2,4-Dichloro-5-trifluoromethylpyrimidine

Bezeichnung:2,4-Dichloro-5-trifluoromethylpyrimidine

CAS-Nr3932-97-6

Englisch Name:2,4-Dichloro-5-trifluoromethylpyrimidine

CBNumberCB4237271

SummenformelC5HCl2F3N2

Molgewicht216.98

MOL-Datei3932-97-6.mol

2,4-Dichloro-5-trifluoromethylpyrimidine physikalisch-chemischer Eigenschaften

Siedepunkt	49℃/32mm
Dichte	1.609 g/mL at 25 °C
Brechungsindex	1.4749
Flammpunkt	200 ºF
storage temp.	2-8°C
Löslichkeit	Chloroform, Methanol
pka	-4.89±0.29(Predicted)
Aggregatzustand	Clear Colorless to Pale Yellow Liquid
Aussehen	Colorless to light yellow Liquid
InChI	InChI=1S/C5HCl2F3N2/c6-3-2(5(8,9)10)1-11-4(7)12-3/h1H
InChIKey	VABVSVZAESMOCH-UHFFFAOYSA-N
SMILES	C1(Cl)=NC=C(C(F)(F)F)C(Cl)=N1
CAS Datenbank	3932-97-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,C,T
R-Sätze:	36/37/38-36-25
S-Sätze:	26-36/37/39-45
RIDADR	UN 2810
WGK Germany	3
Hazard Note	Irritant
HazardClass	CORROSIVE
HazardClass	8
PackingGroup	Ⅲ
HS Code	29335990
Speicherklasse	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 2 Oral Eye Irrit. 2

Gefahreninformationscode (GHS)

2,4-Dichloro-5-trifluoromethylpyrimidine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R36:Reizt die Augen.
R25:Giftig beim Verschlucken.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Chemische Eigenschaften
White liquid or solid
Verwenden
2,4-Dichloro-5-trifluoromethylpyrimidine is a reactant in the preparation of pyrimidine derivatives as inhibitors of gene ALK protein Kinase phosphorylating kinase and as cell proliferation inhibitors.
Synthese

54-20-6

3932-97-6

The general procedure for the synthesis of 2,4-dichloro-5-trifluoromethylpyrimidine from 5-trifluoromethyluracil is as follows: 1. 5-Trifluoromethyluracil (250 g, 1.39 mol) and phosphorus trichloride (655 mL, 6.94 mol, 5 eq.) were added to a 3L four-neck flask fitted with an overhead stirrer, a reflux condenser, a dosing funnel, and an internal thermocouple under nitrogen protection. 2. concentrated phosphoric acid (85 wt%, 9.5 mL, 0.1 eq.) was added to the reaction mixture in a single addition and a moderate exothermic phenomenon was observed. 3. Diisopropylethylamine (245 mL, 1.39 mol, 1 eq.) was added slowly dropwise over 15 minutes, controlling the dropwise acceleration so that the internal temperature of the reaction reached 85-90 °C at the end of the dropwise acceleration. Upon completion of the dropwise addition, the reaction mixture changed to a homogeneous light orange solution. 4. The reaction mixture was heated to 100 °C and held for 20 hours until HPLC analysis showed complete consumption of the feedstock. 5. The heating was stopped and the reaction mixture was cooled to 40 °C and then slowly added dropwise to a pre-cooled mixture of 3N HCl (5 L, 10 eq.) and ether (2 L), maintaining the temperature of the quench tank. 6. Separate the organic and aqueous layers, the aqueous layer being extracted once with ether (1 L). The organic layers were combined and washed with water until the washings were neutral (5 times, 1.5 L each), then dried over MgSO4 and concentrated to give 288 g (95% yield) of a light yellow-orange oily product with 96% HPLC purity. 7. The product can be extracted under reduced pressure from aqueous solution of 1.5 L of ether (2 L). 7. The product was further purified by reduced pressure distillation (boiling point 109 °C, 79 mmHg).
Einzelnachweise
[1] Patent: US2005/256145, 2005, A1. Location in patent: Page/Page column 43
[2] Patent: US2005/256125, 2005, A1. Location in patent: Page/Page column 29
[3] Patent: US2005/256144, 2005, A1. Location in patent: Page/Page column 20
[4] Patent: US2014/135497, 2014, A1. Location in patent: Paragraph 0060; 0061; 0062; 0063; 0064
[5] Patent: WO2014/76085, 2014, A1. Location in patent: Page/Page column 9-10

2,4-Dichloro-5-trifluoromethylpyrimidine Upstream-Materialien And Downstream Produkte

2,4-Dichloro-5-trifluoromethylpyrimidine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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