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109789

Sigma-Aldrich

2-Amino-6-chlorpurin

≥99%

Synonym(e):

6-Chlor-2-purinamin, 6-Chlor-guanin

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About This Item

Empirische Formel (Hill-System):
C5H4ClN5
CAS-Nummer:
10310-21-1
Molekulargewicht:
169.57
Beilstein:
9626
EG-Nummer:
233-686-7
MDL-Nummer:
MFCD00075252
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24846937
NACRES:
NA.22

Assay

≥99%

mp (Schmelzpunkt)

>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)

InChIKey

RYYIULNRIVUMTQ-UHFFFAOYSA-N

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Anwendung

2-Amino-6-chloropurine has been used in the enzymatic production of DAPdR and 2-amino-6-chloropurine-2,-deoxyriboside (ACPdR).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

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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
L L Bennett et al.
Biochemical pharmacology, 33(2), 261-271 (1984-01-15)
2-Amino-6-chloro-1-deazapurine is of interest as a purine analog with demonstrated in vivo activity against mouse leukemia L1210. That the active form of this agent is a nucleotide and that the nucleotide is formed by the action of hypoxanthine (guanine) phosphoribosyltransferase
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.
Lak Shin Jeong et al.
Nucleosides, nucleotides & nucleic acids, 26(6-7), 721-724 (2007-12-11)
Novel apio carbocyclic nucleosides 18-21 were asymmetrically synthesized as potential antiviral and antitumor agent, starting from D-ribose employing aldol reaction, RCM reaction and Mitsunobu reaction as key reactions.
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
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