Ethyl 2-amino-4-phenylthiophene-3-carboxylate

Base Information

• Chemical Name: Ethyl 2-amino-4-phenylthiophene-3-carboxylate
• CAS No.: 4815-36-5
• Molecular Formula: C13H13NO2S
• Molecular Weight: 247.318
• Hs Code.: 29349990
• European Community (EC) Number: 674-826-0
• NSC Number: 171773,149683
• DSSTox Substance ID: DTXSID50197439
• Nikkaji Number: J364.510J
• Wikidata: Q72472574
• Mol file: 4815-36-5.mol

Synonyms:Ethyl 2-amino-4-phenylthiophene-3-carboxylate;4815-36-5;2-Amino-4-phenyl-thiophene-3-carboxylic acid ethyl ester;2-Amino-4-phenylthiophene-3-carboxylic acid ethyl ester;ethyl 2-amino-4-phenyl-3-thiophenecarboxylate;NSC149683;NSC 149683;BRN 1429620;3-Thiophenecarboxylic acid, 2-amino-4-phenyl-, ethyl ester;Thiophene-3-carboxylic acid, 2-amino-4-phenyl-, ethyl ester;MFCD00126391;Amino-2 ethoxycarbonyl-3 phenyl-4 thiophene [French];2-amino-4-phenyl-3-thiophenecarboxylic acid ethyl ester;Amino-2 ethoxycarbonyl-3 phenyl-4 thiophene;Ethyl 2-Amino-4-phenyl-thiophene-3-Carboxylate;ethyl-2-amino-4-phenyl Thiophene-3-Carboxylate;5-18-12-00255 (Beilstein Handbook Reference);CBMicro_024541;Ethyl-2-amino-4-phenylthiophene-3-carboxylate;Enamine_004212;2-Amino-4-Phenyl-Thiophene-3-CarboxylicAcidEthylEster;SCHEMBL1190649;DTXSID50197439;HMS1405P10;AMY28654;BBL008315;NSC171773;STK347691;AKOS000112156;CCG-241818;NSC-149683;NSC-171773;SB66958;2-amino-3-carboethoxy-4-phenylthiophene;AS-43108;SY030964;2-amino-3-ethoxycarbonyl-4-phenylthiophene;LS-152979;A7331;CS-0038271;Ethyl2-amino-4-phenylthiophene-3-carboxylate;FT-0625929;EN300-02862;J-507880;2-amino-4-phenyl-3-thiophenecarboxylic acidethyl ester;Ethyl 2-amino-4-phenylthiophene-3-carboxylate, 97%;Z56860274;2-amino-4-phenyl-3-thiophenecarboxylic acid, ethyl ester;F1018-1557;3-Thiophenecarboxylic acid,2-amino-4-phenyl-,Ethyl ester

Chemical Property of Ethyl 2-amino-4-phenylthiophene-3-carboxylate

Chemical Property:

• Appearance/Colour: Yellow Solid
• Vapor Pressure: 2.54E-06mmHg at 25°C
• Melting Point: 92-97 °C
• Refractive Index: 1.612
• Boiling Point: 391 °C at 760 mmHg
• PKA: -0.14±0.10(Predicted)
• Flash Point: 190.3 °C
• PSA: 80.56000
• Density: 1.231 g/cm³
• LogP: 3.75520
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 247.06669983
• Heavy Atom Count: 17
• Complexity: 266

Purity/Quality:

99.5% ^*data from raw suppliers

Ethyl 2-Amino-4-phenylthiophene-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=C(SC=C1C2=CC=CC=C2)N
• Uses: 2-Amino-4-phenyl-thiophene-3-carboxylic acid ethyl ester is a synthetic intermediate useful for pharmaceutical synthesis. Ethyl 2-Amino-4-phenylthiophene-3-carboxylate is used in the design and synthesis of thieno[2,3-d]pyrimidine analogs which exhibits antiproliferative activity against human cancer cells such as liver, pancreatic and colorectal cancer.

Technology Process of Ethyl 2-amino-4-phenylthiophene-3-carboxylate

There total 10 articles about Ethyl 2-amino-4-phenylthiophene-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: 97.0%

acetophenone (98-86-2) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-amino-4-phenyl-thiophene-3-carboxylate (4815-36-5)

Guidance literature:

acetophenone; ethyl 2-cyanoacetate; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.5h;

With pyridine; In dichloromethane; at 0 - 20 ℃;

With sulfur; diethylamine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm1008538

Reference yield: 80.0%

benzaldehyde (100-52-7) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-amino-4-phenyl-thiophene-3-carboxylate (4815-36-5)

Guidance literature:

With sulfur; diethylamine; In methanol; ethanol; at 20 ℃; Sonication;

DOI:10.1021/acs.jmedchem.0c02266

Reference yield: 79.0%

morpholine (110-91-8,99108-56-2) + (Z)-2-cyano-3-phenylbut-2-enoic acid ethyl ester (17277-47-3) → ethyl 2-amino-4-phenyl-thiophene-3-carboxylate (4815-36-5)

Guidance literature:

With hydrogen sulfide; In ethanol; ethyl acetate; Petroleum ether;

upstream raw materials:

ethyl 2-cyano-3-phenylbut-2-enoate

acetophenone

ethyl 2-cyanoacetate

(Z)-2-cyano-3-phenylbut-2-enoic acid ethyl ester

Downstream raw materials:

3-phenyl-7,8-dihydro-6H-pyrrolo[1,2-a]thieno[2,3-d]pyrimidin-4-one

3-phenyl-6,7,8,9-tetrahydro-pyrido[1,2-a]thieno[2,3-d]pyrimidin-4-one

2-Isothiocyanato-4-phenyl-thiophene-3-carboxylic acid ethyl ester

2-(3-Ethyl-thioureido)-4-phenyl-thiophene-3-carboxylic acid ethyl ester

Refernces

• 1、 Kaliraj,Jeyalakshmi,Kathiravan,Madhavan,Devi, Arikketh. "Design, molecular docking and biological evaluation of fused thienopyrimidines and quinazoline". . p. 537 - 544. Retrieved 2021/02/27.
• 2、 -. "BENZOTHIADIAZINE DERIVATIVES AND COMPOSITIONS COMPRISING THE SAME FOR TREATING DISORDERS MEDIATED BY ADENOSINE". Page/Page column 30-31; 33. . Retrieved 2020/07/15.