2-Methyl-3,1-benzoxaza-4-one supplier

Name
2-METHYL-3,1-BENZOXAZA-4-ONE
EINECS 208-381-7
CAS No. 525-76-8
Article Data182
CAS DataBase
Density 1.25 g/cm³
Solubility
Melting Point 79-82 °C(lit.)
Formula C₉H₇NO₂
Boiling Point 283.5 °C at 760 mmHg
Molecular Weight 161.16
Flash Point 144.7 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Methyl-3,1-benzoxaza-4-one;2-Methyl-3,1-benzoxazin-4-one;2-Methyl-3,1-benzoxazine-4-one;2-Methyl-4-oxo-3,1-benzoxazine;2-Methyl-4-oxo-4H-3,1-benzoxazine;2-Methyl-4H-3,1-benzoxazin-4-one;2-Methyl-4H-benzo[d][1,3]oxazin-4-one;2-Methylbenzo(1,3)oxazin-4-one;Acetanthranil;Acetylanthranil;Acetylanthranyl;NSC 10119;NSC 521353;
PSA 43.10000
LogP 1.49640

Synthetic route

: 108-24-7
acetic anhydride

: 118-92-3
anthranilic acid

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
Heating;	100%
at 130℃; for 0.166667h; Irradiation;	100%
at 130℃; for 3h;	100%

: 201230-82-2
carbon monoxide

: 615-43-0
2-iodophenylamine

: 75-36-5
acetyl chloride

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; N-ethyl-N,N-diisopropylamine; palladium diacetate In tetrahydrofuran at 100℃; under 15514.9 Torr; for 24h;	99%
With N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran at 100℃; under 15001.5 Torr; for 24h; Autoclave;	94%
With C22H28Br2N4Pd; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 80℃; under 3000.3 Torr; for 40h; Autoclave;	60%

...Expand

: 89-52-1
o-acetylamino-benzoic acid

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With triphenyl phosphite In pyridine at 100℃; for 2h;	90%
With acetic anhydride at 130℃; for 1h;	90%
With acetic anhydride for 3h; Cyclization; Heating;	88%

: 118-92-3
anthranilic acid

: 78-39-7
Triethyl orthoacetate

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
for 0.1h; Irradiation;	90%
at 100℃; for 0.75h; Time; Microwave irradiation; Inert atmosphere;	82%
With acetic acid Reflux;	75%

: 201230-82-2
carbon monoxide

: 108-24-7
acetic anhydride

: 615-36-1
2-bromoaniline

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With potassium tetrachloropalladate(II); N-ethyl-N,N-diisopropylamine; catacxium A In toluene at 100℃; under 1500.15 Torr; for 16h; Catalytic behavior; Solvent; Reagent/catalyst; Autoclave;	90%

...Expand

: 101646-18-8
2-carboxymalonanilic acid ethyl ester

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With PPA; Polyphosphoric acid (PPA) for 1h;	89%

: 5234-26-4
N-(2-acetylphenyl)acetamide

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
Stage #1: N-(2-acetylphenyl)acetamide With iodine; sodium hydrogencarbonate In dimethyl sulfoxide at 20℃; for 0.0333333h; Stage #2: With tert.-butylhydroperoxide In nonane; dimethyl sulfoxide at 95℃; for 3h;	89%

: 118-92-3
anthranilic acid

CH3COX: CH3COX

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
	85%

: 33047-12-0
1-Acetyl-2,1-benzisoxazol-3(1H)-one

A: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

B: N-Acetylanthranilic acid

Conditions

Conditions	Yield
at 550℃; under 0.01 Torr; Elimination; Cyclization;	A 80% B 6%

: 31162-13-7
2-azidobenzoic acid

: 75-36-5
acetyl chloride

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate); triethylamine; triphenylphosphine In toluene at 110℃; Aza-Wittig Reaction; Reflux;	73%

: C9H7N3O3

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With triphenylphosphine In toluene at 20℃; Aza-Wittig Reaction;	73%

: 19591-17-4
o-iodoacetanilide

: 1864-94-4
phenyl formate

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;	63%

: 3-azido-3-methylphthalide

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
In xylene Heating;	62%

: 108-24-7
acetic anhydride

: 118-92-3
anthranilic acid

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

A: 491-36-1
4-Hydroxyquinazoline

B: 1769-24-0
2-methyl-4-quinazolone

C: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
at 150℃; for 0.333333h; Niementowski quinazoline reaction; Microwave irradiation; Sealed tube;	A 60% B n/a C 20%

...Expand

: 95-20-5
2-methyl-1H-indole

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With potassium phosphate; 5,6-bis(5-methoxythiophen-2-yl)pyrazine-2,3-dicarbonitrile; oxygen; acetic acid In water; acetonitrile at 25℃; pH=12.7; Irradiation; chemoselective reaction;	58%

: 50-00-0
formaldehyd

: 614-76-6
N-acetyl-2-bromoaniline

A: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

B: 103-84-4
Acetanilid

Conditions

Conditions	Yield
With potassium acetate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In o-xylene at 110℃; for 18h; Schlenk technique; Inert atmosphere;	A 45% B 50%

...Expand

: 95-20-5
2-methyl-1H-indole

A: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

B: 23740-95-6
2-methyl-2-(2-methyl-1H-indol-3-yl)-1,2-dihydro-3H-indol-3-one

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); Trimethylacetic acid In toluene at 60℃;	A 30% B 48%

: 201230-82-2
carbon monoxide

: 19591-17-4
o-iodoacetanilide

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 250℃; under 49403.3 Torr; for 16h; Heck Reaction; Autoclave;	36%

: 201230-82-2
carbon monoxide

: 615-43-0
2-iodophenylamine

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With oxygen; copper diacetate; palladium diacetate; potassium carbonate In acetonitrile at 100℃; under 2280.15 Torr; for 24h;	14%

: 271-58-9
anthranil

: 108-24-7
acetic anhydride

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
at 130 - 150℃;

: 3342-77-6
N-formylanthranilic acid

: 108-24-7
acetic anhydride

A: 19555-60-3
bis-4H-3,1-benzoxazine-4-one

B: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

...Expand

: 3740-52-1
2-(2-nitrophenyl)acetic acid

: 108-24-7
acetic anhydride

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 108-24-7
acetic anhydride

: 41470-93-3
2-((ethoxycarbonyl)amino)benzoic acid

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 541-41-3
chloroformic acid ethyl ester

: 89-52-1
o-acetylamino-benzoic acid

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With triethylamine In benzene Ambient temperature;

: 82666-35-1
2-[1-Methoxy-eth-(Z)-ylideneamino]-benzoic acid

A: 67-56-1
methanol

B: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
Equilibrium constant;

: 118-92-3
anthranilic acid

: 64-19-7
acetic acid

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With <(chlorosulfinyloxy)methylene>dimethylammonium chloride; triethylamine 1.) CH2Cl2, 0-5 deg C, 10 min, 2.) CH2Cl2, RT, overnight; Yield given. Multistep reaction;
With triphenyl phosphite In pyridine at 150℃; for 0.166667h; microwave irradiation;
With pyridine Reflux;

: 103-84-4
Acetanilid

CO: CO

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
With Tl(OOCCF3)2; magnesium oxide; lithium chloride; palladium dichloride 1)Tl(OOCCF3)2/CF3COOH,r.t.,overnight 2)PdCl2/MgO/LiCl/MeOH,r.t.,overnight; Yield given. Multistep reaction;

: 271-58-9
anthranil

formic acetic anhydride: formic acetic anhydride

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

Conditions

Conditions	Yield
at 100℃;

: 108-24-7
acetic anhydride

N.N'-methyl-di-anthranilic acid: N.N'-methyl-di-anthranilic acid

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 67-56-1
methanol

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 2719-08-6
methyl 2-(acetylamino)benzoate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane for 1h; Product distribution; Ambient temperature; various acylanthraniles; various alcohols; other bases, temperatures and times;	100%
With 1,4-diaza-bicyclo[2.2.2]octane for 1h; Ambient temperature;	100%
With ammonia In methanol for 1h; Ambient temperature;	95%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 100-37-8
2-(Diethylamino)ethanol

: 82679-12-7
β-(diethylamino)ethyl o-acetamidobenzoate

Conditions

Conditions	Yield
at 100℃; for 1h;	100%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 6665-97-0
1,3-dimethoxy-2-nitrobenzene

: 52898-79-0
3-(2,6-dimethoxyphenyl)-2-methyl-3H-quinazolin-4-one

Conditions

Conditions	Yield
With acetic acid Heating / reflux;	100%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 1898-06-2
3-amino-2-methyl-4-oxoquinazoline

Conditions

Conditions	Yield
Stage #1: 2-methyl-4-oxo-3,1-benzoxazine With hydrazine hydrate In tetrahydrofuran Stage #2: With sodium hydroxide In tetrahydrofuran; water	99%
Stage #1: 2-methyl-4-oxo-3,1-benzoxazine In ethanol at 20℃; for 0.0833333h; Stage #2: With hydrazine hydrate In ethanol at 100℃; for 6h;	99.54%
With pyridine; hydrazine hydrate for 5h; Heating;	82%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 75-65-0
tert-butyl alcohol

: 19849-22-0
tert-butyl o-acetamidobenzoate

Conditions

Conditions	Yield
With sodium t-butanolate for 3h; Heating;	99%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 143-27-1
hexadecylamine

: 3-hexadecyl-2-methylquinazolin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: 2-methyl-4-oxo-3,1-benzoxazine In ethanol at 20℃; for 0.0833333h; Stage #2: hexadecylamine In ethanol at 100℃; for 6h;	98.1%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 3544-24-9
3-Aminobenzamide

: 24295-53-2
3-(3-carbamoylphenyl)-2-methylquinazolin-4(3H)-one

Conditions

Conditions	Yield
With acetic acid Reflux;	98%
In acetic acid Reflux;

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 64-17-5
ethanol

: 20628-20-0
ethyl N-acetylanthranilate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane for 0.166667h; Inert atmosphere; Sealed tube; Microwave irradiation; Heating;	97%
In ethanol for 1h; Ambient temperature;	90%
With sodium methylate for 1h; Ambient temperature;	88%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 91-59-8
naphthalen-2-ylamine

: 4207-03-8
2-methyl-3-(naphthalen-2-yl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: 2-methyl-4-oxo-3,1-benzoxazine In ethanol at 20℃; for 0.0833333h; Stage #2: naphthalen-2-ylamine In ethanol at 100℃; for 6h;	96.44%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 108-95-2
phenol

: 33163-29-0
phenyl 2-acetamidobenzoate

Conditions

Conditions	Yield
With sodium hydroxide for 3h; Heating;	96%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 106-40-1
4-bromo-aniline

: 1788-95-0
3-(4-bromophenyl)-2-methylquinazolin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: 2-methyl-4-oxo-3,1-benzoxazine In ethanol at 20℃; for 0.0833333h; Stage #2: 4-bromo-aniline In ethanol at 100℃; for 6h;	95.13%
at 80℃; for 2.5h; Molecular sieve; Green chemistry;	53%
Heating;	30%
With trichlorophosphate Heating;

: 80-05-7
BPA

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 32001-92-6
2,2-Bis-<4-(2-N-acetylamino-benzoyloxy)-phenyl>-propan

Conditions

Conditions	Yield
With pyridine for 3h; Heating;	95%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 105-56-6
ethyl 2-cyanoacetate

: 1026672-88-7
3-(2-Acetylamino-phenyl)-2-cyano-3-oxo-propionic acid ethyl ester

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol 1.) r.t., 1 h, 2.) r.t., 2 h;	95%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 10073-89-9
2-methyl-6-nitro-4H-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
With sulfuric acid; nitric acid Heating;	95%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 106-47-8
4-chloro-aniline

: 1788-93-8
3-(4-chlorophenyl)-2-methyl-3H-quinazolin-4-one

Conditions

Conditions	Yield
Stage #1: 2-methyl-4-oxo-3,1-benzoxazine In ethanol at 20℃; for 0.0833333h; Stage #2: 4-chloro-aniline In ethanol at 100℃; for 6h;	94.78%
With sodium acetate In acetic acid for 5h; Reflux;	89%
at 80℃; for 2h; Molecular sieve; Green chemistry;	89%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 629-11-8
1,6-hexanediol

: 82679-11-6
hexamethylene bis(o-acetamidobenzoate)

Conditions

Conditions	Yield
With pyridine for 0.5h; Ambient temperature;	94%

: 6298-19-7
2-chloro-3-aminopyridine

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 20091-81-0
2-methyl-3-(2'-chloropyrid-3'-yl)quinazolin-4-one

Conditions

Conditions	Yield
at 140℃; for 2h;	92%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 123-30-8
4-amino-phenol

: 1789-09-9
1-(2-methyl-4-oxo-4H-quinazolin-3-yl)-4-hydroxybenzene

Conditions

Conditions	Yield
With acetic acid for 4h; Reflux;	92%
In N,N-dimethyl-formamide at 140℃; for 4h;	79%
In N,N-dimethyl-formamide for 2h; Heating;	71%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 56982-15-1
2-methyl-3-(3-carboxyphenyl)-quinazolin-4(3H)-one

Conditions

Conditions	Yield
With methanol vapor at 25℃; for 15h;	92%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 99-05-8
meta-aminobenzoic acid

