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

Base Information

• Chemical Name: Ethyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate
• CAS No.: 91076-94-7
• Molecular Formula: C13H12ClNO2S
• Molecular Weight: 281.76
• Hs Code.: 2934999090
• European Community (EC) Number: 622-023-0
• DSSTox Substance ID: DTXSID70366625
• Wikidata: Q82151925
• Mol file: 91076-94-7.mol

Synonyms:Ethyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate;91076-94-7;SCHEMBL1143359;DTXSID70366625;MFCD06336766;AKOS000352201;BB 0218724;CS-0229832;EN300-10123;Z56995168;Ethyl3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate;Ethyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate, 97%;2-Thiophenecarboxylicacid,3-amino-5-(4-chlorophenyl)-,ethyl ester;3-Amino-5-(4-chlorophenyl)-thiophen-2-ylcarboxylic acid ethylester;3-amino-5-(4-chlorophenyl)-thiophene-2-carboxylic acid ethyl ester

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

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 4.16E-09mmHg at 25°C
• Melting Point: 107-111 °C(lit.)
• Refractive Index: 1.62
• Boiling Point: 472.8 °C at 760 mmHg
• Flash Point: 239.7 °C
• PSA: 80.56000
• Density: 1.323 g/cm³
• LogP: 4.40860
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 281.0277275
• Heavy Atom Count: 18
• Complexity: 295

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

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

There total 4 articles about Ethyl 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: 72.0%

2-chloro-3-(4-chlorophenyl)acrylonitrile (90272-22-3) + ethyl 2-sulfanylacetate (623-51-8) → 5-(p-chlorophenyl)-3-amino-thiophene-2-carboxylic acid ethyl esther (91076-94-7)

Guidance literature:

With sodium ethanolate; In ethanol; for 0.5h;

DOI:10.1134/S1070428002120138

Reference yield:

(E)-3-Chloro-3-(4-chloro-phenyl)-acrylonitrile (78583-86-5) + ethyl bromoacetate (105-36-2) → 5-(p-chlorophenyl)-3-amino-thiophene-2-carboxylic acid ethyl esther (91076-94-7)

Guidance literature:

With sodiumsulfide nonahydrate; In N,N-dimethyl-formamide; at 60 ℃; for 3h;

DOI:10.1055/s-0030-1258469

Reference yield:

(4-chlorophenyl)acetaldehyde (4251-65-4) → 5-(p-chlorophenyl)-3-amino-thiophene-2-carboxylic acid ethyl esther (91076-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trichlorophosphate / 5 h / 60 °C

1.3: Reflux

2.1: sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 3 h / 60 °C

With sodiumsulfide nonahydrate; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1055/s-0030-1258469

upstream raw materials:

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

ethyl 2-sulfanylacetate

2-chloro-3-(4-chlorophenyl)acrylonitrile

(4-chlorophenyl)acetaldehyde

Downstream raw materials:

2-amino-6-(4-chlorophenyl)thieno[3,2-d]pyrimidin-4(3H)-one

3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylic acid

Refernces

• 1、 Shastin,Golubinskii,Lenkova,Balenkova,Nenaidenko. "Synthesis of ethyl 3-amino-5-arylthiophene-2-carboxylates based on α-chlorocinnamonitriles". . p. 238 - 240. Retrieved 2007/10/03.