5-Chlorothiophene-2-carboxylic acid

Base Information

• Chemical Name: 5-Chlorothiophene-2-carboxylic acid
• CAS No.: 24065-33-6
• Molecular Formula: C5H3ClO2S
• Molecular Weight: 162.597
• Hs Code.: 29349990
• European Community (EC) Number: 480-060-6,607-311-6
• NSC Number: 14776
• UNII: XV5SRC3PJ3
• DSSTox Substance ID: DTXSID10178800
• Nikkaji Number: J48.863A
• Wikidata: Q69756857
• Pharos Ligand ID: GWD6D5RHBD2W
• ChEMBL ID: CHEMBL4280438
• Mol file: 24065-33-6.mol

Synonyms:5-Chlorothiophene-2-carboxylic acid;24065-33-6;5-Chloro-2-thiophenecarboxylic acid;2-Thiophenecarboxylic acid, 5-chloro-;MFCD00041426;C5H3ClO2S;NSC 14776;XV5SRC3PJ3;5-Chloro thiophene-2-carboxylic acid;BRN 0118361;AI3-61740;CHEMBL4280438;NSC-14776;5-18-06-00177 (Beilstein Handbook Reference);5-Chlorothiophene-2-carboxylicacid;NSC14776;Rivaroxaban Impurity C;Maybridge3_003717;UNII-XV5SRC3PJ3;SCHEMBL77196;5-chlorothiophenecarboxylic acid;RIVAROXABAN CTCA IMPURITY;2-Chlorothiophene-5-Formic Acid;DTXSID10178800;5-chloro-2-thiophenecarboxylicacid;HMS1441I21;5-chloro-2-thiophencarboxylic acid;5-chlorthiophene-2-carboxylic acid;2-CHLORO-5-CARBOXYTHIOPHENE;2-chloro-5-thiophenecarboxylic acid;BCP05839;CS-M1254;STR03101;5-chloro thiophen-2-carboxylic acid;5-chloro-thiophen-2-carboxylic acid;5-Chlorothiophene 2-carboxylic acid;BBL037515;BDBM50467736;GEO-00807;STK502364;5-chloro-2-thiophene carboxylic acid;5-chloro-2-thiophene-carboxylic acid;5-chloranylthiophene-2-carboxylic acid;AKOS000278212;FS-1378;PB12047;IDI1_015104;AC-25302;SY001039;5-CHLOROTHIOPHEN-2-CARBOXYLIC ACID;5-Chlorothiophene-2-carboxylic acid, 97%;LS-152999;A4985;AM20090264;C1230;FT-0620284;RIVAROXABAN IMPURITY F [EP IMPURITY];EN300-00711;W-200249;Z56346822;F2182-0126;2-Chloro-5-carboxythiophene;5-Chloro-2-thenoic acid;9E9

Chemical Property of 5-Chlorothiophene-2-carboxylic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 0.00119mmHg at 25°C
• Melting Point: 154-158 °C(lit.)
• Boiling Point: 287 °C at 760 mmHg
• PKA: 3.32±0.10(Predicted)
• Flash Point: 127.4 °C
• PSA: 65.54000
• Density: 1.572 g/cm³
• LogP: 2.09970
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 161.9542282
• Heavy Atom Count: 9
• Complexity: 128

Purity/Quality:

99.00% ^*data from raw suppliers

5-Chloro-2-thiophenecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(SC(=C1)Cl)C(=O)O
• Description: 5-Chlorothiophene-2-carboxylic acid is a powdered chemical substance. It is classified as a hazardous chemical to water and should be handled with care.
• Uses: In chemistry and materials science, it serves as a ligand in the synthesis of ruthenium complexes, influencing their photophysical and electrochemical properties.^[1]; In organic synthesis, it is used as a precursor for the preparation of pharmaceuticals, dyes, and aroma compounds.^[2]; It can be utilized in step-down reduction reactions of carboxylic acids to aromatic hydrocarbons via palladium catalysis.^[3]; It is also involved in the synthesis of selective T-type calcium channel inhibitors.^[4]
• Production Methods: Chemical synthesis methods for 5-Chlorothiophene-2-carboxylic acid involve reactions starting from appropriate precursors, such as oxalyl chloride and thiosemicarbazide.
• Analysis Method: Analytical techniques such as FT-IR spectroscopy, FT-Raman spectroscopy, NMR spectroscopy, and mass spectrometry are used for characterization and analysis of 5-Chlorothiophene-2-carboxylic acid and its derivatives.
• References: [1] Mono and binuclear ruthenium(II) complexes containing 5-chlorothiophene-2-carboxylic acid ligands: Spectroscopic analysis and computational studies; DOI 10.1016/j.molstruc.2016.07.048; [2] Vibrational Spectroscopic (FT-IR, FT-Raman) and DFT analysis of a potent NLO molecule 5-Chlorothiopene-2-Carboxylic acid; [3] Highly-chemoselective step-down reduction of carboxylic acids to aromatic hydrocarbons via palladium catalysis; DOI 10.1039/C9SC00892F; [4] SYNTHESIS OF 1,3,4-OXADIAZOLES AS SELECTIVE T-TYPE CALCIUM CHANNEL INHIBITORS; DOI 10.3987/com-19-s(f)5

Technology Process of 5-Chlorothiophene-2-carboxylic acid

There total 19 articles about 5-Chlorothiophene-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: 98.8%

5-Chloro-2-thiophenecarboxaldehyde (7283-96-7) → 5-Chlorothiophene-2-carboxylic acid (24065-33-6)

Guidance literature:

5-Chloro-2-thiophenecarboxaldehyde; With sodium hydroxide; at -5 - 0 ℃; for 2h; Large scale;

With chlorine; at 15 - 30 ℃; for 8h; Large scale;

Reference yield: 96.7%

5-bromo-2-chlorothiophene (2873-18-9) + carbon dioxide (124-38-9,18923-20-1) → 5-Chlorothiophene-2-carboxylic acid (24065-33-6)

Guidance literature:

5-bromo-2-chlorothiophene; With iodine; magnesium; In tetrahydrofuran; at 22 - 28 ℃; Inert atmosphere;

carbon dioxide; With hydrogenchloride; In water; at -15 ℃; for 1.5h;

Reference yield: 95.0%

5-chloro-2-trichloroacetylthiophene → 5-Chlorothiophene-2-carboxylic acid (24065-33-6)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In toluene; at 20 ℃; for 2h; Reagent/catalyst; Solvent;

upstream raw materials:

2-thienyl chloride

diethyl ether

2,5-diclorothiophene

2-thiophenylcarboxylic acid

Downstream raw materials:

methyl 5-chloro-2-thiophenecarboxylate

ethyl 5‐chlorothiophene‐2‐carboxylate

5-chlorothiophene-2-carbonyl chloride

tert-butyl 4-{4-[(5S)-5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}piperazine-1-carboxylate

Refernces

• 1、 -. "Method for synthesizing 5-chlorothiophene-2-formic acid with thiophene-2-formic acid as raw material". Paragraph 0027; 0031-0036. . Retrieved 2019/10/22.
• 2、 -. "Low cost preparation method of high purity 5-chlorothiophene-2-formyl chloride". Paragraph 0056-0062. . Retrieved 2019/03/26.