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2-Aminopurine
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Name

2-Aminopurine

 EINECS 207-197-4
CAS No. 452-06-2 Density 1.612 g/cm3
PSA 80.48000 LogP 0.51630
Solubility Soluble in acid, slightly soluble in hot ethanol, insoluble in alkaline solution Melting Point 280-282 °C(lit.)
Formula C5H5N5 Boiling Point 616.3 °C at 760 mmHg
Molecular Weight 135.128 Flash Point 362.9 °C
Transport Information N/A Appearance White to light yellow crystal powder
Safety 22-36-26 Risk Codes 22-36/37/38-20/21/22
Molecular Structure Molecular Structure of 452-06-2 (2-Aminopurine) Hazard Symbols HarmfulXn
Synonyms

1H-Purin-2-amine(9CI);Purine, 2-amino- (6Cl,8Cl);2-Aminopurine;Isoadenine;NSC 24129;SQ22451;CCRIS 759;Purine, 2-amino-;

Article Data 23

2-Aminopurine Synthetic route

33512-51-5

2-(methylthio)-9H-purine

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
With potassium amide In ammonia for 70h; Mechanism; 2-halogenated purines;90%
10310-21-1

2-Amino-6-chloropurin

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
In hydrogenchloride at 50℃; electrolysis, -0.75V, initial current 50-60 mA;85%
palladium on charcoal In sodium hydroxide; water

1,2-diaminopurinium mesitylenesulphonate

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
With methylamine In methanol at 100℃; for 17h;80%

1,2-diaminopurinium mesitylenesulphonate

A

120-73-0

purine

B

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
With ammonia In methanol at 100℃; for 17h; Mechanism; Product distribution;A 70%
B 20%
3546-50-7

pyrimidine-2,4,5-triamine

14036-53-4

dimethoxymethyl acetate

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
1.) RT, 6 h, 2.) reflux, 30 min;61%

1-amino-2-(methylthio)purinium mesitylenesulfonate

A

33512-51-5

2-(methylthio)-9H-purine

B

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
With ammonia In methanol at 100℃; for 17h; Product distribution; Mechanism; ANRORC and no ANRORC mechanism determined by reaction with 15N labelled ammonia; var. temp. and time;A 55%
B 25%
61991-08-0

amipurimycin

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
With trifluoroacetic acid at 130℃;48%

6-(2-acetylvinylthio)-2-aminopurine

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
With nickel In water for 7.5h; Heating;35.7%
107550-74-3

iso-2',3'-dideoxyadenosine

A

122999-44-4

2,3-Didesoxy-β-D-glycero-pentofuranose

B

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
With hydrogenchloride at 22℃; rate of hydrolysis relative to dideoxyadenosine;
3616-24-8

2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine

A

18620-60-5

2,4-diamino-5-formamidopyrimidine

B

452-06-2

9H-purin-2-amine

Conditions
ConditionsYield
With sodium cacodylate buffer; water at 110℃; for 22h; Kinetics; Thermodynamic data; Mechanism; ΔH(excit.); var. temp. and times;

2-Aminopurine Specification

The 2-Aminopurine with CAS registry number of 452-06-2 is also known as Purine, 2-amino- (6Cl,8Cl). The IUPAC name is 7H-Purin-2-amine. It belongs to product categories of Pyrimidine; Purine; Nucleotides and Nucleosides; Purines; Biochemistry; Nucleobases and Their Analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic Acids; Bases & Related Reagents; Nucleotides; Nucleoside Analogs; Nucleosides, Nucleotides, Oligonucleotides; Biochemicals and Reagents. Its EINECS registry number is 207-197-4. In addition, the formula is C5H5N5 and the molecular weight is 135.15.

Physical properties about 2-Aminopurine are: (1)ACD/LogP: -0.52; (2)ACD/LogD (pH 5.5): -0.57; (3)ACD/LogD (pH 7.4): -0.53; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 11.11; (7)ACD/KOC (pH 7.4): 12.31; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 0; (11)Index of Refraction: 1.837; (12)Molar Refractivity: 37.03 cm3; (13)Molar Volume: 83.8 cm3; (14)Surface Tension: 122.7 dyne/cm; (15)Density: 1.612 g/cm3; (16)Flash Point: 362.9 °C; (17)Enthalpy of Vaporization: 91.41 kJ/mol; (18)Boiling Point: 616.3 °C at 760 mmHg; (19)Vapour Pressure: 4.03E-15 mmHg at 25 °C.

Preparation of 2-Aminopurine: it is prepared by reaction of 1,2-diaminopurinium mesitylenesulphonate. The reaction needs reagent methylamine and solvent methanol at the temperature of 100 °C for 17 hours. The yield is about 80%. It is a fluorescent molecular marker used in nucleic acid research and sometimes used in the laboratory for mutagenesis.

2-Aminopurine is prepared by reaction of 1,2-diaminopurinium mesitylenesulphonate.

Uses of 2-Aminopurine: it is used to produce 2-benzylaminopurine by reaction with phenylmethanol; sodium salt. The reaction occurs at the temperature of 130 °C for 17 hours. The yield is about 63%.

2-Aminopurine is used to produce 2-benzylaminopurine by reaction with phenylmethanol; sodium salt.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. What's more, it is harmful by inhalation, in contact with skin and if swallowed. During using it, wear suitable protective clothing and do not breathe dust. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=C2C(=NC(=N1)N)N=CN2
2. InChI: InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
3. InChIKey: MWBWWFOAEOYUST-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type

Route

 Reported Dose (Normalized Dose) Effect Source
rat LD50 intraperitoneal 270mg/kg (270mg/kg)   Japanese Kokai Tokyo Koho Patents. Vol. #78-55733,
rat LD50 oral 723mg/kg (723mg/kg)   Japanese Kokai Tokyo Koho Patents. Vol. #78-55733,

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