Tag: 100-200

Speciation Analysis and Thermodynamic Criteria of Solvated Ionic Liquids: Ionic Liquids or Superconcentrated Solutions? was written by Arai, Nana;Watanabe, Hikari;Nozaki, Erika;Seki, Shiro;Tsuzuki, Seiji;Ueno, Kazuhide;Dokko, Kaoru;Watanabe, Masayoshi;Kameda, Yasuo;Umebayashi, Yasuhiro. And the article was included in Journal of Physical Chemistry Letters in 2020.HPLC of Formula: 112-49-2 This article mentions the following:

Lithium-glyme solvate ionic liquids (Li-G SILs) and super-concentrated electrolyte solutions (SCESs) are expected as a promising electrolyte for the next generation lithium secondary batteries. The former consists of only the oligoether glyme solvated lithium ion and its counter anion and the latter contains no full solvated Li⁺ ion by the solvents due to the extremely high Li salt concentration Although both of them are similar with each other, it is still unclear that both should be room-temperature ionic liquids (RTILs). To reveal the distinct definition for them, speciation analyses were performed to the Li-G SIL and the aqueous SCES to evaluate the free solvent concentration in these solutions with a new Raman/IR spectral anal. technique called complementary least square anal. (CLSA). Furthermore, from a thermodn. point of views, we investigated the solvent activity/activity coefficient in the gas phase equilibrated with sample solutions and found they can be a good criterion for SILs. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2HPLC of Formula: 112-49-2).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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. 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.HPLC of Formula: 112-49-2

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

N-(2-Benzoylphenyl)-L-tyrosine PPARγ Agonists. 2. Structure-Activity Relationship and Optimization of the Phenyl Alkyl Ether Moiety was written by Collins, Jon L.;Blanchard, Steven G.;Boswell, G. Evan;Charifson, Paul S.;Cobb, Jeff E.;Henke, Brad R.;Hull-Ryde, Emily A.;Kazmierski, Wieslaw M.;Lake, Debra H.;Leesnitzer, Lisa M.;Lehmann, Juergen;Lenhard, James M.;Orband-Miller, Lisa A.;Gray-Nunez, Yolanda;Parks, Derek J.;Plunkett, Kelli D.;Tong, Wei-Qin. And the article was included in Journal of Medicinal Chemistry in 1998.Application of 3929-47-3 This article mentions the following:

We previously reported the identification of (2S)-((2-benzoylphenyl)amino)-3-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propanoic acid (I) (PPARγ pK_i = 8.94, PPARγ pEC₅₀ = 9.47) as a potent and selective PPARγ agonist. We now report the expanded structure-activity relationship around the Ph alkyl ether moiety by pursuing both a classical medicinal chem. approach and a solid-phase chem. approach for analog synthesis. The solution-phase strategy focused on evaluating the effects of oxazole and Ph ring replacements of the 2-(5-methyl-2-phenyloxazol-4-yl)ethyl side chain of I with several replacements providing potent and selective PPARγ agonists with improved aqueous solubility Specifically, replacement of the Ph ring of the phenyloxazole moiety with a 4-pyridyl group to give (2S)-((2-benzoylphenyl)amino)-3-{4-[2-(5-methyl-2-pyridin-4-yloxazol-4-yl)ethoxy]phenyl}propionic acid (PPARγ pK_i = 8.85, PPARγ pEC₅₀ = 8.74) or a 4-methylpiperazine to give (2S)-((2-benzoylphenyl)amino)-3-(4-{2-[5-methyl-2-(4-methylpiperazin-1-yl)thiazol-4-yl]ethoxy}phenyl)propionic acid (PPARγ pK_i = 8.66, PPARγ pEC₅₀ = 8.89) provided two potent and selective PPARγ agonists with increased solubility in pH 7.4 phosphate buffer and simulated gastric fluid as compared to I. The second strategy took advantage of the speed and ease of parallel solid-phase analog synthesis to generate a more diverse set of Ph alkyl ethers which led to the identification of a number of novel, high-affinity PPARγ ligands (PPARγ pK_i‘s 6.98-8.03). The combined structure-activity data derived from the two strategies provide valuable insight on the requirements for PPARγ binding, functional activity, selectivity, and aqueous solubility In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Application of 3929-47-3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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 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.Application of 3929-47-3

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Organophotoredox-catalyzed cyanoalkylation of 1,4-quinones was written by Kulthe, Arun D.;Jaiswal, Sunidhi;Golagani, Durga;Mainkar, Prathama S.;Akondi, Srirama Murthy. And the article was included in Organic & Biomolecular Chemistry in 2022.Quality Control of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

A visible-light-induced metal-free cyanoalkylation of 1,4-quinones under mild and redox-neutral conditions to afford desired cyanoalkylated quinones I [R = H, Ph, Bn, etc.; R¹ = H, Me, OH, etc.; X = CHR², CH₂, O; R² = 4-t-BuPh, Bu, etc.] was described. This reaction proceeded at room temperature without the need of extra base or additive and was suitable for a variety of 1,4-quinones and differently substituted cyclobutanone oxime esters. Further transformation of cyano functionality to tetrazole and amine had also been demonstrated to showcase the advantage of this method to prepare drug-like mols. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Quality Control of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. 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.Quality Control of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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Ether – Wikipedia,
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Isatogens. V. Hydroxyhydroquinol derivatives of the isatogen series was written by Ruggli, Paul;Leonhardt, Werner. And the article was included in Helvetica Chimica Acta in 1924.Product Details of 5367-32-8 This article mentions the following:

Thiele’s reaction in which a hydroxhydroquinol is formed from p-C₆H₄O₂ and Ac₂O containing some H₂SO₄ (Ber. 31, 1247) may be applied to the isatogen series. Thus when 3 g. 6-nitro-2-phenylisatogen is added to 15 cc. Ac₂O containing 0.25 cc. concentrated H₂SO₄ and warmed to 50° for 15 min., there results, in addition to 1 g. of a by-product to be described later, 2 g. (45%) of 1,3,5-triacetoxy-2-phenyl-6-nitroindole (I), bright yellow, m. 194-5°. Aqueous alkali gives a deep red solution; concentrated H₂SO₄ gives a deep violet solution containing III. Boiling 2 g. I with 20 cc. EtOH and 1.25 cc. concentrated HCl about 30 min. gives the 1,3-Ac₂ derivative, orange-yellow, m. 214-5° (70% yield); with concentrated H₂SO₄ it gives the same violet solution as I. The 5-chloroacetoxy derivative is yellow and m. 156-8° (decomposition). The 5-MeO derivative (II), greenish yellow, m. 221-2°, results by the action of CH₂N₂. Concentrated H₂SO₄ reacts with I to give 2-phenyl-5-hydroxy-6-nitro-3-ketoindolenine (III), brick-red, m. 188°; very dilute alkali gives an emerald-green solution, from which black flakes soon sep. A large excess of H₂NOH.HCl gives the oxime (IV), red, m. 280° (decomposition), which gives a Me ether, dark red, m. 172°, with Me₂SO₄; this with Ac₂O-H₂SO₄ gives the 5-Ac derivative, brick-red, m. 152°. The 5-MeO derivative (V), dark red, m. 205°, results by the action of concentrated H₂SO₄ upon II; warmed with aqueous alkali, it gradually decomposes Ac₂O regenerates II. The oxime (VI), orange-red, m. 263-4°, whose Me ether is deep red and m. 157°; this is also formed from IV and CH₂N₂. Oxidation of VI in AcOH with CrO₃ gives 2-phenyl-3,6-dinitro-5-methoxyindole, bright yellow, m. 303-6° (decomposition), in 40-45% yields, while oxidation of V gives 4-nitro-5-methoxybenzoylanthranilic acid (VII), golden yellow, m. 272°. Heated with H₃PO₄ up to 170°, VII gives 2-amino-4-nitro-5-methoxybenzoic acid, violet-black, m. 217-8°; the aqueous solution is orange-red. 4-Amino-5-methoxybenzoylanthranilic acid, decompose 200°, results by the reduction of the Na salt of VII by H and Ni; the 4-Ac derivative decomposes 275°. The reduction of the diazo compound yields 5-methoxybenzoylanthranilic acid, m. 200°, which was synthesized from 2-nitro-5-methoxytoluene, yellow, m. 50°, through reduction with Sn and HCl and subsequent treatment with NaOH and BzCl, yielding the 2-benzoylamino-5-methoxytoluene, m. 200°, and oxidation with KMnO₄. The 3-methoxybenzoylanthranilic acid, prepared in a similar manner, m. 204.5°, but depressed the m. p. of the 5-derivative 25°. 2-Nitro-6-methoxytoluene, yellow, m. 52°. 2-Benzoylamino-6-methoxytoluene, m. 177°. 6-Methoxybenzoylanthranilic acid, m. 120°. The action of SnCl₂ in AcOH saturated with HCl upon II gives 2-phenyl-3-acetoxy-5-methoxy-6-aminoindole, m. 212°; with Ac₂O and concentrated H₂SO₄ this forms 1-acetyl-2-phenyl-3-acetoxy-5-methoxy-6-diacetaminoindole, m. 220°. Me isatogenate treated with Ac₂O and H₂SO₄ gives a yellow compound, C₁₆H₁₅O₈N, m. 193-5°, which may be the corresponding triacetoxyhydroquinol derivative In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Product Details of 5367-32-8).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Product Details of 5367-32-8

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Reduction of Synthetic Ubiquinone QT Catalyzed by Bovine Mitochondrial Complex I Is Decoupled from Proton Translocation was written by Okuda, Kenji;Murai, Masatoshi;Aburaya, Shunsuke;Aoki, Wataru;Miyoshi, Hideto. And the article was included in Biochemistry in 2016.SDS of cas: 605-94-7 This article mentions the following:

We previously succeeded in site-specific chem. modifications of the inner part of the quinone binding pocket of bovine mitochondrial complex I through ligand-directed tosylate (LDT) chem. using specific inhibitors as high-affinity ligands for the enzyme [Masuya, T., et al. (2014) Biochem.53, 2304-2317, 7816-7823]. To investigate whether a short-chain ubiquinone, in place of these specific inhibitors, serves as a ligand for LDT chem., we herein synthesized a LDT reagent QT possessing ubiquinone scaffold and performed LDT chem. with bovine heart submitochondrial particles (SMP). Detailed proteomic analyses revealed that QT properly guides the tosylate group into the quinone binding pocket and transfers a terminal alkyne to nucleophilic amino acids His150 and Asp160 in the 49 kDa subunit. This result clearly indicates that QT occupies the inner part of the quinone binding pocket. Nevertheless, we noted that QT is a unique electron acceptor from complex I distinct from typical short-chain ubiquinones such as ubiquinone-1 (Q₁) for several reasons; for example, QT reduction in NADH-QT oxidoredn. was almost completely insensitive to quinone-site inhibitors (such as bullatacin and piericidin A), and this reaction did not produce a membrane potential. On the basis of detailed comparisons of the electron transfer features between QT and typical short-chain quinones, we conclude that QT may accept electrons from an N2 cluster at a position different from that of typical short-chain quinones because of its unique side-chain structure; accordingly, QT reduction is unable to induce putative structural changes inside the quinone binding pocket, which are critical for driving proton translocation. Thus, QT is the first ubiquinone analog, to the best of our knowledge, the catalytic reduction of which is decoupled from proton translocation through the membrane domain. Implications for mechanistic studies on QT are also discussed. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7SDS of cas: 605-94-7).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. 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: 605-94-7

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1,2,4-dithiazolidines; synthesis, antibacterial and antifungal activity was written by Deohate, Pradip P.;Berad, B. N.. And the article was included in Chemistry: An Indian Journal in 2004.Related Products of 57179-35-8 This article mentions the following:

3,5-Diphenylimino-4-alkylbenzylidene amidino-1,2,4-dithiazolidines, e.g., I, have been obtained by the basification of their hydrochlorides, which were prepared by efficient method of interaction of N-phenyl-S-chloro isothiocarbamoyl chloride and 1-(substituted) alkylbenzylidene amidino-3-Ph thiocarbamides. The latter were synthesized by the condensation of 1-amidino-3-Ph thiocarbamide and different aliphatic and aromatic aldehydes. 3,5-Diphenylimino-4-alkylbenzylidene amidino-1,2,4-dithiazolidines underwent acylation to afford monoacetyl derivatives, and on reaction with sodium nitrite in acidic medium afforded mononitroso derivatives The title compounds were assayed for their antibacterial and antifungal activity against gram pos. as well as gram neg. microorganisms. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Related Products of 57179-35-8).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) 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. 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.Related Products of 57179-35-8

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Ether – Wikipedia,
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Analogs of the cyclic hydroxamic acid 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one (DIMBOA): decomposition to benzoxazolinones and reaction with β-mercaptoethanol was written by Atkinson, Jeffrey;Morand, Peter;Arnason, John T.;Niemeyer, Hermann M.;Bravo, Hector R.. And the article was included in Journal of Organic Chemistry in 1991.Name: 3-Methyl-4-nitroanisole This article mentions the following:

Analogs I (R = OH, OMe, H; R¹ = OH, H; R² = H, 5-Me, 6-OMe, 8-OMe; R³ = OMe, CMe₃, Me, H, Cl, F, CO₂Me, CO₂Et, NO₂, CF₃, cyano; R²R³ = 6,7-OCH₂O) of the aglycons of naturally occurring cyclic hydroxamic acids from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the α-(O-nitrophenoxy)-α-methoxyacetates II, followed by demethylation of the C-2 methoxy group. A structure-activity series was produced, i.e., I (R = R¹ = OH, R² = H, R³ = OMe, CMe₃, Me, H, Cl, F, CO₂Me). The pK_a values for the hydroxamic acid and the phenol moieties were determined for each member of this series. They correlated well with σ in a linear free energy relationship (LFER) yielding values of ρ = 0.71 (with σ_p) for pK_a1 (the hydroxamic acid) and ρ = 1.6 (with σ_m) for pK_a2 (the phenol). A LFER also existed between the rate constants for the unimol. decomposition of these hydroxamic acids to benzoxazolinones and σ⁺ (ρ = -1.1). The rates of hydroxamic acid reduction to lactams by β-mercaptoethanol were also investigated. Only I (R = R¹ = OH; R² = H, 6-OMe, 8-OMe, R³ = OMe; R²R³ = 6,7-OCH₂O) had measurable rates of reduction ¹H NMR spectra recorded during this reaction in D₂O buffers (pD 9), however, showed that I (R = R¹ = OH, R² = H, R³ = OMe, CMe₃, Me, H, Cl) formed a hemithioacetal at C-2 even though only I (R = R¹ = OH, R² = H, R³ = OMe) has a measurable rate of reduction by the same thiol. The remarkable rate enhancement provided by an oxa functionality suggests that reduction occurs by direct attack of thiolate on the hydroxamic N of a resonance-stabilized ion pair. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Name: 3-Methyl-4-nitroanisole).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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. 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).Name: 3-Methyl-4-nitroanisole

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

Electrochemical chlorination and bromination of electron-deficient C-H bonds in quinones, coumarins, quinoxalines and 1,3-diketones was written by Yu, Dan;Ji, Ruixue;Sun, Zhihui;Li, Wenjie;Liu, Zhong-Quan. And the article was included in Tetrahedron Letters in 2021.Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:

The electrochem.-promoted chlorination and bromination of electron-deficient C-H bonds was developed, using quinones, coumarins, quinoxalines and 1,3-diketones. This protocol features readily available and safe halogen sources (hydrochloric acid and KBr), high site-selectivity and mild reaction conditions. It could provide an efficient access to a series of chlorinated and brominated quinones, coumarins, quinoxalines and 1,3-diketones. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Safety of 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

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

Dipeptide-type inhibitors targeting plasmepsins from Plasmodium falciparum was written by Kiso, Aiko;Hidaka, Koushi;Tsuchiya, Yumi;Kimura, Tooru;Hayashi, Yoshio;Nezami, Azin;Liu, Jun;Goldberg, Daniel E.;Freire, Ernesto;Kiso, Yoshiaki. And the article was included in Peptide Science in 2003.Recommanded Product: 1877-75-4 This article mentions the following:

A symposium report. A series of dipeptide-type inhibitors containing allophenylnorstatine-dimethylthioproline scaffold against malarial aspartic protease plasmepsin II (Plm II) was synthesized. Among these compounds, KNI-10006 which has aminoindanol at the P2′ position was found to inhibit Plm II with a K_i value of 0.5 nM. From a SAR study, it is concluded that both the hydroxyl group and the indan structure of the aminoindanol of KNI-10006 are important for its tight binding. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Recommanded Product: 1877-75-4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Recommanded Product: 1877-75-4

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The influence of nitro groups on the reactivity of substituents in the benzene nucleus. II. The dinitrotoluenes was written by Kenner, James;Parkin, Michael. And the article was included in Journal of the Chemical Society, Transactions in 1920.Safety of 3-Methyl-4-nitroanisole This article mentions the following:

The dinitrotoluenes used were prepared according to the directions of Meisenheimer and Hesse (C. A. 14, 52). 2,3-Dinitrotoluene (A) heated for 9 hrs. on a water bath with NaOMe gave a dark oil, 2,6-Me(O₂N)C₆H₃OMe, b₂₄ 140°, leaving a small tarry residue. [3,2-Me(O₂N)C₆H₃]₂N₂O was also produced in small amount and separated from alc. in diamond-shaped prisms, m. 144°. A was unaffected by treatment on a water bath with 2.5 N NH₃ in MeOH. The mixture was then heated under pressure for 15 hrs. at 150-60°, leaving a residue, m. 97°, corresponding to 3-nitro-o-toluidine. H₂S passed for 3 hrs. through a boiling solution of A in alc. to which NH₃ had been added gave yellow prisms from C₆H₆, m. 150°, of dinitroditolyl sulfide, most probably the 2,2′,6,6′-isomeride. The more readily soluble product, after recrystallization from C₆H₆, m. 54°, but it is uncertain whether it is the 2-nitro-m-toluidine as prepared by Limpricht (Ber. 18, 1452 (1885)), as it was not acetylated under ordinary conditions. SnCl₂ and HCl in absolute alc. was dropped into A in cold alc. The solution was extracted with ether and the residue after evaporation treated with light petroleum. The soluble portion consisted of unchanged A and the residue separated from ether and light petroleum in long, stout, deep red prisms of dinitroazotoluene, m. 106° probably the 2,2′,3,3′-isomeride. NaOMe acting on 3,4-dinitrotoluene (B) gave 3,6-Me(O₂N)C₆H₃OMe and possibly some of the 4,2-isomer. Alc. NH₃ and B heated for 6 hrs. at 150° gave pure 4-nitro-m-toluidine, m. 109°, and a mixture of the latter with 3-nitro-p-toluidine. 2,5-Cl(O₂N)-C₆H₃Me and NaOMe interact to give 2,4-Me(O₂N)C₆H₃OMe in long, radiating needles from light petroleum, m. 63°. NaOMe acting on 2,5-dinitrotoluene gave 3,4-Me-(O₂N)C₆H₃OMe, m. 55°. 6-Nitro-m-toluidine was prepared by nitrating m-toluidine after the method of Noelting and Stoecklin (Ber. 24, 564(1891)). It m. 133° rather than 138° as given by N. and S. Its Ac derivative crystallines from dilute alc. in small prisms, m. 104°, and is easily hydrolyzed by concentrated HCl. 2,5-O₂N(ON)C₆H₃Me, prepared by shaking 6-nitro-m-toluidine with Caro’s acid from K₂S₂O₈ and H₂SO₄, for 16 hrs., crystals from alc., m. 113°. Fuming HNO₃ easily oxidizes it to 2,5-dinitrotoluene. The latter treated with alc. NH₃ at 150° for 15 hrs. gave 5-nitro-o-toluidine. K. and P. attempt to explain the influence of NO₂ groups on the various substituents in the C₆H₆ nucleus from their exptl. data. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Safety of 3-Methyl-4-nitroanisole).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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.Safety of 3-Methyl-4-nitroanisole

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