O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine
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O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine
structure -
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CAS No:
6723-30-4
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Formula:
C5H11NO2
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Chemical Name:
O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine
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Synonyms:
O-(oxan-2-yl)hydroxylaMine;2-(Aminooxy)tetrahydro-2H-pyran;O-(TETRAHYDRO-PYRAN-2-YL)-HYDROXYLAMINE;O-tertrahydroxy-pyran-2-yl-hydroxylamine;O-(2H-Tetrahydropyran-2-yl)hydroxylamine;O-(TETRAHYDRO-2H-PYRAN-2-YL)HYDROXYLAMINE;O-(Tetrahydropyran-2-yl)hydroxylamine;O-(Tetrahydropyran-2-yl)-hydroxylaMine, 95+%;HYDROXYLAMINE, O-(TETRAHYDRO-2H-PYRAN-2-YL)-
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CAS No:
O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine Basic Attributes
117.15
117.078979
1308068-626-2
DTXSID50408719
2932999099
Characteristics
44.5
0.2
White Low Melting Solid
1.1±0.1 g/cm3
34-37 °C(lit.)
81 °C20 mm Hg(lit.)
180 °F
1.464
Safety Information
3
36/37/38
26-36
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine Use and Manufacturing
A 250 mL three-necked flask was charged with N-hydroxyphthalimide (10 g, 0.061 mol)Dihydropyran (6.1 g, 0.073 mol), Tetrahydrofuran 100mL, After dissolution, p-toluenesulfonic acid (1.1 g, 6.1 mmol) was added, Reaction at room temperature 2h.The tetrahydrofuran was distilled off under reduced pressure, To the residue was added 200 mL of water, Dichloromethane 3 × 200mL extraction, Saturated NaHCO3 aqueous solution 3 × 200mL wash, Saturated NaCl aqueous solution 200mL washed once, Anhydrous sodium sulfate, filtration, evaporated to dryness, A yellow-green solid, 15.3g.The resulting solid was added to a 1000 mL three-necked flask, Ethanol 450mL, stirred to dissolve, 80percent hydrazine hydrate (10.4 mL, 0.17 mol) was added dropwise, Reaction at room temperature 1h.The reaction solution was directly suction filtered, The filtrate evaporated to give crude product 10.6g, was added ethyl acetate 500mL, After full mixing, Vacuum filtration insoluble matter, The filtrate was washed with water 3 × 100mL, Saturated brine solution 200mL washed once, Anhydrous sodium sulfate, filtration, evaporated to dryness, Had pale yellow oil, vacuum-dried yellow solid 5.39g, m.p. 35-37 ° C, yield 75.3percent.Synthesis of 9-4:; to a solution of 2-(tetrahydro-2H-pyran-2-yloxy)isoindoline-l, 3-dione (13.4 g, 54.25 mmol, 1.00 equiv) in MeOH(200mL) was added hydrazine (6 mL). The resulting solution was stirred for 30mins at 60°C in an oil bath. The reaction mixture was cooled with a water/ice bath. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 5.6 g (88percent) of HTo a solution of compound 2 (200 g, 0.80 mol) in methyl tert-butyl ether (1.8 L), hydrazine hydrate (48.6 g, 0.97 mol) was added drop wise at 25–30°C. The resulting reaction mass refluxed at 80°C over a period of 1 h. Reaction completion was monitored by TLC. The resulting reaction mass was cooled to 10°C and reaction mass was filtered through celite pad to remove phthalimide impurities. Then filtrate was dried with sodium sulfate and concentrated. The product was further purified by high vacuum distillation (120°C, 1 mmHg) to obtain compound 3 (80 g, 84percent) as colorless oil which was solidified upon storage at 4–8°C as a white solid.
Used as an oximation reagent in the synthesis of a marine alkaloid which shows significant inhibitory activity against mycothiol S-conjugate amidase.1
Computed Properties
Molecular Weight:117.15
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:117.078978594
Monoisotopic Mass:117.078978594
Topological Polar Surface Area:44.5
Heavy Atom Count:8
Complexity:67.4
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine
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