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161179

Sigma-Aldrich

6-Chloropurine

≥99%

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About This Item

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

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.

Application

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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)
Takayuki Ando et al.
Carbohydrate research, 342(17), 2641-2648 (2007-09-14)
1',2'-cis-beta-Glycosyladenine nucleosides, such as beta-altroside, beta-mannoside, and beta-idoside, were efficiently synthesized from the corresponding 1',2'-trans-beta-6-chloropurine derivatives, beta-glucoside, and beta-galactoside. Nucleophilic substitution of the O-trifluoromethanesulfonyl groups at the C-2' and/or 3' was carried out using tetrabutylammonium acetate or cesium acetate under
Michal Sála et al.
Bioorganic & medicinal chemistry letters, 22(5), 1963-1968 (2012-02-09)
We report on the synthesis and the study of the structure-activity relationship of novel 9-norbornyl-6-chloropurine derivatives, which exert selective antiviral activity on the replication of Coxsackievirus B3. In particular, the synthetic approaches towards norbornyl derivatives bearing diverse side chains were

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