2-Aminopurine supplier | CasNO.452-06-2

Name
2-Aminopurine
EINECS 207-197-4
CAS No. 452-06-2
Article Data23
CAS DataBase
Density 1.612 g/cm³
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
Appearance White to light yellow crystal powder
Safety 22-36-26
Risk Codes 22-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms 1H-Purin-2-amine(9CI);Purine, 2-amino- (6Cl,8Cl);2-Aminopurine;Isoadenine;NSC 24129;SQ22451;CCRIS 759;Purine, 2-amino-;
PSA 80.48000
LogP 0.51630

Synthetic route

: 33512-51-5
2-(methylthio)-9H-purine

: 452-06-2
9H-purin-2-amine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With trifluoroacetic acid at 130℃;	48%

: 6-(2-acetylvinylthio)-2-aminopurine

: 452-06-2
9H-purin-2-amine

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: 154-42-7
thioguanine

: 452-06-2
9H-purin-2-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / NaOH / dioxane; H2O / 5 - 10 °C 2: 35.7 percent / Raney nickel / H2O / 7.5 h / Heating View Scheme

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 452-06-2
9H-purin-2-amine

Conditions

Conditions	Yield
With Canyon Diablo iron meteorites at 140℃; for 24h; Reagent/catalyst; Temperature;

: 452-06-2
9H-purin-2-amine

: 2-aminopurine thallium salt

Conditions

Conditions	Yield
With thallium (I) ethoxide In ethanol at 15 - 20℃; for 36h;	92%

: 452-06-2
9H-purin-2-amine

: 56287-17-3, 69123-94-0, 784-71-4
2'-deoxy-2'-fluorouridine

: 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine

Conditions

Conditions	Yield
In water at 37℃; for 48h; thymidine phosphorylase, purine nucleoside phosphorylase, phosphate buffer, pH 7;	89%

: 452-06-2
9H-purin-2-amine

: 951-77-9
2'-Deoxycytidine

: 3616-24-8
2-amino-9-(β-D-2'-deoxyribofuranosyl)-purine

Conditions

Conditions	Yield
With citrate buffer; N-deoxyribosyltransferase from L. leichmannii In ethanol at 40℃; for 48h;	86%

: 110661-91-1
tert-butyl 4-bromobutyrate

: 452-06-2
9H-purin-2-amine

: 1043904-91-1
C13H19N5O2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 80℃;	85%

: 452-06-2
9H-purin-2-amine

: 157363-84-3
1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol

: 1-(2-amino-9H-purin-9-yl)-2,5-anhydro-3,4-di-O-benzyl-1-deoxy-D-glucitol

Conditions

Conditions	Yield
Stage #1: 9H-purin-2-amine With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol In N,N-dimethyl-formamide at 110℃;	66%

: 20194-18-7
sodium phenyl-methanolate

: 452-06-2
9H-purin-2-amine

: N-(phenylmethyl)-aminopurine

Conditions

Conditions	Yield
at 130℃; for 17h;	63%

: 36016-40-7
mesitylenesulfonylhydroxylamine

: 452-06-2
9H-purin-2-amine

: 1,2-diaminopurinium mesitylenesulphonate

Conditions

Conditions	Yield
In methanol; dichloromethane for 4h; Ambient temperature;	62%

: 3083-77-0
araU

: 452-06-2
9H-purin-2-amine

: 2-amino-9-(β-D-arabinofuranosyl)purine

Conditions

Conditions	Yield
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0;	61%

: 127047-77-2
4-acetoxy-3-(acetoxymethyl)-1-iodobutane

: 452-06-2
9H-purin-2-amine

A: 131266-15-4
7-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

B: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 18h; Ambient temperature;	A 15% B 59%

...Expand

: 13831-03-3
tert-butyl prop-2-ynoate

: 452-06-2
9H-purin-2-amine

A: 1043904-89-7
C12H15N5O2

B: 1043904-90-0
C12H15N5O2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 80℃;	A 57% B 23%

...Expand

: 452-06-2
9H-purin-2-amine

: cis/trans-1-acetoxymethyl-2-bromo-2-(bromomethyl)cyclopropane

A: (Z,E)-2-amino-7-[(2-acetoxymethyl)cyclopropylidenemethyl]purine

B: (Z,E)-2-amino-9-[(2-acetoxymethyl)cyclopropylidenemethyl]purine

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 65℃; for 8h;	A 20% B 53%

...Expand

: 105-36-2
ethyl bromoacetate

: 452-06-2
9H-purin-2-amine

: 933477-63-5
2-(2-amino-9H-purin-9-yl)acetic acid

Conditions

Conditions	Yield
Stage #1: 9H-purin-2-amine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide for 2h; Inert atmosphere; Stage #3: With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	51%

: 1134003-26-1
(5aS,7S)-7-[(1R/S)-2-bromo-1-methylethyl]-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran

: 452-06-2
9H-purin-2-amine

: 1134003-03-4
(5aS,7S)-7-[(1R/S)-2-(2-amino-9H-purin-9-yl)-1-methylethyl]-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran

Conditions

Conditions	Yield
Stage #1: 9H-purin-2-amine With caesium carbonate In N,N-dimethyl-formamide at 25℃; for 1h; Inert atmosphere; Stage #2: (5aS,7S)-7-[(1R/S)-2-bromo-1-methylethyl]-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran In N,N-dimethyl-formamide at 25℃; for 24h; Inert atmosphere;	48%

: 4362-40-7
5-chloromethyl-2,2-dimethyl-1,3-dioxolane

: 452-06-2
9H-purin-2-amine

A: 120139-11-9
9-(RS)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl-2-aminopurine

B: 120139-12-0
7-(RS)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl-2-aminopurine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 14h;	A 44% B 15%

...Expand

: 452-06-2
9H-purin-2-amine

: 5983-09-5
2',3'-Dideoxyuridine

: 107550-74-3
iso-2',3'-dideoxyadenosine

Conditions

Conditions	Yield
at 50℃; for 2h; Escherichia coli JA-300 cells, pH 6.5;	44%

: 116384-57-7
Diethyl 2-Bromoethoxymethanephosphonate

: 452-06-2
9H-purin-2-amine

: 126354-35-6
[2-(2-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide a) At 80 deg C for 1 h 2) addition of IIc,80 deg C for 16 h;	40%

: 51385-79-6
diethyl-2-(2-bromoethylidene)malonte

: 452-06-2
9H-purin-2-amine

: 134470-59-0
2-amino-9-(2,2-dicarboethoxycyclopropyl)purine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	39%

: 452-06-2
9H-purin-2-amine

: 3840-30-0
5-(chloromethyl)-1,2,3-trimethoxybenzene

: 9-(3,4,5-trimethoxybenzyl)-9H-purin-2-ylamine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;	36%

: 452-06-2
9H-purin-2-amine

: 850883-62-4
2-deoxy-2-fluoro-α-D-arabinofuranose 1-phosphate

: 2-Amino-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine

Conditions

Conditions	Yield
purine nucleoside phosphorylase In water at 50℃; for 216h; pH=7.5; Aqueous phosphate buffer; Enzymatic reaction;	32%

: 108-24-7
acetic anhydride

: 452-06-2
9H-purin-2-amine

: 23567-61-5
2-(N-acetylamino)purine

Conditions

Conditions	Yield
With ethanol 1) EtOH, 25 min, reflux, 2) 15 min, reflux; Yield given. Multistep reaction;

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,

Product Name

2-Aminopurine

Synthetic route

2-Aminopurine Specification

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