2,4-Dichlorpyrimidin

Bezeichnung:2,4-Dichlorpyrimidin

CAS-Nr3934-20-1

Englisch Name:2,4-Dichloropyrimidine

CBNumberCB6202781

SummenformelC4H2Cl2N2

Molgewicht148.98

MOL-Datei3934-20-1.mol

Synonyma

2,4-Dichlorpyrimidin

2,4-Dichlorpyrimidin physikalisch-chemischer Eigenschaften

Schmelzpunkt	57-61 °C (lit.)
Siedepunkt	101 °C/23 mmHg (lit.)
Dichte	1.6445 (rough estimate)
Brechungsindex	1.6300 (estimate)
Flammpunkt	101°C/23mm
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
pka	-2.84±0.20(Predicted)
Aggregatzustand	Powder, Crystals and/or Chunks
Farbe	White to yellow to beige or grayish
Wasserlöslichkeit	Soluble in water (partly), methanol, chloroform, and ethyl acetate.
Sensitive	Moisture Sensitive
BRN	110911
InChIKey	BTTNYQZNBZNDOR-UHFFFAOYSA-N
CAS Datenbank	3934-20-1(CAS DataBase Reference)
NIST chemische Informationen	Pyrimidine, 2,4-dichloro-(3934-20-1)
EPA chemische Informationen	Pyrimidine, 2,4-dichloro- (3934-20-1)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-28A
RIDADR	1759
WGK Germany	3
TSCA	Yes
HazardClass	8
PackingGroup	III
HS Code	29335990

Gefahreninformationscode (GHS)

2,4-Dichloropyrimidine 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:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
White Solid
Verwenden
2,4-Dichloropyrimidine was used in the synthesis of medicinally important 4-aryl-5-pyrimidinylimidazoles.
synthetische
Obtained by chlorination of uracil. Add uracil, phosphorus trichloride, and xylene amine into the reaction pot, heat to 130 ℃, reflux for about 45min, slightly cool, put in crushed ice, that is, the precipitation of purple solid, filtered while hot and not dissolved, washed with ice water, vacuum drying, a kind of purple crude, decolorized with petroleum ether (boiling range of 60-90 ℃), recrystallized, obtained 2,4-dichloropyrimidine.
Allgemeine Beschreibung
2,4-Dichloropyrimidine is a human skin sensitizer. It undergoes effective one-pot, regioselective double Suzuki coupling reaction to yield diarylated pyrimidines.
Reaktivität anzeigen
The reaction of N-substituted cyclic amines with 2,4-dichloroquinazoline and 2,4-dichloro-5-methyl-pyrimidine afforded 2-amino-4-chloroquinazolines and 2-amino-4-chloro-5-methylpyrimidines, respectively—the reaction of these amines with 2,4-dichloropyrimidine 3a afforded not only 2-amino-4-chloropyrimidines but also the isomeric 4-amino-2-chloropyrimidines. An effective one-pot, regioselective double Suzuki coupling of 2,4-dichloropyrimidine has been developed. This method enables the quick and efficient synthesis of diarylated pyrimidines. The choice of solvent proved critical to the success of this reaction sequence, with alcoholic solvent mixtures affording much greater reactivity and correspondingly lower temperatures than polar aprotic solvents[5-6].
Einzelnachweise
[1] DR. AGNES FIZIA. Cyclopalladation in the Periphery of a NHC Ligand as the Crucial Step in the Synthesis of Highly Active Suzuki–Miyaura Cross-Coupling Catalysts[J]. Chemistry - A European Journal, 2017. DOI:10.1002/chem.201702877.
[2] FABIAN BRUENING Lucie E L. Highly Regioselective Organocatalytic SNAr Amination of 2,4-Dichloropyrimidine and Related Heteroaryl Chlorides[J]. European Journal of Organic Chemistry, 2017. DOI:10.1002/ejoc.201700459.
[3] ANDERSONSAMANTHA C HandyScott T. One-pot Double Suzuki Couplings of Dichloropyrimidines.[J]. Synthesis-Stuttgart, 2010. DOI:10.1055/s-0030-1258150.
[4] TOMá? KUBELKA. Synthesis of 2,4-Disubstituted Pyrimidin-5-yl C-2′-Deoxyribonucleosides by Sequential Regioselective Reactions of 2,4-Dichloropyrimidine Nucleosides[J]. European Journal of Organic Chemistry, 2010. DOI:10.1002/ejoc.201000164.
[5] Kenji Yoshida, M. Taguchi. “Reaction of N-substituted cyclic amines with 2,4-dichloroquinazoline, 2,4-dichloropyrimidine, and its 5-methyl derivative.” Journal of The Chemical Society-perkin Transactions 1 102 1 (1992): 919–922.
[6] Samantha C Anderson, Scott T Handy. “One-pot Double Suzuki Couplings of Dichloropyrimidines.” Synthesis-Stuttgart 2010 16 (2010): 2721–2724.

2,4-Dichloropyrimidine Upstream-Materialien And Downstream Produkte

2,4-Dichlorpyrimidin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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