Tag: M.W:100-200

Synthetic Route of C3H4BrN. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Bromopropanenitrile, is researched, Molecular C3H4BrN, CAS is 19481-82-4, about Atom-transfer radical polymerization of acrylonitrile under microwave irradiation. Author is Hou, Chen; Guo, Zhenliang; Liu, Junshen; Ying, Liang; Geng, Dongdong.

A single-pot atom-transfer radical polymerization under microwave irradiation was first used to successfully synthesize polyacrylonitrile. This was achieved with FeBr2/isophthalic acid as the catalyst and 2-bromopropionitrile as the initiator. With the same exptl. conditions, the apparent rate constant under microwave irradiation was higher than that under conventional heating. An FeBr2/isophthalic acid ratio of 1:2 not only gave the best control of mol. weight and its distribution but also provided a rather rapid reaction rate. The polymers obtained were end-functionalized by bromine atoms, and they were used as macroinitiators to proceed the chain extension polymerization

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, Non-U.S. Gov’t, Organic Letters called NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes, Author is Qu, Zhonghua; Chen, Xing; Zhong, Shuai; Deng, Guo-Jun; Huang, Huawen, which mentions a compound: 376581-24-7, SMILESS is OB(C1=CC=C2N=CC=CC2=C1)O, Molecular C9H8BNO2, Computed Properties of C9H8BNO2.

A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerated a broad range of reducible functional groups such as halogen (Cl, Br and even I), aldehyde, ketone, carboxyl and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Aminobenzothiazoles. XI. Synthesis of 5,4′-disubstituted 1-anilinobenzothiazoles from nuclear substituted thiocarbenilides》. Authors are Dyson, George M.; Hunter, Robert F.; Soyka, Charles.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).Reference of 1,2-Benzisoxazole. Through the article, more information about this compound (cas:271-95-4) is conveyed.

cf. C. A. 23, 835. (p-BrC6H4NH)2CS and Br in CHCl3 yield a perbromide, which, on heating, gives a hydropentabromide(I), C13H8N2Br2S.HBr.Br4, orange-red needles, m. 170° (decomposition) and rapidly loses Br on exposure to moist air suspended in H2SO3 and treated with SO2, there results 5,4′-dibromo-1-anilinobenzothiazole(II), m. 221°; Ac derivative, m. 205-6°; HBr salt, m. 250° (decomposition); Br gives I. 1-Chloro-5-bromobenzothiazole, m. 89°, b13 157-9°, results by heating p-BrC6H4NCS and PCl5 30-40 hrs. at 170-80° warming with p-BrC6H4NH2 gives II. p-BrC6H4NHCSNHPh and Br in CHCl3 give the hydrotribromide, m. 148° (decomposition), which is reduced to 4′-bromo-1-anilinobenzothiazole (III), m. 214-5°, also obtained from 1-chlorobenzothiazole and p-BrC6H4NH2. Bromination of III gives II. 1-Anilinobenzothiazole yields a hexabromide, m. 140°, which yields II on being dissolved in boiling absolute EtOH. Hugershoff’s dibromoanilinobenzothiazole (Ber. 36, 3121(1903)) appears to consist mainly of II, although the m. p. could not be raised above 200°. Bromination of II gives an unstable orange hexabromide, m. 254°, which gives with hot absolute EtOH a tetra-Br substitution derivative, m. 196-8°. (p-ClC6H4NH)2CS and Br in CHCl3 yield a hydrotribromide, orange, m. 165-7° (decompm); reduction gives 5,4′-dichloro-1-aminobenzothiazole, m. 224°; Ac derivative, m. 186-7°; HBr salt. yellow, m. 217°; hexabromide, orange, m. 263° (decomposition). p-ClC6H4NHCSNHPh yields a Br addition compound, orange, m. 130° (decomposition); 4′-chloro-1-anilinobenzothiazole, m. 196°; this is also obtained from 1-chlorobenzothiazole and p-ClC6H4NH2. (p-IC6H4NH)2CS and Br in CHCl3 yield a red bromide, m. 185°, and a yellow, m. 211°; both, on reduction, yield 5,4′-diiodo-1-anilinobenzothiazole, m. 193° (decomposition); this also results by treating 1-anilinobenzothiazole in AcOH with ICl, warming the solution and diluting with H2O. (p-FC6H4NH)2CS gives a hydrotribromide, orange, m. 150-2° (decomposition); 5,4′-difluoro-1-anilinobenzothiazole, m. 227-8°. 5,4′-Dinitro-1-anilinobenzothiazole, brilliant yellow, in. 280°; this also results on nitration of 1-anilinobenzothiazole. (p-NCC6H4NH)2CS and Br give an addition product, golden, m. 159-60° (decomposition): 5,4′-dicyano-1-anilinobenzothiazole, m. 222°. (p-EtO2CC6H4NH)2CS yields a hydropentabromide, orange, m. 110° (decompn); reduction gives Et 1-anilinobenzothiazole-5,4′-dicarboxylate, m. 190-2°; hydrolysis gives the free acid, does not m. 290°. (p-MeOC6H4NH)2CS yields a brick-red bromide, m. 137° (decomposition), reduced to a dibromo-5,4′-dimethoxy-1-anilinobenzothiazole, m. 240°. PhNHCSNAcPh yields a hydrotribromide, orange, m. 167° (decomposition); the same compound is obtained from 1-acetanilinobenzothiazole, HBr and Br (Hugershoff, Ber. 36, 3136(1903)); Br in CHCl3 gives an orange hexa-Br addition compound, m. 163° (decomposition).

