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)

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

F 

10

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29339900

MSDS

• Language:English Provider:6-Chloroguanine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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).

6-Chloroguanine(10310-21-1)Related Product Information

• 2-Amino-4-chloro-6-methoxypyrimidine
• 4,6-Dimethoxy-2-methylthiopyrimidine
• 2-Amino-4,6-dimethylpyrimidine
• 6-Chloroguanine
• 6-CHLOROGUANINE RIBOSIDE,6-Chloroguanine nucleoside,(-)-2-Amino-6-chloropurine riboside, 6-Chloroguanine riboside
• 9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine
• 8-CHLOROGUANINE,CHLOROGUANINE
• 2-Aminopurine
• Purine
• 6-Chloropurine
• 6-Methoxypurine
• 2-ACETAMIDO-6-CHLOROPURINE
• 2-ACETAMIDO-6-CHLORO-9-(2',3',5'-TRI-O-ACETYL-BETA-D-RIBOFURANOSYL)PURINE
• 2-AMINO-6-CHLORO-9-(3,5-DI-O-(P-TOLUOYL)-BETA-D-2-DEOXYRIBOFURNANOSYL)PURINE
• 2-AMINO-6-CHLORO-9H-PURINE-9-ACETIC ACID
• 9-(4-ACETOXY-3-ACETOXYMETHYLBUTYL)-2-AMINO-6-CHLOROPURINE-D4
• 2',3',5'-Tri-O-acetyl-2-aMino-6-chloropurine Riboside
• 2-AMINO-6-CHLORO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE