Product Name

  • Name

    2-Amino-4-methylbenzoic acid

  • EINECS 218-976-3
  • CAS No. 2305-36-4
  • Article Data26
  • CAS DataBase
  • Density 1.254 g/cm3
  • Solubility
  • Melting Point 174-177 ºC
  • Formula C8H9 N O2
  • Boiling Point 329.8 °C at 760 mmHg
  • Molecular Weight 151.165
  • Flash Point 153.3 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety S26;S37/39
  • Risk Codes R36/37/38   
  • Molecular Structure Molecular Structure of 2305-36-4 (2-Amino-4-methylbenzoic acid)
  • Hazard Symbols
  • Synonyms p-Toluicacid, 2-amino- (6CI,7CI,8CI); 2-Amino-4-methylbenzoic acid; 2-Amino-p-toluicacid; 4-Methylanthranilic acid; NSC 39155
  • PSA 63.32000
  • LogP 1.85660

Synthetic route

4-methyl-2-nitrobenzoic acid
27329-27-7

4-methyl-2-nitrobenzoic acid

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr;100%
With platinum (IV) oxide; hydrogen In methanol for 3h;98%
With palladium on activated carbon; hydrogen In ethyl acetate at 20℃; for 14h; Saturated gas;95%
With hydrogenchloride; tin
With iron(III) chloride; hydrazine hydrate; sodium hydroxide In water at 70℃; for 1h; Temperature;
2-bromo-4-methylbenzoic acid
7697-27-0

2-bromo-4-methylbenzoic acid

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 12h;87%
mononitro-p-xylene
89-58-7

mononitro-p-xylene

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With selenium; nitrobenzene; sodium hydroxide In methanol; water; dimethyl sulfoxide at 90℃; for 5h; Inert atmosphere;70%
2-bromo-5-methylaniline
53078-85-6

2-bromo-5-methylaniline

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With tert.-butyl lithium In hydrogenchloride; diethyl ether; water; pentane59%
6-methylindoline-2,3-dione
1128-47-8

6-methylindoline-2,3-dione

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide
7-methyl-3-m-tolyl-1H-quinazoline-2,4-dione
33900-96-8

7-methyl-3-m-tolyl-1H-quinazoline-2,4-dione

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With potassium hydroxide
2-amino-4-methylbenzamide
39549-79-6

2-amino-4-methylbenzamide

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With potassium hydroxide
5-methyl-2-cyanoaniline
26830-96-6

5-methyl-2-cyanoaniline

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With potassium hydroxide
methanol
67-56-1

methanol

6-methylindoline-2,3-dione
1128-47-8

6-methylindoline-2,3-dione

A

methyl 4-methylanthranilate
18595-17-0

methyl 4-methylanthranilate

B

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium methylate 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;
6-methylindoline-2,3-dione
1128-47-8

6-methylindoline-2,3-dione

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-2H-3,1-benzoxazin-2,4(1H)-dione
63480-11-5

7-methyl-2H-3,1-benzoxazin-2,4(1H)-dione

acid

acid

A

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

B

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-2H-3,1-benzoxazin-2,4(1H)-dione
63480-11-5

7-methyl-2H-3,1-benzoxazin-2,4(1H)-dione

alkaline solution

alkaline solution

A

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

B

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

hydrogenchloride
7647-01-0

hydrogenchloride

4-methyl-2-nitrobenzoic acid
27329-27-7

4-methyl-2-nitrobenzoic acid

tin

tin

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

4,4'-dimethyl-2,2'-triazenediyl-di-benzonitrile
85167-56-2

4,4'-dimethyl-2,2'-triazenediyl-di-benzonitrile

alkaline solution

alkaline solution

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

4-methyl-2-nitrobenzonitrile
26830-95-5

4-methyl-2-nitrobenzonitrile

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated hydrochloric acid / im Druckrohr
2: tin; hydrochloric acid
View Scheme
2-acetylamino-4-methylbenzoic acid
81115-52-8

2-acetylamino-4-methylbenzoic acid

aniline
62-53-3

aniline

A

Acetanilid
103-84-4

Acetanilid

B

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
In toluene at 20 - 110℃; for 10h;A 0.12 g
B 0.1 g
methyl 4-methylanthranilate
18595-17-0

methyl 4-methylanthranilate

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; ethanol; water at 50℃; for 3h; Inert atmosphere;
4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

methyl 4-methylanthranilate
18595-17-0

methyl 4-methylanthranilate

Conditions
ConditionsYield
In diethyl ether for 1h; Inert atmosphere;100%
urea
57-13-6

urea

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-quinazoline-2,4(1H,3H)-dione
62484-15-5

7-methyl-quinazoline-2,4(1H,3H)-dione

Conditions
ConditionsYield
at 160℃; for 10h;99%
at 180℃; for 2h;85%
Stage #1: urea; 4-methylanthranilic acid at 160℃; for 6h;
Stage #2: With water at 100℃; for 0.0833333h;
41%
triphosgene

triphosgene

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-2H-3,1-benzoxazin-2,4(1H)-dione
63480-11-5

7-methyl-2H-3,1-benzoxazin-2,4(1H)-dione

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate at 20℃; for 0.25h;99%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-3-phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

7-methyl-3-phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With triethylamine In ethanol for 3h; Reflux;97%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-2H-3,1-benzoxazin-2,4(1H)-dione
63480-11-5

7-methyl-2H-3,1-benzoxazin-2,4(1H)-dione

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 5h; Inert atmosphere; Large scale;93%
In tetrahydrofuran at 20℃;
In tetrahydrofuran at -5℃; for 5h;
Stage #1: 4-methylanthranilic acid In 1,4-dioxane Reflux;
Stage #2: bis(trichloromethyl) carbonate In 1,4-dioxane Reflux;
1,1-dichloro-2-nitro ethylene
6061-04-7

1,1-dichloro-2-nitro ethylene

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

4-methyl-2-(2-nitroacetamido)benzoic acid

4-methyl-2-(2-nitroacetamido)benzoic acid

Conditions
ConditionsYield
In water at 50℃; for 5h; Green chemistry;92%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

C13H16N2O
1309763-88-9

C13H16N2O

Conditions
ConditionsYield
at 150℃; for 2h; Neat (no solvent);90%
4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

2-benzoylamino-4-methyl-benzoic acid

2-benzoylamino-4-methyl-benzoic acid

Conditions
ConditionsYield
With triethylamine at 20℃;90%
tetrahydrobetacarboline
16502-01-5

tetrahydrobetacarboline

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

(2-amino-4-methylphenyl)(1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)methanone

(2-amino-4-methylphenyl)(1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)methanone

Conditions
ConditionsYield
With triethylamine; HATU90%
methanol
67-56-1

methanol

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

methyl 4-methylanthranilate
18595-17-0

methyl 4-methylanthranilate

Conditions
ConditionsYield
With thionyl chloride89%
With sulfuric acid for 48h; Reflux;84%
Stage #1: methanol; 4-methylanthranilic acid With sulfuric acid at 0℃; for 16h; Reflux;
Stage #2: With sodium hydrogencarbonate In water
82%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

benzylamine
100-46-9

benzylamine

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

3-benzyl-2-(4-chlorophenyl)-7-methylquinazolin-4(3H)-one

3-benzyl-2-(4-chlorophenyl)-7-methylquinazolin-4(3H)-one

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In ethyl acetate at 20℃; for 5h;89%
4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

(2-amino-4-methylphenyl)methanol
81335-87-7

(2-amino-4-methylphenyl)methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h;87%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 45℃;70%
With sulfuric acid at 25℃; durch elektrolytische Reduktion an einer Bleikathode;
chloroacetyl chloride
79-04-9

chloroacetyl chloride

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

2-(2-chloroacetamido)-4-methylbenzoic acid
65077-83-0

2-(2-chloroacetamido)-4-methylbenzoic acid

Conditions
ConditionsYield
Stage #1: 4-methylanthranilic acid With potassium carbonate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: chloroacetyl chloride at 0 - 20℃;
87%
In benzene for 0.5h; Heating;
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

1-isocyanato-3-trifluoromethyl-benzene
329-01-1

1-isocyanato-3-trifluoromethyl-benzene

4-methyl-2-[3-(3-trifluoromethyl-phenyl)-ureido]-benzoic acid

4-methyl-2-[3-(3-trifluoromethyl-phenyl)-ureido]-benzoic acid

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;87%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

C15H18N2O
1309763-87-8

C15H18N2O

Conditions
ConditionsYield
at 150℃; for 2h; Neat (no solvent);87%
1,1,3,3-tetramethylbutane isonitrile
14542-93-9

1,1,3,3-tetramethylbutane isonitrile

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

C17H24N2O
1309763-89-0

C17H24N2O

Conditions
ConditionsYield
at 150℃; for 2h; Neat (no solvent);86%
4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

Bis-(2-carboxy-5-methyl-phenyl)-diselenid

Bis-(2-carboxy-5-methyl-phenyl)-diselenid

Conditions
ConditionsYield
Stage #1: 4-methylanthranilic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: With sodium diselenide In water at 50℃; for 2.5h;
86%
4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

methyl 4-methylanthranilate
18595-17-0

methyl 4-methylanthranilate

Conditions
ConditionsYield
In methanol85.7%
2-bromo-1-chloro-3-iodobenzene

2-bromo-1-chloro-3-iodobenzene

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

C14H11BrClNO2

C14H11BrClNO2

Conditions
ConditionsYield
With potassium acetate; copper diacetate; copper at 140℃; Inert atmosphere;85%
With potassium acetate; copper diacetate; copper at 140℃; Inert atmosphere;82.2%
C11H15BrClNO

C11H15BrClNO

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

C19H23ClN2O3

C19H23ClN2O3

Conditions
ConditionsYield
With potassium acetate; copper diacetate; copper In water at 20 - 140℃; Inert atmosphere;84.8%
potassium cyanate
590-28-3

potassium cyanate

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-quinazoline-2,4(1H,3H)-dione
62484-15-5

7-methyl-quinazoline-2,4(1H,3H)-dione

Conditions
ConditionsYield
Stage #1: potassium cyanate; 4-methylanthranilic acid With acetic acid In water at 20℃; for 0.5h;
Stage #2: With sodium hydroxide In water at 50℃;
83%
thiourea
17356-08-0

thiourea

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

C9H8N2OS
1463501-49-6

C9H8N2OS

Conditions
ConditionsYield
at 40℃; for 2.5h; Inert atmosphere; Ionic liquid;83%
4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-quinazolin-4(3H)-one
75844-40-5

7-methyl-quinazolin-4(3H)-one

Conditions
ConditionsYield
at 140℃;82%
at 150℃; for 1h; Temperature; Microwave irradiation;63%
at 120 - 130℃;
benzoyl chloride
98-88-4

benzoyl chloride

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

7-methyl-2-phenyl-4H-benzo[d][1,3]oxazin-4-one

7-methyl-2-phenyl-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 3h; Inert atmosphere;82%
With pyridine
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

4-methylanthranilic acid
2305-36-4

4-methylanthranilic 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
82%
bis-silyl-1,3-dienediolate

bis-silyl-1,3-dienediolate

benzaldehyde
100-52-7

benzaldehyde

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

C21H21NO4

C21H21NO4

Conditions
ConditionsYield
Stage #1: bis-silyl-1,3-dienediolate; benzaldehyde; 4-methylanthranilic acid With water; samarium(III) trifluoromethanesulfonate In dichloromethane; tert-butyl alcohol at -20℃; Inert atmosphere;
Stage #2: With 2,4-dinitrobenzenesulfonic acid In dichloromethane; tert-butyl alcohol at -20℃; Inert atmosphere; diastereoselective reaction;
80%
4-chloropyrido<3,2-d>pyrimidine
51674-77-2

4-chloropyrido<3,2-d>pyrimidine

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

C14H12N4O
1304513-65-2

C14H12N4O

Conditions
ConditionsYield
With hydrogenchloride; water In isopropyl alcohol at 140℃; for 1h; Microwave irradiation;79%
methyllithium
917-54-4

methyllithium

4-methylanthranilic acid
2305-36-4

4-methylanthranilic acid

2’-amino-4’-methylacetophenone
122710-21-8

2’-amino-4’-methylacetophenone

Conditions
ConditionsYield
In 1,2-dimethoxyethane; monoethylene glycol diethyl ether at 0℃; for 2h; Inert atmosphere;79%

2-Amino-4-Methylbenzoic Acid Chemical Properties

Molecular Formula: C8H9NO2
Molar mass:151.16256 g/mol
Structure of 2-Amino-4-methylbenzoic acid(2305-36-4):
                                       
Synonyms of2-Amino-4-methylbenzoic acid(2305-36-4):Benzoic acid, 2-amino-4-methyl-;4-METHYLANTHRANILIC ACID;Benzoic acid, 2-amino-4-methyl- (9CI)
Melting point:174-177 oC
Density:1.254 g/cm3
Flash Point:153.3 °C
Boiling Point: 329.8 °C at 760 mmHg

2-Amino-4-Methylbenzoic Acid Safety Profile

Hazard Codes:Xi
Risk Statements:
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin 
Safety Statements:  
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
37:  Wear suitable gloves
39:  Wear eye/face protection

2-Amino-4-Methylbenzoic Acid Specification

Product Categories of 2-Amino-4-methylbenzoic acid(2305-36-4):CARBOXYLICACID;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Carboxylic Acids;Phenyls & Phenyl-Het;Benzoic acid;Phenyls & Phenyl-Het;API intermediates
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