511617
6-Chloropurine
99%
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About This Item
Empirical Formula (Hill Notation):
C5H3ClN4
CAS Number:
Molecular Weight:
154.56
NACRES:
NA.22
UNSPSC Code:
12352100
PubChem Substance ID:
EC Number:
201-745-6
Beilstein/REAXYS Number:
5774
MDL number:
Assay:
99%
Quality Segment
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
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.
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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