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511617 Sigma-Aldrich

6-Chloropurine

99%

  • CAS Number 87-42-3

  • Empirical Formula (Hill Notation) C5H3ClN4

  • Molecular Weight 154.56

  •  Beilstein/REAXYS Number 5774

  •  EC Number 201-745-6

  •  MDL number MFCD00075825

  •  PubChem Substance ID 24873552

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Properties

Related Categories Building Blocks, Chemical Synthesis, Halogenated Heterocycles, Heterocyclic Building Blocks, Purines More...
Quality Level   100
assay   99%
mp   >300 °C (dec.) (lit.)
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.

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
UO7520000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles

Related Content

Indoles, Purines, and Their Isosteres

Substituted indoles and purines have frequently been referred to as “privileged structures” since they are capable of binding to multiple receptors with high affinity, and thus have applications acro...
Keywords: Building blocks, Medicinal chemistry

Peer-Reviewed Papers
15

References

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