511617

6-Chloropurine

99%

• Empirical Formula (Hill Notation): C₅H₃ClN₄
• CAS Number: 87-42-3
• Molecular Weight: 154.56
• Beilstein/REAXYS Number: 5774
• EC Number: 201-745-6
• MDL number: MFCD00075825
• UNSPSC Code: 12352100
• PubChem Substance ID: 24873552
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 99%
• mp: >300 °C (dec.) (lit.)
• functional group: 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)
• InChI key: ZKBQDFAWXLTYKS-UHFFFAOYSA-N

Description

General description

6-Chloropurine (6-CIPH), a 6-substituted purine derivative, is an antileukemic drug. It can be prepared by the chlorination of hypoxanthine with phosphorus oxychloride in the presence of dimethylaniline. 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. 6-CIPH can undergo palladium-catalyzed cross coupling with organostannanes at 6-position to form the corresponding arylated or alkylated products.

Application

6-Chloropurine may be used:

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves