6-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 0 - 20℃; | 100% |
With borane-THF In tetrahydrofuran at 5 - 20℃; for 24.5h; Inert atmosphere; | 95% |
With borane-THF In tetrahydrofuran at 0 - 20℃; for 24.5h; Inert atmosphere; | 95% |
2-((2,5-dimethoxyphenyl)amino)ethane-1-ol
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
With SO42-/ZrO2-MnO2 In water at 110℃; for 4h; Reagent/catalyst; | 79.8% |
With hydrogen bromide for 2h; cyclocondensation; demethylation; Heating; | 76% |
6-methoxy-3,4-dihydro-2H-benzo[1,4]oxazine
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at -78 - 20℃; for 2h; Inert atmosphere; | 69% |
2,5-dimethoxyaniline
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 41 percent / CaCO3 / H2O / 4 h / Heating 2: 76 percent / 62 percent HBr / 2 h / Heating View Scheme |
2-amino-4-methoxyphenol
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 10 h / 80 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 3: boron tribromide / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere View Scheme |
6-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere View Scheme |
4-methoxy-2-nitrophenol
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ammonium chloride; iron / tetrahydrofuran; methanol; water / 4 h / 80 °C / Inert atmosphere 2: potassium carbonate / acetonitrile / 10 h / 80 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 4: boron tribromide / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere View Scheme |
2-chloro-N-(2',5'-dimethoxyphenyl)acetamide
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: boron tribromide / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice 2: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice 3: borane-THF / tetrahydrofuran / 24.5 h / 5 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 3: borane-THF / tetrahydrofuran / 24.5 h / 0 - 20 °C / Inert atmosphere View Scheme |
2,5-dimethoxyaniline
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine / acetonitrile / 1 h / Inert atmosphere; Cooling with ice 2: boron tribromide / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice 3: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice 4: borane-THF / tetrahydrofuran / 24.5 h / 5 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: 1 h / 0 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere 3: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 4: borane-THF / tetrahydrofuran / 24.5 h / 0 - 20 °C / Inert atmosphere View Scheme |
2-chloro-N-(2,5-dihydroxyphenyl)acetamide
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice 2: borane-THF / tetrahydrofuran / 24.5 h / 5 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2: borane-THF / tetrahydrofuran / 24.5 h / 0 - 20 °C / Inert atmosphere View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
acetic anhydride
1-(6-hydroxy-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)ethan-1-one
Conditions | Yield |
---|---|
In water at 20℃; Sonication; Heating; | 95% |
In water at 20 - 50℃; Sonication; | 95% |
In water for 0.25h; Acetylation; Heating; | 65% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
tert-butyldimethylsilyl chloride
6-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-benzo[1,4]oxazine
Conditions | Yield |
---|---|
Stage #1: 3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.333333h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil for 1h; Time; | 94% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
4-nitrobenzenediazonium tetrafluoroborate
Conditions | Yield |
---|---|
Stage #1: 3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine With hydrogenchloride In methanol; water for 0.25h; Cooling with ice; Stage #2: 4-nitrobenzenediazonium tetrafluoroborate In methanol; water at 0℃; for 1.25h; | 87% |
Stage #1: 3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine With hydrogenchloride In methanol; water at 0℃; for 0.25h; Stage #2: 4-nitrobenzenediazonium tetrafluoroborate In methanol; water at 0℃; for 1.25h; | 87% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
propionic acid anhydride
1-(6-hydroxy-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propan-1-one
Conditions | Yield |
---|---|
In water for 0.25h; Acylation; Heating; | 84% |
butanoic acid anhydride
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
1-(6-hydroxy-2,3-dihydro-benzo[1,4]oxazin-4-yl)-butan-1-one
Conditions | Yield |
---|---|
In water for 0.25h; Acylation; Heating; | 79% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
benzoic acid anhydride
4-benzoyl-6-hydroxy-3,4-dihydro-2H-1,4-benzoxazine
Conditions | Yield |
