2,6-Diaminopurine supplier | CasNO.1904-98-9

Name
2,6-Diaminopurine
EINECS 217-605-2
CAS No. 1904-98-9
Article Data25
CAS DataBase
Density 1.743 g/cm³
Solubility water: 2.38 g/L (20 °C)
Melting Point 117-122 °C(lit.)
Formula C₅H₆N₆
Boiling Point 748.992 °C at 760 mmHg
Molecular Weight 150.143
Flash Point 447.815 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-45-36/37-36/37/39-27-36-22
Risk Codes 22-36/37/38-40-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms Purine, 2, 6-diamino-;1H-Purine-2,6-diamine;SQ 21065;Purine, 2,6-diamino-;Purine, 2,6-diamino- (VAN 8CI);2-Aminoadenine;X 79;5H-purine-2,6-diamine;2,6-Dichloropurine;purine-2,6-diyldiamine;2,6-Diaminopurine 98%;9H-purine-2,6-diamine;2,6-diamino-purin;
PSA 106.50000
LogP 0.67970

Synthetic route

: 7280-83-3, 62043-11-2, 63041-03-2, 69369-16-0
2,6-Diaminopurine hemisulfate

: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
With Dowex 50X8 (H-form) In water Ambient temperature;	92%

: 64-17-5
ethanol

: 10536-81-9
2-azidoadenine

A: 131287-56-4
8-ethoxy-2,6-diaminopurine

B: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
Ambient temperature; Irradiation;	A 11% B 75%
Product distribution; Ambient temperature; Irradiation;	A 11% B 75%

...Expand

: 10536-81-9
2-azidoadenine

: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
In isopropyl alcohol Product distribution; Ambient temperature; Irradiation; or tert-butyl alcohol;	65%

: 67-56-1
methanol

: 10536-81-9
2-azidoadenine

A: 131287-55-3
8-methoxy-2,6-diaminopurine

B: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
for 1.16667h; Ambient temperature; Irradiation;	A 37% B 37%
for 1.16667h; Product distribution; Ambient temperature; Irradiation;	A 37% B 37%

...Expand

: 5451-40-1
2,6 dichloropurine

A: 85029-13-6
4-cyano-5-(cyanoamino)imidazole

B: 1839-18-5
2-chloroadenine

C: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
With potassium amide In ammonia at -33℃; for 20h;	A 25% B 12% C 13%

...Expand

: 85029-14-7
4-amidino-5-(cyanamino)imidazole

: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
Heating;

: 10310-21-1
2-Amino-6-chloropurin

A: 85029-13-6
4-cyano-5-(cyanoamino)imidazole

B: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
With potassium amide In ammonia at -33℃; for 20h; Yield given. Yields of byproduct given;

: 9-(2-deoxy-α-L-erythro-pentofuranosyl)-2,6-diaminopurine

A: 1904-98-9
2,6-diaminopurine

B: Phosphoric acid mono-((2S,4R,5S)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl) ester

Conditions

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

: 9-(2-deoxy-β-L-erythro-pentofuranosyl)-2,6-diaminopurine

A: 1904-98-9
2,6-diaminopurine

B: Phosphoric acid mono-((2R,4R,5S)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl) ester

Conditions

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

: 85029-13-6
4-cyano-5-(cyanoamino)imidazole

: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: KNH2 / liquid ammonia 2: Heating View Scheme

: 10310-21-1
2-Amino-6-chloropurin

: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium amide / liquid ammonia / 20 h / -33 °C 2: KNH2 / liquid ammonia 3: Heating View Scheme

: 5451-40-1
2,6 dichloropurine

: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 25 percent / potassium amide / liquid ammonia / 20 h / -33 °C 2: KNH2 / liquid ammonia 3: Heating View Scheme

: 2-amino-5'-deoxyadenosine

: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
adenosine phosphorilase In water pH=7.4; Enzymatic reaction; Phosphate buffer;

: 105-36-2
ethyl bromoacetate

A: 1187357-51-2
ethyl 2-[6-amino-2-{3-(t-butoxycarbonylamino)-propyl}amino-9H-purin-9-yl]acetate

B: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
With NaH In N,N-dimethyl-formamide; mineral oil

: ({[Mg4(adipate)4(N,N-dimethylacetamide)(H2O)]*5(N,N-dimethylacetamide)*2methanol*4H2O})

A: 719-41-5
1-hydroxy-9H-xanthen-9-one

B: 935-92-2
2,3,5-Trimethyl-1,4-benzoquinone

C: 825-25-2
2-cyclopentylidenecyclopentan-1-one

D: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
at 330 - 400℃;

...Expand

: 2096-10-8
adenosine-2-amine

A: C5H9O8P(2-)*2K(1+)

