Category: 616-43-3

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Pyrrole Syntheses from Amino Ketones with Ketones and Ketone Esters》. Authors are Piloty, O.; Hirsch, P..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).HPLC of Formula: 616-43-3. Through the article, more information about this compound (cas:616-43-3) is conveyed.

The following pyrrole derivatives have been prepared by treating aqueous solutions of the HCl salts of amino ketones containing an excess of alk. with a ketone or ketone ester and allowing to stand a long time at a slightly elevated temperature in closed vessels. α-β’-Dimethylpyrrole, from Ac2NH2.HCl and AcMe; yield, 30%. α-Phenyl-β’-methylpyrrole, from 10 g. AcCH2NH2.HCl and 5 g. AcPh, m. 152°; yield, 1 g. α,β,β’-Trimethylpyrrole, from AcEt; yield, 28%. α-Ethyl-β,β’-dimethylpyrrole, b10 77-8° (yield, 0.4 g. from 14 g. AcCH3NH2.HCl and 10 g. Et2CO); picrjate, bright yellow, striated prisms, m. 122.5°. α,β,α’-Trimethylpyrrole, from AcCHMeNH2 and AcMe; yield, 50%. Some tetramethylpyrazine is formed in this reaction. AcCHMeNH2 and AcEt react only slowly and incompletely; the chief product is the pyrazine, but a little α,β,α’,β’-tetramethylpyrrole picrate (cf. Fischer and Bartholomäus, C. A., 7, 780) was isolated. Et α,β’-dimethylpyrrole-β-carboxylate, from AcCH2NH2 and AcCH2CO2Et. Monoethyl β-methylpyrrole-α’,β’-dicarboxylate, from 19 g. HO2CCOCH2CO2Et and 11 g. AcCH2NH2.HCl, monoclinic prisms, m. 196° (yield, 2-3 g.), converted by 20 hrs. b. with excess of 20% KOH into β-methylpyrrole-β’ (or α’)-carboxylic acid, flocks, m. 149°, losing CO2 and forming β-methylpyrrole, b11 45°. Monoethyl α,β-dimethylpyrrole-α’,β’-dicarboxylate, from AcCHMeNH2 and HO2CCOCH2CO2Et, prisms, m. 201° (loss of CO2). α,β-Dimethylpyrrole-β’ (or α’)-carboxylic acid, m. 188°. α,β-Dimethylpyrrole, b11 62°; picrate, bright yellow, felted needles, m. 146-5°; contrary to all other pyrrole derivatives, it has the comp. C18H21O7N5, i. e., 2 mols. pyrrole: 1 mol. picric acid.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Name: 3-Methyl-1H-pyrrole. 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: 3-Methyl-1H-pyrrole, is researched, Molecular C5H7N, CAS is 616-43-3, about Immunochemical Detection of Protein Modification Derived from Metabolic Activation of 8-Epidiosbulbin E Acetate. Author is Zhou, Shenzhi; Zhang, Na; Hu, Zixia; Lin, Dongju; Li, Weiwei; Peng, Ying; Zheng, Jiang.

Furanoid 8-epidiosbulbin E acetate (EEA) is one of the most abundant diterpenoid lactones in herbal medicine Dioscorea bulbifera L. (DB). Our early work proved that EEA could be metabolized to EEA-derived cis-enedial (EDE), a reactive intermediate, which is required for the hepatotoxicity observed in exptl. animals exposed to EEA. Also, we found that EDE could modify hepatic protein by reaction with thiol groups and/or primary amines of protein. The present study was inclined to develop polyclonal antibodies to detect protein modified by EDE. An immunogen was prepared by reaction of EDE with keyhole limpet hemocyanin (KLH), and polyclonal antibodies were raised in rabbits immunized with the immunogen. Antisera collected from the immunized rabbits demonstrated high titers evaluated by enzyme-linked immunosorbent assays (ELISAs). Immunoblot anal. showed that the polyclonal antibodies recognized EDE-modified bovine serum albumin (BSA) in a hapten load-dependent manner but did not cross-react with native BSA. Competitive inhibition experiments elicited high selectivity of the antibodies toward EDE-modified BSA. The antibodies allowed us to detect and enrich EDE-modified protein in liver homogenates obtained from EEA-treated mice. The developed immunoprecipitation technique, along with mass spectrometry, enabled us to succeed in identifying multiple hepatic proteins of animals given EEA. We have successfully developed polyclonal antibodies with the ability to recognize EDE-derived protein adducts, which is a unique tool for us to define the mechanisms of toxic action of EEA.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Practical synthesis of thieno[3,2-b]pyrrole》. Authors are Matteson, Donald S.; Snyder, H. S..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Electric Literature of C5H7N. Through the article, more information about this compound (cas:616-43-3) is conveyed.

cf. C.A. 51, 16422a. KCNS(200 g.) in 250 ml. MeOH at -75° (Dry Ice-Me2CO bath) stirred with dropwise addition of 159.6 g. Br in 125 ml. MeOH at -75° and the mixture kept below -60°, the thiocyanogen solution cooled to -75° and treated rapidly with 67.1 g. redistilled pyrrole in 250 ml. MeOH at -75° and the mixture stirred (with cooling bath removed) until the temperature rose to -25°, poured onto 2 kg. crushed ice and stirred with 300 g. NaCl, filtered through a 5-6-in. Buchner funnel and the ice and solids washed freely with H2O, the crude 3-thiocyanopyrrole (I) dried in vacuo and clarified in 100 ml. CH2Cl2 and 500 ml. methylcyclohexane (MgSO4 and Darco) at 40°, the colorless solution chilled and seeded, kept 17 hrs. at 0°, and chilled to -20° gave 62 g. I, m. 40-4°, infrared spectrum identical with that of I prepared from Cu(CNS)2 and pyrrole. I stains the skin deep red and may cause burning or itching sensations. The use of rubber gloves is mandatory and contacted areas should be washed immediately with soap and H2O and treated with 3% H2O2. Pyrrole (0.71 g.) in 75 ml. MeOH stirred at 0-5° (N atm.) with portionwise addition of 0.2 mole Cu(CNS)2 [on basis of (NCS)2 analysis] in a few min. and stirring continued 50 min. at 0-5°, the mixture filtered and the CuCNS washed with 50 ml. MeOH, the filtrate and washings poured onto 300 g. crushed ice and 100 g. NaCl added, the mixture filtered and the solids extracted with 225 ml. methylcyclohexane, the solution treated with Darco and cooled, seeded, and kept 17 hrs. at 0° gave 5.83 g. I, m. 41.5-43° (methylcyclohexane). As a route to 3-(alkylthio)pyrroles, attempts to isolate 3-mercaptopyrrole (II), 3-RSC4H4N (R = H) (IIa), were made but abandoned when a more promising way was found. Mg (1.87 g.) in 125 ml. MeOH (N atm.) at -20° kept 1 hr. with 6.2 g. I and the mixture poured into 500 ml. H2O, 200 ml. Et2O, and sufficient solid CO2 to dissolve the precipitated Mg(OH)2, the aqueous phase extracted with Et2O and the dried Et2O solutions evaporated in vacuo, the residue sublimed at 75°/0.1 mm. and the product (6.8 g.) recrystallized from PhMe, resublimed, recrystallized from dilute MeOH, and resublimed at 55-65°/0.1 mm. gave S-3-pyrrolyl O-Me thioimidocarbonate, II [R = C(:NH)OMe], m. 77-80°. I(6.21 g.) and 8.5 g. MeI in 50 ml. MeOH at -20° (N atm.) stirred with dropwise addition in 10 min. of 7.9 g. 85% KOH in 20 ml. H2O and 20 ml. MeOH and stirring continued 1.5 hrs. without cooling, the excess alkali neutralized with solid CO2 and the mixture poured into 500 ml. H2O containing 100 g. NaCl, the mixture extracted 3 times with 50 ml. CH2Cl2 and the dried solution (K2CO3) evaporated in vacuo, the residue distilled, and the product (5.1 g.) redistilled gave II (R = Me) (IIb), b12-13 88-9°. The excellent (90%) yield of IIb showed that the extremely unstable anion of IIa exists long enough to displace halide ions from a moderately active alkyl halide. I (62.1 g.) and 83.5 g. BrCH2CO2H in 500 ml. MeOH at -50° stirred rapidly with addition of 123 g. 85% KOH in 500 ml. 50% dilute MeOH in 10 min. and stirring continued 2 hrs. without cooling, the mixture brought to pH 8 with solid CO2 and the solvent evaporated in vacuo (warm H2O bath to avoid bumping), the solid residue taken up in 500 ml. CH2Cl2 and the mixture stirred with controlled addition of 375 ml. ice-cold 4N HCl, the aqueous phase extracted twice with 250 ml. CH2Cl2 and the combined dried CH2Cl2 solutions treated with Darco and filtered, the filtrate saturated with excess dry NH3, and filtered gave 78 g. II (R = CH2CO2NH4) (IIc), m. 127-33°, purified by treatment of IIc with N HCl and extraction with CH2Cl2, dehydration over MgSO4, and crystallization by treatment with anhydrous NH3 to give IIc, m. 125-33°; Ca salt-2H2O, m. 112-20° (decomposition). IIc in MeOH refluxed 20 hrs. with ZnCl2 and the product purified by extraction followed by distillation in a sublimation apparatus at 80°/0.1 mm. gave the liquid ester II (R = CH2CO2Me). BrCH2CH(OEt)2 failed to react with I under the above conditions and active alkyl halides such as PhCOCH2Br, BrCH2CO2Et, and ClCH2COCO2H appeared to be attacked by OH- more rapidly than was I and also failed to give sulfides. IIc (17.42 g.) and 250 ml. CH2Cl2 shaken with 30 ml. ice-cold 6N HCl and the aqueous phase extracted twice with 250 ml. CH2Cl2, the combined CH2Cl2 extracts dried (MgSO4) and treated with Darco, filtered and the filtrates combined with the 150 ml. CH2Cl2 washings of the Mg2SO4, the CH2Cl2 solution added dropwise in 50 min. to the most vigorously agitated region of 400 g. well-stirred polyphosphoric acid at 120-3° with free vaporization of the CH2Cl2, the mixture cooled below 100° and added slowly with stirring to 1200 ml. H2O and 750 ml. EtOAc, the stirring continued 30 min. and the aqueous layer extracted with 250 ml. EtOAc, the aqueous layer saturated with 300 g. NaCl and extracted twice with 250 ml. EtOAc, the emulsion layer neutralized with Na2CO3 and warmed on a steam bath prior to a 3-fold extraction with 100 ml. portions of EtOAc, the combined EtOAc solutions washed with aqueous NaHCO3 and dried over MgSO4, evaporated in vacuo, and the residue sublimed twice at 120°/0.1 mm. gave 5.0 g. product, m. 183-8.5°, purified by sublimation twice, recrystallization twice from aqueous HCONMe2 and sublimation twice, treatment with Darco, and recrystallization from MeOH to give 2H,3H-thieno[3,2-b]pyrrol-3-one (III), m. 187-90°, λ 330, 303 (min.), 279, 236 (min.) mμ (ε 7400, 3900, 16,000, 500, 95% alc.), ν 3140, 1635 cm.-1 (Nujol). III (0.28 g.) in 35 ml. 95% alc. refluxed 1 hr. with 2.5 g. Raney Ni (W6) and the solution filtered, the residue washed with alc. and the alc. solutions evaporated in vacuo, the residue sublimed, and the product (0.06 g.) recrystallized from H2O gave 23 mg. 2-acetylpyrrole, m. 89-91°, identical with that prepared from C4H4NMgBr and AcCl. III (1.39 g.) and 1.5 g. NaBH4 in 50 ml. MeOH refluxed 16 hrs. under N and the mixture poured into 200 ml. 15% aqueous NaCl, extracted 3 times with 50 ml. CH2Cl2 and the dried extract evaporated, the residue sublimed at 6070°/0.1 mm., and the 0.76 g. product recrystallized from Et2O-C5H12 at -70° and resublimed 3 times gave thieno[3,2-b]pyrrole, m. 25-8°, λ 260, 233 (min.) mμ (ε 11,800, 4900, 95% alc.), infrared spectrum and that of a less pure sample synthesized from thiophene (cf. Snyder, et al., C.A. 51, 13846b) given.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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, Soil Biology & Biochemistry called Management induced organic matter differentiation in grassland and arable soil: a study using pyrolysis techniques, Author is Nierop, Klaas G. J.; Pulleman, Mirjam M.; Marinissen, Joke C. Y., which mentions a compound: 616-43-3, SMILESS is CC1=CNC=C1, Molecular C5H7N, Quality Control of 3-Methyl-1H-pyrrole.

Differences in agricultural management and land use lead to differences in soil structure, soil organic matter (SOM) dynamics and composition We investigated the SOM composition at 3 depth layers in a permanent pasture (PP), an organic arable (OA) and a conventional arable (CA) field within one soil series in marine loam deposits in The Netherlands. Both arable fields were in the grass phase of the rotation. The chem. composition of SOM was determined by a combination of conventional pyrolysis-gas chromatog./mass spectrometry (Py-GC/MS) and of thermally-assisted hydrolysis and methylation (THM) with tetramethylammonium hydroxide (TMAH). In PP, SOM was composed of relatively little decomposed, mainly grass-derived material comprising polysaccharides, lignin, aliphatic compounds (extractable lipids, cutin, suberin) and proteins. With depth, plant-derived constituents decreased, whereas microbial and humified material predominated. Both arable soils contained mainly strongly humified plant material and microbially altered proteineous material that showed heterocyclic N-compounds together with alkylbenzenes and phenols upon pyrolysis. With THM, small traces of plant-derived alkanols and cutin/suberin were observed in the arable soils. The upper layers of OA contained little lignin, which can only be derived from the grass vegetation or manure inputs since last plowing (2 yr before), since it was not found in the whole plow layer. Overall SOM composition is therefore hardly affected by organic farming compared to conventional management. The differences in SOM content and composition between the pasture and arable fields can be ascribed to differences in input and depth distribution of fresh organic materials. A difference in phys. protection of easily mineralizable SOM between pasture and arable soils is also likely to contribute.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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: 616-43-3, is researched, Molecular C5H7N, about Theoretical and experimental study of monosubstituted pyrroles, the main research direction is pyrrole UV spectra; formation energy pyrrole; electronic transition pyrrole.Recommanded Product: 616-43-3.

The energies of formation of 2-substituted pyrroles and 3-substituted pyrroles are almost the same; and the wavelengths of the π → π* electronic transition increase in the following order: H < Me < CN < CO2H < CH:NOH < CHO < NO2. Exptl. studies confirm the theoretical relation between wavelength and substituent. The larger bathochromic shifts are observed for the 2-substituted compounds When you point to this article, it is believed that you are also very interested in this compound(616-43-3)Recommanded Product: 616-43-3 and due to space limitations, I can only present the most important information.

Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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, Journal of Organic Chemistry called Conjugated Macrocycles Related to the Porphyrins. 25.Proton NMR Spectroscopic Evidence for a Preferred [18]Annulene Substructure in Carbaporphyrins from the Magnitude of Selected 4JH,H CH:C-CH3 Coupling Constants, Author is Liu, Dachun; Lash, Timothy D., which mentions a compound: 616-43-3, SMILESS is CC1=CNC=C1, Molecular C5H7N, COA of Formula: C5H7N.

Two new benzocarbaporphyrins with four or five alkyl substituents have been synthesized by the “”3 + 1″” MacDonald methodol. At lower temperatures, the proton NMR spectrum of the asym. substituted carbaporphyrin I gave two NH resonances, while carbaporphyrin II, which retains a plane of symmetry, gave only one resonance of this kind. As no addnl. peaks were seen for the remaining protons, these data strongly support the proposal that a single tautomer predominates in solution where the two NH protons flank the interior CH. Carbaporphyrin I, which has a CH:CMe unit on the pyrrolic ring opposite the indene moiety, gave a long-range coupling constant of 4JMe,H = 1.3-1.4 Hz. On the other hand, the CH:CMe units of II, which correspond to the pyrrole rings on each side of the carbocyclic moiety, gave 4JMe,H = 0.9-1.0 Hz. These values are in accord with those expected if the exterior carbon-carbon bonds of the pyrrole units next to the indene ring are part of a fully delocalized 18π electron system, while the C:C bond of the remaining pyrrole ring retains substantial olefinic character.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3-Methyl-1H-pyrrole( cas:616-43-3 ) is researched.Category: chiral-oxygen-ligands.Groves, J. K.; Anderson, Hugh J.; Nagy, H. published the article 《Pyrrole chemistry. XIII. New syntheses of 3-alkylpyrroles》 about this compound( cas:616-43-3 ) in Canadian Journal of Chemistry. Keywords: pyrrole alkyl preparation. Let’s learn more about this compound (cas:616-43-3).

3-n-Alkylpyrroles are prepared in good yield by a combined Wolff-Kishner reduction and hydrolysis and decarboxylation of 4-acyl-2-pyrrole-thiolcarboxylates. Me 4-isopropyl-2-pyrrolecarboxylate and 4-tert-butyl-2-pyrrolecarbonitrile are prepared by alkylation of Me 2-pyrrolecarboxylate and 2-pyrrolecarbonitrile, resp. Hydrolysis and decarboxylation of these disubstituted compounds afford the corresponding-3-alkylpyrroles. Mass spectral data for some 1-, 2-, and 3-alkylpyrroles are reported.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Electric Literature of C5H7N. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 3-Methyl-1H-pyrrole, is researched, Molecular C5H7N, CAS is 616-43-3, about Scientific investigation of the paint and adhesive materials used in the Western Han dynasty polychromy terracotta army, Qingzhou, China. Author is Wei, Shuya; Ma, Qinglin; Schreiner, Manfred.

A royal tomb of early period of the Western Han dynasty (206 B.C-8 A.D) was excavated by archaeologists in Qingzhou County, Shandong Province in 2006. Over 2000 polychromy terracotta soldiers, horses, chariots, servants etc. were unearthed from the tomb. All the terracotta figures are one quarter or one sixth as large as the livings, most of them were painted with well designed patterns. In order to gain complete information about the materials and techniques used for the polychromy on the terracotta army, five samples from the painted areas were taken. In addition, one sample from the area to adhere one leg to the polychromy horse body was also obtained. The anal. techniques applied include XRF, FTIR, Py-GC/MS and GC/MS. Chinese purple, cinnabar, lead red and ochre were used as pigments, while animal glue was identified as binding medium and adhesive in the polychromy terracotta army in the Han Dynasty. The results definitely will provide new evidence about the materials and technologies used in Han Dynasty. Especially, the binding medium identified is different in comparison with Qin Shihuang’s terracotta army (259-210 BC).

When you point to this article, it is believed that you are also very interested in this compound(616-43-3)Electric Literature of C5H7N and due to space limitations, I can only present the most important information.

Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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, Pontif. Acad. Sci. Acta called Polarographic reducibility of pyrrole and pyrrole substitutes, Author is Bonino, G. B., which mentions a compound: 616-43-3, SMILESS is CC1=CNC=C1, Molecular C5H7N, Computed Properties of C5H7N.

cf. C.A. 38, 1230.6. 1-Methylpyrrole, 2-methylpyrrole, 1-allylpyrrole, 2,4-dimethylpyrrole, 2,5-dimethylpyrrole, 3-methylpyrrole, 4-ethylpyrrole, 2,3,5-trimethylpyrrole, 2,5-dimethylpyrrole, 3-ethylpyrrole, 2,4-dimethylpyrrole, and pure 2,3,4,5-tetramethylpyrrole (I) (the latter obtained by the action of K methylate on trimethylpyrrole) in 0.1 N LiCl solution in 80% EtOH were not reduced polarographically. I obtained by the Piloty and Hirsch method (cf. C.A. 7, 1365), containing tetramethylpyrazine (II) as an impurity, showed the same polarographic wave of reduction as II. The findings of Dezelic (Boll. intern. acad. croata sci. e belle arti, 1941) are not correct.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Thermal reactions of organic nitrogen compounds. III. 1-Isopropylpyrrole》. Authors are Jacobson, I. A. Jr.; Jensen, H. B..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Safety of 3-Methyl-1H-pyrrole. Through the article, more information about this compound (cas:616-43-3) is conveyed.

cf. CA 57, 9781i. 1-Isopropylpyrrole isomerized irreversibly to 2-isopropylpyrrole, which in turn isomerized reversibly to 3-isopropylpyrrole. The temperature range was 340-575°. The entropies and heats of activation were calculated for the isomerization reactions 1-alkylpyrrole → 2-alkylpyrrole ⇄ 3-alkylpyrrole at 500° for methyl-, butyl-, and isopropylpyrrole.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate