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2,6-Diaminopurine

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Name

2,6-Diaminopurine

EINECS 217-605-2
CAS No. 1904-98-9 Density 1.743 g/cm3
PSA 106.50000 LogP 0.67970
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 N/A 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 Molecular Structure of 1904-98-9 (2,6-Diaminopurine) Hazard Symbols HarmfulXn
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;

Article Data 25

2,6-Diaminopurine Synthetic route

1904-98-9

2,6-diaminopurine

Conditions
ConditionsYield
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
ConditionsYield
Ambient temperature; Irradiation;A 11%
B 75%
Product distribution; Ambient temperature; Irradiation;A 11%
B 75%
10536-81-9

2-azidoadenine

1904-98-9

2,6-diaminopurine

Conditions
ConditionsYield
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
ConditionsYield
for 1.16667h; Ambient temperature; Irradiation;A 37%
B 37%
for 1.16667h; Product distribution; Ambient temperature; Irradiation;A 37%
B 37%
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
ConditionsYield
With potassium amide In ammonia at -33℃; for 20h;A 25%
B 12%
C 13%
85029-14-7

4-amidino-5-(cyanamino)imidazole

1904-98-9

2,6-diaminopurine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;
85029-13-6

4-cyano-5-(cyanoamino)imidazole

1904-98-9

2,6-diaminopurine

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

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.

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