2,6-Dichlor-1H-purin

Bezeichnung:2,6-Dichlor-1H-purin

CAS-Nr5451-40-1

Englisch Name:2,6-Dichloropurine

CBNumberCB1720642

SummenformelC5H2Cl2N4

Molgewicht189

MOL-Datei5451-40-1.mol

Synonyma

2,6-Dichlor-1H-purin

2,6-Dichlor-1H-purin physikalisch-chemischer Eigenschaften

Schmelzpunkt	185-195 °C (dec.) (lit.)
Siedepunkt	310.62°C (rough estimate)
Dichte	1.7265 (rough estimate)
Brechungsindex	1.6300 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	soluble
Aggregatzustand	Crystalline Powder
pka	5.22±0.20(Predicted)
Farbe	White to yellow
Wasserlöslichkeit	soluble
BRN	9354
InChI	InChI=1S/C5H2Cl2N4/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H,8,9,10,11)
InChIKey	RMFWVOLULURGJI-UHFFFAOYSA-N
SMILES	N1C2C(=NC(Cl)=NC=2Cl)NC=1
CAS Datenbank	5451-40-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	36/37/38-22
S-Sätze:	22-24/25-37/39-26-36
RIDADR	UN2811
WGK Germany	3
HazardClass	IRRITANT
HS Code	29349990
Speicherklasse	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral

Gefahreninformationscode (GHS)

2,6-Dichloropurine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
2,6-Dichloropurine is an important pharmaceutical intermediate. It is widely used in the preparation of purine nucleosides and purine nucleotides^[1].
Chemische Eigenschaften
white to light yellow crystal powder
Verwenden
2,6-Dichloropurine is used in the synthesis of 2,6-diamino-substituted purine derivatives as potential cardiomyogenesis inducing agents.
Verwenden
Suzuki-Miyaura cross-coupling between halopurines and arylboronic acids in water-acetonitrile.1
Synthesis Reference(s)
Journal of the American Chemical Society, 80, p. 404, 1958 DOI: 10.1021/ja01535a040
Synthese
2,6-Dichloropurine is prepared in two main ways:
(1) By chlorination of the purine ring structure, e.g., chlorination of xanthine (2,6-dihydroxypurine) with pyrophosphoryl chloride at high temperatures in sealed tubes in the presence of a phase-transfer catalyst or with phosphorus oxychloride under reflux, and chlorination of 6-chloropurine, hypoxanthine, or their N-oxides with phosphorus oxychloride, and chlorination with chlorine gas at low temperatures. Chlorination of 2,6-dithiopurine.
(2) The purine ring is constructed using barbituric acid derivatives or 2,4-dichloro-5,6-diaminopyridine as starting materials. However, both methods are not very suitable for industrial production.
The industrial preparation of 2,6-dichloropurine involves the direct chlorination of xanthine with phosphorus trichloride and a weakly nucleophilic organic base (e.g., amidine, guanidine base, or proton sponge)^[1]. The reaction process is shown below:
läuterung methode
It can be recrystallised from 150 parts of boiling H2O and dried at 100o to constant weight. It is soluble in EtOAc. The HgCl2 salt separates from EtOH solution. UV: max 275nm ( 8.9K) at pH 1; and 280nm ( 8.5K) at pH 11 [Elion & Hitchings J Am Chem Soc 78 3508 1956, Schaeffer & Thomas J Am Chem Soc 80 3738 1958, Beaman & Robins J Appl Chem (London) 12 432 1962, Montgomery J Am Chem Soc 78 1928 1956]. [Beilstein 26 III/IV 1747.]
Einzelnachweise
[1] QI ZENG. Facile and Practical Synthesis of 2,6-Dichloropurine[J]. Organic Process Research & Development, 2004, 8 6: 962-963. DOI:10.1021/op049878r.

2,6-Dichloropurine Upstream-Materialien And Downstream Produkte

2,6-Dichlor-1H-purin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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