Category: 2199-49-7

Porphyrins. VI. The relative reactivities of substituted pyrroles was written by Badger, G. M.;Harris, R. L. N.;Jones, R. Alan. And the article was included in Australian Journal of Chemistry in 1964.Formula: C8H11NO2 This article mentions the following:

The comparative reactivities of a series of substituted pyrroles was examined by use of the diazo-coupling reaction and the Ehrlich reaction. The method used was that of Treibs and Fritz (CA 52, 13705g), but some modifications were introduced, p-AcNHC₆H₄N₂Cl was used instead of p-PhNHC₆H₄N₂Cl, and PhN₂Cl and 2,4,6-Br₃C₆H₂N₂OAc were included to improve the accuracy of classification. Six aryldiazonium salts (I-VI) were used. With I-IV the reaction was carried out by mixing an alc. solution of the pyrrole (5 mL. 1.5 鑴?10^-3M) with an aqueous solution of the diazonium salt (0.15 mL., 5 鑴?10^-2M) and with V-VI an HOAc solution of the pyrrole was mixed with an HOAc solution of the Na salt of the anti-diazotate, both with and without the addition of HCl (0.15 mL., 2N). Tests were carried out at pH 3, 5, and 7 with the following pyrroles (substituents given): 3-Me; 2,4-Me₂; 3-CO₂Et; 2,4-Me₂, 3-CO₂Et; 2-Z, 3-Me, 4-CO₂Et; 2-Q, 3-Me, 4-Ac; 3-CO₂Et, 4-Me; 3-Ac, 4-Me; 2-CO₂Et, 3,4-Me₂; 2-CO₂Et, 3,5-Me₂; 2-CO₂Et, 3,5-Me₂; 2-CO₂Et, 3-CH₂CH₂CO₂Et, 5-Me; 2-CO₂Et; 2-CH:C(CN)₂, 3,4-Me₂; 2-CH:C(CN)₂, 3-CH₂CH₂-CO₂Et, 4-Me; 2-CH:C(CN)₂, 4-Me; 2-CH:C(CN)₂, 3-Me; and 2-CH:C(CN)₂. The results showed that the dicyanovinyl group exerted a very pronounced deactivating influence on pyrroles. The dicyanovinyl group was much more deactivating than an ethoxycarbonyl group. Most of the pyrroles used were prepared earlier. Other pyrroles were prepared as follows: A solution of 50 g. 2-carboxy-3-ethoxycarbonyl-4-methylpyrrole in ethanol-amine was refluxed 1 h. and poured into 1 l. H₂O, the mixture extracted 24 h. with ether, and the aqueous solution acidified with dilute HCl to give 36 g. 2-carboxy-3-(2-hydroxyethylcarbonyl)-4-methylpyr-role (VII), m. 219鎺?(decomposition) (EtOH). VII (2.5 g.) in 10 mL. 25% aqueous NaOH was heated 15 h. in a sealed tube at 140-50鎺? the mixture extracted with ether, and the extract dried and evaporated to yield 0.67 g. 3-methylpyrrole (VIII), b. 142-3鎺? Formylation of VIII by the Vilsmeier-Haack method at 0鎺?yielded 2-formyl-3-methylpyrrole (IX), m. 92鎺? Condensation of 0.1 g. IX with 0.05 g. malononitrile in a few drops MeOH and I drop Et₂NH yielded 2-(-dicyanovinyl)-3-methylpyrrole, m. 194.5-5.5鎺?(decomposition) (MeOH). A mixture of 1 g. 2-ethoxycarbonyl-3,4-dimethylpyrrole, 1 mL. EtOH, and 10 mL. 10% aqueous KOH was refluxed 90 min. and the solution cooled and brought to pH 5-6 (HOAc) to yield 0.8 g. 2-carboxy-3,4-dimethylpyrrole (X). Refluxing 5 g. X and 5 mL. ethanolamine 1 h. and working up the mixture yielded 2.56 g. 3,4-dimethylpyrrole (XI), b₇₆₀ 164-6鎺? m. 32-3鎺? Formylation of XI (as in VIII) yielded 2-formyl-3,4-dimethylpyrrole (XII), m. 129-30鎺? XII was converted into 2-(-dicyanovinyl)-3,4-dimethylpyrrole by the method of Fischer and Hoefelman (CA 32, 3389₄). In the experiment, the researchers used many compounds, for example, Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7Formula: C8H11NO2).

Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Formula: C8H11NO2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Simple Formation of an Abiotic Porphyrinogen in Aqueous Solution was written by Lindsey, Jonathan S.;Ptaszek, Marcin;Taniguchi, Masahiko. And the article was included in Origins of Life and Evolution of Biospheres in 2009.Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate This article mentions the following:

Porphyrins have long been proposed as key ingredients in the emergence of life yet plausible routes for forming their essential pyrrole precursor have heretofore not been identified. Here we show that the anaerobic reaction of δ-aminolevulinic acid (ALA, 1-5 mM) with the β-ketoester Me 4-methoxyacetoacetate (2-40 mM) in water (pH 5-7) at 70-100° for >6 h affords the porphyrinogen, which upon chem. oxidation gives the corresponding porphyrin in overall yield of up to 10%. The key intermediate is the α-methoxymethyl-substituted pyrrole, which undergoes tetramerization and macrocycle formation under kinetic control. The resulting type-I porphyrin bears four propionic acid and four carbomethoxy groups, is distinct from porphyrins (e.g., uroporphyrin or coproporphyrin) derivable from ALA alone via the extant universal biosynthetic path to tetrapyrroles, and is photoactive upon assembly into cationic micelles in aqueous solution The simple self-organization of eight acyclic mols. into a tetrapyrrole macrocycle, from which a porphyrin is derived that is photoactive in lipid assemblies, augurs well for the spontaneous origin of catalysts and pigments essential for prebiotic metabolism and proto-photosynthesis. In the experiment, the researchers used many compounds, for example, Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate).

Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Palladium-Catalyzed C2-Regioselective Perfluoroalkylation of the Free (NH)-Heteroarenes was written by Qin, Hong;Zhang, Jie;Qiao, Kai;Zhang, Dong;He, Wei;Liu, Chengkou;Fang, Zheng;Guo, Kai. And the article was included in Journal of Organic Chemistry in 2021.Formula: C8H11NO2 This article mentions the following:

A highly regioselective and atom-efficient strategy for the construction of fused free (NH) heteroarenes I (R = 3-Me, 4-Cl, 7-F, etc.) and II (R¹ = 2-C(O)₂Me, 3-C(O)₂Me, 3-C(O)₂Et-4-Me) through a palladium-catalyzed perfluoroalkyl insertion reaction has been accomplished. This protocol employed multiple iodofluoroalkanes R²I [R² = 1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl, 1,1,2,2,3,3,3-heptafluoropropyl, (benzenesulfonyl)difluoromethyl, etc.] as practical and available perfluoroalkyl sources to provide an operationally simple and versatile route for the synthesis of perfluoroalkylated indoles III. Moreover, indoles I without the assistance of guide groups were utilized as substrates, achieving C(sp2)-H site-selective functionalization of indoles I in yields up to 95%. Furthermore, this protocol was also used for late-stage C2 perfluoroalkylation of bioactive compounds such as auxin, tryptophan, and melatonin analogs. In the experiment, the researchers used many compounds, for example, Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7Formula: C8H11NO2).

Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Formula: C8H11NO2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Pyrrole and polypyrrole-based liquid crystals containing azobenzene mesogenic groups was written by Chen, Yu;Harrison, William T. A.;Imrie, Corrie T.;Ryder, Karl S.. And the article was included in Journal of Materials Chemistry in 2002.Category: esters-buliding-blocks This article mentions the following:

The thermotropic and electrochem. properties and polymerization of a series of N-substituted pyrrole monomers bearing mesogenic 4-substituted azobenzene attached as a pendant group via alkyl spacers were discussed. The effects of azobenzene moiety substitution with methoxy, cyano and nitro terminal groups upon mol. properties were discussed. Addnl. the first crystal structure determination and anal. of two N-alkylpyrroles bearing mesogenic groups was presented. In the experiment, the researchers used many compounds, for example, Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7Category: esters-buliding-blocks).

Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some rearrangements of β-methyl-β’-carbethoxypyrrole was written by Fischer, H.;Wiedemann, O.. And the article was included in Z. physiol. Chem. in 1926.Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate This article mentions the following:

β,β’-Disubstituted pyrroles are of especial interest for syntheses in the field of blood and bile pigments. The α-position of the pyrrole ring, however, becomes less reactive when both β-positions are occupied, particularly with respect to condensations with CH₂O, H₂CO₂ and (CHO)₂. Introduction of an aldehyde group by treatment with HCN and HCl furnished the starting point for the synthesis of a number of new derivatives Piloty’s 3-methyl-4-carbethoxypyrrole-5-carboxylic acid (I) was converted into 3-methyl-4,5-dicarbethoxypyrrole (II), m. 63°, by esterification with EtOH and HCl; into 3-methyl-4-carbethoxy-5-carbomethoxypyrrole, m. 59°, by esterification with CH₂N₂; and into 3-methyl-4-carbethoxypyrrole (III), m. 73°, by heating above the m. p. to expel CO₂. Treatment of III with anhydrous HCN and HCl in Et₂O gave 2-formyl-3-methyl-4-carbethoxypyrrole (IV), m. 121°, and this by reduction with EtONa and (NH₂)₂ at 150-60° was converted into 2,3-dimethylpyrrole; picrate, m. 146-7°; phenylhydrazone, m. 154°; semicarbazone, m. 224°; azlactone, m. 192°; oxime, m. 167°. The oxime when refluxed with Ac₂O and NaOAc gave the nitrile, m. 135°, and an acetylated nitrile. Condensation of III with IV by means of concentrated HCl gave bis-[3-methyl-4-carbethoxypyrryl]methene-HCl (V), m. 195°; free base m. 129°. In like manner a Me derivative of V, m. 218°, was obtained from IV and 2,4-dimethyl-3-carbethoxypyrrole. Saponification of IV with 20% KOH gave 2-formyl-3-methylpyrrole-4-carboxylic acid, m. 255°, and this when heated in vacuo at 190-200° gave 2-formyl-3-methylpyrrole, m. 95°. 2-Acetyl-3-methyl-4-carbethoxypyrrole (VI), m. 117°, was obtained by treatment of III in Et₂O with MeCN and HCl and warming the intermediate imine-HCl with H₂O. Reduction of VI by means of EtONa and (NH₂)₂.H₂O at 150° gave 2-ethyl-3-methylpyrrole, isolated as the picrate, m. 137°. Saponification of VI gave 2-acetyl-3-methylpyrrole-4-carboxylic acid, m. 272°; this loses CO₂ when melted and forms 2-acetyl-3-methylpyrrole, m. 98°. 2-Chloroacetyl-3-methyl-4-carbethoxypyrrole, m. 115°, was prepared by treatment of III with ClCH₂CN and HCl and hydrolysis of the intermediate imine-HCl with dilute NH₄OH. A dimethyldicarbethoxypyrocoll, m. 168°, was obtained by refluxing I with Ac₂O and NaOAc. The hydrazide of I, m. 165°, was prepared by refluxing II in EtOH with (NH₂)₂.H₂O, while further refluxing with excess of the reagent gave pyrryldiketodiazine, which sublimes at 190-310° but does not m. 360°. 3-Methyl-4-carbohydrazidopyrrole-5-carboxylic acid, m. 235°, was obtained by treatment of the K salt of the ester acid with excess of (NH₂)₂.H₂O in EtOH. The following derivatives of the pyrryl-α-acid hydrazide are described: benzoylhydrazide, m. 232°; phenylthiosemicarbazide, m. 185°; condensation product with glyoxal, m. 330°; condensation product with II, m. 221°. The hydrazide of I formed a HCl salt which reacted with NaNO₂ to yield the azide, explosive at 80°. Treatment of the latter with MeOH gave Me 3-methyl-4-carbethoxypyrrole-5-carbamate, m. 108°. 3-Methylpyrrole-4,5-dicarboxylic acid, m. 221°, was prepared by saponification of the ester acid. β-Methylpyrrole reacts with MgEtBr and EtOCOCl to yield 2-carbethoxy-3-methylpyrrole, m. 56°, and this when treated with HCN and HCl yields 2-carbethoxy-3-methyl-5-formylpyrrole, m. 107°; semicarbazone, m. 230°. Distillation of the Ba salt of I converts it into 3-methyl-4-carbethoxypyrrole. In the experiment, the researchers used many compounds, for example, Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate).

Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis and Michael reaction of 3,4-dimethylpyrrole was written by Cheng, D. O.;Bowman, T. L.;LeGoff, E.. And the article was included in Journal of Heterocyclic Chemistry in 1976.COA of Formula: C8H11NO2 This article mentions the following:

MeCH:CHCO2Et and 4-MeC6H4SO2CH2NC gave 3-carbethoxy-4-methylpyrrole, which was reduced with NaAlH2(OCH2CH2OMe)2 to 3,4-dimethylpyrrole (I). Michael addition of Me vinyl ketone and butyn-2-one to I gave the bisadducts, 2,5-bis(3-oxobutyl)-3,4-dimethylpyrrole and 2,5-bis(3-oxobutenyl)-3,4-dimethylpyrrole, resp., while Et propiolate gave only the monoadduct, Et 3-(3,4-dimethylpyrrol-2-yl)propenoate (II). Catalytic reduction of II gave Et 3-(3,4-dimethylpyrrol-2-yl)propanoate, which with Et propiolate gave Et 3-(5-carboethoxyethyl-3,4-dimethylpyrrol-2-yl)propenoate (III). In the experiment, the researchers used many compounds, for example, Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7COA of Formula: C8H11NO2).

Ethyl 4-methyl-1H-pyrrole-3-carboxylate (cas: 2199-49-7) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.COA of Formula: C8H11NO2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics