Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate
• CAS No.: 91076-93-6
• Molecular Formula: C12H10ClNO2S
• Molecular Weight: 267.736
• Hs Code.: 2934999090
• European Community (EC) Number: 673-106-3
• DSSTox Substance ID: DTXSID60380537
• Wikidata: Q72486817
• ChEMBL ID: CHEMBL1384146
• Mol file: 91076-93-6.mol

Synonyms:methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate;91076-93-6;methyl 3-amino-5-(4-chlorophenyl)-thiophene-2-carboxylate;MLS000851464;MFCD00052591;SMR000457907;2-Thiophenecarboxylic acid, 3-amino-5-(4-chlorophenyl)-, methyl ester;Methyl-3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate;3-amino-5-(4-chlorophenyl)thiophene-2-carboxylic acid methyl ester;Methyl3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate;Maybridge1_003891;SCHEMBL1531346;CHEMBL1384146;BDBM76603;cid_2777492;HMS552I19;DTXSID60380537;MELGGDOYSMRBGA-UHFFFAOYSA-N;HMS2796N03;AMY18042;CCG-43615;AKOS000352107;AC-4412;PS-4342;SY004531;CS-0197498;FT-0628537;EN300-3278146;SR-01000633520-1;Methyl 3-amino-5-(4-chlorophenyl)thiophene-2carboxylate;Z384975562;methyl 3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylate;methyl 3-azanyl-5-(4-chlorophenyl)thiophene-2-carboxylate;3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylic acid methyl ester;methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate, AldrichCPR

Chemical Property of Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 7.43E-09mmHg at 25°C
• Melting Point: 140-141 °C
• Refractive Index: 1.633
• Boiling Point: 465.9 °C at 760 mmHg
• Flash Point: 235.5 °C
• PSA: 80.56000
• Density: 1.363 g/cm³
• LogP: 4.01850
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 267.0120774
• Heavy Atom Count: 17
• Complexity: 282

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 22-26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=C(S1)C2=CC=C(C=C2)Cl)N

Technology Process of Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

There total 8 articles about Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-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: 81.0%

3-amino-5-bromo-thiophene-2-carboxylic acid methyl ester (107818-55-3) + 4-Chlorophenylboronic acid (1679-18-1) → methyl 3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylate (91076-93-6)

Guidance literature:

With palladium diacetate; sodium carbonate; triphenylphosphine; In 1,4-dioxane; water; at 80 ℃;

DOI:10.1016/j.tet.2021.132247

Reference yield: 73.0%

(E)-3-Chloro-3-(4-chloro-phenyl)-acrylonitrile (78583-86-5) + Methyl thioglycolate (2365-48-2) → methyl 3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylate (91076-93-6)

Guidance literature:

With sodium methylate; In methanol; for 3h; Reflux;

DOI:10.1016/j.tetlet.2019.151185

Reference yield:

para-chloroacetophenone (99-91-2) + Methyl thioglycolate (2365-48-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → methyl 3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylate (91076-93-6)

Guidance literature:

para-chloroacetophenone; N,N-dimethyl-formamide; With trichlorophosphate; at 20 ℃;

With hydroxylamine hydrochloride; at 0 - 100 ℃;

Methyl thioglycolate; With sodium methylate; In N,N-dimethyl-formamide; at 0 ℃; Further stages.;

DOI:10.1021/jm060572f

upstream raw materials:

(E)-3-Chloro-3-(4-chloro-phenyl)-acrylonitrile

Methyl thioglycolate

para-chloroacetophenone

N,N-dimethyl-formamide

Downstream raw materials:

3-(3-Chloro-2,2-dimethyl-propionylamino)-5-(4-chloro-phenyl)-thiophene-2-carboxylic acid methyl ester

6-(4'-chlorophenyl)-2,4-dihydro-1H-thieno[3,2-d][1,3]oxazine-2,4-dione

3-bromo-5-(4-chloro-phenyl)-thiophene-2-carboxylic acid methyl ester

methyl 5-(4-chlorophenyl)-3-((dimethylamino)methyleneamino)thiophene-2-carboxylate

Refernces

• 1、 Irgashev, Roman A.,Steparuk, Alexander S.,Rusinov, Gennady L.. "One-pot synthesis of 2-substituted thieno[3,2-b]indoles from 3-aminothiophene-2-carboxylates through in situ generated 3-aminothiophenes". supporting information. . Retrieved 2019/09/30.
• 2、 Hinsberger, Stefan,De Jong, Johannes C.,Groh, Matthias,Haupenthal, J?rg,Hartmann, Rolf W.. "Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections". . p. 343 - 351. Retrieved 2014/03/21.