---|---|
In ethyl acetate for 1h; Acylation; Heating; | 61% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Chloroacetic anhydride
4-chloroacetyl-6-hydroxy-3,4-dihydro-2H-1,4-benzoxazine
Conditions | Yield |
---|---|
In ethyl acetate Acylation; Heating; | 57% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
With perchloric acid In water; isopropyl alcohol at 80℃; | 55% |
With perchloric acid In water; isopropyl alcohol at 80℃; | 55% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
5-ethylamino-4-methyl-2-nitrosophenol hydrochloride
Conditions | Yield |
---|---|
With perchloric acid In water; isopropyl alcohol at 80℃; | 44% |
With perchloric acid In water; isopropyl alcohol at 80℃; | 44% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
ethyl bromide
4-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-ol
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 18h; | 38% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
With perchloric acid In water; isopropyl alcohol at 80℃; | 32% |
With perchloric acid In water; isopropyl alcohol at 80℃; | 32% |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
1-(6-oxiranylmethoxy-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 65 percent / H2O / 0.25 h / Heating 2: 59 percent / K2CO3 / 3 h / 90 - 95 °C View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 65 percent / H2O / 0.25 h / Heating 2: 59 percent / K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating 4: aq. KOH / methanol / 3 h / 65 - 70 °C View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
1-(6-oxiranylmethoxy-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84 percent / H2O / 0.25 h / Heating 2: K2CO3 / 3 h / 90 - 95 °C View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
4-diethylaminoacetyl-6-hydroxy-3,4-dihydro-2H-1,4-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 57 percent / ethyl acetate / Heating 2: 63 percent / ethanol / 3 h / Heating View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 65 percent / H2O / 0.25 h / Heating 2: 59 percent / K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating 4: aq. KOH / methanol / 3 h / 65 - 70 °C View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
1-(6-oxiranylmethoxy-2,3-dihydro-benzo[1,4]oxazin-4-yl)-butan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 79 percent / H2O / 0.25 h / Heating 2: K2CO3 / 3 h / 90 - 95 °C View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
1-[6-(2-hydroxy-3-isopropylamino-propoxy)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 65 percent / H2O / 0.25 h / Heating 2: 59 percent / K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 61 percent / ethyl acetate / 1 h / Heating 2: K2CO3 / 3 h / 90 - 95 °C View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
4-acetyl-6-(3-tert-butylamino-2-hydroxy-propoxy)-3,4-dihydro-2H-1,4-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 65 percent / H2O / 0.25 h / Heating 2: 59 percent / K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
2-diethylamino-1-(6-oxiranylmethoxy-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 57 percent / ethyl acetate / Heating 2: 63 percent / ethanol / 3 h / Heating 3: K2CO3 / 3 h / 90 - 95 °C View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 84 percent / H2O / 0.25 h / Heating 2: K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 84 percent / H2O / 0.25 h / Heating 2: K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 79 percent / H2O / 0.25 h / Heating 2: K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 79 percent / H2O / 0.25 h / Heating 2: K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating View Scheme |
3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 61 percent / ethyl acetate / 1 h / Heating 2: K2CO3 / 3 h / 90 - 95 °C 3: propan-2-ol / 3 h / Heating View Scheme |
IUPAC Name: 3,4-Dihydro-2H-1,4-benzoxazin-6-ol
Synonyms of 2H-1,4-Benzoxazin-6-ol, 3,4-dihydro- (CAS NO.26021-57-8): 3,4-Dihydro-2H-1,4-benzoxazin-6-ol ; Hydroxybenzomorpholine ; EINECS 247-415-5
CAS NO: 26021-57-8
Molecular Formula of 2H-1,4-Benzoxazin-6-ol, 3,4-dihydro- (CAS NO.26021-57-8): C8H9NO2
Molecular Weight: 151.1626
Molecular Structure:
Polar Surface Area: 21.7 Å2
Index of Refraction: 1.582
Molar Refractivity: 40.65 cm3
Molar Volume: 121.7 cm3
Surface Tension: 51.3 dyne/cm
Density of 2H-1,4-Benzoxazin-6-ol, 3,4-dihydro- (CAS NO.26021-57-8): 1.241 g/cm3
Flash Point: 156.2 °C
Enthalpy of Vaporization: 60.06 kJ/mol
Boiling Point: 334.7 °C at 760 mmHg
Vapour Pressure: 6.46E-05 mmHg at 25°C
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