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N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine

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N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine Basic information
Product Name:N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine
Synonyms:N6-BENZYL-9-(2-TETRAHYDROPYRANYL)ADENINE (BPA);9-(oxan-2-yl)-N-(phenylmethyl)purin-6-amine;benzyl-(9-tetrahydropyran-2-ylpurin-6-yl)amine;2-(phenylmethyl)-8-(2H-pyran-2-yl)-7H-purin-6-amine;PYRANYL BENZYLADENINE;N-(Phenylmethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine;n-benzyl-9-(tetrahydro-2h-pyran-2-yl)adenine;N-BENZYL-9-(2'-TETRAHYDROPYRANYL)ADENINE
CAS:2312-73-4
MF:C17H19N5O
MW:309.37
EINECS:
Product Categories:Plant Hormones
Mol File:2312-73-4.mol
N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine Structure
N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine Chemical Properties
Melting point 108-110 °C
Boiling point 449.64°C (rough estimate)
density 1.0874 (rough estimate)
refractive index 1.7500 (estimate)
storage temp. −20°C
pka3.51±0.10(Predicted)
form Solid
color White to off-white
CAS DataBase Reference2312-73-4(CAS DataBase Reference)
EPA Substance Registry SystemN-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine (2312-73-4)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 26-36
WGK Germany 3
RTECS UO7510000
ToxicityLD50 orl-rat: 1640 mg/kg 85AREA 3,48,76/77
MSDS Information
ProviderLanguage
SigmaAldrich English
N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine Usage And Synthesis
Chemical PropertiesWhite crystals
UsesN-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine is a highly mobile synthetic cytokinin. Foliar spray of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine increased branching in carnation, chrysan-themum, pointsettia, petunia and fuchsia. Application of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine to flower buds at an early stage increased both the diameter and the fresh weight of carnation flowers or chrysanthemum infloresences.
PreparationDissolve alcohol in PrOH (14 ml). Add TEA (0.95 ml, 6.9 mmol) and 6-chloro-9-(tetrahydropyran-2-yl)purine (1.64 g) to the reaction mixture. Heat the reaction mixture at 45 °C for 6 hours. Cool the reaction mixture. Filter the mixture. Evaporate the filtrate partly. Purify the filtrate by CC (60.3 g of silica gel, mobile phase CHCl3-Me2CO 4:1, flow rate 7.5 ml/min). The product is a light yellow viscous substance that starts to crystallize after two weeks of drying over P2O5 in a vacuum desiccator.
Preparation of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine Figure Preparation of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine
Safety ProfileModerately toxic by ingestion.Experimental reproductive effects. When heated todecomposition it emits toxic vapors of NOx.
N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine Preparation Products And Raw materials
Raw materials6-methylsulfonyl-5H-purine-->6-Chloro-9-(tetrahydro-2-pyranyl)-purine-->6-(Methylthio)purine-->6-Benzylaminopurine-->Benzylamine-->3,4-Dihydro-2H-pyran-->6-Chloropurine
Tag:N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine(2312-73-4) Related Product Information
Centchroman Adenine Benzyl benzoate Tetrahydro-4H-pyran-4-one Benzyl alcohol Bis(2-ethylhexyl)amine Benzyl chloride Triallylamine N-Methylformamide Triethylamine 6-Benzylaminopurine Benzyl nicotinate Dibenzylamine Triethanolamine Benzyl N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine