2-Amino-5-phenylthiophene-3-carboxamide

Base Information

• Chemical Name: 2-Amino-5-phenylthiophene-3-carboxamide
• CAS No.: 4815-35-4
• Molecular Formula: C11H10 N2 O S
• Molecular Weight: 218.279
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID60351580
• Nikkaji Number: J3.006.852A
• Wikidata: Q82128104
• ChEMBL ID: CHEMBL382565
• Mol file: 4815-35-4.mol

Synonyms:2-amino-5-phenylthiophene-3-carboxamide;4815-35-4;2-Amino-5-phenyl-thiophene-3-carboxylic acid amide;2-AMINO-5-PHENYL-3-THIOPHENECARBOXAMIDE;CHEMBL382565;MFCD01314303;CBMicro_037044;Cambridge id 5914467;Oprea1_326775;Oprea1_445444;SCHEMBL3510525;DTXSID60351580;UHEGYTDIDBFUJD-UHFFFAOYSA-N;HMS1757A19;AMY12179;BDBM50186655;STK346852;AKOS000274130;BS-14000;PD158739;BIM-0036903.P001;(S)-Modafinil-d10 Carboxylate Methyl Ester;FT-0731297;EN300-04586;2-AMINO-5-PHENYL-THIOPHENE-3-CARBOXYLIC;AB00100625-01;ACETICACID,[(2-FURANYLMETHYL)SULFINYL]-;A854717;SR-01000223155;2-Amino-5-Phenylthiophene-3-Carboxylic Acid Amide;SR-01000223155-1;Z56884070;F0863-0293;2-amino-5-phenyl-thiophene-3-carboxylic acid amide, AldrichCPR

Chemical Property of 2-Amino-5-phenylthiophene-3-carboxamide

Chemical Property:

• Vapor Pressure: 1.87E-06mmHg at 25°C
• Melting Point: 218-220 °C
• Boiling Point: 395.2°Cat760mmHg
• PKA: 15.48±0.50(Predicted)
• Flash Point: 192.8°C
• PSA: 98.34000
• Density: 1.321g/cm³
• LogP: 3.56160
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 218.05138412
• Heavy Atom Count: 15
• Complexity: 241

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-Amino-5-phenyl-3-thiophenecarboxamide ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=C(S2)N)C(=O)N
• Uses: 2-AMino-5-phenyl-thiophene-3-carboxylic acid aMide is an 2-Aminothiophene-3-carboxamide derivative and a known inhibitor of janus kinases used in the treatment of myeloproliferative disorders and cancers.

Technology Process of 2-Amino-5-phenylthiophene-3-carboxamide

There total 9 articles about 2-Amino-5-phenylthiophene-3-carboxamide 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: 80.0%

phenylacetaldehyde (122-78-1) + cyanoacetic acid amide (107-91-5) → 2-Amino-5-phenyl-thiophene-3-carboxylic acid amide (4815-35-4)

Guidance literature:

With morpholine; sulfur; In ethanol; at 70 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1055/s-0030-1261032

Reference yield:

C19H16N2O3S → 2-Amino-5-phenyl-thiophene-3-carboxylic acid amide (4815-35-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; at 80 ℃;

DOI:10.1016/j.bmcl.2014.02.064

Reference yield:

phenylacetic acid (103-82-2) → 2-Amino-5-phenyl-thiophene-3-carboxylic acid amide (4815-35-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sulfuric acid / 3 h / Reflux

2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 20 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 2 h / 80 °C

4: morpholine; sulfur / ethanol / 0.33 h / 70 °C / Microwave irradiation

With morpholine; sulfuric acid; diisobutylaluminium hydride; sulfur; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; toluene; acetonitrile; 1: Fischer esterification / 4: Gewald reaction;

DOI:10.1055/s-0030-1261032

upstream raw materials:

phenylacetic acid

2-phenylethanol

phenylacetaldehyde

cyanoacetic acid amide

Downstream raw materials:

6-phenylthieno<2,3-d>pyrimidine-2,4-dione

2-[(4-fluoropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide

2-[(4-methylpyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide

2-[(5-fluoropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide

Refernces

• 1、 Revelant, Germain,Dunand, Sandrine,Hesse, Stephanie,Kirsch, Gilbert. "Microwave-assisted synthesis of 5-substituted 2-aminothiophenes starting from arylacetaldehydes". . p. 2935 - 2940. Retrieved 2011/11/01.
• 2、 -. "Novel Compounds". . . Retrieved 2008/06/13.