of their syntheses, which has hampered the development of new reagents of the same family. Herein, we use d. functional theory calculations to understand the reasons for the divergent behaviors between the CF3 and SCF3 reagents. We demonstrate that they follow different mechanisms of formation and that the metals involved in the syntheses (potassium in the case of the trifluoromethyl reagent and silver in the trifluoromethylthio analog) play key roles in the mechanisms and greatly influence the possibility of their rearrangements from the hypervalent (I-CF3, I-SCF3) to the corresponding ether-type form (O-CF3, O-SCF3).

Journal of Organic Chemistry published new progress about Free energy of activation. 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, SDS of cas: 1391728-13-4.

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

Klimankova, Iveta; Hubalek, Martin; Matousek, Vaclav; Beier, Petr published the artcile< Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols>, Application In Synthesis of 1391728-13-4, the main research area is fluoroalkyl iodonium benzoiodoxole preparation water soluble fluoroalkylation reagent; stability chemoselectivity fluoroalkylation thiol cysteine fluoroalkyl iodonium benzoiodoxole.

Water-soluble fluoroalkyl iodonium compounds and fluoroalkyl benzoiodanes were prepared and tested for their ability to alkylate the sulfur atoms of cysteine and cysteine-containing peptides under biocompatible conditions. Some of the reagents displayed excellent reactivity despite their limited stability in aqueous media. In reactions with a cysteine-containing heptapeptide, in addition to the expected S-fluoroalkylated product, a range of side-products were obtained, with the amounts of side-products depending on the conditions used (type of reagent, concentration, and pH). With highly activated hypervalent iodine reagents, a new reactive mode was observed – reaction with disulfides to form fluoroalkyl thiols.

Organic & Biomolecular Chemistry published new progress about Disulfides Role: RCT (Reactant), RACT (Reactant or Reagent). 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Application In Synthesis of 1391728-13-4.

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

D’Auria, Maurizio; Mauriello, Giacomo published the artcile< Bis(trifluoroacetoxy)iodobenzene-iodine system: an efficient and selective reagent for iodination of thiophene derivatives>, Application In Synthesis of 88105-22-0, the main research area is iodination thiophene trifluoroacetoxyiodobenzene iodide.

Bis-(trifluoroacetoxy)iodobenzene-iodine system is a good iodinating reagent of thiophene derivatives giving products with iodine atom in α-position on the thiophene ring. For example, iodination of 2-thiophenecarboxylic acid Me ester with bis(trifluoroacetoxy)iodobenzene/iodine gave 5-iodo-2-thiophenecarboxylic acid Me ester in 78% yield.

Tetrahedron Letters published new progress about Iodination, regioselective. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Application In Synthesis of 88105-22-0.

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

D’Auria, Maurizio; De Mico, Antonella; D’Onofrio, Franco; Mendola, Daniele; Piancatelli, Giovanni published the artcile< Photochemical behavior of halothiophenes: synthesis of 5-arylthiophene-2-carboxylic esters>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is photolysis halothiophene derivative reactivity mechanism; bithiophenecarboxylic acid propynyl; arylation photochem halothiophene derivative.

The arylation of 5-halothiophene-2-carbonitrile and Me 5-halothiophene-2-carboxylate by a photochem. process was investigated. Whereas 5-bromothiophene-2-carbonitrile is completely unreactive, the corresponding iodo derivative furnishes the dehalogenation product. In contrast, Me 5-iodothiophene-2-carboxylate gives the corresponding aryl and heteroaryl derivatives in good yields on irradiation in the presence of various aromatic substrates (benzene, p-xylene, naphthalene, thiophene, 2-bromothiophene and 2-chlorothiophene). The different reactivities of these compounds are explained. An application of this conversion to the synthesis of 5′-(1-propynyl)-2,2′-bithiophene-5-carboxylic acid is reported.

Journal of Photochemistry and Photobiology, A: Chemistry published new progress about Phosphorescence. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

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

Yang, Peng-Fei; Shu, Wei published the artcile< Orthogonal Access to α-/β-Branched/Linear Aliphatic Amines by Catalyst-Tuned Regiodivergent Hydroalkylations>, Name: tert-Butyl (3-iodopropyl)carbamate, the main research area is amine preparation regioselective; chiral amine preparation regioselective enantioselective; alkenyl amine alkyl halide hydroalkylation metal catalyst; Amines; Chain Walking; Cobalt Catalysis; Hydroalkylations; Regiodivergent Reactions.

Herein, a catalyst-controlled synthesis of α-branched e.g., N-(1-phenylpentan-3-yl)benzamide, β-branched e.g., N-(2-methyl-4-phenylbutyl)benzamide and linear aliphatic amines e.g., N-(5-phenylpentyl)benzamide from Ni/Co-catalyzed regio- and site-selective hydroalkylations of alkenyl amines e.g., N-(prop-2-en-1-yl)benzamide with alkyl halides RX (R = butan-2-yl, Bn, 2-phenylethyl, 2-(1,3-dioxolan-2-yl)ethyl, etc.; X = I, Br) is developed. This catalytic protocol features the reliable prediction and control of the coupling position of alkylation to provide orthogonal access to α-branched, β-branched and linear alkyl amines from identical starting materials. This platform unlocks orthogonal reactivity and selectivity of nickel hydride and cobalt hydride chem. to catalytically repurpose three types of alkyl amines under mild conditions.

Angewandte Chemie, International Edition published new progress about Aliphatic amines Role: SPN (Synthetic Preparation), PREP (Preparation). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Name: tert-Butyl (3-iodopropyl)carbamate.

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

Matsumoto, Koki; Nakajima, Masaya; Nemoto, Tetsuhiro published the artcile< Determination of the best functional and basis sets for optimization of the structure of hypervalent iodines and calculation of their first and second bond dissociation enthalpies>, Recommanded Product: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole, the main research area is hypervalent iodine bond dissociation enthalpy substituent effect.

Hypervalent iodines are widely used in organic chem., and their most important feature is the three-center four-electron bond. However, there have been few reports on the measurement of their bond dissociation enthalpy (BDE). Therefore, in many cases, BDE is estimated by computational calculations However, the value of a calculated BDE usually varies depending on the choice of functional and basis set, and the best method for making an accurate evaluation of the three-center four-electron bond has not been determined We succeeded in determining the best functional and basis set to calculate the three-center four-electron bond to within 0.79% error and 0.53 standard deviation. Using the optimal functional and basis set, the first and second BDEs of several hypervalent iodines are calculated, and as the effect of benzene substituents was investigated, neg. correlation was observed in the Hammett plot. In addition, the effect of ortho-substituent in cyclic hypervalent iodine was found to be significant. Furthermore, the decomposition route of hypervalent iodine is calculated The value of a calculated BDE usually varies depending on the choice of functional and basis set. We succeeded in determining the best functional and basis sets to calculate the three-center four-electron bond of hypervalent iodine to within 0.79% error and 0.53 standard deviation. Using the optimal functional and basis sets, the first and second BDEs of several hypervalent iodines are calculated, and addnl., the decomposition route of hypervalent iodine is calculated

Journal of Physical Organic Chemistry published new progress about Bond cleavage. 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Recommanded Product: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole.

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

Hughes, Gregory; Kreher, David; Wang, Changsheng; Batsanov, Andrei S.; Bryce, Martin R. published the artcile< Ethynyl π-extended 2,5-diphenyl-1,3,4-oxadiazoles and 2-phenyl 5-(2-thienyl)-1,3,4-oxadiazoles: synthesis, X-ray crystal structures and optical properties>, SDS of cas: 88105-22-0, the main research area is butylphenyl ethynylphenyl oxadiazole heteroaryl iodide Sonogashira cross coupling palladium; heteroarylethynylphenyl oxadiazole preparation optical property; ethynylthienyl oxadiazole heteroaryl iodide Sonogashira cross coupling palladium; oxadiazole phenyl ethynylthienyl preparation optical property crystal structure.

2-(4-Tert-Butylphenyl)-5-(4-ethynylphenyl)-1,3,4-oxadiazole (I, R = H) reacted with a series of heteroaryl iodides under standard Sonogashira cross-coupling conditions to yield products I [R = 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrazyl (II), 5-bromo-2-pyrimidyl, 2-thienyl (III) and 3-thienyl (IV)] in 40-79% yields. Compound III was lithiated followed by electrophilic iodination using perfluorohexyl iodide to give the corresponding iodothienyl derivative, which by a two-step sequence gave the terminal ethynylthienyl derivative V (R’ = H) . Conversion of V into the terminal ethynylaldehyde derivative V (R’ = CHO) via acetal derivative proceeded in high yield. Starting from 2-iodo-5-methoxycarbonylthiophene, a five-step sequence afforded 2-(4-tert-butylphenyl)-5-(4-ethynylthienyl)-1,3,4-oxadiazole (VI, R = H) (13% overall yield). Sonogashira cross-coupling reactions of VI with heteroaryl iodides gave 2-phenyl-5-(2-thienyl)-1,3,4-oxadiazoles VI (R = 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrazyl (VII), 5-bromo-2-pyrimidyl, 2-thienyl and 3-thienyl). Two-fold reaction of V with 2,5-diiodothiophene gave the bis(ethynylthienyl)thiophene derivative (30% yield). Solution UV-Vis absorption and photoluminescence spectra establish that replacement of the Ph ring in the 2,5-diphenyl-1,3,4-oxadiazole series I by a thienyl ring as in VI leads to a red shift in the lowest energy band in both the absorption spectra and emission spectra. The X-ray crystal structures of compounds II, IV, V and VII·CHCl3 reveal that the mol. structures are approx. planar although there are substantial differences in the conformations.

Organic & Biomolecular Chemistry published new progress about Aryl iodides Role: RCT (Reactant), RACT (Reactant or Reagent). 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, SDS of cas: 88105-22-0.

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