5-Bromo-2-chloropyrimidine

Bezeichnung:5-Bromo-2-chloropyrimidine

CAS-Nr32779-36-5

Englisch Name:5-Bromo-2-chloropyrimidine

CBNumberCB4748175

SummenformelC4H2BrClN2

Molgewicht193.43

MOL-Datei32779-36-5.mol

5-Bromo-2-chloropyrimidine physikalisch-chemischer Eigenschaften

Schmelzpunkt	73-79 °C (lit.)
Siedepunkt	95°C 15mm
Dichte	1.859±0.06 g/cm3(Predicted)
Flammpunkt	95°C/15mm
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	soluble in Methanol
pka	-2.84±0.22(Predicted)
Aggregatzustand	Crystalline Powder
Farbe	Off-white to beige
Wasserlöslichkeit	insoluble
BRN	507955
Stabilität	Hygroscopic
InChI	InChI=1S/C4H2BrClN2/c5-3-1-7-4(6)8-2-3/h1-2H
InChIKey	XPGIBDJXEVAVTO-UHFFFAOYSA-N
SMILES	C1(Cl)=NC=C(Br)C=N1
CAS Datenbank	32779-36-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36/39-37/39-36
RIDADR	UN 3335
WGK Germany	3
HazardClass	IRRITANT
HS Code	29335990

Gefahreninformationscode (GHS)

5-Bromo-2-chloropyrimidine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
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.
S36/39:Bei der Arbeit geeignete Schutzkleidung und Schutzbrille/Gesichtsschutz tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
5-Bromo-2-chloropyrimidine is a halogenated pyrimidine analogue containing chloro and bromo substituents at positions 2 and 5 of the benzene ring structure. The compound is used as a pharmaceutical intermediate in the preparation of macitentan, an endothelin receptor antagonist drug for the treatment of pulmonary hypertension.
Chemische Eigenschaften
Off-white to beige crystalline powder
Verwenden
5-Bromo-2-chloropyrimidine is applied as a pharmaceutical intermediate, in the synthesis of pharmaceutical goods such as inhibitors. It is also employed in the cross-coupling reactions of indium organometallics with 2,5-dihalopyrimidines.
Verwenden
5-Bromo-2-chloropyrimidine is a intermediate in the synthesis of pharmaceutical goods such as inhibitors.
synthetische
Under nitrogen protection, 35 g (0.2 mol) of 2-hydroxy-5-bromopyrimidine, 61.3 g (0.4 mol) of phosphorus oxychloride, and 200 mL of toluene were added into the reaction flask. At 35 ℃, triethylamine 40.5g was added and then heated up at 80-85 ℃. Stir the reaction for 6 hours, sampling HPLC to detect the raw material (less than 2%), and lower the temperature. After concentrating the mixture under reduced pressure to remove most of the toluene and Phosphorus oxychloride, put the reaction solution into 10°C water, and adjust pH=8-9 with 20% sodium carbonate aqueous solution. Finally, 5-Bromo-2-chloropyrimidine was obtained after purification.
Reaktivität anzeigen
5-Bromo-2-chloropyrimidine, a 2,5-dihalopyrimidine, is a useful organic electrophiles. It could react with tri(3-indolyl)indium reagent through cross-coupling reaction. Other aryl- and heteroarylindium reagents, such as thiophenyl-, pyridyl-, naphthyl-, and alkynylindium reagents, also reacted with 5-bromo-2- chloropyrimidine to afford the corresponding 2-chloro-5-substituted pyrimidines[1].
Einzelnachweise
[1] Mosquera A, et al. Cross-Coupling Reactions of Indium Organometallics with 2,5-Dihalopyrimidines: Synthesis of Hyrtinadine A?. Organic Letters, 2008; 10: 3745–3748.

5-Bromo-2-chloropyrimidine Upstream-Materialien And Downstream Produkte

5-Bromo-2-chloropyrimidine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

32779-36-5, 5-Bromo-2-chloropyrimidine Verwandte Suche:

Send Inquriy