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Gazzetta Chimica Italiana called Reactions with hydrazoic acid in sulfuric acid solutions. XIX. Formation of oxazoles and isoxazoles, Author is Caronna, Gaetano; Palazzo, Salvatore, which mentions a compound: 271-95-4, SMILESS is C12=CC=CC=C1ON=C2, Molecular C7H5NO, Application In Synthesis of 1,2-Benzisoxazole.

cf. CA 45, 2007b; 52, 15481c. The addition of HN3 to o-hydroxy aldehydes occurred without addition of the entire mol. of HN3. 2,5-HO(O2N)C6H3CHO (5 g.) added to 50 ml. CHCl3 and the yellow solution stratified with 15 ml. concentrated H2SO4 (d. 1.84), treated portionwise with 4.2 g. NaN3 with evolution of N and the mixture kept 12 hrs., the colorless CHCl3 layer decanted and the residue washed by decantation with CHCl3, poured slowly onto ice and the H2O-washed product crystallized (alc., C) gave 5-nitro-1,2-benzisoxazole (I), m. 126-7°, also obtained from the CHCl3 mother liquors to give a final yield of 85%. I hydrolyzed in dilute alkali and the orange red solution acidified with dilute HCl gave 2,5-HO(O2N)C6H3CN, m. 190-4°. The original dilute H2SO4 mother liquor made alk. with Na2CO3 and extracted repeatedly with Et2O, the extract evaporated and the residue crystallized from alc. yielded authentic 2-amino-5-nitrobenzoxazole, m. 288°. 5,2-Cl(OH)C6H3CHO (5 g.) in 30 ml. CHCl3 and 10 ml. concentrated H2SO4 treated portionwise with 4.5 g. HN3 and the mixture worked up as before gave 5-chloro-1,2-benzisoxazole, m. 70°, hydrolyzed to the corresponding 5,2-Cl(O2N)C6H3CN, m. 164-5° (H2O), and 2-amino-5-chlorobenzoxazole, m. 184°, together with a small amount of 5,2-Cl(HO)C6H3CN. 2,3,5-HO(Cl2)C6H2CHO (5 g.) in 30 ml. CHCl3, stratified with 30 ml. concentrated H2SO4 and treated portionwise with 4 g. NaN3 yielded, on working up, 5,7-dichloro-1,2-benzisoxazole, m. 107°, converted by alk. hydrolysis to 2,3,5-HO(Cl2)C6H2CN, m. 139°, and 2-amino-5,7-dichlorobenzoxazole, m. 251°. The average yields of benzisoxazoles from the corresponding aldehydes were about 90%. A probable mechanism for the cyclization was discussed.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Computed Properties of C3H4BrN. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-Bromopropanenitrile, is researched, Molecular C3H4BrN, CAS is 19481-82-4, about MALDI-ToF mass spectrometry detection of intramolecular composition gradient in copolymers. Author is Trhlikova, Olga; Janata, Miroslav; Walterova, Zuzana; Kanizsova, Livia; Cadova, Eva; Horsky, Jiri.

Since their addition to the polymer-architecture portfolio, gradient copolymers have attracted significant attention. Up to now, however, the existence of the intramol. composition gradient must have been ascertained by sampling during living copolymerization because a reliable method for the detection of the composition gradient in the finalized copolymer had not been established yet. Here we show that MALDI-ToF mass spectrometry not only identifies imperfect, i.e. prematurely terminated copolymers but these copolymers can be used as “”time capsules”” which provide information on composition evolution and the intramol. composition gradient.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Matyjaszewski, Krzysztof; Poli, Rinaldo researched the compound: 2-Bromopropanenitrile( cas:19481-82-4 ).Application of 19481-82-4.They published the article 《Comparison of Bond Dissociation Energies of Dormant Species Relevant to Degenerative Transfer and Atom Transfer Radical Polymerization》 about this compound( cas:19481-82-4 ) in Macromolecules. Keywords: bond dissociation energy dormant species transfer atom radical polymerization; dithiobenzoate bond dissociation energy transfer atom radical polymerization; dithioacetate bond dissociation energy transfer atom radical polymerization. We’ll tell you more about this compound (cas:19481-82-4).

D. functional calculations are reported for the bond dissociation energy (BDE) of a number of dithioacetates, CH3C(S)S-R and selected dithiobenzoates, PhC(S)S-R, of relevance to reversible addition-fragmentation transfer (RAFT) controlled radical polymerization In comparison with previously reported calculations [Gillies, M. B.; Matyjaszewski, K.; Norrby, P.-O.; Pintauer, T.; Poli, P.; Richard, R. Macromols. 2003, 36, 8551-8559] at the same level on corresponding R-X systems (X = Cl, Br, I, N3, S2CNMe2), the results reveal significant steric and polar effects on the BDE. Particularly bulky R groups (tBu, C(CH3)2COOMe) yield relatively weaker R-S2CZ (Z = Me, Ph) bonds, such that the radical transfer process to R’-S2CZ where R’ is less sterically encumbering (e.g., CH(CH3)COOMe) is less favorable, when compared to the same transfer to R’-Cl (or R’-Br). As indicated by an anal. of DFT computed natural charges, electroneg. substituents in the α position of the R group (F, OMe, OAc, and also multiple substitution with Cl atoms) reinforce the ionic component of the R-X bond when X is a more electroneg. group (i.e., Cl, Br) relative to S2CZ. Therefore, transfer of these radicals is also disfavored for R’-S2CZ relative to R’-Cl or R’-Br. These effects rationalize exptl. observations and can be used as a guiding tool for the rational design of ATRP initiators and RAFT transfer agents.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Lewis acid-catalyzed [4+2] annulation between propargylic alcohols with benzo[d]isoxazoles, published in 2017, which mentions a compound: 271-95-4, Name is 1,2-Benzisoxazole, Molecular C7H5NO, Quality Control of 1,2-Benzisoxazole.

An unprecedented copper(II) trifluoromethanesulfonate-catalyzed [4+2] cascade annulation of propargylic alcs. with benzo[d]isoxazoles proceeded through a sequential ring opening/Meyer-Schuster rearrangement/intermol. cyclization. This protocol tolerated a broad variety of functional groups, offers a versatile, modular and atom-economical access to a new class of fascinating quinoline derivatives in good yields under mild conditions. The transformation could be scaled up to a gram scale efficiently, thus highlighting the synthetic utility of this methodol.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Formation and constitution of indoxazenes》. Authors are Lindemann, Hans; Pickert, Walter.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).COA of Formula: C7H5NO. Through the article, more information about this compound (cas:271-95-4) is conveyed.

Heating o-HOC6H4CMeNOAc with NaOH on the H2O bath gives 2-methylindoxazene (I); with an excess of NaOH the corresponding oxime is obtained. 2-Hydroxy-4,6-dimethylbenzaldoxime, m. 130°; Ac derivative, m, 109°; with the calculated amount of NaOH this gives 3,5-dimethylindoxazene (II), b14 117°; with 20% NaOH on the H2O bath II gives 2-hydroxy-4,6-dimethylbenzonitrile, m. 180° (Ac derivative, m. 54°). Reduction of 2,4-dimethylindoxazene (III) in AcOH with Pd on BaSO4. gives 5,2-Me(OH)C6H3COMe; in absolute Et2O the corresponding imine, yellow, m. 167° (decomposition) is formed. In concentrated H2SO4-HNO3, II gives a 4-nitro derivative, m. 112°; NaOH transforms this into 2-hydroxy-4,6-dimethyl-5-nitrobenzonitrile, m. 193°. Indoxazene, d420.4 1.1729, n 1.5554, 1.56161, 1.57721 and 1.59124 for α, D, β and γ at 20.4°; 1, d419.9 1.1260, n 1.54472, 1.55098, 1.56624, 1.58074 at 19.9°; 111, d419.8 1.0955, n 1.53887, 1.54461, 1.55841, – at 19.8°; II, d420.2 1.1061, n, 1.54755, 1.55362, 1.56823, 1.58186 at 20.2°. The constitutions of these compounds are discussed in the light of the spectrochem. data.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Diimino- and diaminopyridine complexes of CuBr and FeBr2 as catalysts in atom transfer radical polymerization (ATRP), published in 2000-09-28, which mentions a compound: 19481-82-4, mainly applied to pyridine complex atom transfer radical polymerization; catalyst ATRP pyridine copper iron complex; methacrylate atom transfer radical polymerization catalyst; acrylate atom transfer radical polymerization catalyst; styrene atom transfer radical polymerization catalyst, Reference of 2-Bromopropanenitrile.

