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511617

Sigma-Aldrich

6-Chloropurine

99%

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About This Item

Empirical Formula (Hill Notation):
C5H3ClN4
CAS Number:
Molecular Weight:
154.56
Beilstein/REAXYS Number:
5774
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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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.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Adenine ≥99%

Sigma-Aldrich

A8626

Adenine

Synthesis and anti-HIV activity of dihydroisoxazole 6-chloropurine and adenine.
Xiang Y, et al.
Bioorganic & Medicinal Chemistry Letters, 6(9), 1051-1054 (1996)
REACTIONS OF RIBONUCLEOTIDE DERIVATIVES OF PURINE ANALOGUES AT THE CATALYTIC SITE OF INOSINE 5'-PHOSPHATE DEHYDROGENASE.
A HAMPTON
The Journal of biological chemistry, 238, 3068-3074 (1963-09-01)
The Synthesis and Properties of 6-Chloropurine and Purine1.
Bendich A, et al.
Journal of the American Chemical Society, 76(23), 6073-6077 (1954)
Synthesis of Nucleosides and Related Compounds. Part XXV. The Alkylation of 6-Chloropurine with Alcohols by Mitsunobu Reaction.
Toyota A, et al.
Chemical & Pharmaceutical Bulletin, 40(4), 1039-1041 (1992)
6-Chloropurines and organostannanes in palladium catalyzed cross coupling reactions.
Gundersen LL.
Tetrahedron Letters, 35(19), 3155-3158 (1994)

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