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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Diazo compounds of ferrocene》. Authors are Nesmeyanov, A. N.; Drozd, V. N.; Sazonova, V. A..The article about the compound:Bromoferrocenecas:1273-73-0,SMILESS:Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25).Application of 1273-73-0. Through the article, more information about this compound (cas:1273-73-0) is conveyed.

cf. CA 52, 14579b. Since ferrocenediazonium salts cannot be prepared with HNO2 owing to destruction of the ring by this acid, an indirect method was devised. Diazoaminoferrocene was added at -4(1° to concentrated HCl and the mixture gradually warmed to -20°, when a violet color of the diazonium salt appeared, while at -15°, N evolution commenced and terminated at -5°; crystals of chloroferrocene precipitated After dilution and extraction with Et2O, the organic extract was washed with aqueous KOH and H2O, and evaporated yielding 72% chloroferrocene (I), m. 57-8°. The mother liquor after neutralization and extraction with Et2O gave 62% ferrocenylamine, m. 154-5°. Similar treatment of benzenediazoaminoferrocene gave 76% I and traces of ferrocenylamine; similar decompn, in concentrated HBr or HI gave 70% bromoferrocene, m. 32-3°, or 72% iodoferrocene, m. 42 4°, resp. Similar reaction with 40% H2SO4 in the presence of Et2O gave a solution containing hydroxyferrocene, which was isolated as the benzoyl derivative, m. 108.5-9 5° in 3% yield. Benzenediazoaminoferrocene hydrolyzed as above in concentrated HCl, warmed to -20° to form the diazonium salt solution, and treated with 2-C10H7OH in 10% KOH in the cold gave, after chromatog. purification on Al2O3, 48% 1-ferroceneazo-2-naphthol (II), m. 151-2°, a green solid, along with 28% I; II gave violet solutions in organic solvents and was insoluble in alkalies. 1,1′-Bis(benzenediazoamino)ferrocene treated similarly in the cold with concentrated HCl gave a violet solution of the bis(diazonium salt), which with 2-C10H7OH as above gave a little II, 35% red 1-benzeneazo-2-naphthol, and 24% black ferrocene-1,1′-bis(1-azo-2-naphthol), decompg 212-13°.

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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 Preparation of chlorinated 3-indolylacetic acids, published in 1977, which mentions a compound: 63352-97-6, mainly applied to indoleacetic acid chloro; phenylhydrazine cyclization formylpropionate; hydrazine phenyl reaction formylpropionate; propionate formyl reaction phenylhydrazine, SDS of cas: 63352-97-6.

Indoleacetic acids I (Rn = 4-Cl, 6-Cl) were prepared in 38-40% yield by reaction of the resp. chloro(diethylaminomethyl)indole with NaCN followed by hydrolysis. I (Rn = 5-Cl, 7-Cl, 4,6-Cl2, 4,7-Cl2, 5,7-Cl2, 6,7-Cl2, 5-Cl-7-Me, 7-Br) were prepared in 7-28% yield by reaction of HCOCH2CH2CO2H with the appropriate phenylhydrazine hydrochlorides.

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Synthetic Route of C10H8BrNO2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-(7-Bromo-1H-indol-3-yl)acetic acid, is researched, Molecular C10H8BrNO2, CAS is 63352-97-6, about Substituted indoleacetic acids tested in tissue cultures. Author is Engvild, Kjeld C..

Monochloro substituted indole-3-acetic acids inhibited shoot induction in tobacco tissue cultures about as much as IAA. Dichloro substituted indole-3-acetic acids inhibited shoot formation less. Other substituted indoleacetic acids except 5-fluoro- and 5-bromoindole-3-acetic acid were less active than IAA. Callus growth was quite variable and not correlated with auxin strength measured in the Avena coleoptile test.

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Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Electrophilic heteroaromatic substitutions. XI. Thallium in pyrrole chemistry. Formation of C-pyrrylthallium derivatives. Author is Monti, Donato; Sleiter, Giancarlo.

