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342300

Sigma-Aldrich

2-Amino-6-chloropurine

97%

Sinonimo/i:

6-Chloro-2-purinamine, 6-Chloroguanine

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About This Item

Formula empirica (notazione di Hill):
C5H4ClN5
Numero CAS:
10310-21-1
Peso molecolare:
169.57
Beilstein:
9626
Numero CE:
233-686-7
Numero MDL:
MFCD00075252
Codice UNSPSC:
12352100
ID PubChem:
24861051
NACRES:
NA.22

Saggio

97%

Punto di fusione

>300 °C (lit.)

Stringa SMILE

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)
RYYIULNRIVUMTQ-UHFFFAOYSA-N

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Categorie correlate

Descrizione generale

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.

Applicazioni

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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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)
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
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
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.
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
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