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342300

Sigma-Aldrich

2-Amino-6-chloropurine

97%

Sinónimos:

6-Chloro-2-purinamine, 6-Chloroguanine

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About This Item

Fórmula empírica (notación de Hill):
C5H4ClN5
Número de CAS:
10310-21-1
Peso molecular:
169.57
Beilstein/REAXYS Number:
9626
EC Number:
233-686-7
MDL number:
MFCD00075252
UNSPSC Code:
12352100
PubChem Substance ID:
24861051
NACRES:
NA.22

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

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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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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.
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
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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