: 56982-15-1
2-methyl-3-(3-carboxyphenyl)-quinazolin-4(3H)-one

Conditions

Conditions	Yield
With acetic acid for 5h; Reflux;	92%
With acetic acid for 5h; Reflux;	92%
In acetic acid Reflux;
With acetic acid for 5h; Reflux;

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 1769-24-0
2-methyl-4-quinazolone

Conditions

Conditions	Yield
With ammonium hydroxide In ethanol at 20℃; for 48h; Substitution;	91%
With ammonia In ethanol for 2h; Reflux;	85%
With formamide for 3h; Heating;	85%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine

: 854-08-0
3-[2-(3,4-dimethoxy phenyl)-ethyl]-2-methyl-3H-quinazoline-4-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Reflux; Inert atmosphere;	90%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 61-54-1
tryptamine

: 103970-47-4
3-[2-(3-indolyl)ethyl]-2-methyl-4(3H)-quinazolinone

Conditions

Conditions	Yield
at 205℃; for 1.5h;	89%
With acetic acid for 5h; Reflux;

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 62-53-3
aniline

: 2385-23-1
2-Methyl-3-phenyl-4(3H)-quinazolinone

Conditions

Conditions	Yield
With pyridine; phosphorus pentoxide at 90 - 95℃; for 26h;	89%
With pyridine; phosphorus pentoxide at 90 - 95℃; for 26h;	89%
at 80℃; for 3h; Molecular sieve; Green chemistry;	74%

: 525-76-8
2-methyl-4-oxo-3,1-benzoxazine

: 33809-77-7
2-acetamidobenzamide

Conditions

Conditions	Yield
With ammonium hydroxide In benzene at 23℃; for 1h; Product distribution;	89%
With ammonium hydroxide In tetrahydrofuran at 20℃; for 0.25h;
With ammonia In water at 20℃; for 4h;

2-Methyl-3,1-benzoxaza-4-one Specification

The CAS register number of 2-Methyl-3,1-benzoxaza-4-one is 525-76-8. It also can be called as 4H-3,1-Benzoxazin-4-one, 2-methyl- and the IUPAC name about this chemical is 2-methyl-3,1-benzoxazin-4-one. The molecular formula about this chemical is C₉H₇NO₂ and the molecular weight is 161.16. It belongs to the following product categories, such as API intermediates; Benzoxazines; Building Blocks; Heterocyclic Building Blocks and so on.

Physical properties about 2-Methyl-3,1-benzoxaza-4-one are: (1)ACD/LogP: 1.04; (2)ACD/LogD (pH 5.5): 1.04; (3)ACD/LogD (pH 7.4): 1.04; (4)ACD/BCF (pH 5.5): 3.65; (5)ACD/BCF (pH 7.4): 3.66; (6)ACD/KOC (pH 5.5): 87.95; (7)ACD/KOC (pH 7.4): 88.14; (8)#H bond acceptors: 3; (9)Polar Surface Area: 38.66Å²; (10)Index of Refraction: 1.604; (11)Molar Refractivity: 44.03 cm³; (12)Molar Volume: 127.9 cm³; (13)Polarizability: 17.45x10^-24cm³; (14)Surface Tension: 43.8 dyne/cm; (15)Flash Point: 144.7 °C; (16)Enthalpy of Vaporization: 52.24 kJ/mol; (17)Boiling Point: 283.5 °C at 760 mmHg; (18)Vapour Pressure: 0.00316 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-acetylamino-benzoic acid. This reaction will need reagent Ac₂O. The reaction time is 1 hour(s) with reaction temperature of 130 ℃. The yield is about 90%.

Uses of 2-Methyl-3,1-benzoxaza-4-one: it can be used to produce 2-acetylamino-benzoic acid methyl ester with methanol at ambient temperature. This reaction is a kind of Bromination. It will need reagent 1,4-diazabicyclo<2.2.2>octane (Dabco) with reaction time of 1 hours. The yield is about 100%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2O\C(=N/c1c2cccc1)C
(2)InChI: InChI=1/C9H7NO2/c1-6-10-8-5-3-2-4-7(8)9(11)12-6/h2-5H,1H3
(3)InChIKey: WMQSKECCMQRJRX-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C9H7NO2/c1-6-10-8-5-3-2-4-7(8)9(11)12-6/h2-5H,1H3
(5)Std. InChIKey: WMQSKECCMQRJRX-UHFFFAOYSA-N

Product Name

2-METHYL-3,1-BENZOXAZA-4-ONE

Synthetic route

2-Methyl-3,1-benzoxaza-4-one Specification

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