2,6-Bis[1-(octylimino)ethyl]- and 2,6-bis[1-(octylamino)ethyl]pyridine complexes of CuBr and FeBr2 were employed successfully in the atom transfer radical polymerization (ATRP) of Me methacrylate, styrene, and Me acrylate. The diiminopyridine ligand formed active catalysts with CuBr and FeBr2. The diaminopyridine ligand formed an active catalyst with CuBr. Comparison of both ligands in the copper-mediated ATRP reactions showed that the change from the imine to the amine ligand increased the catalytic activity.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzisoxazoles. III》. Authors are Borsche, Walther; Scriba, Wilhelm.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).Application In Synthesis of 1,2-Benzisoxazole. Through the article, more information about this compound (cas:271-95-4) is conveyed.

cf. C. A. 33, 8197.5. Meyer (Cathcart and M., Ber. 25, 3291 (1892)) was of the opinion that benzisoxazoles could not be prepared from oximes of o-acylated halo- or nitrobenzenes unless the radical XC6H4C(:NOH) is bound with a neg. group. It is now shown that this is not true. o-BrC6H4CN and MeMgI give 85% of 2-BrC6H4Ac, b16 118-20°; oxime (I), m. 129°. 2-BrC6H4CO2Me and MeMgI give some dimethyl-2-bromophenylcarbinol, b16 128-30°; BrC6H4Ac was not formed. Heating I with KOH in 50% MeOH gives 80% of 3-methylbenzisoxazole, b15 104-8°. o-BrC6H4CN and EtMgBr give 90% of 2-bromopropiophenone, yellowish oil, b16 135-40°; 2,4-dinitrophenylhydrazone, orange-yellow, m. 115-16°; oxime, b16 164-72°; with KOH in 50% MeOH (9 h. at 120°) there results a mixture of unchanged oxime and ethylindoxazene. o-BrC6H4CN (18.2 g.) and PhCH2MgCl give about 12 g. of 2-bromophenyl benzyl ketone, b15 206-8° (2,4-dinitrophenylhydrazone, orange, m. 149°; oxime, m. 116°); KOH in 50% MeOH (8 h. at 110-15°) gives 85% of 3-benzylbenzisoxazole, m. 87°. 4,3-Br(H2N)C6H3Me gives about 70% of 3-cyano-4-bromotoluene, m. 65°; MeMgI gives 3-acetyl-4-bromotoluene, b15 132-6°; 2,4-dinitrophenylhydrazone, orange, m. 170°; oxime, m. 131-2° (cf. Claus, J. prakt. Chem. 46, 26(1892), who states that it could not be converted to II); KOH in 50% MeOH (9 h. at 150°) gives 3,5-dimethylbenzisoxazole (II), b14 116-18° (NO2 derivative, m. 72°). 2-ClC6H4CN (6.4 g.) gives 4 g. 2-ClC6H4Ac; 2,4-dinitrophenylhydrazone, dark yellow, m. 206°; semicarbazone, m. 178-9°. 2-BrC6H4Ac, BzH and 10% NaOH in MeOH give 2-cinnamoylbromobenzene, b14 234-8°, as a yellow, viscous oil; 2,4-dinitrophenylhydrazone, red, m. 236-7°; an oxime could not be prepared 6,3-Br (O2N)C6H3Ac (4.88 g.) and 4 g. PhNHNH2.HCl in MeOH, heated 18 h. at 150°, give 3.1 g. of 3-methyl-1-phenyl-5-nitroisoindazole, yellow, m. 131-2°; catalytic reduction gives the 5-NH2 derivative, m. 127-8° (Bz derivative, m. 160-1°); a byproduct, yellow, m. 336°, is probably the corresponding azoxy compound Removal of the NH2 group gives 3-methyl-1-phenylisoindazole, m. 73-4°.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI