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Chemical Structure| 68-94-0 Chemical Structure| 68-94-0
Chemical Structure| 68-94-0

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Hypoxanthine, a naturally occurring purine derivative, an intermediate product of uric acid synthesis, formed from adenylic acid and itself a precursor of xanthine.

Synonyms: Purin-6-ol; Sarcine; 1,7-Dihydro-6H-purin-6-one

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of Hypoxanthine

CAS No. :68-94-0
Formula : C5H4N4O
M.W : 136.11
SMILES Code : O=C1NC=NC2=C1N=CN2
Synonyms :
Purin-6-ol; Sarcine; 1,7-Dihydro-6H-purin-6-one
English Name :1,9-Dihydro-6H-purin-6-one
MDL No. :MFCD00005725
InChI Key :FDGQSTZJBFJUBT-UHFFFAOYSA-N
Pubchem ID :135398638

Safety of Hypoxanthine

Application In Synthesis of Hypoxanthine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 68-94-0 ]

[ 68-94-0 ] Synthesis Path-Downstream   1~9

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  • [ 21802-48-2 ]
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  • [ 16370-43-7 ]
YieldReaction ConditionsOperation in experiment
1: 87% 2: 2% 3: 2% With sodium hydroxide at 100℃; for 7h;
With water at 70℃; for 96h; pH 10.47, ionic strength 1.0; other time and pH;
With water at 70℃; pH 6.92, half-life 41 h;
With water at 70℃; pH 6.97, half-life 37 h;
With water at 70℃; pH 8.70, half-life 19 h;
With water at 70℃; pH 10.47, half-life 4.6 h;
With sodium hydroxide; water at 70℃; half-life 3.1 h;

  • 4
  • [ 21436-98-6 ]
  • [ 68-94-0 ]
  • [ 82760-83-6 ]
YieldReaction ConditionsOperation in experiment
40% With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 150℃; for 24h;
  • 5
  • [ 137-04-2 ]
  • [ 68-94-0 ]
  • [ 6296-90-8 ]
YieldReaction ConditionsOperation in experiment
56% With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 150℃; for 24h;
  • 6
  • [ 4551-95-5 ]
  • [ 58-63-9 ]
  • [ 4338-48-1 ]
  • [ 68-94-0 ]
YieldReaction ConditionsOperation in experiment
6.1 mg With purine nucleoside phosphorylase from Aeromonas hydrophyla, covalently immobilized on aminopropylsilica particles In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 0.166667h; Flow reactor; Enzymatic reaction;
  • 7
  • [ 13146-72-0 ]
  • [ 1839-18-5 ]
  • [ 68-94-0 ]
  • [ 115044-75-2 ]
YieldReaction ConditionsOperation in experiment
40% With potassium dihydrogenphosphate; recombinant E. coli purine nucleoside phosphorylase In water at 50℃; for 192h; Enzymatic reaction; 2-Chloro-9-(3-deoxy-β-D-ribofuranosyl)adenine (9) 2-Chloroadenine (50 mg, 0.295 mmol) was dissolved in H2O (660 mL) under heating and stirring. The solution was cooled to 50 °C, 3′-deoxyinosine (8, 0.1 g, 0.396 mmol) and KH2PO4 (180 mg, 1.323 mmol) were added, and the pH of the mixture was adjusted to 7.0 (2.0 mM); PNP (1320 IU) was added and the mixture was incubated at 50 °C for 8 d under stirring. The precipitate was filtered off, the solution was concentrated and the desired product was isolated by column chromatography (silica gel 100 C18-RP, 2.5 × 19 cm, 10% aq EtOH, flow rate 5 mL/min) as a lyophilized powder; yield: 34 mg (0.119 mmol, 40%); purity 99.3%; HPLC (method II); tR = 11.41 min. 1H and 13C NMR spectra are in agreement with the literature data. 1H NMR (700 MHz, DMSO-d6): δ = 8.38 (s, 1 H, H-8), 7.77 (s, 2 H, NH2), 5.81 (d, J = 1.9 Hz, 1 H, H-1′), 5.66 (br s, 1 H, OH-2′), 4.99 (m, 1 H, OH- 5′), 4.53 (m, 1 H, H-2′), 4.36 (m, 1 H, H-4′), 3.69 and 3.53 (2 m, 2 H, H- 5′), 2.22 (ddd, J = 13.1, 8.9, 5.7 Hz, 1 H, H-3a′), 1.91 (ddd, J = 13.1, 6.1, 2.8 Hz, 1 H, H-3b′). 13C NMR (176 MHz, DMSO-d6): δ = 157.18 (C6), 150.36 (C4), 139.83 (C8), 118.55 (C5), 91.15 (C1′), 81.36 (C4′), 75.17 (C2′), 62.77 (C5′), 34.21 (C3′). 15N NMR (71 MHz, DMSO-d6): δ = 241.41 (N7), 220.38 (N3), 174.09 (N9), 86.94 (NH2). HRMS (ESI+): m/z [M + H]+ calcd for C10H13N5O3Cl: 288.0677/286.0707, 37Cl/35Cl; found: 288.0691/286.0721, 37Cl/35Cl; m/z [base + H]+ calcd for C5H5N5Cl: 172.0204/170.0233, 37Cl/35Cl; found: 172.0219/170.0249, 37Cl/35Cl. UV (H2O, pH 7.0): λ (ε) = 264 (12,100, max), 232 nm (4,700, min) [Lit.9 UV (H2O): λ = 265 nm (max)].
  • 8
  • [ 68-94-0 ]
  • [ CAS Unavailable ]
  • [ 1214-39-7 ]
YieldReaction ConditionsOperation in experiment
18.2 g In N,N-dimethyl-formamide at 75℃; for 4h; 2 Example 2 In a three-neck reaction vessel, 0.1 mol (13.6 g) of hypoxanthine, 0.15 mol (16 g) of benzylamine, 4 g (I2-P2O5-ZnCl2) catalyst and 100 mL of DMF solvent were added.The mass ratio of P2O5:ZnCl2:I2 is 1:0.2:0.02. Then, the temperature is raised to about 75 DEG C., and the temperature is controlled at 75 DEG C for 4 hours. After the reaction,Slowly add 1mol (18g) of process water and control the temperature at 75°C to adjust the pH to neutral. After adjustment, a large amount of solids are precipitated and directly heated.After suction filtration, the crude product of 6-benzylaminopurine (6-BA) was obtained. After drying, the yield was 21.7 g. The equivalent yield was 96.2% and the content was 98.1%.The obtained crude product was tested for chloride ion content and the chloride ion content was ≤ 0.1 ppm. In order to better improve the purity of the product, you can further refine it, specifically:Into another three-necked flask was added 20 g of the crude 6-benzylaminopurine (6-BA) obtained above and 250 g of ethanol, and the mixture was heated to reflux, dissolved, and 1.6 g of activated charcoal was added while hot.Decoloring treatment by stirring for 30 minutes, while hot suction filtration, the filtrate was stirred and slowly cooled to 5 °C -10 °C for analysis, filtration, drying, to obtain refined product 6-benzylaminopurine 18.2g, the content is 99.6 %.The quality product will be tested for chloride ion content, chloride ion content ≤ 0.05ppm. The mother liquor can be applied to the next batch.
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