ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate

Base Information

• Chemical Name: ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS No.: 2386-26-7
• Molecular Formula: C11H15 N O3
• Molecular Weight: 209.245
• Hs Code.: 2933990090
• European Community (EC) Number: 640-502-2
• NSC Number: 10765
• UNII: MVH7P0EOA6
• DSSTox Substance ID: DTXSID50178566
• Nikkaji Number: J87.067F
• Wikidata: Q72472192
• Mol file: 2386-26-7.mol

Synonyms:2386-26-7;ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate;3-Acetyl-2,4-dimethyl-5-carbethoxypyrrole;1H-Pyrrole-2-carboxylic acid, 4-acetyl-3,5-dimethyl-, ethyl ester;2,4-DIMETHYL-3-ACETYL-5-CARBETHOXYPYRROLE;NSC 10765;MVH7P0EOA6;PYRROLE-2-CARBOXYLIC ACID, 4-ACETYL-3,5-DIMETHYL-, ETHYL ESTER;AI3-18675;4-Acetyl-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester;NSC-10765;4-Acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester;Ethyl-4-acetyl-3,5-dimethylpyrrole-2-carboxylate;ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate;NSC10765;Maybridge1_002117;UNII-MVH7P0EOA6;CBMicro_013151;SCHEMBL1450411;HMS547I05;DTXSID50178566;SMSF0004185;MFCD00022373;STK500704;AKOS000266693;AS-9832;CB03785;CCG-234162;SB62132;NCGC00336964-01;AC-26701;BIM-0013287.P001;LS-136821;BB 0218545;CS-0298816;FT-0626065;A23190;AB00074975-01;AB00074975-03;SR-01000388216;SR-01000388216-1;BRD-K69414438-001-01-6;Z53845389;ETHYL 3-ACETYL-2,4-DIMETHYL-5-PYRROLECARBOXYLATE;F0091-0056;4-Acetyl-3,5-Dimethyl-2-pyrrolecarboxylic acid, ethyl ester;3,5-Dimethyl-4-acetyl-1H-pyrrole-2-carboxylic acid ethyl ester

Chemical Property of ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate

Chemical Property:

• Vapor Pressure: 4.89E-05mmHg at 25°C
• Melting Point: 143 °C
• Refractive Index: 1.5080 (estimate)
• Boiling Point: 359.2°Cat760mmHg
• PKA: 14.65±0.50(Predicted)
• Flash Point: 171°C
• PSA: 59.16000
• Density: 1.123g/cm³
• LogP: 2.01080
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 209.10519334
• Heavy Atom Count: 15
• Complexity: 265

Purity/Quality:

99% ^*data from raw suppliers

Ethyl-4-acetyl-3,5-dimethylpyrrole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: 20/21/22
• Safety Statements: 22-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C(=C(N1)C)C(=O)C)C
• Uses: It is utilized as pharmaceutical intermediate.

Technology Process of ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate

There total 17 articles about ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

ethyl acetoacetate (141-97-9) + acetylacetone (123-54-6,81235-32-7) → ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate (2386-26-7)

Guidance literature:

ethyl acetoacetate; With acetic acid; sodium nitrite; In water; at 0 - 20 ℃; for 3h;

acetylacetone; With zinc; In water; at 0 - 85 ℃; for 4h;

DOI:10.1016/j.ejmech.2021.113953

Reference yield: 86.0%

3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole (2199-44-2) + acetyl chloride (75-36-5) → ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate (2386-26-7)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 2h; Heating;

DOI:10.1016/0040-4020(90)80003-Z

Reference yield: 83.0%

3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole (2199-44-2) + acetic acid (64-19-7,77671-22-8) → ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate (2386-26-7)

Guidance literature:

acetic acid; With trifluoroacetic anhydride; In acetonitrile;

With phosphoric acid; trifluoroacetic anhydride; In acetonitrile;

3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole; In acetonitrile; at 20 ℃;

DOI:10.1021/jo051906w

upstream raw materials:

3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole

acetic anhydride

acetyl chloride

ethyl 4-iodo-3,5-dimethyl-1H-pyrrole-2-carboxylate

Downstream raw materials:

2,4-dimethyl-3-ethyl-pyrrole

2,4-dimethyl-3-acetylpyrrole

ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate

4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid

Refernces

• 1、 Bian, Yuanyuan,Chen, Yadong,Hong, Qianqian,Jiang, Fei,Kong, Bo,Li, Hongmei,Lu, Tao,Ma, Yu,Ran, Ting,Tang, Weifang,Wang, Cong,Yang, Na,Zhang, Zhimin,Zheng, Wan,Zhu, Jiapeng,Zhu, Zhaohong. "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". . . Retrieved 2021/11/03.
• 2、 -. "SPIROBODIPYs with spiropyran structure compound, preparation method and its use". Paragraph 0020; 0057-0058. . Retrieved 2016/11/02.