- Vilsmeier-Haack preparation of 2-acylpyrroles using bis(trichloromethyl)carbonate and N,N-dimethylacylaminesShi, X. J.; Su, W. K.; Shan, W. G., Journal of the Indian Chemical Society, 2005, 82(11), 1019-1021
Cas no 932-16-1 (2-Acetyl-1-methylpyrrole)
2-Acetyl-1-methylpyrrole Chemical and Physical Properties
Names and Identifiers
-
- 1-(1-Methyl-1H-pyrrol-2-yl)ethanone
- Methyl 1-methyl-2-pyrrolyl ketone
- 2-Acetyl-1-methylpyrrole
- 1-(1-methylpyrrol-2-yl)ethanone
- N-Methyl-2-acetyl pyrrole
- 1-(1-Methyl-1H-pyrrol-2-yl)ethanone (ACI)
- Ketone, methyl 1-methylpyrrol-2-yl (6CI, 7CI, 8CI)
- 1-(1-Methyl-1H-pyrrol-2-yl)ethan-1-one
- 1-Methyl-2-acetylpyrrole
- 2-Acetyl-N-methylpyrrole
- N-Methyl-2-acetylpyrrole
- N-Methyl-2-pyrrolylethanone
- N-Methyl-5-acetylpyrrole
- NSC 87239
-
- MDL: MFCD00003089
- Inchi: 1S/C7H9NO/c1-6(9)7-4-3-5-8(7)2/h3-5H,1-2H3
- InChI Key: NZFLWVDXYUGFAV-UHFFFAOYSA-N
- SMILES: O=C(C)C1N(C)C=CC=1
- BRN: 111887
Computed Properties
- Exact Mass: 123.06800
- Monoisotopic Mass: 123.068
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 2
- Heavy Atom Count: 9
- Rotatable Bond Count: 1
- Complexity: 122
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Topological Polar Surface Area: 22A^2
- Surface Charge: 0
- Tautomer Count: 2
- XLogP3: 0.7
Experimental Properties
- Color/Form: Colorless oily liquid
- Density: 1.04?g/mL?at 25?°C(lit.)
- Boiling Point: 202°C(lit.)
- Flash Point: Degrees Fahrenheit:154.4°F
Degrees Celsius:68°C - Refractive Index: n20/D 1.542(lit.)
- PSA: 22.00000
- LogP: 1.22770
- Solubility: Soluble in ethanol and aniline
- FEMA: 3184
- Vapor Pressure: 0.3±0.4 mmHg at 25°C
2-Acetyl-1-methylpyrrole Security Information
- Prompt:warning
- Signal Word:warning
- Hazard Statement: H227
- Warning Statement: P210-P280-P370+P378-P403+P235-P501
- Hazardous Material transportation number:NONH for all modes of transport
- WGK Germany:3
- Safety Instruction: S24/25
- HazardClass:IRRITANT
- TSCA:Yes
- Storage Condition:Sealed in dry,Room Temperature
2-Acetyl-1-methylpyrrole Customs Data
- HS CODE:2933990090
- Customs Data:
China Customs Code:
2933990090Overview:
2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%
Declaration elements:
Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date
Summary:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
2-Acetyl-1-methylpyrrole Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Fluorochem | 002488-5g |
2-Acetyl-1-methylpyrrole |
932-16-1 | 98% | 5g |
£10.00 | 2022-03-01 | |
| Fluorochem | 002488-10g |
2-Acetyl-1-methylpyrrole |
932-16-1 | 98% | 10g |
£16.00 | 2022-03-01 | |
| Fluorochem | 002488-25g |
2-Acetyl-1-methylpyrrole |
932-16-1 | 98% | 25g |
£32.00 | 2022-03-01 | |
| Fluorochem | 002488-100g |
2-Acetyl-1-methylpyrrole |
932-16-1 | 98% | 100g |
£93.00 | 2022-03-01 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | A151233-100g |
2-Acetyl-1-methylpyrrole |
932-16-1 | >98.0%(GC) | 100g |
¥603.90 | 2023-09-04 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | A151233-25g |
2-Acetyl-1-methylpyrrole |
932-16-1 | >98.0%(GC) | 25g |
¥196.90 | 2023-09-04 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | A151233-5g |
2-Acetyl-1-methylpyrrole |
932-16-1 | >98.0%(GC) | 5g |
¥60.90 | 2023-09-04 | |
| XI GE MA AO DE LI QI ( SHANG HAI ) MAO YI Co., Ltd. | 160865-1G |
2-Acetyl-1-methylpyrrole |
932-16-1 | 1g |
¥262.88 | 2023-12-10 | ||
| XI GE MA AO DE LI QI ( SHANG HAI ) MAO YI Co., Ltd. | 160865-10G |
2-Acetyl-1-methylpyrrole |
932-16-1 | 10g |
¥1148.44 | 2023-12-10 | ||
| XI GE MA AO DE LI QI ( SHANG HAI ) MAO YI Co., Ltd. | W318418-SAMPLE-K |
2-Acetyl-1-methylpyrrole |
932-16-1 | ≥98%, FG | 587.6 | 2021-05-17 |
2-Acetyl-1-methylpyrrole Production Method
Production Method 1
1.2 0 °C; 1 h, 40 - 50 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ; 0 °C → rt
Production Method 2
- Electronic Asymmetry of an Annelated Pyridyl-Mesoionic Carbene Scaffold: Application in Pd(II)-Catalyzed Wacker-Type Oxidation of OlefinsSaha, Sayantani; Yadav, Suman; Reshi, Noor U. Din ; Dutta, Indranil; Kunnikuruvan, Sooraj; et al, ACS Catalysis, 2020, 10(19), 11385-11393
Production Method 3
- Alkylation of 2-acetylpyrrole and 1-alkyl-2-acetylpyrroles under solid/liquid phase-transfer conditionsGol'dberg, Yu.; Abele, E.; Shymanskaya, M., Synthetic Communications, 1991, 21(4), 557-62
Production Method 4
Production Method 5
- Pyrrole studies. XXVII. Utilization of 1-methyl-2-pyrrolyllithium in the synthesis of 1-methyl-2-substituted pyrrolesBrittain, Judith M.; Jones, R. Alan; Arques, Jose Sepulveda; Saliente, Teresa Aznar, Synthetic Communications, 1982, 12(3), 231-48
Production Method 6
- Synthesis of acylpyrroles and their antiinflammatory and analgesic activitiesMeng, Fanhao; Gao, Wenfang; Zhang, Shoufang, Shenyang Yaoke Daxue Xuebao, 1995, 12(3), 165-70
Production Method 7
- Michael addition of [1H]pyrroleMatoba, Katsuhide; Yamazaki, Takao, Chemical & Pharmaceutical Bulletin, 1982, 30(7), 2586-9
Production Method 8
- Regioselective photoaddition of pyrroles and aliphatic carbonyl compounds. A new synthesis of 3(4)-substituted pyrrolesJones, Guilford II; Gilow, Helmuth M.; Low, Julie, Journal of Organic Chemistry, 1979, 44(16), 2949-51
Production Method 9
Production Method 10
- Formation of N-alkyl-2-acylpyrroles and aliphatic aldimines in model nonenzymic browning reactionsRizzi, George P., Journal of Agricultural and Food Chemistry, 1974, 22(2), 279-82
Production Method 11
- Ytterbium(III) trifluoromethanesulfonate catalyzed Friedel-Crafts acylation of 1-methylpyrrole in ionic liquidSu, Weike; Wu, Chunlei; Su, Hao, Journal of Chemical Research, 2005, (1), 67-68
Production Method 12
Production Method 13
1.2 Reagents: Hydrochloric acid Solvents: Water
- Oxidative coupling of enolates using memory of chirality: An original enantioselective synthesis of quaternary α-amino acid derivativesMambrini, Antonin; Gori, Didier; Guillot, Regis; Kouklovsky, Cyrille; Alezra, Valerie, Chemical Communications (Cambridge, 2018, 54(90), 12742-12745
Production Method 14
- Green N-Methylation of Electron Deficient Pyrroles with DimethylcarbonateLaurila, Michael L.; Magnus, Nicholas A.; Staszak, Michael A., Organic Process Research & Development, 2009, 13(6), 1199-1201
Production Method 15
- New method for the synthesis of 2-acetylfuran, 2-acetylthiophene, and 2-acetyl-N-methylpyrroleYan, Shenggang; Wang, Shihua, Huaxue Shiji, 1993, 15(4),
Production Method 16
- Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary aminesGiles, Robert G.; Heaney, Harry; Plater, M. John, Tetrahedron, 2015, 71(39), 7367-7385
Production Method 17
- Desulfonylation reactionsAlonso, Diego A.; Najera, Carmen, Organic Reactions (Hoboken, 2008, 72, 367-656
Production Method 18
- Oxidative radical cyclization to pyrroles under reducing conditions. Reductive desulfonylation of α-sulfonylpyrroles with tri-n-butyltin hydrideAntonio, Yulia; De la Cruz, Maria Elizabeth; Galeazzi, Edvige; Guzman, Angel; Bray, Brian L.; et al, Canadian Journal of Chemistry, 1994, 72(1), 15-22
Production Method 19
- Pyrrole chemistry. XVII. Alkylation of the pyrrolyl ambident anionWang, Nam-Chiang; Teo, Kang-Er; Anderson, Hugh J., Canadian Journal of Chemistry, 1977, 55(23), 4112-16
Production Method 20
- Preparation and photolysis of acyloins. Acylation of pyrroles and indoleRyang, Hong-Son; Sakurai, Hiroshi, Journal of the Chemical Society, 1972, (2),
Production Method 21
1.2 Reagents: Sodium hydroxide Solvents: Water ; neutralized, 0 °C
- Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic SynthesesLiang, Fengying; Eda, Kazuo ; Okazoe, Takashi; Wada, Akihiro; Mori, Nobuaki; et al, Journal of Organic Chemistry, 2021, 86(9), 6504-6517
2-Acetyl-1-methylpyrrole Raw materials
- 18-Crown-6
- Lithium, (1-methyl-1H-pyrrol-2-yl)-
- 1-[1-methyl-5-(methylsulfonyl)-1H-pyrrol-2-yl]-Ethanone
- N,N-Dimethylacetamide
- N-[1-(1-Methyl-1H-pyrrol-2-yl)ethylidene]methanamine
- N-(1-chloroethylidene)-N-methylmethanaminium chloride
- 2-Acetylpyrrole
- N-Methylpyrrole
- 1-Methyl-2-(tributylstannyl)-1H-pyrrole
- 1H-Pyrrole, 2-ethenyl-1-methyl-
2-Acetyl-1-methylpyrrole Preparation Products
2-Acetyl-1-methylpyrrole Suppliers
2-Acetyl-1-methylpyrrole Related Literature
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P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
-
Govind Reddy Mol. Syst. Des. Eng., 2021,6, 779-789
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Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392
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Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao You Analyst, 2015,140, 1827-1831
Additional information on 2-Acetyl-1-methylpyrrole
Introduction to 2-Acetyl-1-methylpyrrole (CAS No. 932-16-1)
2-Acetyl-1-methylpyrrole, identified by the Chemical Abstracts Service Number (CAS No.) 932-16-1, is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical chemistry and materials science due to its versatile structural framework and potential biological activities. This compound belongs to the pyrrole derivatives, which are known for their broad spectrum of applications ranging from pharmaceuticals to agrochemicals and specialty chemicals. The presence of both an acetyl group and a methyl substituent in the pyrrole ring endows 2-Acetyl-1-methylpyrrole with unique chemical properties that make it a valuable scaffold for further derivatization and functionalization.
The structural motif of 2-Acetyl-1-methylpyrrole consists of a five-membered aromatic ring containing one nitrogen atom, with an acetyl group attached to the 2-position and a methyl group at the 1-position. This specific arrangement contributes to its reactivity and makes it a suitable candidate for various chemical transformations, including condensation reactions, nucleophilic additions, and metal-catalyzed coupling reactions. These properties have been exploited in synthetic chemistry to develop more complex molecules with tailored functionalities.
In recent years, 2-Acetyl-1-methylpyrrole has been extensively studied for its potential applications in drug discovery. The pyrrole core is a common structural feature in many bioactive molecules, including antiviral, antibacterial, and anticancer agents. The acetyl group can serve as a pharmacophore or a site for further modifications, while the methyl group can influence the electronic properties of the molecule, thereby affecting its biological activity. Preliminary studies have suggested that derivatives of 2-Acetyl-1-methylpyrrole may exhibit inhibitory effects on certain enzymes and receptors, making them promising candidates for therapeutic intervention.
One of the most intriguing aspects of 2-Acetyl-1-methylpyrrole is its role as a precursor in the synthesis of more complex heterocyclic compounds. For instance, it can be used to construct fused ring systems such as indoles and benzothiophenes through cyclization reactions. These fused heterocycles are known for their diverse biological activities and are frequently encountered in natural products and pharmaceuticals. The ability to efficiently synthesize these complex structures from 2-Acetyl-1-methylpyrrole highlights its importance as a building block in synthetic organic chemistry.
Recent advancements in computational chemistry have also contributed to a deeper understanding of the reactivity and properties of 2-Acetyl-1-methylpyrrole. Molecular modeling studies have revealed insights into how the acetyl and methyl groups influence the electronic distribution within the molecule, which in turn affects its interactions with biological targets. These computational approaches have been instrumental in guiding experimental design and optimizing synthetic routes.
The pharmaceutical industry has shown particular interest in 2-Acetyl-1-methylpyrrole due to its potential as an intermediate in the synthesis of novel drug candidates. Researchers have explored its use in developing small molecule inhibitors targeting various disease pathways. For example, modifications of the acetyl group have been investigated for their ability to enhance binding affinity to specific protein targets, while alterations at the methyl position have been explored for their impact on metabolic stability.
Moreover, 2-Acetyl-1-methylpyrrole has found applications beyond pharmaceuticals. In materials science, it serves as a precursor for synthesizing functional materials such as organic semiconductors and ligands for metal complexes used in catalysis. The unique electronic properties of pyrrole derivatives make them attractive for applications in optoelectronic devices, where they can contribute to efficient charge transport and light emission.
The synthesis of 2-Acetyl-1-methylpyrrole itself is well-documented, with several efficient methods available depending on the starting materials and desired scale of production. Common synthetic routes involve condensation reactions between appropriate precursors followed by functional group transformations to introduce the acetyl and methyl groups. Advances in green chemistry have also led to the development of more sustainable synthetic pathways, reducing waste and improving atom economy.
In conclusion, 2-Acetyl-1-methylpyrrole (CAS No. 932-16-1) is a multifaceted compound with significant potential in both pharmaceuticals and materials science. Its unique structural features make it a valuable scaffold for drug discovery and a versatile building block for synthesizing complex heterocyclic molecules. As research continues to uncover new applications and synthetic strategies, the importance of this compound is expected to grow further, solidifying its role as a key player in modern chemical research.
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