5-Chlorothiophene-2-carboxylic acid

Bezeichnung:5-Chlorothiophene-2-carboxylic acid

CAS-Nr24065-33-6

Englisch Name:5-Chlorothiophene-2-carboxylic acid

CBNumberCB3189269

SummenformelC5H3ClO2S

Molgewicht162.59

MOL-Datei24065-33-6.mol

5-Chlorothiophene-2-carboxylic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	154-158 °C(lit.)
Siedepunkt	287.0±20.0 °C(Predicted)
Dichte	1.466 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
pka	3.32±0.10(Predicted)
Aggregatzustand	Powder
Farbe	Cream-yellow
BRN	118361
InChI	InChI=1S/C5H3ClO2S/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H,7,8)
InChIKey	QZLSBOVWPHXCLT-UHFFFAOYSA-N
SMILES	C1(C(O)=O)SC(Cl)=CC=1
CAS Datenbank	24065-33-6(CAS DataBase Reference)
NIST chemische Informationen	5-Chloro-2-thiophenecarboxylic acid(24065-33-6)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36-43-36/37/38
S-Sätze:	26-36-37/39
WGK Germany	3
RTECS-Nr.	XM8400000
HazardClass	IRRITANT
HS Code	29349990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1

Gefahreninformationscode (GHS)

5-Chlorothiophene-2-carboxylic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36:Reizt die Augen.
R43:Sensibilisierung durch Hautkontakt möglich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
5-Chlorothiophene-2-carboxylic acid is a biochemical reagent that can be used as a biological material or organic compound for life science-related research. It is also used as a ligand to synthesise the New Mono and Binuclear Ruthenium(II) Complexes[1].
Chemische Eigenschaften
White to light yellow crystal powder
Verwenden
A metabolite of Rivaroxaban (R538000).
Verwenden
5-Chlorothiophene-2-carboxylic acid can be used in the synthesis of the following:
- rivaroxaban, an oxazolidinone derivative used in the treatment of thromboembolic disorders
- 5-chloro-4-nitrothiophene-2-carboxylic acid, which can be used in the synthesis of thieno[2,3-b][1,4]thiapezine-5-ones
Synthese
The compound 5-chlorothiophene-2-carboxylic acid is a crucial intermediate in the synthesis of rivaroxaban. Due to its significance, numerous researchers have investigated various methods of synthesizing it. The synthesis of this compound involves the utilization of different starting materials, namely, 2-chlorothiophene, 2-chloro-5-bromothiophene, and 5-chloro-2-acetylthiophene, depending on the specific approach employed.

1. This method takes 2-chlorothiophene as an initial raw material, carrying out Friedel-crafts acylation with trichloroacetyl chloride under the action of aluminum trichloride to generate 2-trichloroacetyl-5-chlorothiophene, and then carrying out liquid alkali hydrolysis to obtain a target product.
2. This method reacts 5-chloro-2-bromothiophene with magnesium to generate a Grignard reagent, introducing carbon dioxide for inserting carbonyl and performing acid-base treatment to obtain a product.
3. 5-chloro-2-acetylthiophene is used as a raw material and is oxidized by sodium chlorite and potassium dihydrogen phosphate system to obtain a target compound.
Einzelnachweise
[1] Kalaiyar Swarnalatha, Ramasamy Subramanian, Subramaniam Kamalesu . “Mono and binuclear ruthenium(II) complexes containing 5-chlorothiophene-2-carboxylic acid ligands: Spectroscopic analysis and computational studies.” Journal of Molecular Structure 1123 (2016): Pages 416-425.

5-Chlorothiophene-2-carboxylic acid Upstream-Materialien And Downstream Produkte

5-Chlorothiophene-2-carboxylic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

24065-33-6, 5-Chlorothiophene-2-carboxylic acid Verwandte Suche:

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