Reaction of several pyrrole derivatives with Tl(III) salts was investigated under different exptl. conditions. C-Thallation is dependent on what position (α or β) of the pyrrole nucleus is amenable to attack, and on the nature of the thallating agent. Yields are strongly influenced by electronic and steric effects of the substituents already present in the pyrrole nucleus and by the nature of the reaction medium. Spectroscopic and anal. data for the C-pyrrylthallium derivatives prepared are reported. E.g., treating pyrroles I (R = H; R1 = Me, Et) with Tl(OAc)3 in MeCN or CH2ClCH2Cl gave 37-79% I [R = (AcO)2Tl; same R1].

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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Redox-Rich Metallocene Tetrazene Complexes: Synthesis, Structure, Electrochemistry, and Catalysis.Application of 1273-73-0.

Thermal or photochem. metal-centered cycloaddition reactions of azidocobaltocenium hexafluorophosphate or azidoferrocene with (cyclooctadiene)(cyclopentadienyl)Co(I) afforded the first metallocenyl-substituted tetrazene cyclopentadienyl cobalt complexes together with azocobaltocenium or azoferrocene as side products. The trimetallic CpCo compounds are highly conjugated, colored and redox-active metallo-aromatic compounds, as shown by their spectroscopic, structural and electrochem. properties. The CpCo-tetrazenido complex with two terminally appended cobaltocene units catalyzes electrochem. proton reduction from acetic acid at a mild overpotential (0.35 V). Replacing cobaltocene with ferrocene moieties rendered the complex inactive toward catalysis.

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 1273-73-0, is researched, Molecular C10BrFe, about Metallosupramolecular cluster assemblies based on donor-acceptor type structural frameworks. Syntheses, crystal structures and spectroscopic properties of novel triosmium alkylidyne carbonyl clusters bearing remote ferrocenyl units as electron donors, the main research direction is metallosupramol cluster donor acceptor framework; osmium alkylidyne ferrocenyl tetranuclear cluster; crystal structure osmium alkylidyne ferrocenyl cluster; mol structure osmium alkylidyne ferrocenyl cluster.Formula: C10BrFe.

Two pyridyl ligands containing redox-active ferrocenyl groups [Fe(η5-C5H5)(η5-C5H4C6H4R)] [R = C5H4N (I), NCH(C5H4N) (II)] have been prepared using a palladium-catalyzed aromatic cross-coupling reaction. Treatment of the cluster [Os3(μ-H)3(CO)9(μ3-CCl)] with one equivalent of 1,8-diaza-bicyclo[5.4.0]undec-7-ene in the presence of a ten-fold excess of the ferrocenyl ligands I and II produces the compounds [Os3(μ-H)2(CO)9(μ3-CNC5H4R’)] [R’ = C6H4(η5-C5H4)Fe(η5-C5H5) 1, R’ = CHNC6H4(η5-C5H4)Fe(η5-C5H5) 2] resp. in good yields. Both compounds 1 and 2 exhibit donor-π-acceptor structural frameworks and show considerable neg. solvatochromism in their UV/VIS spectra. Unlike 1 and 2 which possess extended donor-π-acceptor nature, the ferrocenyl-phosphine cluster derivative [Os3(μ-H)2(CO)9{μ3-CPPh2(η5-C5H4)Fe(η5-C5H4PPh2)}] 3 has also been synthesized in moderate yield by the same synthetic route using 1,1′-bis(diphenylphosphino)ferrocene as the nucleophile. The new clusters 1-3 have all been fully characterized by both spectroscopic and crystallog. methods. Conceptually, the classification of 1-3 as supermols. is straightforward, since mol. subunits with well defined intrinsic properties can be easily identified, thus affording a new type of covalently linked donor-acceptor system. Both structural features and spectroscopic data for compounds 1-3 are fully consistent with a zwitterionic formulation for these supramol. species. These results suggest that a strong interaction exists between the ferrocenyl moiety and the OS3C core in their ground states.

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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 Improved synthesis of covalently strapped porphyrins. Application to highly deformed porphyrin synthesis, published in 1988-04-01, which mentions a compound: 2199-44-2, Name is Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, Molecular C9H13NO2, Category: thiazolidine.

