Category: 75581-11-2

FeCl₃/PPh₃-catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes was written by Sawant, Dinesh N.;Tambade, Pawan J.;Wagh, Yogesh S.;Bhanage, Bhalchandra M.. And the article was included in Tetrahedron Letters in 2010.SDS of cas: 75581-11-2 This article mentions the following:

Conditions for a FeCl₃/PPh₃-catalyzed and palladium-, copper-, amine free-Sonogashira coupling reaction of aryl halides with terminal alkynes are reported. The protocol was applicable to a wide variety of substituted aryl iodides and alkynes with different steric and electronic properties and gave excellent yields of the desired coupling products. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).SDS of cas: 75581-11-2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

One-pot preparation of arylalkynes by a tandem catalytic iodination of arenes and palladium-catalyzed coupling of iodoarenes with terminal alkynes was written by Wan, Shun;Wang, Sunewang R.;Lu, Wenjun. And the article was included in Journal of Organic Chemistry in 2006.Category: ethers-buliding-blocks This article mentions the following:

Iodination of activated arenes by air-oxidation was carried out in the presence of catalytic bismuth salts at room temperature Subsequently, the formed iodoarenes reacted with terminal alkynes to give arylalkynes under a selected palladium-catalyzed coupling condition in the same pot. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Category: ethers-buliding-blocks).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides was written by Wang, Xuan;Ma, Guobin;Peng, Yu;Pitsch, Chloe E.;Moll, Brenda J.;Ly, Thu D.;Wang, Xiaotai;Gong, Hegui. And the article was included in Journal of the American Chemical Society in 2018.Synthetic Route of C8H9IO This article mentions the following:

This work illustrates the reductive coupling of electron-rich aryl halides with tertiary alkyl halides under Ni-catalyzed cross-electrophile coupling conditions, which offers an efficient protocol for the construction of all carbon quaternary stereogenic centers. The mild and easy-to-operate reaction tolerates a wide range of functional groups. The utility of this method is manifested by the preparation of cyclotryptamine derivatives, wherein successful incorporation of 7-indolyl moieties is of particular interest as numerous naturally occurring products are composed of these key scaffolds. DFT calculations have been carried out to investigate the proposed radical chain and double oxidative addition pathways, which provide useful mechanistic insights into the part of the reaction that takes place in solution In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Synthetic Route of C8H9IO).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Synthetic Route of C8H9IO

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Ether – Wikipedia,
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The synthesis and properties of some alkyliodophenols was written by Suter, C. M.;Schuetz, Robert D.. And the article was included in Journal of Organic Chemistry in 1951.SDS of cas: 75581-11-2 This article mentions the following:

Some alkyliodophenols are prepared to be tested for their bactericidal properties. Adding dropwise 58 g. Ac₂O containing 0.1 cc. concentrated H₂SO₄ to 100 g. o-EtC₆H₄OH containing 0.1 cc. concentrated H₂SO₄ over a period of 3 hrs. and fractionally distilling the mixture through a 50-cm. Vigreux column give 81% o-EtC₆H₄OAc, b₄ 77-8°, d₄²⁵ 1.0334, n_D²⁵ 1.5002. The following alkylphenyl acetates are prepared in the same way: o-Pr, b₃ 77-8°, d₄²⁵ 1.0165, n_D²⁵ 1.5040, mol. refraction (MR) 51.958; o-Bu, b₃ 100-3°, d₄²⁵ 0.9881, n_D²⁵ 1.4897, MR 56.227; o-Am, b₃ 104-6°, d₄²⁵ 0.9697, n_D²⁵ 1.4888, MR 59.949; o-C₆H₁₃OH b₄ 113-16°, d₄²⁵ 0.9500, n_D²⁵ 1.4973. o-MeC₆H₄OAc with ICl gives 4,2-IMeC₆H₃OAc, m. 55-6°, which, saponified with 10% NaOH 10 min. on a steam bath, gives 4,2-IMeC₆H₃, (I), m. 64-5°. Adding dropwise 0.81 g. Me₂SO₄ to 3 g. I in 5% NaOH within 0.5 hr. at 30° gives 4,2-IMeC₆H₃OMe, crystals from AcOH, m. 75-6°. Adding 150 g. iodine in 400 cc. H₂O containing 98.5 g. KI to 75 g. p-MeC₆H₄OH in 400 cc. H₂O containing 120 g. NaHCO₃, shaking the mixture 3 hrs., extracting it with ether, and fractionating the residue of the washed (H₂O, 5% Na₂S₂O₃) and dried ether solution in vacuo give 12.4% 2,4-IMeC₆H₃OH, b₃ 96-8°, d₄²⁵ 1.684, n_D²⁵ 1.5331, solubility in H₂O 0.08%, in 20% EtOH 0.29%. In the same way the following substituted phenols are prepared (yield, b.p., d₄²⁵, n_D²⁵, solubility (%) at 25° in H₂O and in 20% EtOH, in the order given): I, 5.2%, b₂ 105-10°, m. 64-5°, -, -, 0.09, 0.16; 2-methyl-6-iodo, 4.2%, b₂ 70-5°, m. 15-16°, 1.661, 1.6100, 0.17, 0.34; 2-ethyl-4-iodo, 3%, b₃ 126-9°, m. 48-50°, -, -, 0.21, 0.28; 2-ethyl-6-iodo, 2.5%, b₃ 98-100°, 1.679, 1.6017, 0.09, 0.86; 4-ethyl-2-iodo, 26.2%, b₄ 98-100°, 1.670, 1.5750, 0.31, 0.45; 2-propyl-4-iodo, 1.5%, b₂ 119-20°, -, -, -, -; 2-propyl-6-iodo, 1.8%, b₂ 94-5°, 1.681, 1.5846, -, -; 4-propyl-2-iodo, 11%, b₄ 132-5°, 1.655, 1.5568, 0.009, 0.014; 4-butyl-2-iodo, 5.3%, b₄ 150-2°, 1.637, 1.5895, 0.00, 0.00. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.SDS of cas: 75581-11-2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

The Synthesis of Benzofulvenes through Palladium-Catalyzed Sequential Three-Component Reactions was written by Zhou, Bo;Wu, Zhuo;Qi, Weixin;Sun, Xueliang;Zhang, Yanghui. And the article was included in Advanced Synthesis & Catalysis in 2018.Recommanded Product: 75581-11-2 This article mentions the following:

An approach for the synthesis of benzofulvenes was developed through palladium-catalyzed sequential three-component reactions. The reactions likely involved C,C-palladacycles as the key intermediates. The palladacycles were generated through cascade reactions of aryl halides and alkynes, and then reacted with CH₂Br₂ to form benzofulvenes as the final products. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Recommanded Product: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Recommanded Product: 75581-11-2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid was written by Castanet, Anne-Sophie;Colobert, Francoise;Broutin, Pierre-Emmanuel. And the article was included in Tetrahedron Letters in 2002.SDS of cas: 75581-11-2 This article mentions the following:

A variety of aromatic compounds substituted with methoxy or Me groups were regioselectively iodinated with N-iodosuccinimide and catalytic HO₂CCF₃ with excellent yields under mild conditions and short reaction times. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.SDS of cas: 75581-11-2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Complementary site-selectivity in arene functionalization enabled by overcoming the ortho constraint in palladium/norbornene catalysis was written by Wang, Jianchun;Li, Renhe;Dong, Zhe;Liu, Peng;Dong, Guangbin. And the article was included in Nature Chemistry in 2018.Name: 4-Iodo-1-methoxy-2-methylbenzene This article mentions the following:

Achieving site-selectivity in arene functionalization that is complementary to the site-selectivity from electrophilic aromatic substitution reactions has been a long-standing quest in organic synthesis. Palladium/norbornene cooperative catalysis potentially offers a unique approach to this problem, but its use has been hampered by the ortho constraint, which is the requirement of an ortho substituent for mono ortho functionalization of haloarenes. Here, we show that such a challenge could be addressed using a new class of bridgehead-modified norbornenes, thereby enabling a broadly useful strategy for arene functionalization with complementary site-selectivity. A range of ortho-unsubstituted aryl iodides, previously problematic substrates, can now be employed to provide mono ortho-functionalized products effectively. This method is applicable for late-stage functionalization of complex bioactive mols. at positions that are difficult to reach by conventional approaches. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Name: 4-Iodo-1-methoxy-2-methylbenzene).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Name: 4-Iodo-1-methoxy-2-methylbenzene

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones was written by Yao, Qiuli;Liu, Wenbo;Liu, Peng;Ren, Linjing;Fang, Xuehong;Li, Chao-Jun. And the article was included in European Journal of Organic Chemistry in 2019.SDS of cas: 75581-11-2 This article mentions the following:

The acylation of aryl halides to prepare aryl ketones without metal catalyst represents an important yet challenging topic towards more sustainable ketone synthesis. A simple and efficient metal-free protocol for the acylation of aryl halides with diketone under the irradiation of light utilizing N-methylpiperidine as base under an air atm. is described. This reaction can tolerate a wide range of functional groups and the corresponding ketones can be obtained in modest to good yields. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.SDS of cas: 75581-11-2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Palladium-catalyzed triple coupling of 2-iodoanisoles with aryl iodides to access 6H-dibenzopyrans was written by Chen, Li-Ping;Cheng, Shu-Lin;Fan, Xin-Yue;Zhu, Ji-Fa;Wang, Bi-Qin;Feng, Chun;Xiang, Shi-Kai. And the article was included in Organic Chemistry Frontiers in 2022.HPLC of Formula: 75581-11-2 This article mentions the following:

A palladium-catalyzed triple coupling of 2-iodoanisoles with aryl iodides was developed. 3-Methyl-2-pyridone was used as a ligand to accelerate the cross-coupling and suppress the homo-coupling of 2-iodoanisoles. A variety of 6H-dibenzopyran derivatives such as I [R = H, F, Cl, etc., R¹ = 4-Me, 4-F, 4-MeO, etc.; R² = 8-Me, 8-Cl, 8-Ph, etc.] was prepared by this method. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2HPLC of Formula: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.HPLC of Formula: 75581-11-2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Ambident reactivity of anisole and p-iodoanisole toward phenylium cations and evidence for ipso-attack in cationic phenylation was written by Eustathopoulos, Helene;Court, Jean;Bonnier, Jane Marie. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1983.Quality Control of 4-Iodo-1-methoxy-2-methylbenzene This article mentions the following:

The phenylation of p-IC₆H₄OMe in the thermolysis of PhN₂BF₄ gave, inter alia,p-MeOC₆H₄Ph and 4-IC₆H₄OPh, showing ipso-attack and attack on O by Ph⁺. With PhOMe, the O atom of the MeO substituent is also attacked by Ph⁺ giving Ph₂O through the initial formation of Ph₂O⁺Me followed by intermol. demethylation. No intramol. rearrangement occurs with the oxonium ion. The mechanism involves kinetically predominant C-phenylation of both substrates. BF₃ promotes deiodination of p-IC₆H₄OMe and its phenylated isomers. This deiodination invalidates the conclusions drawn from isomer distributions; therefore the presence of BF₃ must be carefully controlled in a mechanistic study. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Quality Control of 4-Iodo-1-methoxy-2-methylbenzene).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Quality Control of 4-Iodo-1-methoxy-2-methylbenzene

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem