Methyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

Base Information

• Chemical Name: Methyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
• CAS No.: 108354-78-5
• Molecular Formula: C10H13NO2S
• Molecular Weight: 211.285
• Hs Code.: 2934999090
• European Community (EC) Number: 672-032-9
• DSSTox Substance ID: DTXSID10373419
• Nikkaji Number: J455.884G
• Wikidata: Q82161574
• ChEMBL ID: CHEMBL1632051
• Mol file: 108354-78-5.mol

Synonyms:108354-78-5;methyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate;2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid methyl ester;2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid methyl ester;CBMicro_029799;Oprea1_515014;Oprea1_612476;2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-;SCHEMBL2179728;CHEMBL1632051;DTXSID10373419;DKYYKIHEIOOWRB-UHFFFAOYSA-N;HMS1648K22;BBL005237;MFCD00130099;STK039450;AKOS000111620;FS-1352;SB66902;s10367;BIM-0029921.P001;BB 0242384;CS-0042661;EU-0099890;FT-0678120;EN300-05522;A801863;AK-968/37166331;SR-01000397768;SR-01000397768-1;Z56904670;F1443-4670;methyl-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate;methyl 2-amino-4, 5, 6, 7-tetrahydro-1-benzothiophene-3-carboxylate;methyl 2-amino-4,5,6,7-tetrahydro-1-benzo[b]thiophene-3-carboxylate;2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophen e-3-carboxylic acid methyl ester;2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid methyl ester, AldrichCPR

Chemical Property of Methyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

Chemical Property:

• Appearance/Colour: light yellow solid
• Vapor Pressure: 1.42E-06mmHg at 25°C
• Melting Point: 128-131 °C
• Refractive Index: 1.608
• Boiling Point: 398.993 °C at 760 mmHg
• PKA: 0.52±0.20(Predicted)
• Flash Point: 195.104 °C
• PSA: 80.56000
• Density: 1.273 g/cm³
• LogP: 2.57690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 211.06669983
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

99%, ^*data from raw suppliers

Methyl2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(SC2=C1CCCC2)N

Technology Process of Methyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

There total 6 articles about Methyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-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: 95.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + methyl 2-cyanoacetate (105-34-0) → methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (108354-78-5)

Guidance literature:

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

DOI:10.1016/j.ejmech.2019.02.067

Reference yield: 87.0%

methanol (67-56-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + cyanoacetic acid (372-09-8) → methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (108354-78-5)

Guidance literature:

cyanoacetic acid; With dmap; poly(ethylene glycol) 3400; dicyclohexyl-carbodiimide; for 0.0833333h; microwave irradiation;

cyclohexanone; With sulfur; N-ethyl-N,N-diisopropylamine; for 0.333333h; microwave irradiation;

methanol; With potassium cyanide; at 20 ℃;

Reference yield: 75.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + ethyl 2-cyanoacetate (105-56-6) → methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (108354-78-5)

Guidance literature:

With sulfur; diethylamine; In ethanol; at 45 - 50 ℃; for 1h;

upstream raw materials:

methanol

ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

cyclohexanone

cyanoacetic acid

Downstream raw materials:

methyl 2-[(3-carboxy-1-oxopropyl)amino]-4,5,6,7-tetra-hydrobenzo[b]thiophene-3-carboxylate

5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

4-dimethylamino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine

methyl 2-[[(6-carboxy-3-cyclohexen-1-yl)carbonyl] amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Refernces

• 1、 Di Fruscia, Paolo,Zacharioudakis, Emmanouil,Liu, Chang,Moniot, Sébastien,Laohasinnarong, Sasiwan,Khongkow, Mattaka,Harrison, Ian F.,Koltsida, Konstantina,Reynolds, Christopher R.,Schmidtkunz, Karin,Jung, Manfred,Chapman, Kathryn L.,Steegborn, Clemens,Dexter, David T.,Sternberg, Michael J.E.,Lam, Eric W.-F.,Fuchter, Matthew J.. "The discovery of a highly selective 5,6,7,8-Tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one SIRT2 Inhibitor that is Neuroprotective in an in vitro Parkinson's Disease Model". . p. 69 - 82. Retrieved 2015.
• 2、 Adib, Mehdi,Bayanati, Maryam,Soheilizad, Mehdi,Ghazvini, Helia Janatian,Tajbakhsh, Mahmood,Amanlou, Massoud. "A simple synthesis of alkyl 2-aminobenzo[ b ]thiophene-3-carboxylates via an unexpected dehydrogenation of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[ b ]thiophene-3-carboxylates". . . Retrieved 2014.
• 3、 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.
• 4、 Dimo, Kamal Sorel Djeukoua,Doungmo, Giscard,Ekom, Steve Endeguele,Fondjo, Emmanuel Sopbué,Kuiate, Jules-Roger,Siéwé, Désire André,Simon, Peter F. W.,Tamokou, Jean-De-Dieu,Tsopmo, Appolinnaire,Walters, Mallory E.. "Chromium (III) complex of 2-amino-3-carbomethoxy-4,5,6,7-tetrahydrobenzo[B] thiophene: synthesis, characterization and antimicrobial activity". . p. 4908 - 4913. Retrieved 2020/11/16.