3-Thiophenecarboxylic acid

Base Information

• Chemical Name: 3-Thiophenecarboxylic acid
• CAS No.: 88-13-1
• Molecular Formula: C5H4O2S
• Molecular Weight: 128.152
• Hs Code.: 29349990
• European Community (EC) Number: 201-802-5
• NSC Number: 66314
• UNII: 6V3012Q6BE
• DSSTox Substance ID: DTXSID40236745
• Nikkaji Number: J4.287K
• Wikipedia: B-thiophenic acid
• Wikidata: Q27265560
• ChEMBL ID: CHEMBL164585
• Mol file: 88-13-1.mol

Synonyms:thiophene-3-carboxylic acid

Chemical Property of 3-Thiophenecarboxylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00323mmHg at 25°C
• Melting Point: 136-141 °C(lit.)
• Refractive Index: 1.606
• Boiling Point: 271.112 °C at 760 mmHg
• PKA: 4.1(at 25℃)
• Flash Point: 117.765 °C
• PSA: 65.54000
• Density: 1.401 g/cm³
• LogP: 1.44630
• Storage Temp.: Refrigerated.
• Solubility.: water: soluble0.2g/10 mL, clear to almost clear, colorless to sl
• Water Solubility.: 4.3 g/L (25 ºC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 127.99320054
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

3-Thiophenecarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CSC=C1C(=O)O
• Uses: 3-Thiophenecarboxylic Acid was used as a lading compound for the development of a clinic useful D-amino acid inhibitor and have the potential to sever as active site proves to elucidate the structure-function relationships of D-amino acids.

Technology Process of 3-Thiophenecarboxylic acid

There total 44 articles about 3-Thiophenecarboxylic 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: 94.0%

3-Bromothiophene (872-31-1) + carbon dioxide (124-38-9,18923-20-1) → 3-Thiophene carboxylic acid (88-13-1)

Guidance literature:

carbon dioxide; With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate; In 1,4-dioxane; at 65 ℃; for 0.333333h; Schlenk technique;

3-Bromothiophene; With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; toluene; at 100 ℃; for 7h; Schlenk technique; Sealed tube;

DOI:10.1039/c8cc06820h

Reference yield: 90.0%

3-thienyl iodide (10486-61-0) + formic acid (64-18-6) → 3-Thiophene carboxylic acid (88-13-1)

Guidance literature:

With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 80 ℃; for 10h; Inert atmosphere; Sealed tube;

DOI:10.1002/cctc.201700517

Reference yield: 88.0%

5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane (905966-46-3) + carbon dioxide (124-38-9,18923-20-1) → 3-Thiophene carboxylic acid (88-13-1)

Guidance literature:

5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane; carbon dioxide; With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate; In toluene; at 100 ℃; for 15h; under 760.051 Torr; Schlenk technique; Inert atmosphere;

With hydrogenchloride; In water; ethyl acetate; toluene; at 20 ℃;

DOI:10.1039/c4cc03650f

upstream raw materials:

3-Bromothiophene

n-butyllithium

diethyl ether

ethylmagnesium bromide

Downstream raw materials:

3-thiophene carboxylic acid chloride

thiolane-3-carboxylic acid

2-chlorothiophene-4-carboxylic acid

2-bromothiophene-4-carboxylic acid

Refernces

• 1、 Anghel, C?t?lin C.,Stroia, Ioan,Pop, Alexandra,Bende, Atilla,Grosu, Ion,H?dade, Niculina D.,Roncali, Jean. "An attempt to synthesize a terthienyl-based analog of indacenedithiophene (IDT): unexpected synthesis of a naphtho[2,3-b]thiophene derivative". . p. 9894 - 9900. Retrieved 2021/03/23.
• 2、 Kim, Seongwoo,Lee, Ha-Eun,Suh, Jong-Min,Lim, Mi Hee,Kim, Min. "Sequential Connection of Mutually Exclusive Catalytic Reactions by a Method Controlling the Presence of an MOF Catalyst: One-Pot Oxidation of Alcohols to Carboxylic Acids". supporting information. p. 17573 - 17582. Retrieved 2020/12/22.