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Usage

Uses

Used in Pharmaceutical Synthesis:
3,4-Dimethyl-1H-pyrrole-2-carboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Organic Compounds Synthesis:
3,4-Dimethyl-1H-pyrrole-2-carboxylic acid is used as a versatile starting material in the synthesis of a wide range of organic compounds. Its reactivity and functional groups allow for the formation of various derivatives, expanding its applications in organic chemistry.
Used in Disease Treatment Research:
3,4-Dimethyl-1H-pyrrole-2-carboxylic acid has been investigated for its potential use in the treatment of various diseases, including cancer and inflammation. Its unique chemical properties and biological activity make it a promising candidate for further research and development as a therapeutic agent.
Used in New Material and Chemical Synthesis:
3,4-Dimethyl-1H-pyrrole-2-carboxylic acid has been studied for its potential as a building block for the synthesis of new materials and chemicals. Its versatile structure and functional groups can be utilized to create novel compounds with unique properties and applications in various industries.

InChI:InChI=1/C7H9NO2/c1-4-3-8-6(5(4)2)7(9)10/h3,8H,1-2H3,(H,9,10)

Upstream product

• 954-92-7 3,4-dimethyl-pyrrole-2-carboxylic acid benzyl ester 
• 2199-64-6 ethyl 3,5-dimethyl-4-formyl-1H-pyrrole-2-carboxylate 
• 2199-46-4 2-(ethoxycarbonyl)-3,4,5-trimethylpyrrole 
• 4868-30-8 benzyl 4,5-dimethyl-1H-pyrrole-3-carboxylate 
• 938-75-0 3,4-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester 
• 85057-78-9 5-ethoxycarbonyl-3,4-dimethylpyrrole-2-carboxylic acid 

Downstream Products

• 4030-22-2 3,4-dimethyl-3-pyrrolin-2-one 

Relevant academic research and scientific papers

Synthesis and dihydrogen phosphate binding properties of pyrrole containing ansa-ferrocenes

Pyrrole-substituted α,ω-diamines varying in length and number of heteroatoms between the amine functionalities were reacted with 1,1′-ferrocenedimethanol to form ansa-ferrocenes. 1H-NMR binding studies in a 2% dimethylsulfoxide-d6 solution of dichloromethane-d2 establish a correlation between the affinity for tetrabutylammonium dihydrogen phosphate and the number of heteroatoms in the diamine. Further support for this conclusion came from electrochemical analyses.

Synthetic Studies Relevant to Biosynthetic Research on Vitamin B12. Part 7. Synthesis of (+/-)-Bonellin Dimethyl Ester

The dimethyl ester of the green marine pigment, bonellin, has been synthesized in racemic form by a rational photochemical route.The two propionate residues of this biologically active pigment have been introduced synthetically in differentiated form which opens the way to the synthesis of the naturally occuring amino acid derivatives of bonellin.

Methoxyl-induced fluorescence quenching in N,N′-bridged 9H-dipyrrinones and an X-ray crystal structure

Strongly fluorescent dipyrrinones can be prepared by bridging the pyrrole and lactam nitrogens with a carbonyl group, from reaction with N,N′-carbonyldiimidazole in the presence of a strong, non-nucleophilic base. The yellow, N,N′-carbonyl-bridged dipyrrinones typically have fluorescent quantum yields (φF) approaching 1.0. Thus, in chloroform, N,N′-bridged 9H-dipyrrinones with β-alkyl substituents: 2,3-diethyl-7,8-dimethyl has φF = 0.90 (λem = 465 nm) and 2,3-dimethyl-7,8-dimethoxy has φF = 0.84 (λem = 482 nm). In contrast, 2,3-dimethoxy-7,8-dimethyl and 2,3,7,8-tetramethoxy show red-shifted λem but with strongly reduced φF: φF = 0.10 (λem = 511 nm) and 0.08 (λem = 511 nm), respectively. Methoxy substituents on the lactam, but not the pyrrole ring act to quench the fluorescence and shift the emission and excitation wavelengths bathochromically. The first X-ray crystal structure of an N,N′-carbonyl-bridged dipyrrinone was obtained from 7,8-dimethoxy-2,3-dimethyl-10H-dipyrrin-1-one.

Corrole-Substituted Fluorescent Heme Proteins

Although fluorescent proteins have been utilized for a variety of biological applications, they have several optical limitations, namely weak red and near-infrared emission and exceptionally broad (>200 nm) emission profiles. The photophysical properties of fluorescent proteins can be enhanced through the incorporation of novel cofactors with the desired properties into a stable protein scaffold. To this end, a fluorescent phosphorus corrole that is structurally similar to the native heme cofactor is incorporated into two exceptionally stable heme proteins: H-NOX from Caldanaerobacter subterraneus and heme acquisition system protein A (HasA) from Pseudomonas aeruginosa. These yellow-orange emitting protein conjugates are examined by steady-state and time-resolved optical spectroscopy. The HasA conjugate exhibits enhanced fluorescence, whereas emission from the H-NOX conjugate is quenched relative to the free corrole. Despite the low fluorescence quantum yields, these corrole-substituted proteins exhibit more intense fluorescence in a narrower spectral profile than traditional fluorescent proteins that emit in the same spectral window. This study demonstrates that fluorescent corrole complexes are readily incorporated into heme proteins and provides an inroad for the development of novel fluorescent proteins.

Shape-persistent poly-porphyrins assembled by a central truxene: Synthesis, structure, and singlet energy transfer behaviors

Four dyad systems composed of a central truxene and either one or three β-substituted zinc(II) porphyrins (ZnP: TruZnP (7) and TruTriZnP (9)) or free-bases (H2P: TruP (6) and TruTriP (8)) have been prepared. The presence of β-methyl groups minimizes π-conjugation through the quasi right angle made by the porphyrin and the truxene planes, and renders these dyads relatively rigid. The position of the absorption and emission 0-0 peaks confirms the role of the truxene and porphyrin as the energy donor and acceptor, respectively. Selective excitation of the truxene results in an efficient singlet energy transfer (S1 ET) from the truxene to the porphyrin unit. The rates for S1 ET (kET) are extracted from the change in the fluorescence lifetime of truxene in the presence and absence of the acceptor, and are temperature independent, (TruP (6), TruTriP (8), TruZnP (7) and TruTriZnP (9) are 5.0, 1.4, 1.0 and 1.4 at 298 K and 5.9, 1.3, 2.6, and 0.86 (ns)-1 at 77 K, respectively), consistent with their relative rigidity. These kET's are similar to other related but more flexible systems reported by one of us (Inorg. Chem. 2011, 50, 11493-11505). The k ET's time scale was assumed, based on modeling, to be related with hindered rotations about the truxene-porphyrin C-C bonds due to steric hexyl-hexyl interactions. This work confirms this earlier conclusion was correct. Copyright

Facile synthesis of 2,3,7,8-tetramethyl-2,2′-dipyrrin trifluoroacetate and its X-ray crystal structure

3,4-Dimethyl-1H-pyrrole-2-carboxylic acid was converted to 2,3,7,8-tetramethyl-2,2′-dipyrrin by the action of trifluoroacetic acid and ethyl orthoformate. A crystal of the dipyrrin was grown from dichloromethane-n-hexane and an X-ray crystallographic structure of its trifluoroacetate salt was determined.

Intermolecularly hydrogen-bonded dimeric helices: tripyrrindiones

A rare and unusual class of tripyrrolic compounds, violet-colored tripyrrin-1,14-diones, can be prepared easily and in moderately high yields from base (piperidine)-catalyzed condensation of 3-pyrrolin-2-ones with 2,5-diformylpyrroles. Dipyrrinones adopt the all-syn-Z conformation leading to helical, lock-washer like structures, which form dimers that are held together by intermolecular hydrogen bonds in nonpolar solvents and in the crystal. Strong bathochromic spectral shifts of the tripyrrindione ～480 nm long wavelength UV-visible absorption band are seen with added base: DBU, 615 nm; TFA, 573 nm; and Zn(OAc)2, 586 nm.

Large scale, efficient synthesis of 9-unsubstituted dipyrrinone

9-Unsubstituted dipyrrinone 8, the useful precursor for the synthesis of biliverdins, bilirubins, and other bile pigments, was synthesized in large scale and high yield starting from acetaldehyde and nitroethane in eight steps with overall yield 10%. The key intermediate 3,4-dimethyl-2-ethoxycarbonylpyrrole 3 was synthesized via Zard-Barton's method in high yield.

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.

Exciton Coupling from Dipyrrinone Chromophores

2,3,7,8-Tetramethyl-(10H)-dipyrrin-1-one-9-carboxylic acid and p-(dimethylamino)benzoic acid are reacted separately with (1R,2R)-cyclohexanediol to form the corresponding diesters (1 and 3, respectively).These diesters exhibit intense bisignate circular dichroism (CD) spectra characteristic of exciton coupling and show a negative exciton chirality: Δεmax408 -122.5, Δεmax360 +95 (1 in CH2Cl2) and Δεmax318 -88.5 , Δεmax292 +41.5 (3 in CH2Cl2).In (CH3)2SO solvent the Cotton effect signs become inverted for the bis(dipyrrinone ester) but remain unchanged for the bis.