132253-56-6

Basic information

• Product Name: 1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE
• Synonyms: 1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE;AKOS BB-3535;N-(2-BROMOPHENYL)-2,5-DIMETHYLPYRROLE;1-(2-BroMophenyl)-2,5-diMethylpyrrole
• CAS NO: 132253-56-6
• Molecular Formula: C₁₂H₁₂BrN
• Molecular Weight: 250.13
• Mol File: 132253-56-6.mol

Chemical Properties

• Boiling Point: 329.8±30.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• PKA: -3.37±0.70(Predicted)
• CAS DataBase Reference: 1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE(132253-56-6)
• EPA Substance Registry System: 1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE(132253-56-6)

Safety Data

• Hazardous Substances Data: 132253-56-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE is used as a key intermediate in organic synthesis for the creation of more complex organic molecules. Its presence of a bromine atom in the phenyl group enhances its reactivity and utility in the synthesis process.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE is utilized as a starting material or intermediate in the development of new medicinal compounds. Its unique structure contributes to the design of potential drugs with novel therapeutic properties.
Used in the Development of New Materials:
1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE's structural attributes also make it a candidate for the development of new materials with specific properties, such as in polymer chemistry or as part of advanced material systems.
Overall, 1-(2-BROMO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE is a versatile chemical intermediate with applications spanning across organic synthesis, pharmaceutical research, and material science, highlighting its importance in the advancement of various fields.

Upstream product

• 615-36-1 2-bromoaniline 
• 74-86-2 acetylene 
• 110-13-4 2,5-hexanedione 

Downstream Products

• 1616734-31-6 1-(2-(diphenylphosphino)phenyl)-2,5-dimethyl-1H-pyrrole 
• 688010-78-8 C₁₈H₁₈BrN₃OS 
• 662154-13-4 1-(2-bromophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde 
• 1237588-09-8 2-(2',5'-dimethylpyrrole)(di(1-adamantyl)phosphino)benzene 
• 1147015-07-3 4-{[2-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]ethynyl}-7H-pyrrolo[2,3-d]pyrimidine 
• 188825-09-4 6-[2-(2,5-Dimethyl-pyrrol-1-yl)-phenyl]-7-hydroxy-8,9-diisopropoxy-6H-oxazolo[5,4,3-ij]quinolin-2-one 
• 188825-10-7 6-(2-Amino-phenyl)-7-hydroxy-8,9-diisopropoxy-6H-oxazolo[5,4,3-ij]quinolin-2-one 
• 188825-08-3 1-(tert-butoxycarbonyl)-4-[2-(2,5-dimethylpyrrol-1-yl)phenyl]-1,4-dihydropyridine 

Relevant articles and documents

Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles

A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5- dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C = N bond of the intermediate aldimine (aza-Favorsky reaction).

Fluxional chloro-pyrrole-Pd(ii) complex to cationic η2-pyrrole-Pd(ii) complex: subtlety in structure-directed bonding mode

Fluxionality in η1-aromatic carbocyclic-ligated Pd(ii) complexes is retained if the η1-carbon is replaced with an N atom through “hemilabile” palladium-carbon η1-pyrrole ligation. Herein, we report and characterize a tetra

Design and development of pyrrole carbaldehyde: An effective pharmacophore for enoyl-ACP reductase

Enoyl-ACP reductase is the key enzyme involved in FAS-II synthesis of mycolic acid in bacterial cell wall and is a promising target for discovering new chemical entity. The designed pharmacophores are the possible better tools to combat mutation in enoyl-ACP enzyme, which leads to a decrease in volume of triclosan binding site. Compound 3a showed H-bonding interactions similar to that of triclosan with enoyl-ACP enzyme and with a better docking score (C score 8.81), while the compound 3f showed additional interaction with MET98.H amino acid residue. The 3D-QSAR computations also support the docking study to develop novel pyrrole-based derivatives. Graphical abstract: Molecular docking 3D-QSAR studies and synthesis of active analogs of pyrrole carbaldehyde as better receptor fit pharmacophore for enoyl-ACP reductase along with in vitro antitubercular activity. (Figure Presented).

Steric vis-à-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes

In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design.

Steric vis-??-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes

In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design.

A "hemilabile" palladium-carbon bond: Characterization and its implication in catalysis

An unusual palladium-carbon bond was identified in the crystal structure of a Pd(II) complex (VI) derived from 1-(2-diphenylphosphinophenyl)-2,5-dimethyl- 1H-pyrrole (L4). Theoretical calculations indicate that the Pd-C bond is covalent in nature. The com

Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3- alkyl-2-(alkylimino)thiazolidin-4-one chemotype

High affinity and selective S1P4 receptor (S1P4-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H- pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P4-R agonist hit distinct from literature S1P4-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P4-R agonist activity and exquisite selectivity over the other S1P 1-3,5-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P4-R signaling cascade and elucidate the molecular basis of the receptor function.

Chemoselective benzylic C-H activations for the preparation of condensed N-heterocycles

Buttoning up: A chemoselective domino reaction including one or two successive C-H activations serves to convert a range of readily available N-arylpyrroles into complex polycondensed N-heterocycles. The reaction is catalyzed by Pd(OAc)2 (5 mol%), and p-Tol3P (10 mol%) is added as the ligand (see scheme; Tol = tolyl).

Versatile Synthesis of Dihydroquinolines and Quinoline Quinones Using Cyclobutenediones. Construction of the Pyridoacridine Ring System

1-BOC-2-lithio-1, 4-dihydropyridines were condensed with 3,4-disubstituted cyclobutenediones to produce 1,2-adducts. Neat thermolysis under oxygen-free conditions produced substituted 1,4-dihydroquinoline hydroquinones in which the tert-butoxy residue of the BOC group was displaced by a phenolic residue, generating an oxazolone ring that functioned to protect both rings of the dihydroquinoline hydroquinone from untimely oxidation. Oxidative aromatization with concomitant loss of the oxazolone ring was achieved using 2 equiv of o-chloranil in acetic acid and provided substituted quinoline quinones in good yields. By use of this strategy, a concise synthesis of the pyridoacridine ring system was achieved.