Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

405191

Sigma-Aldrich

2,5-Thiophenedicarboxylic acid

99%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

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
Pricing and availability is not currently available.

Quality Level

100

Assay

99%

mp

>300 °C (lit.)

functional group

carboxylic acid

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.[1] Due to its diverse coordination modes, it is an excellent choice as an aromatic linker to generate coordination networks.[2] The enthalpies of combustion and sublimation of 2,5-thiophenedicarboxylic acid have been evaluated by rotary-bomb combustion calorimetry.[3]

Application

2,5-Thiophenedicarboxylic acid may be used as a thiophene based linker in the preparation of magnesium coordination networks.[2] It may also be used as a precursor in the synthesis of 2,5-bis-benzoxazoyl-thiophene (EBF).[1]
It may be used in the synthesis of the following:
  • new cobalt(II) thiophenedicarboxylate coordination polymer[4]
  • novel mesogenic thiophene based supramolecular liquid crystals[5]
  • 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)[6]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
WXBF5170V
WXBF3402V
WXBF0129V
MKCS8393
WXBD9267V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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-
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)
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 +/-
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service