Skip to Content
Merck
CN
All Photos(1)

Documents

342300

Sigma-Aldrich

2-Amino-6-chloropurine

97%

Sign Into View Organizational & Contract Pricing

Synonym(s):
6-Chloro-2-purinamine, 6-Chloroguanine
Empirical Formula (Hill Notation):
C5H4ClN5
CAS Number:
Molecular Weight:
169.57
Beilstein:
9626
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

mp

>300 °C (lit.)

SMILES string

Nc1nc(Cl)c2nc[nH]c2n1

InChI

1S/C5H4ClN5/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H3,7,8,9,10,11)

InChI key

RYYIULNRIVUMTQ-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

2-Amino-6-chloropurine is a 6-substituted purine. Tautomeric purine forms of 2-amino-6-chloropurine were investigated by vibrational spectroscopy and quantum chemical method.

Application

2-Amino-6-chloropurine may be used:
  • in the enzymatic synthesis of 2′-deoxyguanosine
  • in the synthesis of 9-alkyl purines
  • in the synthesis of (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis of enantiomeric N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. II. The synthon approach.
Holy A, et al.
Collection of Czechoslovak Chemical Communications, 60(8), 1309-1409 (1995)
Jan Novák et al.
Organic letters, 5(5), 637-639 (2003-02-28)
Protecting the hydroxyl group in both 2-bromo-2-phenylethanol and 2-bromo-1-phenylethanol enhanced the alkylation of 2-amino-6-chloropurine to give corresponding 7- and 9-alkylated products. Subsequent hydrolysis and deprotection led to 7- and 9-hydroxy(phenyl)ethylguanines. 7-Hydroxy(phenyl)ethylguanines are major guanine adducts formed by interaction of styrene
V Balachandran et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 96, 340-351 (2012-06-19)
Two purine tautomers of 2-amino-6-chloropurine (ACP), in labeled as N(9)H(10) and N(7)H(10), were investigated by vibrational spectroscopy and quantum chemical method. The FT-IR and FT-Raman spectra of ACP have been recorded in the regions 4000-400 cm(-1) and 3500-100 cm(-1), respectively.
K Kim et al.
Combinatorial chemistry & high throughput screening, 3(2), 125-129 (2000-05-02)
A new application of solid-supported reagents was developed to separate the alkylated N7/N9 regioisomers derived from commercially available 2-amino-6-chloropurine. Simple filtration through an alumina/H+ pad or scavenging by AG/Dowex-50W-X8 resin provides diverse N9 regioisomers selectively in moderate yields with high
Kiyoshi Okuyama et al.
Bioscience, biotechnology, and biochemistry, 67(5), 989-995 (2003-07-02)
Nucleoside deoxyribosyltransferase-II (NdRT-II) of Lactobacillus helveticus, which catalyzes the transfer of a glycosyl residue from a donor deoxyribonucleoside to an acceptor base, has a broad specificity for the acceptor bases. Six-substituted purines were found to be substrates as acceptor bases

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service