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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:
4282-31-9
Molecular Weight:
172.16
EC Number:
224-284-2
MDL number:
MFCD00016896
UNSPSC Code:
12352100
PubChem Substance ID:
24865298
NACRES:
NA.22

Quality Level

100

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

Related Categories

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Preliminary communication Properties of nonlinear supramolecular liquid crystals containing thiophenedicarboxylic acids.
Lin H-C, et al.
Liq. Cryst., 25(2), 277-283 (1998)
Terbium (III) and dysprosium (III) 8-connected 3D networks containing 2, 5-thiophenedicarboxylate anion: Crystal structures and photoluminescence studies.
Marques LF, et al.
Polyhedron, 38(1), 149-156 (2012)
María Victoria Roux et al.
The journal of physical chemistry. A, 110(45), 12477-12483 (2006-11-10)
The enthalpies of combustion and sublimation of 2,5-thiophenedicarboxylic acid [CASRN 4282-31-9] were measured by rotary-bomb combustion calorimetry and the method of transference in a saturated stream of nitrogen, and the gas-phase enthalpy of formation was determined, Delta(f)H(o)(m)(g) = -(632.6 +/-
Solid-liquid equilibrium and thermodynamic of 2, 5-thiophenedicarboxylic acid in different organic solvents.
Zhi W, et al.
Fluid Phase Equilibria, 375, 110-114 (2014)
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
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