Product Name

  • Name

    3-Methylanthranilic acid

  • EINECS 224-505-2
  • CAS No. 4389-45-1
  • Article Data51
  • CAS DataBase
  • Density 1.254 g/cm3
  • Solubility
  • Melting Point 174-177 °C(lit.)
  • Formula C8H9NO2
  • Boiling Point 315.1 °C at 760 mmHg
  • Molecular Weight 151.165
  • Flash Point 144.4 °C
  • Transport Information
  • Appearance pink to grey-brown crystalline powder
  • Safety 24/25-36-26
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 4389-45-1 (3-Methylanthranilic acid)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms m-Toluicacid, 2-amino- (6CI,7CI,8CI);2-Amino-3-methylbenzoic acid;2-Amino-m-toluicacid;3-Methyl-2-aminobenzoic acid;
  • PSA 63.32000
  • LogP 1.85660

Synthetic route

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr;99%
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 25857.4 Torr;99%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr;99%
2-chloro-3-methylbenzoic acid
15068-35-6

2-chloro-3-methylbenzoic acid

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With ammonia; sodium carbonate; copper(l) chloride In dimethyl sulfoxide at 130 - 150℃; for 5h;93.1%
7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide90%
With potassium chloride; dihydrogen peroxide; sodium hydroxide In water at 0 - 20℃; for 2.25h;80%
60%
3-methyl-2-nitrobenzoyl chloride
50424-93-6

3-methyl-2-nitrobenzoyl chloride

methyl 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilate
83325-79-5

methyl 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilate

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

methyl 3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilate
83334-85-4

methyl 3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilate

Conditions
ConditionsYield
With lithium hydroxide In water; benzeneA n/a
B 61%
8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione
857203-66-8

8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With potassium hydroxide
methanol
67-56-1

methanol

7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

A

methyl 2-amino-3-methylbenzoate
22223-49-0

methyl 2-amino-3-methylbenzoate

B

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium methylate 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;
7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

butan-1-ol
71-36-3

butan-1-ol

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

3-Methylanthranilsaeure-n-butylester
79101-84-1

3-Methylanthranilsaeure-n-butylester

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydride 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;
3-methyl-2-nitrobenzonitrile
1885-77-4

3-methyl-2-nitrobenzonitrile

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
(i) H2, Pd-C, (ii) aq. NaOH; Multistep reaction;
3-methyl-2-nitrobenzoyl chloride
50424-93-6

3-methyl-2-nitrobenzoyl chloride

3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilic acid
78877-00-6

3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilic acid

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilic acid
83325-80-8

3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilic acid

Conditions
ConditionsYield
With lithium hydroxide In water; benzene Title compound not separated from byproducts;
7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

alkali

alkali

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione
857203-66-8

8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione

aqueous NaOH

aqueous NaOH

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

o-toluidine
95-53-4

o-toluidine

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

ammonia
7664-41-7

ammonia

iron(II) sulfate

iron(II) sulfate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

hydrogenchloride
7647-01-0

hydrogenchloride

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

tin

tin

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

ethanol
64-17-5

ethanol

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

zinc dust

zinc dust

alkali

alkali

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

hydrogenchloride
7647-01-0

hydrogenchloride

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

tin

tin

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

o-toluidine
95-53-4

o-toluidine

3-methyl-2-nitrobenzonitrile
1885-77-4

3-methyl-2-nitrobenzonitrile

alcoholic ammonium sulfide

alcoholic ammonium sulfide

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
at 100℃; im Rohr;
(2-amino-3-methyl-phenyl)-glyoxylic acid
859770-30-2

(2-amino-3-methyl-phenyl)-glyoxylic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

diluted NaOH-solution

diluted NaOH-solution

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

(2-amino-3-methyl-phenyl)-glyoxylic acid
859770-30-2

(2-amino-3-methyl-phenyl)-glyoxylic acid

sodium perborate

sodium perborate

diluted NaOH-solution

diluted NaOH-solution

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

m-Toluic acid
99-04-7

m-Toluic acid

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / HNO3 / 1 h / -10 °C
2: 99 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr
View Scheme
Multi-step reaction with 2 steps
1: fuming nitric acid
2: tin; hydrochloric acid
View Scheme
Multi-step reaction with 2 steps
1: fuming nitric acid
2: tin; hydrochloric acid
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / -10 - -5 °C
2: palladium 10% on activated carbon; hydrogen / methanol
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / 1 h / -10 °C
2: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 50 °C
View Scheme
m-Toluic acid
99-04-7

m-Toluic acid

aqueous ammonium polysulfide

aqueous ammonium polysulfide

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 49 percent / fuming nitric acid / 1 h / -10 °C
2: 89 percent / tin, hydrochloric acid / ethanol / 1.5 h / 70 °C
View Scheme
2-(hydroxyimino)-N-(2-methylphenyl)acetamide
1132-03-2

2-(hydroxyimino)-N-(2-methylphenyl)acetamide

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86percent H2SO4 / 1) 55 deg C, 10 min, 2) 75 deg C, 30 min
2: H2O2, NaOH
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / 0.33 h / 80 °C
2: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sulfuric acid / 60 - 80 °C
2.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
2.2: pH 4
View Scheme
3-Methylbenzonitrile
620-22-4

3-Methylbenzonitrile

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: concentrated hydrochloric acid / im Druckrohr
2: fuming nitric acid
3: tin; hydrochloric acid
View Scheme
3-Methyl-2-nitrobenzenecarboxamide
60310-07-8

3-Methyl-2-nitrobenzenecarboxamide

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3
2: (i) H2, Pd-C, (ii) aq. NaOH
View Scheme
o-toluidine
95-53-4

o-toluidine

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium sulfate / water / 40 °C
1.2: Reflux
2.1: sulfuric acid / 0.33 h / 80 °C
3.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium sulfate / water / 40 °C
1.2: 0.17 h / Reflux
2.1: sulfuric acid / 60 - 80 °C
3.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
3.2: pH 4
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 55 °C
2: sulfuric acid / neat (no solvent) / 55 - 80 °C
3: sodium hydroxide; dihydrogen peroxide; potassium chloride / water / 2.25 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 0.17 h / Reflux
2: sulfuric acid / 0.83 h / 70 - 80 °C
3: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1: hydroxylamine hydrochloride; sodium sulfate; hydrogenchloride / water / 12 h / 55 °C / Inert atmosphere
2: sulfuric acid / 0.67 h / Heating; Inert atmosphere
3: dihydrogen peroxide; sodium hydroxide / water / 5.5 h / 80 °C / Inert atmosphere
View Scheme
3-methyl-DL-kynurenine
1446522-57-1

3-methyl-DL-kynurenine

A

L-alanin
56-41-7

L-alanin

B

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With Pseudomonas fluorescens kynureninase In aq. phosphate buffer at 37℃; pH=8; Kinetics; Enzymatic reaction;
ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate
582319-05-9

ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / water / 2 h / 55 - 60 °C
2: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice
3: hydrogenchloride / water / 4 h / Reflux
4: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction
View Scheme
ethyl 7-methylindole-3-(3-acetamido-3-carboethoxy)butanoate

ethyl 7-methylindole-3-(3-acetamido-3-carboethoxy)butanoate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice
2: hydrogenchloride / water / 4 h / Reflux
3: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction
View Scheme
ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(2-formamido-3-methylphenyl)pentanoate
1446522-63-9

ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(2-formamido-3-methylphenyl)pentanoate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 4 h / Reflux
2: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction
View Scheme
methyl 2-amino-3-methylbenzoate
22223-49-0

methyl 2-amino-3-methylbenzoate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; ethanol; water at 50℃; for 3h; Inert atmosphere;
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-3-methylbenzyl alcohol
57772-50-6

2-amino-3-methylbenzyl alcohol

Conditions
ConditionsYield
Stage #1: 3-methylantranilic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;
Stage #2: With water; sodium hydroxide In tetrahydrofuran
100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h;97%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-5-bromo-3-methylbenzoic acid
206548-13-2

2-amino-5-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1h;100%
With bromine; acetic acid at 20 - 25℃;97%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 70 - 80℃; for 0.5h;95.6%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

methyl iodide
74-88-4

methyl iodide

methyl 2-amino-3-methylbenzoate
22223-49-0

methyl 2-amino-3-methylbenzoate

Conditions
ConditionsYield
Stage #1: 3-methylantranilic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.666667h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;
100%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 18.5h;92%
Stage #1: 3-methylantranilic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide for 24h;
77%
Stage #1: 3-methylantranilic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 24h;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;
3-carboxyphthalic anhydride
3786-39-8

3-carboxyphthalic anhydride

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
at 150℃; for 12h;100%
6-[(R)-5-(3-amino-propyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one
1221280-89-2

6-[(R)-5-(3-amino-propyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-4-methyl-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-yl]-propyl}-benzamide

2-amino-4-methyl-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-yl]-propyl}-benzamide

Conditions
ConditionsYield
100%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-5-chloro-3-methylbenzoic acid
20776-67-4

2-amino-5-chloro-3-methylbenzoic acid

Conditions
ConditionsYield
With chlorine In 1,2-dichloro-ethane at 50℃; for 3h; Solvent;98.1%
With N-chloro-succinimide In N,N-dimethyl-formamide at 70 - 80℃; for 0.5h;97.8%
With N-chloro-succinimide In N,N-dimethyl-formamide at 75℃;91%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

2-<(2-carboxyphenyl)amino>-3-methylbenzoic acid
80841-45-8

2-<(2-carboxyphenyl)amino>-3-methylbenzoic acid

Conditions
ConditionsYield
With copper; potassium carbonate; copper(I) bromide In various solvent(s) at 160℃; for 0.5h;98%
piperidine
110-89-4

piperidine

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

(2-amino-3-methylphenyl)(piperidin-1-yl)methanone

(2-amino-3-methylphenyl)(piperidin-1-yl)methanone

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 16h;98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

4-Chlorophenylsulfonyl isocyanate
5769-15-3

4-Chlorophenylsulfonyl isocyanate

3-(4-chlorobenzenesulfonyl)-8-methyl-2,4(1H,3H)-quinazolinedione

3-(4-chlorobenzenesulfonyl)-8-methyl-2,4(1H,3H)-quinazolinedione

Conditions
ConditionsYield
98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

C17H15NO4
698393-13-4

C17H15NO4

Conditions
ConditionsYield
at 110℃; for 16h; Inert atmosphere; neat (no solvent);98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-3-methylbenzamide
1885-32-1

2-amino-3-methylbenzamide

Conditions
ConditionsYield
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere;
Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide
98%
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere;
Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 16h; Inert atmosphere;
98%
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere;
Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 16h; Inert atmosphere;
98%
p-chlorophenyl isoselenocyanate
14223-48-4

p-chlorophenyl isoselenocyanate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-(4-chlorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

2-(4-chlorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃; for 4.5h;98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-5-iodo-3-methylbenzoic acid
108857-24-5

2-amino-5-iodo-3-methylbenzoic acid

Conditions
ConditionsYield
With dipotassium peroxodisulfate; iodine In tetrachloromethane at 77℃; for 6h;97.7%
With N-iodo-succinimide In N,N-dimethyl-formamide at 20 - 80℃; for 2h;97%
With N-iodo-succinimide In N,N-dimethyl-formamide at 75℃; for 1h; Inert atmosphere;96%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

6,6'-dimethyl-1,1'-biphenyl-2,2'-dicarboxylic acid
57024-47-2, 108146-85-6, 19634-85-6

6,6'-dimethyl-1,1'-biphenyl-2,2'-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: 3-methylantranilic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #2: With copper(I) In water
97%
With Cu(I)-salt; sodium nitrite78%
Stage #1: 3-methylantranilic acid With sodium hydroxide; sodium nitrite at 0℃; for 0.5h;
Stage #2: With hydroxyammonium sulfate; copper(II) sulfate In water
72%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

2′-iodo-[1,1′-biphenyl]-2-yl benzoate

2′-iodo-[1,1′-biphenyl]-2-yl benzoate

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; sodium carbonate In 1,4-dioxane at 95℃; for 17h; Molecular sieve; Green chemistry;97%
phosgene
75-44-5

phosgene

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

6-methylisatoic anhydride
66176-17-8

6-methylisatoic anhydride

Conditions
ConditionsYield
In 1,4-dioxane; benzene Ambient temperature;96%
With sodium hydrogencarbonate In toluene at 0 - 20℃; for 0.25h;86%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

α,α-diphenylsuccinic acid anhydride
14702-32-0

α,α-diphenylsuccinic acid anhydride

2-(2,5-dioxo-3,3-diphenylpyrrolidin-1-yl)-3-methylbenzoic acid
297757-12-1, 297757-33-6, 297757-34-7

2-(2,5-dioxo-3,3-diphenylpyrrolidin-1-yl)-3-methylbenzoic acid

Conditions
ConditionsYield
at 150℃; for 12h; Condensation;96%
at 150℃; neat (no solvent, solid phase);
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

formamidine acetic acid
3473-63-0

formamidine acetic acid

8-methyl-4-quinazolinone

8-methyl-4-quinazolinone

Conditions
ConditionsYield
In formamide at 160℃; for 12h;96%
With formamide at 160℃;96%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

1-fluoro-4-isoselenocyanatobenzene
154592-60-6

1-fluoro-4-isoselenocyanatobenzene

2-(4-fluorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

2-(4-fluorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃; for 4.5h;96%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

