26260

Sigma-Aldrich

6-Chloropurine

≥95.0% (HPLC)

Empirical Formula (Hill Notation):
C5H3ClN4
CAS Number:
Molecular Weight:
154.56
Beilstein/REAXYS Number:
5774
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

≥95.0% (HPLC)

color

yellow-orange

mp

>300 °C (dec.) (lit.)

solubility

DMF: soluble 0.2 g/10 mL, clear, colorless to light greenish-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
  • 6-succinoaminopurine

Quantity

λmax. 264 nm, mol. absorption 8700 (0.1 M HCl)

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
Lak Shin Jeong et al.
Nucleosides, nucleotides & nucleic acids, 26(6-7), 725-728 (2007-12-11)
Synthesis of 2' -beta-hydroxymethyl nucleosides 3-6 was accomplished, using stereoselective hydroxymethylation as a key step. Adenine nucleoside 3 showed potent anti-HCV activity, implying that 2' -beta-hydroxymethyl group has the appropriate electronic properties interfering with HCV polymerase.
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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