B: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; E-purine nucleoside phosphorylase-0002 In aq. buffer at 40℃; for 0.233333h; pH=9; Equilibrium constant; Thermodynamic data; Temperature; Enzymatic reaction;

: 4546-70-7
2-amino-2'-deoxyadenosine

A: C5H9O7P(2-)*2K(1+)

B: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; E-purine nucleoside phosphorylase-0002 In aq. buffer at 40℃; for 0.233333h; pH=9; Equilibrium constant; Thermodynamic data; Temperature; Enzymatic reaction;

: 60456-26-0
(R)-glycidyl butyrate

: 1904-98-9
2,6-diaminopurine

: Butyric acid (R)-3-(2,6-diamino-purin-9-yl)-2-hydroxy-propyl ester

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;	100%

: 1904-98-9
2,6-diaminopurine

: 212970-74-6
Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

: 1341074-82-5
(2R,3R,4S,5S)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(2,6-diamino-9H-purin-9-yl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

Conditions

Conditions	Yield
Stage #1: 2,6-diaminopurine; Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 65℃; for 1.5h; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 65℃; for 3h; Vorbrüggen coupling; Inert atmosphere; Stage #3: With sodium hydrogencarbonate In water; acetonitrile Inert atmosphere;	100%

Yield

Stage #1: 2,6-diaminopurine; Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 65℃; for 1.5h; Inert atmosphere;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 65℃; for 3h; Vorbrüggen coupling; Inert atmosphere;
Stage #3: With sodium hydrogencarbonate In water; acetonitrile Inert atmosphere;

100%

: 24424-99-5
di-tert-butyl dicarbonate

: 1904-98-9
2,6-diaminopurine

: 1354832-39-5
9,N2,N2,N6,N6-penta(Boc)-2,6-diaminopurine

Conditions

Conditions	Yield
With dmap In tetrahydrofuran at 0 - 20℃; for 18.0833h;	96%
With dmap In tetrahydrofuran at 0 - 20℃; for 18.08h; Inert atmosphere;	81%
With dmap In tetrahydrofuran at 20℃; for 18h;	76%

: 14316-61-1
phenoxyacetic anhydride

: 1904-98-9
2,6-diaminopurine

: N2,N6-bis(phenoxyacetyl)-2,6-diaminopurine

Conditions

Conditions	Yield
In pyridine at 85℃; for 3h;	95%

: 1904-98-9
2,6-diaminopurine

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

: 134444-47-6
2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine

Conditions

Conditions	Yield
In water at 37 - 50℃; for 48h; thymidine phosphorylase, purine nucleoside phosphorylase, phosphate buffer, pH 7;	94%
With E. coli BMT-4D Substitution;

: 591-50-4
iodobenzene

: 1904-98-9
2,6-diaminopurine

: 6318-28-1
9-phenylpurine-2,6-diamine

Conditions

Conditions	Yield
With N4,N7-bis(2-hydroxyethyl)-1,10-phenanthroline-4,7-diamine; sodium L-ascorbate; potassium hydroxide; copper(I) bromide In water; N,N-dimethyl-formamide at 120℃; for 21h; Inert atmosphere; Sealed tube; regioselective reaction;	94%

: 1904-98-9
2,6-diaminopurine

: 3373-53-3
isoguanine (6-amino-1H-purin-2(9H)-one)

Conditions

Conditions	Yield
Stage #1: 2,6-diaminopurine With sodium hydroxide; sodium nitrite for 1h; Inert atmosphere; Stage #2: With sulfuric acid at 20 - 60℃; Inert atmosphere;	91%

: 7732-18-5
water

: 1904-98-9
2,6-diaminopurine

: 402846-48-4
2,6-diaminopurine monohydrate

Conditions

Conditions	Yield
Heating;	91%

: 56035-66-6
5-bromo-2-chloro-4-methyl-6-morpholinopyrimidine

: 1904-98-9
2,6-diaminopurine

: 9-(5-bromo-4-methyl-6-morpholinopyrimidin-2-yl)-9Hpurine-2,6-diamine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	90%

: 52026-43-4
4-(2-chloro-6-methylpyrimidin-4-yl)morpholine

: 1904-98-9
2,6-diaminopurine

: 9-(4-methyl-6-morpholinopyrimidin-2-yl)-9H-purine-2,6-diamine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	89%

: 1904-98-9
2,6-diaminopurine

A: 1146697-82-6
difluoropurine

B: 700-49-2
2-fluoroadenine

C: 3373-53-3
2-Hydroxyadenine

Conditions

Conditions	Yield
With tert.-butylnitrite In pyridine; hydrogen fluoride at 0℃; Kinetics; Balz-Schiemann Reaction; liquid HF; regioselective reaction;	A 8.8% B 88.5% C 0.5%

...Expand

: 38775-52-9
diethyl 2,2'-(sulfonylbis(4,1-phenylene)bis(oxy))diacetate

: 1904-98-9
2,6-diaminopurine

: C42H32N12O12S2

Conditions

Conditions	Yield
In ethanol at 80℃; Solvent;	87%

: 16114-05-9
N,N'-bis(dimethylaminomethylene)hydrazine

: 1904-98-9
2,6-diaminopurine

: 306302-08-9
2-amino-6-(1,2,4-triazol-4-yl)-9-H-purine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Cycloaddition; Heating;	85%

: 3083-77-0
araU

: 1904-98-9
2,6-diaminopurine

: 34079-68-0
2,6-diamino-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;	83%
With dipotassium hydrogenphosphate; sodium azide; purine nucleoside phodphorylase ( EC 2.4.2.1 ); uridine phosphorylase ( EC 2.4.2.3 ) at 37℃; for 288h; pH=7.1; Yield given;
With potassium phosphate; Geobacillus thermoglucosidasius purine nucleoside phosphorylase; Thermus thermophilus pyrimidine nucleoside phosphorylase In water at 70℃; for 3h; pH=7; Enzymatic reaction;

: 1904-98-9
2,6-diaminopurine

A: 1480-90-6
2-hydroxy-6-fluoro purine

B: 69-89-6
2,6-dihydroxypurine

C: 3373-53-3
2-Hydroxyadenine

Conditions

Conditions	Yield
With tert.-butylnitrite; sulfuric acid; sodium fluoride In water at 25℃; Balz-Schiemann Reaction;	A n/a B n/a C 83%

...Expand

: 1904-98-9
2,6-diaminopurine

A: 1146697-82-6
difluoropurine

B: 1480-90-6
2-hydroxy-6-fluoro purine

C: 700-49-2
2-fluoroadenine

D: 69-89-6
2,6-dihydroxypurine

Conditions

Conditions	Yield
With tert.-butylnitrite In pyridine; hydrogen fluoride at 0℃; Reagent/catalyst; Solvent; Balz-Schiemann Reaction; liquid HF;	A 8% B n/a C 81% D n/a

...Expand

: 1904-98-9
2,6-diaminopurine

: (1RS,5RS,8RS)-8-iodo-2-azabicyclo[3.3.1]nonan-3-one

: (1RS,5RS,8RS)-8-(2,6-diamino-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

Conditions

Conditions	Yield
Stage #1: 2,6-diaminopurine With sodium hydride In N,N-dimethyl-formamide at 25℃; for 1h; Metallation; Stage #2: (1RS,5RS,8RS)-8-iodo-2-azabicyclo[3.3.1]nonan-3-one In N,N-dimethyl-formamide for 15h; Alkylation;	80%

: 105-36-2
ethyl bromoacetate

: 1904-98-9
2,6-diaminopurine

: Ethyl (2,6-diaminopurin-9-yl)acetate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Ambient temperature;	79%
With potassium carbonate In ethanol; N,N-dimethyl-formamide

: 149312-18-5
1,5-anhydro-4,6-O-benzylidene-3-deoxy-2-O-[(4-methylphenyl)sulfonyl]-D-ribo-hexitol

: 1904-98-9
2,6-diaminopurine

: 1’,5’-anhydro-4’,6’-O-benzylidene-2’,3’-dideoxy-2’-(2,6-diaminopurin-9-yl)-D-arabinohexitol

Conditions

Conditions	Yield
Stage #1: 2,6-diaminopurine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,5-anhydro-4,6-O-benzylidene-3-deoxy-2-O-[(4-methylphenyl)sulfonyl]-D-ribo-hexitol In N,N-dimethyl-formamide; mineral oil at 20 - 90℃; for 12h; Inert atmosphere;	79%

: 1904-98-9
2,6-diaminopurine

A: 1146697-82-6
difluoropurine

B: 1480-90-6
2-hydroxy-6-fluoro purine

C: 66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9
adenine

D: 700-49-2
2-fluoroadenine

E: 69-89-6
2,6-dihydroxypurine

Conditions

Conditions	Yield
With tert.-butylnitrite; BF4(1-)H3O(1+)C4H10O In N,N-dimethyl-formamide at 0℃; Balz-Schiemann Reaction;	A 14% B n/a C 1% D 79% E n/a

...Expand

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 1904-98-9
2,6-diaminopurine

: 160308-67-8
9-(3-phthalimido-2-hydroxypropyl)-2,6-diaminopurine

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 6h;	78%

: 1904-98-9
2,6-diaminopurine

: N-(tert-Butyloxycarbonyl)-2-amino-2-propennitril

: [1-Cyano-2-(2,6-diamino-purin-9-yl)-ethyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 72h; Ambient temperature;	78%

