Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate

Base Information

• Chemical Name: Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate
• CAS No.: 2199-59-9
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• Hs Code.: 2933990090
• European Community (EC) Number: 606-886-0
• NSC Number: 13426
• DSSTox Substance ID: DTXSID60176417
• Nikkaji Number: J1.979.950F
• Wikidata: Q72474976
• Mol file: 2199-59-9.mol

Synonyms:2199-59-9;Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate;5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester;ethyl 5-formyl-2,4-dimethylpyrrole-3-carboxylate;2,4-dimethyl-3-ethoxycarbonyl-5-formylpyrrole;Ethyl 2,4-dimethyl-5-formylpyrrole-3-carboxylate;MFCD00030352;1H-Pyrrole-3-carboxylic acid, 5-formyl-2,4-dimethyl-, ethyl ester;5-Formyl-2,4-dimethyl-3-pyrrolecarboxylic Acid Ethyl Ester;NSC13426;Ethyl5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate;SCHEMBL1627475;DTXSID60176417;5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylicacidethylester;BCP04682;BBL101193;NSC 13426;NSC-13426;STL554989;AKOS001132948;AB01501;AC-4254;CS-W002153;PS-6285;NCGC00335024-01;SY020518;AM20090212;E1051;FT-0634119;EN300-13240;A13183;AB01327007-02;ethyl 3,5-dimethyl-2-formylpyrrole-4-carboxylate;Ethyl 5-Formyl-2,4-dimethyl-3-pyrrolecarboxylate;J-521137;4-ethoxycarbonyl-3,5-dimethylpyrrole-2-carboxaldehyde;Z89284937;5-formyl-2,4-dimethyl-pyrrole-3-carboxylic acid ethyl ester;2,4-Dimethyl-5-formyl-1H-pyrrole-3-carboxylic acid ethyl ester

Chemical Property of Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate

Chemical Property:

• Vapor Pressure: 2.56E-05mmHg at 25°C
• Melting Point: 164.0 to 168.0 °C
• Refractive Index: 1.556
• Boiling Point: 358.4 °C at 760 mmHg
• PKA: 14.65±0.50(Predicted)
• Flash Point: 170.5 °C
• PSA: 59.16000
• Density: 1.173 g/cm³
• LogP: 1.62070
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=C1C)C=O)C
• Uses: 5-ForMyl-2,4-diMethyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester is used as an intermediate in the synthesis of receptor tyrosine kinase (RTK) inhibitors and their metabolites.

Technology Process of Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate

There total 21 articles about Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-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: 100.0%

2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester (2199-51-1) → ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate (2199-59-9)

Guidance literature:

With hydrogenchloride; In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; trichlorophosphate;

Reference yield: 100.0%

2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester (2199-51-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate (2199-59-9)

Guidance literature:

2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester; N,N-dimethyl-formamide; With trichlorophosphate; In dichloromethane; for 1.5h; Reflux;

With sodium hydroxide; In dichloromethane; water; for 0.5h; Reflux;

DOI:10.1007/s11164-015-1939-z

Reference yield: 95.0%

→ ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate (2199-59-9)

Guidance literature:

upstream raw materials:

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

chloroform

N,N-dimethyl-formamide

2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

Downstream raw materials:

benzyl 2-(2-chloroethyl)-6-ethoxycarbonyl-4-ethyl-1,3,5,6'-tetramethyltripyrrene-1'-carboxylic acid hydrobromide

sunitinib malate

Refernces

• 1、 Sun, Li,Liang, Chris,Shirazian, Sheri,Zhou, Yong,Miller, Todd,Cui, Jean,Fukuda, Juri Y.,Chu, Ji-Yu,Nematalla, Asaad,Wang, Xueyan,Chen, Hui,Sistla, Anand,Luu, Tony C.,Tang, Flora,Wei, James,Tang, Cho. "Discovery of 5-[5-fluoro-2-oxo-1,2-dihydroindol-(3Z)-ylidenemethyl]-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide, a novel tyrosine kinase inhibitor targeting vascular endothelial and platelet-derived growth factor receptor tyrosine kinase". . p. 1116 - 1119. Retrieved 2003.
• 2、 Agosta. "-". . p. 2258,2260. Retrieved 1960.
• 3、 Rasal, Nishant K.,Sonawane, Rahul B.,Jagtap, Sangeeta V.. "Synthesis, biological evaluation, and in silico study of pyrazoline-conjugated 2,4-dimethyl-1H-pyrrole-3-carboxylic acid derivatives". . . Retrieved 2020/10/22.
• 4、 -. "Preparation method of sunitinib intermediate". . . Retrieved 2019/05/04.