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405191

Sigma-Aldrich

2,5-Thiophenedicarboxylic acid

99%

Synonym(s):

2,5-Dicarboxythiophene, Thiophene-2,5-dicarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C6H4O4S
CAS Number:
Molecular Weight:
172.16
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

mp

>300 °C (lit.)

SMILES string

OC(=O)c1ccc(s1)C(O)=O

InChI

1S/C6H4O4S/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)

InChI key

YCGAZNXXGKTASZ-UHFFFAOYSA-N

General description

2,5-Thiophenedicarboxylic acid (2,5-TDCA, H2TDC) is an important building block in the preparation of fluorescent brightening agent, fungicides and anti-cancer drug. It has been generated by chlorination of adipic acid using thionyl chloride. Due to its diverse coordination modes, it is an excellent choice as an aromatic linker to generate coordination networks. The enthalpies of combustion and sublimation of 2,5-thiophenedicarboxylic acid have been evaluated by rotary-bomb combustion calorimetry.

Application

2,5-Thiophenedicarboxylic acid may be used as a thiophene based linker in the preparation of magnesium coordination networks. It may also be used as a precursor in the synthesis of 2,5-bis-benzoxazoyl-thiophene (EBF).
It may be used in the synthesis of the following:
  • new cobalt(II) thiophenedicarboxylate coordination polymer
  • novel mesogenic thiophene based supramolecular liquid crystals
  • two novel coordination polymers with the formula {[Ln2(2,5-tdc)3(dmso)2]H2O}n (Ln = Tb(III) and Dy(III)), (2,5-tdc2 = 2,5-thiophenedicarboxylate and dmso = dimethylsulfoxide)

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis, characterization, and luminescence properties of magnesium coordination networks using a thiophene-based linker.
Calderone PJ, et al.
Inorgorganica Chimica Acta, 378(1), 109-114 (2011)
Devthade Vidyasagar et al.
Scientific reports, 9(1), 7186-7186 (2019-05-12)
An n-p type homostructural metal-free graphitic carbon nitride (g-C3N4) semiconductor is designed and developed for pollutant abatement and energy storage application. The successful grafting of vibrio-like morphology-based g-C3N4 by 2, 5-Thiophenedicarboxylic acid (TDA) molecule and the development of amide-type linkage
Preliminary communication Properties of nonlinear supramolecular liquid crystals containing thiophenedicarboxylic acids.
Lin H-C, et al.
Liq. Cryst., 25(2), 277-283 (1998)
Nail Altunay
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 189, 167-175 (2017-08-16)
The current study reports, for the first time, the development of a new analytical method employing ultrasound assisted-cloud point extraction (UA-CPE) for the extraction of CH
Aude Demessence et al.
Inorganic chemistry, 46(9), 3423-3425 (2007-03-29)
A new carboxylato-bridged CoII network of formula {Co((kappa1-kappa1)-(kappa1-mu2)-mu4-TDC)(mu2-H2O)0.5(H2O)}n (H2TDC=2,5-thiophenedicarboxylic acid) has been hydrothermally synthesized and characterized by single-crystal X-ray diffraction, thermogravimetric analysis, and IR and UV-visible spectroscopies. The title compound is made of chains of CoII dimers interconnected by TDC2-

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