2386-25-6

Basic information

• Product Name: 3-Acetyl-2,4-dimethylpyrrole
• Synonyms: 1-(2,4-diMethyl-1H-pyrrol-3-yl)ethan-1-one;Ethanone, 1-(2,4-diMethyl-1H-pyrrol-3-yl)-;3-ACETYL-2,4-DIMETHYLPYRROLE;2,4-DIMETHYL-3-ACETYLPYRROLE;2,4-Dimethylpyrrol-3-yl methyl ketone;TIMTEC-BB SBB004194;1-(2,4-Dimethyl-1H-pyrrol-3-yl)-ethanone;Ketone, 2,4-dimethylpyrrol-3-yl methyl
• CAS NO: 2386-25-6
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 219-197-1
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;ACETYLGROUP;Building Blocks;Heterocyclic Building Blocks;Pyrroles
• Mol File: 2386-25-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 136-139 °C(lit.)
• Boiling Point: 173°C/12mmHg(lit.)
• Flash Point: 112.1 °C
• Appearance: Light yellow to pink to purple to brown/Powder or Crystals
• Density: 1.0630 (rough estimate)
• Refractive Index: 1.5470 (estimate)
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 16.40±0.50(Predicted)
• CAS DataBase Reference: 3-Acetyl-2,4-dimethylpyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetyl-2,4-dimethylpyrrole(2386-25-6)
• EPA Substance Registry System: 3-Acetyl-2,4-dimethylpyrrole(2386-25-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• RTECS: OB2885000
• Hazardous Substances Data: 2386-25-6(Hazardous Substances Data)

Usage

Chemical Properties

Brown to purple crystals or powder

Safety Profile

Poison by intravenous and intraperitoneal routes. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx,. See also KETONES.

InChI:InChI=1/C8H11NO/c1-5-4-9-6(2)8(5)7(3)10/h4,9H,1-3H3

Upstream product

• 2386-26-7 ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate 
• 2386-27-8 benzyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate 
• 75-36-5 acetyl chloride 
• 7647-01-0 hydrogenchloride 
• 871890-31-2 tris-(4-acetyl-3,5-dimethyl-pyrrol-2-yl)-methane 
• 10034-85-2 hydrogen iodide 
• 64-19-7 acetic acid 
• 1314994-51-8 C₈H₁₁NO 
• 123-54-6 acetylacetone 
• 91375-42-7 5-N,N-Bis(trimethylsilyl)amino pent-3-yne-2-one 
• 952002-53-8 1-(2,4-dimethyl-5-trityl-pyrrol-3-yl)-ethanone 
• 917-54-4 methyllithium 
• 231609-66-8 2-(2-acetyl-1-methylvinylamino)-N-methoxy-N-methylacetamide 
• 306-44-5 propanone 1-oxime 

Downstream Products

• 952002-53-8 1-(2,4-dimethyl-5-trityl-pyrrol-3-yl)-ethanone 
• 625-82-1 2,4-dimethyl-1H-pyrrole 
• 750611-31-5 3-acetyl-5-chloroacetyl-2,4-dimethyl-pyrrole 
• 517-22-6 2,4-dimethyl-3-ethyl-pyrrole 
• 1500-93-2 1-(3,5-dimethyl-1H-pyrrol-2-yl)ethan-1-one 
• 5666-10-4 2,4-dimethyl-3-ethylpyrrolidine 
• 95883-30-0 3-acetyl-1-(2,6-dichlorobenzoyl)-2,4-dimethylpyrrole 
• 628-35-3 ethylene glycol monoformate 
• 21141-02-6 2,4-Dimethyl-3-acetyl-5-ethyl-pyrrol 

Relevant articles and documents

Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy

As epigenetic readers, bromodomain and extra-terminal domain (BET) family proteins bind to acetylated-lysine residues in histones and recruit protein complexes to promote transcription initiation and elongation. Inhibition of BET bromodomains by small molecule inhibitors has emerged as a promising therapeutic strategy for cancer. Herein, we describe our efforts toward the discovery of a novel series of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as BET inhibitors. Intensive structural modifications led to the identification of compound 35f as the most active inhibitor of BET BRD4 with selectivity against BET family proteins. Further biological studies revealed that compound 35f can arrest the cell cycle in G0/G1 phase and induce apoptosis via decreasing the expression of c-Myc and other proteins related to cell cycle and apoptosis. More importantly, compound 35f showed favorable pharmacokinetic properties and antitumor efficacy in MV4-11 mouse xenograft model with acceptable tolerability. These results indicated that BET inhibitors could be potentially used to treat hematologic malignancies and some solid tumors.

Transition metal-free cyclization of N-boc-N-propargylenamines

An efficient method for the synthesis of multi-substituted pyrroles was developed using basic cyclization of readily accessible N-Boc-N-propargylenamines. Despite the basic conditions, cleavage of the N-Boc group occurred easily. The process was rapid and afforded N-H-pyrroles with wide functional group tolerance in high yields.

SPIROBODIPYs with spiropyran structure compound, preparation method and its use

The invention discloses a SPIROBODIPYs compound with the spiropyrane structure. The compound has the following structural general formula (refer to the Specification), wherein R1, R2, R3 and R4 are alkyl substituents or aromatic substituents, R5 is an alkyl substituent, an alcohol hydroxyl substituent or a substituent with triple bonds at the tail end. The invention further discloses the application of the SPIROBODIPYs compound to a fluorescence molecular probe. The SPIROBODIPYs compound can be applied to controllable detection of physiological and pathological process of cells, and can be used for building living cell acid organelles or used as a novel fluorescent dye of a fluorescence molecular probe for detecting the acid environment of cancer cells.