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525-76-8

Basic Information
CAS No.: 525-76-8
Name: 4H-3,1-Benzoxazin-4-one,2-methyl-
Molecular Structure:
Molecular Structure of 525-76-8 (4H-3,1-Benzoxazin-4-one,2-methyl-)
Formula: C9H7NO2
Molecular Weight: 161.16
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;
EINECS: 208-381-7
Density: 1.25 g/cm3
Melting Point: 79-82 °C(lit.)
Boiling Point: 283.5 °C at 760 mmHg
Flash Point: 144.7 °C
Solubility:
Appearance:
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information:
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
ConditionsYield
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
ConditionsYield
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%
89-52-1

o-acetylamino-benzoic acid

525-76-8

2-methyl-4-oxo-3,1-benzoxazine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
101646-18-8

2-carboxymalonanilic acid ethyl ester

525-76-8

2-methyl-4-oxo-3,1-benzoxazine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In xylene Heating;62%
108-24-7

acetic anhydride

118-92-3

anthranilic acid

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
ConditionsYield
at 150℃; for 0.333333h; Niementowski quinazoline reaction; Microwave irradiation; Sealed tube;A 60%
B n/a
C 20%
95-20-5

2-methyl-1H-indole

525-76-8

2-methyl-4-oxo-3,1-benzoxazine

Conditions
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

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
ConditionsYield
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
ConditionsYield
Equilibrium constant;
118-92-3

anthranilic acid

64-19-7

acetic acid

525-76-8

2-methyl-4-oxo-3,1-benzoxazine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;
525-76-8

2-methyl-4-oxo-3,1-benzoxazine

32001-92-6

2,2-Bis-<4-(2-N-acetylamino-benzoyloxy)-phenyl>-propan

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;
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    4H-3,1-Benzoxazin-4-one,2-methyl-

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    High purity 525-76-8 2-METHYL-3,1-BENZOXAZA-4-ONE

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    525-76-8 4H-3,1-Benzoxazin-4-one,2-methyl-

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    CHemwill -- 2-Methyl-3,1-benzoxazin-4-one

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    English name: 2-METHYL-3,1-BENZOXAZA-4-ONE English Synonyms: TIMTEC-BB SBB000135; 2-methyl-4h-1-benzoxazin-4-one; 2-METHYL-3,1-BENZOXAZA-4-ONE; 2-METHYL-4H-3,1-BENZOXAZIN-4- ONE;ACETYL ANTHRANIL;ACETANTHRANIL;AURORA KA-3785;2-2-METHYL-

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    1.A strong technical force and advanced processing equipments. The quality of the products has been strictly inspected and all kinds of index have reached or exceeded domestic and international standards.2. Now we have established long-term stable re

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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