132281-87-9

Basic information

• Product Name: 3-(2-ForMyl-4-Methyl-1H-pyrrol-3-yl)-propionic acid
• Synonyms: 3-(2-ForMyl-4-Methyl-1H-pyrrol-3-yl)-propionic acid;3-(2-forMyl-4-Methyl-1H-pyrrol-3-yl)propanoic acid
• CAS NO: 132281-87-9
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.18854
• Mol File: 132281-87-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 379.4 °C at 760 mmHg
• Flash Point: 183.3 °C
• Appearance: /
• Density: 1.297g/cm³
• Vapor Pressure: 1.97E-06mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(2-ForMyl-4-Methyl-1H-pyrrol-3-yl)-propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-ForMyl-4-Methyl-1H-pyrrol-3-yl)-propionic acid(132281-87-9)
• EPA Substance Registry System: 3-(2-ForMyl-4-Methyl-1H-pyrrol-3-yl)-propionic acid(132281-87-9)

Safety Data

• Hazardous Substances Data: 132281-87-9(Hazardous Substances Data)

Usage

General Description

3-(2-Formyl-4-Methyl-1H-pyrrol-3-yl)-propionic acid is a compound that falls under the class of organic compounds known as Indoles and derivatives; its molecules feature the indole substructure. The structural makeup implies that it can be categorized as a member of the chemical class of pyrroles. Chemicals in this class are compounds containing a pyrrole ring, which is a five-membered aromatic heterocycle with one nitrogen atom and four carbon atoms. This specific chemical has a rather complex formulation, involving a variety of elements, including carbon, hydrogen, oxygen, and nitrogen. Its relative molecular mass and other physical characteristics can be computed based on the specific proportions and arrangements of these atoms. It can be utilized in different chemical reactions and analytical studies. As of now, however, there isn't much literature available on this chemical's uses or properties as they pertain to pharmacology or industrial applications.

InChI:InChI=1/C9H11NO3/c1-6-4-10-8(5-11)7(6)2-3-9(12)13/h4-5,10H,2-3H2,1H3,(H,12,13)

Upstream product

• 827-84-9 methyl 4-methylpyrrole-3-propionate 
• 68-12-2 N,N-dimethyl-formamide 
• 34463-53-1 2-formyl-3-<2-(methoxycarbonyl)ethyl>-4-methylpyrrole 
• 148317-92-4 2,5-dicarboxy-3-methyl-1H-pyrrole-4-propanoic acid ethyl ester 
• 95196-04-6 2-carboxy-5-(ethoxycarbonyl)-4-methyl-1H-pyrrole-3-propionic acid ethyl ester 
• 132281-90-4 ethyl 4-methyl-1H-pyrrole-3-propanoate 
• 90923-49-2 4-methyl-2,5-dicarboxy-1H-pyrrole-3-propanoic acid 
• 54278-10-3 ethyl 5-(ethoxycarbonyl)-2,4-dimethyl-1H-pyrrole-3-propanoate 

Downstream Products

• 531-14-6 coproporphyrin I 
• 14643-66-4 coproporphyrin III 

Relevant articles and documents

SYNTHESIS AND UNUSUAL PROPERTIES OF C(10)-gem-DIMETHYL BILIRUBIN ANALOGS

The characteristic thermodynamically-favored intramolecularly hydrogen-bonded conformation adopted by bilirubin pigments is destabilized by substituting methyl groups on the C(10) central methylene.These methyl groups impose conformation-destabilizing methyl-methylene non-bonded steric interactions with the propionic acid β-CH2 groups at C(8) and C(12) when the propionic acids are engaged in intramolecular hydrogen bonding with the opposing dipyrrinones.Amphiphilic 10,10-dimethylbilirubins (1) and (2) are found to be more polar, but also more soluble than the parents (3) and (4) in organic solvents; yet, 1H-NMR studies in non-polar solvents indicate that a deformed but folded, intramolecularly hydrogen-bonded conformation is retained.The dimethyl esters of 10,10-dimethylbilirubins 1 and 2 did not exhibit the typical strong tendency of bilirubin dimethyl esters to form intermolecular hydrogen bonds in non-polar solvents such as chloroform and benzene.

The total synthesis of chlorophyll a

The total synthesis of chlorophyll a starting from Knorr's pyrrole (1) is described with full experimental detail. Forty six stages are involved to reach the target molecule, chlorin e6 trimethyl ester (46), from which the preparation of chlorophyll a has already been described. The four pyrroles which are required for rings A, B, C and D are elaborated largely by known reactions, although with considerable improvements. These pyrroles are manipulated to give two dipyrrin derivatives: a left-hand component (26, comprising rings A and D) and a right-hand component (the thioaldehyde 31, comprising rings B and C). These are brought together in a carefully controlled, stepwise, condensation to give a single porphyrin product (35) in 50% yield. This synthesis of an unsymmetrically-substituted porphyrin bearing an electron-withdrawing substituent and a meso-substituent is seen as a very considerable advance, both in conceptual and practical terms, over earlier approaches. During the course of the closure of the macrocycle, intermediates which exemplify a new group of dihydroporphyrins, the phlorins (e.g. 34), are recognised. Eleven steps remain. The porphyrin (35) is shown to undergo dehydrogenation (again via a phlorin intermediate) on brief treatment with acetic acid in air to give the meso-crylic acid derivative (36), which in acetic acid under nitrogen at 110° slowly reaches equilibrium with the purpurin (37). The introduction of the reactive vinyl group at C-3 has been delayed until this point in the synthesis. Photo-oxygenation of the product, the vinylpurpurin (38), cleaves the cyclopenteno-ring giving the methoxalylpurpurin (39). A reverse Claisen reaction now generates the methoxylactone, rac-isopurpurin 5 methyl ester (40), the first substance in this synthetic series which can be compared with a sample (albeit optically active) derived from natural chlorophyll a. rac-Isopurpurin 5 methyl ester (40) is hydrolysed to the lactol, chlorin 5 (41), which is resolved (diastereoisomeric salts with quinine). The less soluble salt gives synthetic act-chlorin 5, identical with a sample of natural provenance. Diazomethane treatment of the free acid (42) yields purpurin 5 dimethyl ester (43), again identical with the naturally-derived compound. Treatment with hydrogen cyanide in triethylamine leads to the cyanolactone (44), reductive cleavage and methylation of which give the chlorin e6 nitrile (45). Methanolysis of this furnishes synthetic crystalline chlorin e6 trimethyl ester (46), identical (mp, mixed mp, electronic spectrum, infra red spectrum) with a naturally-derived sample, so completing the total synthesis.