: 65009-00-9
O-phenyl N,N-diethylcarbamate

: 1904-98-9
2,6-diaminopurine

: 6318-28-1
9-phenylpurine-2,6-diamine

Conditions

Conditions	Yield
With sodium t-butanolate In ethylene glycol at 100℃; for 12h;	78%

: 67-56-1
methanol

: hydrotris(3,5-methylphenylpyrazolyl)boratozinc(II) hydroxide

: 1904-98-9
2,6-diaminopurine

: (HB(N2C3H(CH3)(C6H5))3)Zn(C5N6H5)*CH3OH

Conditions

Conditions	Yield
In methanol; dichloromethane soln. Tp*Zn-OH complex in CH2Cl2 was added to suspn. nucleobase in MeOH and stirred for 4 h; react. mixt. was filtered and concd. and cooled to 0°C; elem. anal.;	77%

...Expand

: 155177-69-8
N-(3-chloropropyl)-3-<(tert-butoxycarbonylamino)-propionamido>propionamide

: 1904-98-9
2,6-diaminopurine

: 155177-52-9
2,6-diamino-9-<3-(3-(3-tert-butoxycarbonylamido)propionamido)-propionamido>propyl-9H-purine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	76%

: 141699-57-2
3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1904-98-9
2,6-diaminopurine

: 898828-75-6
(RS)-9-(N-tert-butoxycarbonyl-3-pyrrolidinyl)-2,6-diaminopurine

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide	76%

: 66950-63-8
phenyl N,N-dimethylsulfamate

: 1904-98-9
2,6-diaminopurine

: 6318-28-1
9-phenylpurine-2,6-diamine

Conditions

Conditions	Yield
With sodium t-butanolate In ethylene glycol at 100℃; for 12h;	76%

: 1904-98-9
2,6-diaminopurine

: 197647-17-9
((2R,3S,4S)-3-(benzoyloxy)-5-bromo-4-fluorothiolan-2-yl)methyl benzoate

: 248601-55-0
9-(2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranosyl)-2,6-diaminopurine

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In acetonitrile at 60℃; glycosylation;	75%

2,6-Diaminopurine Standards and Recommendations

ASSAY of 2,6-Diaminopurine: 99.0% min

2,6-Diaminopurine Specification

The 2,6-Diaminopurine is an organic compound with the formula C₅H₆N₆. The IUPAC name of this chemical is 7H-purine-2,6-diamine. With the CAS registry number 1904-98-9, it is also named as 1H-Purine-2,6-diamine. The product's categories are Amineprimary; Pyrimidine; Pyridines, Pyrimidines, Purines and Pteredines; Purine; Amines; Purines; Amine Monomers; Monomers; Primary Amines. Besides, it is a white to light yellow crystal powder, which should be stored in a closed cool and dry place.

Physical properties about 2,6-Diaminopurine are: (1)# of Rule of 5 Violations: 1; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 7.453; (5)ACD/KOC (pH 7.4): 16.223; (6)#H bond acceptors: 6; (7)#H bond donors: 5; (8)Polar Surface Area: 106.5 Å²; (9)Index of Refraction: 1.94; (10)Molar Refractivity: 41.275 cm³; (11)Molar Volume: 86.103 cm³; (12)Polarizability: 16.363×10^-24cm³; (13)Surface Tension: 157.072 dyne/cm; (14)Density: 1.744 g/cm³; (15)Flash Point: 447.815 °C; (16)Enthalpy of Vaporization: 109.175 kJ/mol; (17)Boiling Point: 748.992 °C at 760 mmHg.

Preparation: this chemical can be prepared by 2,6-Diaminopurine hemisulfate. This reaction will need reagent Dowex 50X8 (H-form) and solvent H₂O. The yield is about 92%.

Uses of 2,6-Diaminopurine: it can be used to produce 9-(2,2-diethoxy-ethyl)-9H-purine-2,6-diamine at temperature of 100 °C. It will need solvent dimethylformamide with reaction time of 10 hours. The yield is about 60%.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. It has limited evidence of a carcinogenic effect. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection, do not breathe dust and take off immediately all contaminated clothing. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: c1[nH]c2c(nc(nc2n1)N)N
(2)InChI: InChI=1/C5H6N6/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H5,6,7,8,9,10,11)
(3)InChIKey: MSSXOMSJDRHRMC-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C5H6N6/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H5,6,7,8,9,10,11)
(5)Std. InChIKey: MSSXOMSJDRHRMC-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD10	unreported	70mg/kg (70mg/kg)	BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE	Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.
mouse	LD50	intraperitoneal	202mg/kg (202mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat	LD50	intraperitoneal	> 200mg/kg (200mg/kg)		Advances in Teratology. Vol. 3, Pg. 181, 1968.

Product Name

2,6-Diaminopurine

Synthetic route

2,6-Diaminopurine Standards and Recommendations

2,6-Diaminopurine Specification

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