The title porphyrins I (n = 1, 2, 3) were prepared α,ω-Dicarboxyalkyl dichloride, was treated with 2 equiv of 2-(ethoxycarbonyl)-3,5-dimethylpyrrole, and the chain-linked bis[5-(ethoxycarbonyl)pyrrole] so obtained was transformed into the pyrrole-2-carboxaldehyde by using standard methodol. Protection of the formyl groups as the dicyanovinyl derivative and the activation of the 2-Me substituents with SO2Cl2 gave the bis[2-(chloromethyl)pyrrol)], which on reaction with a 5-unsubstituted 2-pyrrolecarboxylate, in warm AcOH, afforded the chain-linked dipyrromethane dimer in high yield. Regeneration of the formyl substituents and removal of the ester group produced the 5-formyldipyrromethane dimer II, which was cyclized intramolecularly, under high dilution, to give I. II (n = 0) failed to cyclize.

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Product Details of 2199-44-2. 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. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Fluoropyrroles and tetrafluoroporphyrins.

Photolysis of the pyrrole-β-diazonium tetrafluoroborate I (R = N2+BF4-) gave the β-fluoropyrrole I (R = F) which was oxidized to the alc. II. Treatment of II with K3Fe(CN)6 or Cu(OAc)2 gave the fluoroporphyrins III (M = 2H, Cu) resp.

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Application of 1273-73-0. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Electrochemical Parameterization in Sandwich Complexes of the First Row Transition Metals. Author is Lu, Shuangxing; Strelets, Vladimir V.; Ryan, Matthew F.; Pietro, William J.; Lever, A. B. P..

Applying the ligand electrochem. parameter approach to sandwich complexes and standardizing to the FeIII/FeII couple, the authors obtained EL(L) values for over 200 π-ligands. Linear correlations exist between formal potential (E°) and the ∑EL(L) for each metal couple. In this fashion, the authors report correlation data for many first row transition metal couples. The correlations between the EL(L) of the substituted π-ligand and the Hammett substituent constants (σp) are also explored.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of ferrocene derivatives by means of boron- and halogen-substituted ferrocenes》. Authors are Nesmeyanov, A. N.; Sazonova, V. A.; Drosd, V. N..The article about the compound:Bromoferrocenecas:1273-73-0,SMILESS:Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25).Application In Synthesis of Bromoferrocene. Through the article, more information about this compound (cas:1273-73-0) is conveyed.

