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MilliporeSigma

342300

2-Amino-6-chloropurine

97%

Synonym(s):

6-Chloro-2-purinamine, 6-Chloroguanine

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About This Item

Empirical Formula (Hill Notation):
C5H4ClN5
CAS Number:
10310-21-1
Molecular Weight:
169.57
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24861051
EC Number:
233-686-7
Beilstein/REAXYS Number:
9626
MDL number:
MFCD00075252

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Product Name

2-Amino-6-chloropurine, 97%

InChI key

RYYIULNRIVUMTQ-UHFFFAOYSA-N

InChI

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

SMILES string

Nc1nc(Cl)c2nc[nH]c2n1

assay

97%

mp

>300 °C (lit.)

functional group

chloro

Quality Level

100

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This Item
1269141109789PHR2861
2-Amino-6-chloropurine 97%

Sigma-Aldrich

342300

2-Amino-6-chloropurine

Famciclovir Related Compound F United States Pharmacopeia (USP) Reference Standard

USP

1269141

Famciclovir Related Compound F

2-Amino-6-chloropurine ≥99%

Sigma-Aldrich

109789

2-Amino-6-chloropurine

Famciclovir Related Compound F pharmaceutical secondary standard, certified reference material

Supelco

PHR2861

Famciclovir Related Compound F

assay

97%

assay

-

assay

≥99%

assay

-

Quality Level

100

Quality Level

-

Quality Level

200

Quality Level

300

mp

>300 °C (lit.)

mp

>300 °C (lit.)

mp

>300 °C (lit.)

mp

>300 °C (lit.)

functional group

chloro

functional group

-

functional group

chloro

functional group

-

Application

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

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.[4]

Storage Class

11 - Combustible Solids

wgk

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
MKCZ3835
MKCX7730
MKBN2552V
S41873V
S41873

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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)
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.
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
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
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