5-Fluorothiophene-2-carboxylic acid

Base Information

• Chemical Name: 5-Fluorothiophene-2-carboxylic acid
• CAS No.: 4377-58-6
• Molecular Formula: C5H3FO2S
• Molecular Weight: 146.142
• Hs Code.: 2934999090
• European Community (EC) Number: 821-833-3
• ChEMBL ID: CHEMBL4288339
• DSSTox Substance ID: DTXSID20473015
• Nikkaji Number: J1.412.773I
• Wikidata: Q72477157
• Mol file: 4377-58-6.mol

Synonyms:5-fluorothiophene-2-carboxylic acid;4377-58-6;5-FLUORO-2-THIOPHENECARBOXYLIC ACID;5-FLUORO-THIOPHENE-2-CARBOXYLIC ACID;5-FLUOROTHIOPHEN-2-CARBOXYLIC ACID;CHEMBL4288339;5-Fluoro-2-thiophenecarboxylicacid;MFCD07787557;2-Thiophenecarboxylic acid, 5-fluoro-;SCHEMBL1978930;DTXSID20473015;AKOS B029946;XQURBTZGKJENJS-UHFFFAOYSA-N;5-fluorothiophene-2-carboxylicacid;AMY23549;BCP06836;CS-D0304;BDBM50467737;AKOS000313765;PB22097;DS-12454;SY042026;FT-0646229;EN300-106868;A826422;J-517526;Z1198175121

Chemical Property of 5-Fluorothiophene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 139-141℃
• Refractive Index: 1.574
• Boiling Point: 271.178 °C at 760 mmHg
• PKA: 3.52±0.10(Predicted)
• Flash Point: 117.804 °C
• PSA: 65.54000
• Density: 1.528 g/cm³
• LogP: 1.58540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 145.98377867
• Heavy Atom Count: 9
• Complexity: 128

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Fluorothiophene-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1)F)C(=O)O

Technology Process of 5-Fluorothiophene-2-carboxylic acid

There total 4 articles about 5-Fluorothiophene-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: 82.0%

(E)-5-(2-Benzyloxy-4,5-dimethoxy-phenyl)-hex-2-enoic acid ethyl ester → 5-fluorothiophene-2-carboxylic acid (4377-58-6)

Guidance literature:

With sodium hydroxide; In water; for 3h; Heating;

DOI:10.1080/00397910008087280

Reference yield:

5-fluorothiophene-2-carbonitrile (32415-91-1) → 5-fluorothiophene-2-carboxylic acid (4377-58-6)

Guidance literature:

With sodium hydroxide;

Reference yield:

5-nitro-2-thienyl cyanide (16689-02-4) → 5-fluorothiophene-2-carboxylic acid (4377-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium fluoride; tetraphenylphosphonium bromide; Phthaloyl dichloride / sulfolane / 2 h / 180 °C

2: sodium hydroxide; water / 2 h / 100 °C

With potassium fluoride; water; tetraphenylphosphonium bromide; Phthaloyl dichloride; sodium hydroxide; In sulfolane;

upstream raw materials:

5-fluorothiophene-2-carbonitrile

5-nitro-2-thienyl cyanide

Downstream raw materials:

(5-fluorothiophen-2-yl)formyl chloride

N-[5-allyl-6a-(5-fluoro-2-thienyl)-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-1-carbothioyl]benzamide

N-[[1-allyl-3-(5-fluoro-2-thienyl)-4-(hydroxymethyl)pyrrolidin-3-yl]carbamothioyl]benzamide

N-[(4aR,7aR)-7a-(5-fluorothiophen-2-yl)-4,4a,5,6,7,7a-hexahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Refernces

• 1、 Chambers,Marfat. "An improved synthesis of 5-fluorothiophene-2-carboxylic acid". . p. 3629 - 3632. Retrieved 2007/10/03.
• 2、 -. "Processes and intermediates for preparing 2-fluorothiophene derivatives". . . Retrieved 2008/06/13.