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161179

Sigma-Aldrich

6-Chloropurine

≥99%

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$70.90

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

$70.90


Available to ship onApril 24, 2025Details


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Quality Level

assay

≥99%

form

powder

mp

>300 °C (dec.) (lit.)

solubility

DMF: soluble 5%, clear, colorless to yellow

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

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General description

The acid-catalyzed reaction of 6-chloropurine with 3,4-di-O-acetyl-D-xylal has been investigated.[1]

application

6-Chloropurine has been used in the preparation of 9-alkylpurines via alkylation with various substituted alkyl halides in DMSO.[2] It was also used in the preparation of 6-succinoaminopurine.[3]

pictograms

Exclamation mark

signalword

Warning

hcodes

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


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Synthesis of 6-succinoaminopurine.
C E CARTER
The Journal of biological chemistry, 223(1), 139-146 (1956-11-01)
Heterocyclic N-glycosides-V: Synthesis of unsaturated N-glycosides from 6-chloropurine and derivatives of d-xylal and l-arabinal. A conformational NMR study.
Fuertes M, et al.
Tetrahedron, 26(20), 4823-4837 (1970)
Synthesis of Potential Anticancer Agents. XXVI. The Alkylation of 6-Chloropurine2.
Montgomery JA and Temple Jr C.
Journal of the American Chemical Society, 83(3), 630-635 (1961)
Masahiro Ikejiri et al.
Nucleic acids symposium series (2004), (51)(51), 439-440 (2007-11-22)
A series of nucleoside analogues whose 5'-hydroxyl groups are masked by various protective groups were synthesized and evaluated to develop novel anti- hepatitis C virus (HCV) agents. Among the several analogues that showed anti-HCV potency, a 5'-O-benzoyl-2'-deoxyribonucleoside analogue exhibited high
V Gurvich et al.
Nucleosides & nucleotides, 18(10), 2327-2333 (2000-01-05)
Tetrabutylammonium triphenydifluorosilicate (TBAT) has been found to be a useful reagent for the conversion of 6-chloropurine nucleosides to 6-fluoropurine derivatives. The 6-chloropurine nucleosides were reacted with trimethylamine to form quaternary trimethylammonium salts which were treated in situ with TBAT in

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