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6-Chloroguanine

Basic information Description Safety Supplier Related

6-Chloroguanine Basic information

Product Name:
6-Chloroguanine
Synonyms:
  • Clofarabine Impurity 3
  • AURORA KA-689
  • 2-amino-6-chloro-purin
  • 2-AMINO-6-CHLOROPURINE
  • 6-CHLORO-2-AMINOPURINE
  • 6-CHLORO-9H-PURIN-2-YLAMINE
  • 6-CHLOROGUANINE
  • 6-Chloro-7H-purin-2-ylamine
CAS:
10310-21-1
MF:
C5H4ClN5
MW:
169.57
EINECS:
233-686-7
Product Categories:
  • Biochemistry
  • Nucleobases and their analogs
  • Nucleosides, Nucleotides & Related Reagents
  • Nucleic acids
  • Bases & Related Reagents
  • Nucleotides
  • FINE Chemical & INTERMEDIATES
  • Starting Raw Materials & Intermediates
  • Miscellaneous Biochemicals
  • Amines
  • Purine
  • Nucleotides and Nucleosides
  • Purines
  • Fused Ring Systems
  • Aromatics
  • Heterocycles
  • Building Blocks
  • Chemical Synthesis
  • Halogenated Heterocycles
  • Heterocyclic Building Blocks
Mol File:
10310-21-1.mol
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6-Chloroguanine Chemical Properties

Melting point:
>300 °C (lit.)
Boiling point:
279.76°C (rough estimate)
Density 
1.4937 (rough estimate)
refractive index 
1.6110 (estimate)
storage temp. 
2-8°C
solubility 
Solubility in 1mol/L NaOH
form 
Powder
pka
6.65±0.20(Predicted)
color 
White to yellow
Water Solubility 
1.7 g/L (20 ºC)
BRN 
9626
InChI
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
SMILES
N1C2C(=NC(N)=NC=2Cl)NC=1
CAS DataBase Reference
10310-21-1(CAS DataBase Reference)
EPA Substance Registry System
6-Chloro-2-aminopurine (10310-21-1)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
RTECS 
UO7502000
10
Hazard Note 
Irritant/Keep Cold
HazardClass 
IRRITANT, KEEP COLD
HS Code 
29339900

MSDS

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6-Chloroguanine Usage And Synthesis

Description

6-Chloroguanine, also be known as 2-Amino-6-chloropurine may be used in the enzymatic synthesis of 2′-deoxyguanosine, 9-alkyl purines (R)and (S)-N(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. It is also useful during the synthesis of guanine.

Description

2-Amino-6-chloropurine is a precursor in the synthesis of nucleoside analogs with antiviral activity against Epstein-Barr virus (EBV) and human herpes virus 6 (HHV-6).

Chemical Properties

white to light yellow crystal powder

Uses

2-Amino-6-chloropurine finds its uses in the enzymatic synthesis of 2?-deoxyguanosine, 9-alkyl purines and (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases.

Uses

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

Definition

ChEBI: 6-chloroguanine is an organochlorine compound that is 7H-purin-2-amine substituted by a chloro group at position 6. It is a member of 2-aminopurines and an organochlorine compound.

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.

Synthesis

Preparation of 2-amino-6-chloropurine:
Diacetyl guanine (8.0g, 0.034 moles), triethyimethylammonium chloride (15.45g, 0.102 moles), and triethylamine (4.74 mis, 0.034 moles) were heated together with stirring in acetonitrile (70mls) to 50°C. Phosphorus oxychioride (6.34 mis, 0.068 moles) was then added and stirring continued for 4 hours. The reaction mixture was cooled and then added to aqueous sodium hydroxide solution (20g in 300mls water). The reaction mixture was heated to 80°C for 2 hours and then the volume made up to 300 mis with water. The mixture was cooled to 25°C and the pH adjuster to 7 using 10% hydrochloric acid. The resulting slurry was stirred for fifteen minutes and the product filtered off and washed with water 30 mis and then dried at 80°C under vacuum to give a cream/off white coloured product, 2-amino-6-chioropurine 4.69 g (74.6% yield).

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