Basic information
- CAS
4282-31-9- Standard SMILES
O=C(O)c1ccc(C(=O)O)s1- InChIKey
YCGAZNXXGKTASZ-UHFFFAOYSA-N- Molecular formula
- C6H4O4S
- Average molar mass
- 172.16 g/mol
- Monoisotopic mass
- 171.98302961
Names & identifiers
- Preferred name
- 2,5-Thiophenedicarboxylic acid
- IUPAC
- thiophene-2,5-dicarboxylic acid
- English name
- 2,5-Thiophenedicarboxylic acid
- Molecular formula
- C6H4O4S
- Molecular weight
- 172.16
Names & synonyms
2,5-Thiophenedicarboxylic acidTHIOPHENE-2,5-DICARBOXYLIC ACID2,5-Dicarboxythiophene2,5-Thiophene dicarboxylic acidUNII-5Q8A2G9Y8A5Q8A2G9Y8AEINECS 224-284-2NSC 81789NSC-81789DTXSID7063392RefChem:83027DTXCID1040166
Show more names
thiophene-2,5-dicarboxylateRARECHEM AL BE 06232,5-ThiophenedicarboOTAVA-BB BB70139114252,5-THIOPHENEDICARBOXYLICThiophene-2,5-Dicarboxyl Acid
YCGAZNXXGKTASZ-UHFFFAOYSA-N4282-31-9MFCD00016896TH-2COOHMaybridge4_002021SCHEMBL704932.5-Thiophenedicarboxylic acidorb3214673
Database identifiers
- CAS
4282-31-9- PubChem CID
- 20273
- DTXSID
DTXSID7063392- UNII
- 5Q8A2G9Y8A
- EC Number
- 224-284-2
- Nikkaji
- J205.683F
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 103 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 171
Physicochemical properties
- Melting point
- 300 °C · >300 °C (lit.)
- Boiling point
- 272.46 °C · 272.46°C (rough estimate)
- Density
- 1.473 · 1.473 (estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- form
- solid
- pka
- 2.76 · 2.76±0.10(Predicted)
- color
- White to Light yellow
- Water Solubility
- Very soluble in water.
- BRN
- 136781 · 136781
- InChI
- InChI=1S/C6H4O4S/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)
- InChIKey
- YCGAZNXXGKTASZ-UHFFFAOYSA-N
- SMILES
- C1(C(O)=O)SC(C(O)=O)=CC=1
- CAS DataBase Reference
- 4282 · 4282-31-9(CAS DataBase Reference)
- FDA UNII
- 5 Q8A2G9Y8A · 5Q8A2G9Y8A
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29349990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2,5-Thiophenedicarboxylic acid: ACTIVE
Applications
Uses2,5-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 polymernovel mesogenic thiophene based supramolecular liquid crystalstwo 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)
General Description2,5-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.
Upstream & downstream products
Upstream raw materials
Related reactions
16 records
Compound notes
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