511617

6-Chlorpurin

99%

• Empirische Formel (Hill-System): C₅H₃ClN₄
• CAS-Nummer: 87-42-3
• Molekulargewicht: 154.56
• Beilstein: 5774
• EG-Nummer: 201-745-6
• MDL-Nummer: MFCD00075825
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24873552
• NACRES: NA.22

Eigenschaften

• Assay: 99%
• mp (Schmelzpunkt): >300 °C (dec.) (lit.)
• Funktionelle Gruppe: chloro
• SMILES String: Clc1ncnc2[nH]cnc12
• InChI: 1S/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10)
• InChIKey: ZKBQDFAWXLTYKS-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

6-Chloropurine (6-CIPH), a 6-substituted purine derivative, is an antileukemic drug.[1] It can be prepared by the chlorination of hypoxanthine with phosphorus oxychloride in the presence of dimethylaniline.[2] The NMR-based conformational analysis of the products formed during the reaction of 6-CIPH with 3,4-di-O-acetyl-D-xylal and 3,4-di-O-acetyl-L-arabinal have been reported.[3] 6-CIPH can undergo palladium-catalyzed cross coupling with organostannanes at 6-position to form the corresponding arylated or alkylated products.[4]

Anwendung

6-Chloropurine may be used:

• To prepare purine via catalytic dehydrogenation.[2]
• To prepare 9-alkylated adenines via Mitsunobu reaction with various alcohols.[5]
• As a starting material to synthesize dihydroisoxazole 6-chloropurine.[6]

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H302
• Gefahreneinstufungen: Acute Tox. 4 Oral
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves