Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate

Base Information

• Chemical Name: Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate
• CAS No.: 4815-30-9
• Molecular Formula: C11H15NO4S
• Molecular Weight: 257.31
• Hs Code.: 29349990
• European Community (EC) Number: 225-388-0
• NSC Number: 149763
• DSSTox Substance ID: DTXSID90197438
• Nikkaji Number: J124.106K
• Wikidata: Q72469143
• ChEMBL ID: CHEMBL1319821
• Mol file: 4815-30-9.mol

Synonyms:4815-30-9;Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate;Diethyl 5-amino-3-methyl-2,4-thiophenedicarboxylate;2-Amino-3,5-bis(ethoxycarbonyl)-4-methylthiophene;diethyl 2-amino-4-methylthiophene-3,5-dicarboxylate;MFCD00005450;2,4-diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate;2,4-Thiophenedicarboxylic acid, 5-amino-3-methyl-, diethyl ester;diethyl 5-amino-3-methyl-thiophene-2,4-dicarboxylate;EINECS 225-388-0;2-Amino-4-methyl-3,5-bis(ethoxycarbonyl)thiophene;5-Amino-3-methylthiophene-2,4-dicarboxylic acid diethyl ester;5-Amino-3-methyl-thiophene-2,4-dicarboxylic acid diethyl ester;NSC149763;TimTec1_000494;CBDivE_004167;MLS000779926;BIDD:GT0567;AMY505;SCHEMBL1143421;CHEMBL1319821;DTXSID90197438;HMS1535G10;HMS2795I03;5-Amino-3-methyl-2,4-thiophenedicarboxylic Acid Diethyl Ester;BCP29816;BBL007553;STK242202;AKOS000103702;2, 5-amino-3-methyl-, diethyl ester;CCG-103738;CS-W004484;NSC 149763;NSC-149763;NCGC00246391-01;BP-12350;SMR000420157;SY018475;TS-00826;A7328;BB 0218689;FT-0624829;EN300-16871;2,4-diethoxycarbonyl-3-methyl-5-aminothiophene;2-amino-3,5-diethoxycarbonyl-4-methylthiophene;2-Amino-4-methyl-3,5-bis(ethoxycarbonyl)thiophen;AH-232/03154032;SR-01000396841;diethyl2-amino-4-methylthiophene-3,5-dicarboxylate;J-640125;J-800129;SR-01000396841-1;W-202846;BRD-K04917639-001-01-3;diethyl 5-amino-3-methyl-2,4-thiophene dicarboxylate;Z56802790;F0095-1654;2-Amino-4-methylthiophene-3,5-dicarboxylic acid diethyl ester;5-Amino-3-methyl-thiophene-2,4-dicarboxylic acid diethyl ester;ethyl 2-amino-5-(ethoxycarbonyl)-4-methylthiophene-3-carboxylate

Chemical Property of Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate

Chemical Property:

• Appearance/Colour: slightly yellow to beige-yellow crystalline powder
• Vapor Pressure: 9.51E-06mmHg at 25°C
• Melting Point: 105-108 °C(lit.)
• Refractive Index: 1.558
• Boiling Point: 372.6 °C at 760 mmHg
• PKA: -0.53±0.10(Predicted)
• Flash Point: 179.1 °C
• PSA: 106.86000
• Density: 1.247 g/cm³
• LogP: 2.57330
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 257.07217913
• Heavy Atom Count: 17
• Complexity: 297

Purity/Quality:

99% ^*data from raw suppliers

Diethyl5-Amino-3-methylthiophene-2,4-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-60-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(SC(=C1C)C(=O)OCC)N
• Uses: Diethyl 5-Amino-3-methylthiophene-2,4-dicarboxylate is used as a reagent in the synthesis of novel pyrazolo-pyrimidinones as dipeptidyl peptidase IV (DPP-IV) inhibitors in diabetes. It is also used in the synthesis of N-phenylthieno[2,3-d]pyrimidin-4-amines which act as inhibitors of fibroblast grow factor receptor 1 and therefore may be further used as anticancer agents.

Technology Process of Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate

There total 7 articles about Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate 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) + ethyl 2-cyanoacetate (105-56-6) → diethyl 5-amino-3-methyl-2,4-thiophenedicarboxylate (4815-30-9)

Guidance literature:

With sulfur; triethylamine; In ethanol; at 50 ℃; for 6h;

DOI:10.1016/j.cplett.2021.139103

Reference yield: 65.0%

Ethyl 2-oxobutanoate (15933-07-0) + ethyl 2-cyanoacetate (105-56-6) → diethyl 5-amino-3-methyl-2,4-thiophenedicarboxylate (4815-30-9)

Guidance literature:

With sulfur; diethylamine; In ethanol; at 20 ℃; for 1.25h;

DOI:10.1016/j.ejmech.2016.07.022

Reference yield:

C15H20N3O4S(1+)*BF4(1-) → diethyl 5-amino-3-methyl-2,4-thiophenedicarboxylate (4815-30-9)

Guidance literature:

With sodium ethanolate; In ethanol; at 20 ℃; for 6h;

DOI:10.1080/00397910600588819

upstream raw materials:

ethyl acetoacetate

ethyl 2-cyanoacetate

Ethyl 2-oxobutanoate

Downstream raw materials:

5-(3-Carboxy-propionylamino)-3-methyl-thiophene-2,4-dicarboxylic acid diethyl ester

Refernces

• 1、 Mavrova, Anelia Ts.,Wesselinova, Diana,Tsenov, Jordan A.,Lubenov, Lubomir A.. "Synthesis and antiproliferative activity of some new thieno[2,3-d ]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety". . p. 676 - 683. Retrieved 2014.
• 2、 Fatima, Aysha,Javed, Saleem,Khanum, Ghazala,Kumar Srivastava, Sanjay,Siddiqui, Nazia,Verma, Indresh. "Synthesis, computational, spectroscopic, hirshfeld surface, electronic state and molecular docking studies on diethyl-5-amino-3-methylthiophene-2,4-dicarboxylate". . . Retrieved 2021/10/16.
• 3、 -. "COMPOUND AS ACC INHIBITOR AND USE THEREOF". Paragraph 0190; 0191. . Retrieved 2020/06/15.