5-Acetylthiophene-2-carboxylic acid

Base Information

• Chemical Name: 5-Acetylthiophene-2-carboxylic acid
• CAS No.: 4066-41-5
• Molecular Formula: C7H6O3S
• Molecular Weight: 170.189
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90395811
• Nikkaji Number: J25.420G
• Wikidata: Q72435894
• Mol file: 4066-41-5.mol

Synonyms:5-acetylthiophene-2-carboxylic acid;4066-41-5;5-acetyl-2-thiophenecarboxylic acid;2-Thiophenecarboxylic acid, 5-acetyl-;5-acetyl-thiophene-2-carboxylic acid;MFCD00055512;5-Acetylthiophene-2-carboxylicacid;5-Acetyltiophene-2-Carboxylic acid;5-Acetyl-2-thenoic Acid;5-Carboxy-2-acetylthiophene;SCHEMBL593258;DTXSID90395811;LIKIMWYKJUFVJP-UHFFFAOYSA-N;CS-B1379;STR05216;5-acetyl-thiophen-2-carboxylic acid;AM9902;FD7379;STK427451;5-Acetyl thiophene-2-carboxylic acid;5-acetyl-2-thiophene-carboxylic acid;AKOS001138527;PS-5005;SB67081;NCGC00329121-01;SY050152;FT-0619932;EN300-14656;5-Acetyl-2-thiophenecarboxylic acid, AldrichCPR;AB01323246-02;W-202671;F0001-1150;Z104378254

Chemical Property of 5-Acetylthiophene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.27E-06mmHg at 25°C
• Melting Point: 210-212 °C
• Refractive Index: 1.591
• Boiling Point: 385.2 °C at 760 mmHg
• PKA: 2.95±0.10(Predicted)
• Flash Point: 186.8 °C
• PSA: 82.61000
• Density: 1.383 g/cm³
• LogP: 1.64890
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 170.00376522
• Heavy Atom Count: 11
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

5-Acetylthiophene-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(S1)C(=O)O
• Uses: 5-Acetylthiophene-2-carboxylic acid is a intermediate used in the preparation of various 2,5-disubstituted thiophenes.

Technology Process of 5-Acetylthiophene-2-carboxylic acid

There total 12 articles about 5-Acetylthiophene-2-carboxylic acid 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: 90.0%

5-bromothiophene-2-carboxylic acid (7311-63-9) + acetyl chloride (75-36-5) → 5-acetylthiophene-2-carboxylic acid (4066-41-5)

Guidance literature:

5-bromothiophene-2-carboxylic acid; acetyl chloride; With isopropylmagnesium bromide; In tetrahydrofuran; at -40 - -10 ℃; for 12h;

In dichloromethane; at 20 ℃; for 0.25h; Further stages.;

DOI:10.1021/jo000235t

Reference yield: 81.0%

2-Acetyl-5-methylthiophen (13679-74-8) → 5-acetylthiophene-2-carboxylic acid (4066-41-5)

Guidance literature:

With cerium(III) chloride; 1,1,1-trichloroethanol; oxygen; In acetonitrile; at 60 ℃; Irradiation;

DOI:10.1007/s11426-021-1032-7

Reference yield: 39.0%

2-Acetylthiophene (88-15-3,97511-16-5) + carbon dioxide (124-38-9,18923-20-1) → 5-acetylthiophene-2-carboxylic acid (4066-41-5)

Guidance literature:

With 2,3,6,7-tetramethoxy-9(10H)-anthracenone; caesium carbonate; In dimethyl sulfoxide; at 25 ℃; for 18h; under 2280.15 Torr; regioselective reaction; Irradiation; Sealed tube;

DOI:10.1016/j.chempr.2020.08.022

upstream raw materials:

1-(5-ethanesulfonylmethyl-[2]thienyl)-ethanone

2-Acetyl-5-methylthiophen

2-thiophenylcarboxylic acid

malonic acid

Downstream raw materials:

5-ethyl-2-thiophenecarboxylic acid

5-acetyl-N-(phenylmethyl)-2-thiophenecarboxamide

C₁₄H₁₃NO₃S

5-(1-{[(2-fluorophenyl)sulfonyl]amino}ethyl)-N-hydroxythiophene-2-carboxamide

Refernces

• 1、 Bergonzini, Giulia,Brandt, Peter,Fricke, Florian,Johansson, Magnus J.,K?nig, Burkhard,Schmalzbauer, Matthias,Svejstrup, Thomas D.. "Redox-Neutral Photocatalytic C?H Carboxylation of Arenes and Styrenes with CO2". . p. 2658 - 2672. Retrieved 2020/10/07.
• 2、 Abarbri, Mohamed,Thibonnet, Jerome,Berillon, Laurent,Dehmel, Florian,Rottlaender, Mario,Knochel, Paul. "Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange". . p. 4618 - 4634. Retrieved 2007/10/03.