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161179

Sigma-Aldrich

6-Chloropurine

≥99%

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About This Item

Empirical Formula (Hill Notation):
C5H3ClN4
CAS Number:
87-42-3
Molecular Weight:
154.56
Beilstein:
5774
EC Number:
201-745-6
MDL number:
MFCD00075825
UNSPSC Code:
12352100
PubChem Substance ID:
24849911
NACRES:
NA.22

Assay

≥99%

form

powder

mp

>300 °C (dec.) (lit.)

solubility

DMF: soluble 5%, clear, colorless to yellow

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
GHS07

Signal Word

Warning

Hazard Statements

H302

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

161179-1G:
161179-5G:
161179-VAR:
161179-BULK:

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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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)
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)
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
Dong-Chao Wang et al.
Organic & biomolecular chemistry, 9(22), 7663-7666 (2011-09-22)
An efficient method for the synthesis of 6-alkyl or 6-aryl purines (nucleosides) was developed via nickel-catalyzed Negishi cross-couplings of 6-chloropurines and organozinc halides. The ligand-free process gave good to excellent isolated yields at room temperature.
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