Methyl-2-chlornicotinat

Bezeichnung:Methyl-2-chlornicotinat

CAS-Nr40134-18-7

Englisch Name:Methyl 2-chloronicotinate

CBNumberCB2317331

SummenformelC7H6ClNO2

Molgewicht171.58

MOL-Datei40134-18-7.mol

Synonyma

Methyl-2-chlornicotinat

Methyl-2-chlornicotinat physikalisch-chemischer Eigenschaften

Siedepunkt	150 °C/1 mmHg
Dichte	1.314 g/mL at 25 °C
Brechungsindex	n 20/D 1.537
Flammpunkt	110 °C
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
pka	-1.39±0.10(Predicted)
Aggregatzustand	Liquid
Farbe	Colorless
CAS Datenbank	40134-18-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36
S-Sätze:	26
WGK Germany	3
Hazard Note	Irritant/Keep Cold
HS Code	2933399990

Gefahreninformationscode (GHS)

Methyl 2-chloronicotinate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36:Reizt die Augen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Methyl 2-chloronicotinate is used in proteomics studies.
Verwenden
Methyl 2-chloronicotinate serves as a precursor for synthesizing the key intermediate of riociguat via cyclization with hydrazine hydrate, and reacts with morpholine to produce 2-morpholinonicotinic acid[6][7]. It acts as a reagent in the palladium-catalyzed N-arylation of amides during the synthesis of CXCR3 antagonists[8].
Synthese

67-56-1

2942-59-8

40134-18-7

(1) Preparation of methyl 2-chloronicotinate: 15.0 g (95.2 mmol) of 2-chloronicotinate was dissolved in 150 mL of dichloromethane and 8.37 mL (94.5 mmol) of oxalyl chloride was added slowly and dropwise. Subsequently, N,N-dimethylformamide was added dropwise to the mixture and the reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, 40.1 mL (286 mmol) of triethylamine and 37 mL (914 mmol) of methanol were added dropwise to the reaction mixture under ice-bath cooling conditions and stirring was continued for 30 minutes under ice-bath cooling. The reaction mixture was concentrated under reduced pressure and neutralized by adding aqueous sodium bicarbonate to the residue. The aqueous phase was extracted with ether, the organic phases were combined, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (eluent: ethyl acetate/hexane=1:4) to afford 13.9 g of the target product methyl 2-chloronicotinate as a pale yellow liquid in 86% yield.1H-NMR (CDCl3/TMS, δ ppm): 3.97 (3H, s), 7.33 (1H, dd), 8.17 (1H, dd), 8.53 (1H, dd ).
Einzelnachweise
[1] Patent: CN105061399, 2017, B. Location in patent: Paragraph 0010; 0029; 0030
[2] Patent: US2011/287937, 2011, A1. Location in patent: Page/Page column 72-73
[3] Patent: WO2007/71900, 2007, A1. Location in patent: Page/Page column 94
[4] Yakugaku Zasshi, 1952, vol. 72, p. 1336,1338
[5] Chem.Abstr., 1953, p. 4336
[6] Zhao, B., Lan, Z., Xu, S., & Xiong, Y. (2017). Synthesis of 2-Chloronicotinic Acid Derivatives. Advances in Computer Science Research. https://doi.org/10.2991/emcm-16.2017.119
[7] Bi, S., Diao, W., Zhou, T., Lin, K., & Zhou, W. (2023). Development of a new synthetic route of the key intermediate of riociguat. Synthetic Communications, 53(21), 1844–1853. https://doi.org/10.1080/00397911.2023.2252539
[8] Chan, J., Burke, B., Baucom, K. D., Hansen, K., Bio, M., Divirgilio, E., Faul, M., & Murry, J. (2011). Synthesis of a CXCR3 Antagonist. Synfacts, 2011(06), 0583–0583. https://doi.org/10.1055/s-0030-1259890

Methyl 2-chloronicotinate Upstream-Materialien And Downstream Produkte

Methyl-2-chlornicotinat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

40134-18-7, Methyl 2-chloronicotinate Verwandte Suche:

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