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Sigma-Aldrich

2-Amino-6-chloropurine

97%

Synonym(s):

6-Chloro-2-purinamine, 6-Chloroguanine

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1 G
$45.60
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About This Item

Empirical Formula (Hill Notation):
C5H4ClN5
CAS Number:
10310-21-1
Molecular Weight:
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%

$45.60

Only 5 left in stockDetails
Request a Bulk Order

Quality Level

100

assay

97%

mp

>300 °C (lit.)

functional group

chloro

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.[1] Tautomeric purine forms of 2-amino-6-chloropurine were investigated by vibrational spectroscopy and quantum chemical method.[2]

Application

2-Amino-6-chloropurine may be used:
  • in the enzymatic synthesis of 2′-deoxyguanosine[1]
  • in the synthesis of 9-alkyl purines[3]
  • in the synthesis of (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases[4]

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)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBN2552V
S41873V
S41873
02623PD
08327MD

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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
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)
S Phadtare et al.
Journal of medicinal chemistry, 30(2), 437-440 (1987-02-01)
Alkylation of adenine (5a) or 2-amino-6-chloropurine (5b) with excess trans-1,4-dichloro-2-butene (4), effected by K2CO3 in dimethyl sulfoxide or tetra-n-butylammonium fluoride in tetrahydrofuran, led in 90-95% regioselectivity to 9-alkylpurines 6a and 6b. The title compounds 2a and 2b were obtained by
J T Kusmierek et al.
Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 41(10), 701-707 (1987-11-01)
D.c. polarography of 2-amino-6-chloropurine in aqueous medium over a broad pH range revealed two diffusion waves, the first of which corresponds to reduction of the C(6)-Cl bond, leading to formation of 2-aminopurine in high yield. Condensation of the sodium salt
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