Ethyl 2-aminothiophene-3-carboxylate

Base Information

• Chemical Name: Ethyl 2-aminothiophene-3-carboxylate
• CAS No.: 31891-06-2
• Molecular Formula: C7H9NO2S
• Molecular Weight: 171.22
• Hs Code.: 29349990
• European Community (EC) Number: 672-859-5
• DSSTox Substance ID: DTXSID50365792
• Nikkaji Number: J550.012E
• Wikidata: Q72472708
• Mol file: 31891-06-2.mol

Synonyms:ethyl 2-aminothiophene-3-carboxylate;31891-06-2;2-Aminothiophene-3-Carboxylic Acid Ethyl Ester;2-Amino-thiophene-3-carboxylic acid ethyl ester;3-THIOPHENECARBOXYLIC ACID, 2-AMINO-, ETHYL ESTER;MFCD01566303;ethyl2-aminothiophene-3-carboxylate;ethyl 2-amino-3-thenoate;SCHEMBL225275;2-amino-3-ethoxycarbonylthiophene;DTXSID50365792;MKJQYFVTEPGXIE-UHFFFAOYSA-N;BBL016855;STK436102;AKOS000200207;ethyl 2-amino-thiophene-3-carboxylate;AB09218;AC-5468;CS-W008319;DS-0777;FS-1458;SY003505;AM20090456;BB 0218388;FT-0639003;EN300-02969;A22978;Ethyl 2-amino-3-thiophenecarboxylate, AldrichCPR;(R)-2-Diphenylphosphino,2-hydroxyl-1,1-binaphthyl;J-018564;J-520713;Z56769392;F2146-0062

Chemical Property of Ethyl 2-aminothiophene-3-carboxylate

Chemical Property:

• Appearance/Colour: Brown solid
• Vapor Pressure: 0.006mmHg at 25°C
• Melting Point: 42 °C
• Refractive Index: 1.582
• Boiling Point: 273.6 °C at 760 mmHg
• PKA: 0.11±0.10(Predicted)
• Flash Point: 119.3 °C
• PSA: 80.56000
• Density: 1.263 g/cm³
• LogP: 2.08820
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform, Dichloromethane
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 171.03539970
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl 2-Aminothiophene-3-carboxylate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(SC=C1)N
• Uses: Ethyl 2-aminothiophene-3-carboxylate is used as an organic chemical synthesis intermediate.

Technology Process of Ethyl 2-aminothiophene-3-carboxylate

There total 4 articles about Ethyl 2-aminothiophene-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: 89.0%

1,4-dithiane-2,5-diol (40018-26-6) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-aminothiophene-3-carboxylate (31891-06-2)

Guidance literature:

1,4-dithiane-2,5-diol; ethyl 2-cyanoacetate; In ethanol; at 20 ℃; for 0.166667h;

With N-methylpiperazine-functionalized Polyacrylonitrile Fiber; In ethanol; for 4h; Reagent/catalyst; Reflux;

DOI:10.1055/s-0032-1316821

Reference yield: 75.0%

1,4-dithiane-2,5-dithiol + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-aminothiophene-3-carboxylate (31891-06-2)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 8h; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.08.057

Reference yield:

methanol (67-56-1) + 2-aminothiophene-3-carboxylic acid (56387-08-7) → ethyl 2-aminothiophene-3-carboxylate (31891-06-2)

Guidance literature:

With thionyl chloride; at 0 ℃; for 24h; Reflux;

DOI:10.1016/j.ejmech.2014.02.014

upstream raw materials:

1,4-dithiane-2,5-diol

ethyl 2-cyanoacetate

methanol

2-aminothiophene-3-carboxylic acid

Downstream raw materials:

C₁₄H₁₃N₃O₅S

ethyl 2-(phenylethynyl)thiophene-3-carboxylate

7-iodo-6-phenyl-4H-thieno[3,2-c]pyran-4-one

ethyl-2-(2-iodobenzamido)thiophene-3-carboxylate

Refernces

• 1、 Chen, Zhipeng,Zhang, Lina,Yang, Junjie,Zheng, Lu,Hu, Fanjie,Duan, Siqin,Nandakumar, Kutty Selva,Liu, Shuwen,Yin, Hang,Cheng, Kui. "Design, Synthesis, and Structure-Activity Relationship of N-Aryl- N′-(thiophen-2-yl)thiourea Derivatives as Novel and Specific Human TLR1/2 Agonists for Potential Cancer Immunotherapy". supporting information. p. 7371 - 7389. Retrieved 2021/06/28.
• 2、 Fyfe, Tim J.,Kellam, Barrie,Mistry, Shailesh N.,Scammells, Peter J.,Lane, J. Robert,Capuano, Ben. "Subtle modifications to a thieno[2,3-d]pyrimidine scaffold yield negative allosteric modulators and agonists of the dopamine D2 receptor". . p. 474 - 490. Retrieved 2019/03/07.