ethyl 2-ureidophenylcarbonate
2-Benzoxazolinone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 1h; | 100% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; ammonia In methanol at 0 - 20℃; for 2h; Hofmann Rearrangement; Inert atmosphere; | 99% |
With iodosylbenzene In dichloromethane at 20℃; for 2h; Hofmann rearrangement; | 86% |
With potassium hydroxide; [bis(acetoxy)iodo]benzene In methanol at 0℃; for 1h; | 80% |
With sodium hydroxide; sodium hypochlorite |
A
2-Benzoxazolinone
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium hydride In tetrahydrofuran for 24h; Ambient temperature; | A 99% B 70% |
A
2-Benzoxazolinone
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran Ambient temperature; | A 99% B 78% |
Conditions | Yield |
---|---|
at 120℃; for 0.8h; Temperature; | 98.5% |
In 1,2-dichloro-benzene at 180℃; for 2h; | 98% |
With sulfuric acid at 110℃; for 3h; Temperature; | 97.8% |
A
2-Benzoxazolinone
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran for 3h; | A 98% B 72% |
Conditions | Yield |
---|---|
With oxygen; potassium iodide; palladium(II) iodide at 100℃; under 15001.5 Torr; for 24h; Autoclave; | 98% |
With oxygen; potassium iodide; palladium(II) iodide In 1,2-dimethoxyethane at 100℃; under 15201 Torr; for 15h; | 89% |
With oxygen; palladium diacetate; tetra-(n-butyl)ammonium iodide In acetonitrile at 120℃; under 15001.5 Torr; Reagent/catalyst; Temperature; Pressure; Flow reactor; | 73% |
3-ethylaminocarbonyl-2(3H)-benzoxazolone
2-Benzoxazolinone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.25h; | 98% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 4h; Heating; | 97% |
In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; | 89% |
In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; | 89% |
(1H-benzo[d][1,2,3]triazol-1-yl)(2-hydroxyphenyl)methanone
2-Benzoxazolinone
Conditions | Yield |
---|---|
With sodium azide In tetrahydrofuran; water at 100℃; for 4h; | 97% |
Conditions | Yield |
---|---|
In dichloromethane for 0.166667h; Ambient temperature; | 96% |
3-methanesulfonyl-2,3-dihydro-1,3-benzoxazol-2-one
2-Benzoxazolinone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; | 96% |
benzyl 2-oxobenzo[d]oxazole-3(2H)-carboxylate
2-Benzoxazolinone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; | 96% |
3-tert-butoxycarbonyl-2-benzoxazolinone
2-Benzoxazolinone
Conditions | Yield |
---|---|
In methanol at 120℃; under 5171.62 Torr; for 0.166667h; Microwave irradiation; | 96% |
With sodium carbonate In 1,2-dimethoxyethane; water for 3h; Heating; | 70% |
2-(Benzooxazol-2-ylsulfanylmethyl)-2-benzyl-3-phenyl-propan-1-ol
A
2-Benzoxazolinone
B
3,3-dibenzyl-thietane
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran for 4h; | A 95% B 60% |
3-benzoyl-2(3H)-benzoxazolone
2-Benzoxazolinone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; | 95% |
phenyl tosyloxycarbamate
2-Benzoxazolinone
Conditions | Yield |
---|---|
With meso-tetraphenylporphyrin iron(III) chloride; potassium carbonate In 1,2-dichloro-ethane at 25℃; for 2h; Reagent/catalyst; Molecular sieve; Inert atmosphere; | 94% |
3-(phenylsulfonyl)-1,3-benzoxazol-2(3H)-one
2-Benzoxazolinone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; | 93% |
phenyl carbonazidate
2-Benzoxazolinone
Conditions | Yield |
---|---|
With C19H19Cl3CoNO; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate at 40℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube; | 93% |
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In dichloromethane at 28 - 32℃; for 48h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Molecular sieve; Irradiation; chemoselective reaction; | 81% |
Multi-step reaction with 2 steps 1: 23 percent / 0.67 h / 145 °C 2: 46 percent / CH2Cl2 / 2 h / Irradiation View Scheme |
4-amino-2-benzoxazolone
2-Benzoxazolinone
Conditions | Yield |
---|---|
With sulfuric acid; copper(II) sulfate; sodium nitrite In ethyl acetate; isopropyl alcohol Heating; Large scale; | 92.7% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 80℃; for 18h; Reagent/catalyst; Solvent; Temperature; | 92% |
phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate
2-amino-phenol
2-Benzoxazolinone
Conditions | Yield |
---|---|
Stage #1: phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate; 2-amino-phenol In toluene for 1.5h; Reflux; Green chemistry; Stage #2: With sodium hydrogencarbonate In toluene for 1h; Reagent/catalyst; Solvent; Reflux; Green chemistry; | 92% |
Conditions | Yield |
---|---|
With potassium hydroxide; selenium In N,N-dimethyl-formamide at 110℃; under 760 Torr; for 4h; Product distribution; Further Variations:; Solvents; Reagents; Pressures; Temperatures; | 91% |
With pyridine; ; silica gel In various solvent(s) at 200℃; for 6h; Mechanism; other catalysts; | |
With pyridine; In chlorobenzene at 200℃; under 152000 Torr; for 4h; Product distribution; two other catalyst systems; |
3-acetylbenzo[d]oxazol-2(3H)-one
2-Benzoxazolinone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; | 91% |
With hydrogenchloride; water at 90℃; for 8h; | 49% |
Conditions | Yield |
---|---|
With thionyl chloride In benzene for 1h; Heating; | 90% |
With selenium(IV) oxide | |
Multi-step reaction with 2 steps 1: phosphorus pentachloride 2: alcohol View Scheme | |
Multi-step reaction with 2 steps 1: chloroform; chlorine / Behandeln der entstandenen Loesung mit Wasser 2: diluted hydrochloric acid View Scheme | |
Multi-step reaction with 3 steps 1: chloroform; chlorine / Behandeln der entstandenen Loesung mit Wasser 2: alcoholic NaOH-solution 3: diluted hydrochloric acid View Scheme |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 0.5h; Ambient temperature; | 90% |
trifluoromethyl trifluoromethanesulfonate
2-amino-phenol
2-Benzoxazolinone
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 1h; Sealed tube; | 90% |
S,S"-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate
2-amino-phenol
A
2-Benzoxazolinone
B
1-Phenyl-1H-tetrazole-5-thiol
Conditions | Yield |
---|---|
In acetonitrile for 12h; | A 89% B n/a |
A
2-Benzoxazolinone
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran for 3h; | A 89% B 52% |
2-amino-phenol
carbonic acid dimethyl ester
A
2-Benzoxazolinone
B
3-methylbenzo[d]oxazol-2(3H)-one
Conditions | Yield |
---|---|
With lead acetate at -0.15℃; for 0.5h; | A 89% B n/a |
Conditions | Yield |
---|---|
Alkaline conditions; | 100% |
With sodium hydroxide In water at 70 - 80℃; for 1h; | 90% |
With sodium hydroxide for 0.5h; | 90% |
Conditions | Yield |
---|---|
With triethylamine In pyridine Product distribution; Ambient temperature; further reaction conditions; further phosphorylation agents; further carbamates and urea derivatives; | 100% |
Conditions | Yield |
---|---|
Stage #1: 2-Benzoxazolinone at 20℃; Inert atmosphere; Electrolysis; Ionic liquid; Stage #2: ethyl iodide at 20℃; for 2h; Inert atmosphere; Ionic liquid; | 99% |
With potassium hydroxide | |
With potassium hydroxide In 2-methoxy-ethanol |
2-Benzoxazolinone
1,3-chlorobromopropane
3-(3-chloropropyl)-3H-benzooxazol-2-one
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 18h; | 99% |
Stage #1: 2-Benzoxazolinone With potassium carbonate In acetonitrile for 0.166667h; Reflux; Stage #2: 1.3-chlorobromopropane With potassium iodide for 3h; Reflux; | 85% |
Stage #1: 2-Benzoxazolinone With sodium hydride In N,N-dimethyl-formamide Stage #2: 1.3-chlorobromopropane In N,N-dimethyl-formamide at -5 - 20℃; | 54% |
With potassium hydroxide In 2-ethoxy-ethanol for 6h; | |
With sodium hydride 1.) DMF, RT, 30 min, 2.) DMF, RT, 16 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
for 3h; Heating; | 99% |
Conditions | Yield |
---|---|
With pyridine for 1h; Ambient temperature; | 99% |
With triethylamine In benzene | 68% |
Conditions | Yield |
---|---|
With TEA In tetrahydrofuran for 2h; Heating; | 99% |
With triethylamine In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; Reflux; | 75% |
Stage #1: 2-Benzoxazolinone With sodium hydroxide In water; acetone for 0.25h; Friedel Crafts acylation; Stage #2: propionyl chloride In water; acetone at 20℃; for 0.5h; Friedel Crafts acylation; | |
With triethylamine In tetrahydrofuran at 0℃; for 2h; Reflux; |
Conditions | Yield |
---|---|
With ammonium bromide; ethylenediamine at 70℃; for 2h; Microwave irradiation; | 99% |
In 1,2-dichloro-ethane at 95 - 105℃; under 0 - 1125.11 Torr; Alkaline conditions; Large scale; | 96.5% |
With sodium hydroxide In water at 100℃; for 16h; | 72% |
Alkaline hydrolysis; |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium carbonate for 3h; Reflux; | 98% |
With TEA In tetrahydrofuran for 2h; Heating; | 95% |
With pyridine for 1h; Ambient temperature; | 90% |
2-Benzoxazolinone
o-chlorobenzoyl chloride
3-(2-chloro-benzoyl)-3H-benzooxazol-2-one
Conditions | Yield |
---|---|
With pyridine for 1h; Ambient temperature; | 98% |
With potassium hydroxide | |
With pyridine | |
Stage #1: 2-Benzoxazolinone With sodium hydroxide In water; acetone for 0.25h; Friedel Crafts acylation; Stage #2: o-chlorobenzoyl chloride In water; acetone at 20℃; for 0.5h; Friedel Crafts acylation; |
2-Benzoxazolinone
2-chlorobenzoic anhydride
3-(2-chloro-benzoyl)-3H-benzooxazol-2-one
Conditions | Yield |
---|---|
for 3h; Heating; | 98% |
2-Benzoxazolinone
2-cyano-1-phenylacetylene
3-(3-phenyl-2-propenenitrile)benzoxazol-2-one
Conditions | Yield |
---|---|
With potassium hydroxide In acetonitrile at 20 - 25℃; for 10h; | 98% |
2-Benzoxazolinone
chlorophosphoric acid diphenyl ester
(2-Oxo-benzooxazol-3-yl)-phosphonic acid diphenyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane Ambient temperature; | 98% |
With triethylamine | 95% |
With triethylamine In dichloromethane at 35℃; for 0.75h; |
Conditions | Yield |
---|---|
With TEA In tetrahydrofuran for 2h; Heating; | 98% |
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; for 24h; | 98% |
With polyacrylamide In water at 20℃; | 95% |
In neat (no solvent) at 20℃; for 0.5h; | 95% |
2-Benzoxazolinone
6-iodobenzo[d]oxazol-2(3H)-one
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide; sodium iodide In methanol at 34 - 38℃; Large scale; | 97.03% |
With N-iodo-succinimide In acetic acid at 20℃; for 120h; | 96% |
Stage #1: 2-Benzoxazolinone With Iodine monochloride; acetic acid In water for 48h; Stage #2: With potassium carbonate In water; ethyl acetate | 95% |
Conditions | Yield |
---|---|
Stage #1: 2-Benzoxazolinone at 20℃; Inert atmosphere; Electrolysis; Ionic liquid; Stage #2: acetic anhydride at 20℃; for 2h; Inert atmosphere; Ionic liquid; | 97% |
for 3h; Heating; | 92% |
Conditions | Yield |
---|---|
With TEA In tetrahydrofuran for 2h; Heating; | 97% |
Conditions | Yield |
---|---|
Stage #1: 2-Benzoxazolinone With sodium hydroxide In water; acetone for 0.25h; Friedel Crafts acylation; Stage #2: phenylacetyl chloride In water; acetone at 20℃; for 0.5h; Friedel Crafts acylation; | 97% |
2-Benzoxazolinone
3-Methylbenzoyl chloride
3-(3-methylbenzoyl)-2(3H)-benzoxazolone
Conditions | Yield |
---|---|
Stage #1: 2-Benzoxazolinone With sodium hydroxide In water; acetone for 0.25h; Friedel Crafts acylation; Stage #2: 3-Methylbenzoyl chloride In water; acetone at 20℃; for 0.5h; Friedel Crafts acylation; | 97% |
The Molecular formula of 2-BENZOXAZOLINONE(59-49-4): C7H5NO2
The Molecular Weight of 2-BENZOXAZOLINONE(59-49-4): 135.12
Molecular Structure:
EINECS: 200-430-0
Melting point: 137-139 °C(lit.)
Boiling Point: 299 °C at 760 mmHg
Flash Point: 134.6 °C
Index of Refraction: 1.586
Molar Refractivity: 34.28 cm3
Molar Volume: 102 cm3
Polarizability: 13.59 10-24 cm3
Surface Tension: 46.1 dyne/cm
Density: 1.323 g/cm3
Enthalpy of Vaporization: 56.05 kJ/mol
Vapour Pressure: 0.00069 mmHg at 25°C
Water Solubilit: soluble in hot water
BRN: 119481
IUPAC Name: 3H-1,3-benzoxazol-2-one
Synonyms: 3H-BENZOOXAZOL-2-ONE;2-HYDROXYBENZOXAZOLE;2,3-DIHYDRO-1,3-BENZOXAZOL-2-ONE;2-BENZOXAZOLINONE;2-BENZOXAZOLONE;2 (3H)-BENZOXAZOLONE;AKOS B029757;1,3-BENZOXAZOL-2(3H)-ONE;
2-BENZOXAZOLINONE(59-49-4) is used for the production of dyes and synthetic intermediates.
1. | orl-rat LD50:700 mg/kg | MDCHAG Medicinal Chemistry: A Series of Monographs. 4 (1)(1964),308. | ||
2. | orl-mus LD50:554 mg/kg | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 31 (8)(1987),36. | ||
3. | ipr-mus LD50:400 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . |
Poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.
The Hazard Codes of 2-BENZOXAZOLINONE(59-49-4): Xn
Hazard Note: Harmful
The Risk Statements information of 2-BENZOXAZOLINONE(59-49-4):
22: Harmful if swallowed
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
24/25: Toxic in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements information of 2-BENZOXAZOLINONE(59-49-4):
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
24/25: Avoid contact with skin and eyes
WGK Germany: 3
RTECS: DM4905000
2-Benzoxazolinone is used in the study of the antioxidant activity of heterocyclic chalcones, screening of hydrazines as inhibitors of immune suppressive enzyme indoleamine dioxygenase 1, design and the development of the inhibitors of nitric oxide synthases.
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