5-chlorothiophene-2-carboxylic acid

• ChemBase ID: 7247
• Molecular Formular: C5H3ClO2S
• Molecular Mass: 162.59412
• Monoisotopic Mass: 161.95422802
• SMILES: c1(sc(cc1)Cl)C(=O)O
• Canonical SMILES: OC(=O)c1ccc(s1)Cl
• InChI: InChI=1S/C5H3ClO2S/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H,7,8)
• InChIKey: QZLSBOVWPHXCLT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chlorothiophene-2-carboxylic acid
• IUPAC Traditional name: 5-chlorothiophene-2-carboxylic acid
• Synonyms: 2-Chloro-5-carboxythiophene; 5-Chlorothiophen-2-carboxylic acid; NSC 14776; 5-Chlorothiophene-2-carboxylic acid; 5-Chlorothiophene-2-carboxylic acid; 2-Chlorothiophene-5-carboxylic acid; 5-Chloro-2-thiophenecarboxylic acid; 5-氯噻吩-2-羧酸; 2-氯噻吩-5-甲酸

Database IDs

• CAS Number: 24065-33-6
• EC Number: 000-000-0
• MDL Number: MFCD00041426
• Beilstein Number: 118361
• PubChem SID: 24882532; 160970554
• PubChem CID: 95048

CALCULATED PROPERTIES

• Acid pKa: 3.3326368
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.16191117
• LogD (pH = 7.4): -1.1052303
• Log P: 2.3137507
• Molar Refractivity: 34.1688 cm^3
• Polarizability: 13.449741 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 149-152°C; 151°C; 152-154°C; 154-158 °C(lit.)

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: XM8400000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36-43
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H317-H319
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C5H3ClO2S

DETAILS

Sigma Aldrich - 633003

Packaging
5, 25 g in glass bottle

Toronto Research Chemicals - C420500

A metabolite of Rivaroxaban (R538000).

REFERENCES

• Brickner, S., et al.: J. Med. Chem., 39, 673 (1996)
• Sato, K., et al.: Eur. J. Pharmacol., 347, 231 (1996)
• Chang, P., et al.: IDrugs, 7, 50 (1996)
• Weinz, C., et al.: Drug Metab. Dispos., 37, 1056 (2009)