2-cyclohexyl-8-methyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

2-cyclohexyl-8-methyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
With acetic acid In ethanol for 6h; Reflux;96%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

6-methylisatoic anhydride
66176-17-8

6-methylisatoic anhydride

Conditions
ConditionsYield
In 1,4-dioxane for 6.5h; Reflux;95%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane94%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane94%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

1,2-cis-cyclohexanedicarboxylic anhydride
13149-00-3

1,2-cis-cyclohexanedicarboxylic anhydride

C16H17NO4
1185155-84-3

C16H17NO4

Conditions
ConditionsYield
at 110℃; for 10h; Inert atmosphere; neat (no solvent);95%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

4-bromophenyl isoselenocyanate
147695-56-5

4-bromophenyl isoselenocyanate

2-(4-bromophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

2-(4-bromophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃; for 4.5h;95%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-5-bromo-3-methylbenzoic acid hydrobromide

2-amino-5-bromo-3-methylbenzoic acid hydrobromide

Conditions
ConditionsYield
With bromine; acetic acid In dichloromethane at 20℃; for 1h;95%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

acetic anhydride
108-24-7

acetic anhydride

2-acetylamino-3-methylbenzoic acid
67081-69-0

2-acetylamino-3-methylbenzoic acid

Conditions
ConditionsYield
for 2h; Reflux;94%
for 2h; Heating;87%
for 1h; Acetylation; Heating;85%
at 60℃; Reflux;
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

6-methylisatoic anhydride
66176-17-8

6-methylisatoic anhydride

Conditions
ConditionsYield
With bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 16.5h;94%
Multi-step reaction with 2 steps
1: triethylamine; dmap / acetonitrile / 2 h / 20 °C
2: 2-chloro-1-methyl-pyridinium iodide / acetonitrile / 0.17 h / 20 °C
View Scheme
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

formamidine acetic acid
3473-63-0

formamidine acetic acid

8-methylquinazolin-4(3H)-one
19181-54-5

8-methylquinazolin-4(3H)-one

Conditions
ConditionsYield
at 180℃; for 3h;94%
4-pentynoic acid
6089-09-4

4-pentynoic acid

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

3a,9-dimethyl-3,3a-dihydro-1H-benzo[d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione
1227624-59-0

3a,9-dimethyl-3,3a-dihydro-1H-benzo[d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione

Conditions
ConditionsYield
With Echavarren's catalyst In 1,1-dichloroethane at 120℃; for 12h; Sealed vial;93%

3-Methylanthranilic acid Chemical Properties

IUPAC Name: 2-Amino-3-methylbenzoic acid
Synonyms of 3-Methylanthranilic acid (CAS NO.4389-45-1): 2-Amino-3-methylbenzoic acid ; 3-Methyl-2-aminobenzoic acid ; Benzoic acid, 2-amino-3-methyl- (9CI) ; m-Toluic acid, 2-amino- (8CI)
CAS NO: 4389-45-1
Molecular Formula: C8H9NO2
Molecular Weight: 151.16
Molecular Structure:

H bond acceptors: 3
H bond donors: 3
Freely Rotating Bonds: 2
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.618
Molar Refractivity: 42.24 cm3
Molar Volume: 120.5 cm3
Surface Tension: 58.2 dyne/cm
Density: 1.254 g/cm3
Flash Point: 144.4 °C
Enthalpy of Vaporization: 58.74 kJ/mol
Boiling Point: 315.1 °C at 760 mmHg
Vapour Pressure: 0.000188 mmHg at 25°C 
Melting Point: 174-177 °C(lit.)
Appearance: pink to grey-brown crystalline powder
Product Categories of 3-Methylanthranilic acid (CAS NO.4389-45-1): CARBOXYLICACID;FINE Chemical & INTERMEDIATES;Amines;blocks;Carboxes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Benzoic acid;Organic acids;Carboxylic Acids;Phenyls & Phenyl-Het

3-Methylanthranilic acid Uses

 3-Methylanthranilic acid (CAS NO.4389-45-1) is used as intermediates in organic synthesis.

3-Methylanthranilic acid Safety Profile

Safety Information about 3-Methylanthranilic acid (CAS NO.4389-45-1):
Hazard Codes: HarmfulXn,Xi
Risk Statements: 22-36/37/38
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25: Avoid contact with skin and eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany: 3
F: 10
Hazard Note: Irritant
HazardClass: IRRITANT

3-Methylanthranilic acid Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Keep container closed when not in use.

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