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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

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)
Shi Bai et al.
Magnetic resonance in chemistry : MRC, 48(1), 61-67 (2009-11-26)
The (15)N and (13)C chemical shifts of 6-(fluoro, chloro, bromo, and iodo)purine 2'-deoxynucleoside derivatives in deuterated chloroform were measured. The (15)N chemical shifts were determined by the (1)H-(15)N HMBC method, and complete (15)N chemical-shift assignments were made with the aid
Silvia Zimdars et al.
Organic letters, 13(4), 792-795 (2011-01-21)
Starting from an appropriate 6-chloro-2-TMS-purine derivative, a regioselective functionalization of the purine scaffold was achieved successively at positions 8, 6, and 2 via zinc and magnesium intermediates which were generated either by a direct zincation with TMPZnCl·LiCl or by an
Vincent Roy et al.
Future medicinal chemistry, 2(2), 177-192 (2011-03-24)
In recent decades, nucleosides analogs have been the cornerstone in the treatment of various diseases, such as AIDS, herpes and hepatitis. More than 40 modified nucleosides are officially approved by the US FDA and represent the major compound class for
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