[R = ferrocenyl throughout this abstract] A series of new haloferrocene derivatives was prepared from RB(OH)2 (I) derivatives via RLi. Ferrocenyloxy derivatives and their esters were also synthesized and investigated. B(OBu)3 (92 g.) in Et2O was treated at -78° slowly with stirring with RLi from 17.6 g. ferrocene and BuLi (from 39 g. BuCl and 7.6 g. Li) in about 240 cc. Et2O, the mixture stirred until warmed to room temperature, kept overnight, decomposed with 10% H2SO4, the Et2O layer extracted with 10% aqueous KOH (40 cc., twice 10 cc., and five times 40 cc.). The 1st extract acidified and filtered gave 2.90 g. ferrocenylene-1,1′-diboronic acid (II), decomposed at about 180°; the 4th-8th alkali extracts gave 6.06 g. I, yellow, m. 143-8° (sealed tube); the 2nd and 3rd extracts gave a mixture of I and II which washed with Et2O left 0.44 g. II; the Et2O solution evaporated gave 0.72 g. I. I and II refluxed with aqueous ZnCl2 gave ferrocene. I (0.16 g.) in 20 cc. H2O treated with 0.19 g. HgCl2 in aqueous Me2CO gave 0.22 g. RHgCl, m. 192-4° (decomposition) (xylene). Aqueous I refluxed a few min. with excess ammoniacal Ag2O solution and extracted with Et2O, the extract evaporated, and the residue treated with petr. ether left 0.25 g. R2, m. 230-2° (decomposition) (absolute EtOH); the petr. ether solution evaporated gave 0.15 g. ferrocene. I (1 g.) in 200 cc. H2O treated at 50-60° with 1.70 g. CuCl22H2O in 50 cc. H2O, kept 15 min., steam distilled, and the product isolated from the distillate with Et2O gave 0.76 g. RCl, m. 58-9° (MeOH). In the same manner were prepared the following compounds (% yield and m.p. given): RBr, 80, 32-3°; 1,1′-dichloroferrocene (III), 75, 75-7°; 1,1′-dibromoferrocene (IV), 76, 50-1°. II (3.1 g.), 7 cc. MeOH, 4.7 g. CuCl2.2H2O, 75 cc. H2O, and 60 cc. C6H6 refluxed 2.5 h., cooled, distilled, the C6H6 layer separated, the aqueous layer added to the insoluble precipitate, diluted with 70 cc. C6H6, processed again in the same manner, saturated with NaCl, extracted with Et2O, the combined Et2O and C6H6 solutions concentrated to 50 cc., extracted with 10% aqueous KOH, and the extract acidified with 10% H2SO4 yielded 1.56 g. 1′-chloro-1-ferrocenylboronic acid (V), m. 159-61° (aqueous EtOH). Aqueous V boiled with ZnCl2 gave RCl. II and CuBr2 yielded similarly the 1′-Br analog (VI) of V, softened at about 130°, resolidified, m. 155-7°. Aqueous VI refluxed with ZnBr2 gave RBr. V (0.27 g.) in 5 cc. EtOH and 50 cc. H2O treated with 0.28 g. HgCl2 in aqueous Me2CO, the mixture heated 5 min., and filtered yielded 1′-chloro-1-ferrocenylmercuric chloride (VII), m. 144.5-45° (Me2CO), which with Na2S2O3 yielded bis(1′-chloro-1-ferrocenyl)mercury (VIIa), m. 151-2° (xylene-hexane). VI (0.30 g.) and 0.36 g. HgBr2 gave similarly 0.46 g. 1′-Br analog (VIII) of VII, m. 146.5-47° (Me2CO), which with Na2S2O3 yielded the di-Br analog of VIIa, m. 135-6° (MeNO2). VIII in xylene heated gave RBr. VII (1 g.) in 10 cc. xylene treated with 3 g. iodine in 10 cc. hot xylene, the mixture cooled, filtered, the residue washed with EtOH, shaken with 45 g. Na2S2O3 in 200 cc. H2O and with Et2O, and the Et2O layer evaporated gave 0.49 g. 1-chloro-1′-iodoferrocene, m. 42-4° (MeOH). VIII (0.80 g.) in 10 cc. xylene with 3 g. iodine in 10 cc. xylene yielded similarly 0.44 g. 1-bromo-1′-iodoferrocene, m. 28-30° (MeOH). VI (1 g) and 1.7 g. CuCl2 in 120 cc. H2O treated with steam and the product isolated from the distillate with Et2O gave 0.60 g. III, m. 75-7° (EtOH). RBr (0.60 g.) and 1.5 g. Cu phthalimide heated 2 h. at 135-40°, extracted with Et2O, and the extract worked up gave 0.48 g. N-ferrocenylphthalimide (IX), red crystals, m. 156-7° (EtOH). RCl (0.30 g.) and 1.5 g. Cu phthalimide gave similarly 0.24 g. IX. IX (0.3 g.), 0.5 cc. N2H4.H2O, and 5 cc. EtOH refluxed 40 min., diluted with H2O, extracted with Et2O, the Et2O solution extracted with 10% H2SO4, and the acidic extract basified with 10% aqueous KOH yielded 0.15 g. RNH2, m. 153-5°; N-Ac derivative m. 169-71°. RBr (0.30 g.) and 2 g. CuCN heated 2 h. at 135-40° and the product isolated with Et2O gave 0.20 g. RCN, m. 105.5-6.5°, also obtained in 42% yield from RCl and CuCN in C5H5N during 3 h. at 140-5°. RCl (2.5 g.) and 7.5 g. Cu(OAc)2 in 300 cc. 50% EtOH refluxed 15-20 min., diluted with H2O, and the product isolated with Et2O gave 2.3 g. ROAc, m. 64.5-6.5° (aqueous EtOH). RBr (0.30 g.) and 1.0 g. Cu(OAc)2 in 30 cc. 50% EtOH gave similarly 0.25 g. ROAc. I (2.5 g.) in 250 cc. hot H2O treated with 4.35 g. Cu(OAc)2 in hot H2O, the mixture cooled after 10 min., extracted with Et2O, and the residue from the extract treated with petr. ether left 0.42 g. R2, m. 230-2° (decomposition) (EtOH); the petr. ether solution evaporated gave 1.56 g. ROAc, m. 64.5-66° (EtOH). I (0.5 g.) in 60 cc. H2O and 1.0 g. Cu(O2CEt)2 in 40 cc. H2O yielded 0.30 g. EtCO2R, m. 30-1° (EtOH), and 0.08 g. R2. PhMgBr from 0.7 g. PhBr and 0.14 g. Mg in 10 cc. absolute Et2O treated under N with cooling with 0.44 g. ROAc in 5 cc. Et2O, the mixture stirred 1 h. at room temperature, decomposed with aqueous NH4Cl, and the Et2O phase worked up gave 0.23 g. MePh2COH, m. 79-81° (petr. ether); the alk. extract of the Et2O phase treated with CO2 precipitated 0.22 g. ROH, m. 166-70° (under N)(H2O). ROAc (0.40 g.), 6 cc. 10% aqueous KOH, and 8 cc. EtOH refluxed 50 min., the EtOH evaporated, the residual dark brown solution filtered, diluted to 13 cc., and treated with CO2 gave 0.29 g. ROH. VI (2 g.) in hot H2O refluxed with 5.4 g. Cu(OAc)2, cooled, and the product isolated with Et2O yielded 1.62 g. 1,1′-ferrocenylene diacetate (X), m. 55-6° (hexane). V (0.83 g.) and 2.2 g. Cu(OAc)2 gave similarly 0.66 g. X. II (2 g.) in 400 cc. hot H2O and 5.8 g. Cu(OAc)2 heated 40 min. on the water bath and the product isolated with Et2O yielded 0.90 g. X, m. 55-5.5° (hexane). IV (0.3 g.) and 1 g. Cu(OAc)2 in 30 cc. 50% EtOH refluxed 1 h., diluted with H2O, extracted with Et2O, and the extract worked up gave 0.16 g. X, m. 55.5-56° (hexane). X heated 10 min. with 20% aqueous KOH on the water bath and treated with CO2 gave 1,1′-dihydroxyferrocene (XI), yellow air-sensitive crystals, which with BzCl and alkali gave the dibenzoate. XI (from 0.80 g. X) in dry Et2O treated 1.5 h. with a stream of air, washed, and evaporated yielded 60 mg. dimeric cyclopentadienone, b8 120°, m. 96-8°. The hydrolyzates from ROAc and X treated under N with alkali, BzCl, and PhSO2Cl yielded the following compounds (% yield and m.p. given): ROBz, 85, 108.5-9.5°; ROSO2Ph, 90, 90-90.5°; dibenzoate of XI, 68, 114-15°; dibenzenesulfonate of XI, 72, 119.5-20.5°. ROAc (0.3 g.) and 0.5 cc. Me2SO4 in 5 cc. MeOH treated with 1.25 cc. 50% aqueous KOH gave 90% ROMe, m. 39.5-40.5°. X (0.20 g.) in 20 cc. MeOH treated with 3 cc. Me2SO4 yielded 95% 1,1′-dimethoxyferrocene, m. 35-6° (hexane). ROH and XI in 10% aqueous KOH refluxed 3 h. under N with 100% excess ClCH2CO2H, acidified with 10% H2SO4, and the product isolated with Et2O yielded 82% ROCH2CO2H, m. 136-7.5°, and 76% O,O’-(1,1′-ferrocenylene)diglycolic acid, m. 168.5-9.5° (H2O). ROH (0.30 g.), 1.5 g. powd. K2CO3, and 0.55 cc. CH2:CHCH2Br in 7 cc. absolute Me2CO refluxed 2 h. with stirring under N, diluted with H2O, extracted with Et2O, and the extract worked up gave 0.30 g. ROCH2CH:CH2, m. 28-30° (MeOH), which heated under N at 215-20° gave ROH.

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