2486-75-1

Basic information

• Product Name: 4-Amino-2-methylbenzoic acid
• Synonyms: 2-METHYL-4-AMINO-BENZOIC ACID;4-AMINO-2-METHYLBENZOIC ACID;Benzoic acid, 4-amino-2-methyl- (9CI);4-Amino-o-toluic;4-Amino-2-methybenzoic acid;4-amino-2-methylbenozoic acid;4-azanyl-2-methyl-benzoic acid;4-Amino-o-toluic acid, 4-Carboxy-3-methylaniline
• CAS NO: 2486-75-1
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• Product Categories: CARBOXYLICACID;Amino Acids and Derivatives;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Aromatic Amino AcidsCarbonyl Compounds;C8;Carboxylic Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 2486-75-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 160-165 °C
• Boiling Point: 339.5 °C at 760 mmHg
• Flash Point: 159.1 °C
• Appearance: /Solid
• Density: 1.254 g/cm³
• Vapor Pressure: 3.56E-05mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 4.86±0.25(Predicted)
• CAS DataBase Reference: 4-Amino-2-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-2-methylbenzoic acid(2486-75-1)
• EPA Substance Registry System: 4-Amino-2-methylbenzoic acid(2486-75-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 2486-75-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C8H9NO2/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4H,9H2,1H3,(H,10,11)

Synthetic route

2-methyl-4-nitrobenzoic acid (1975-51-5) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol under 12001.2 Torr; Flow reactor;	98%
With hydrogenchloride; tin
With hydrogen; palladium 10% on activated carbon In methanol at 20℃; for 16h;

2-methyl-4-aminobenzonitrile (72115-06-1) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
With water; sodium hydroxide In ethylene glycol at 100℃; for 6h;	95.6%

5-nitro-3H-isobenzofuran-1-one (67081-02-1) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
With phosphorus; hydrogen iodide at 205℃;

hydrogenchloride (7647-01-0) + 2-methyl-4-nitrobenzoic acid (1975-51-5) + tin → 4-amino-2-methylbenzoic acid (2486-75-1)

hydrogenchloride (7647-01-0) + 4-acetylamino-2-methylbenzoic acid (103204-69-9) → 4-amino-2-methylbenzoic acid (2486-75-1)

2-methyl-4-aminobenzaldehyde (61594-81-8) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium formate; formic acid / 3 h / 100 °C 2: water; sodium hydroxide / ethylene glycol / 6 h / 100 °C View Scheme

1-amino-3-methylbenzene (108-44-1) → 4-amino-2-methylbenzoic acid (2486-75-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: trichlorophosphate / 6 h / 0 - 60 °C 2: hydroxylamine hydrochloride; sodium formate; formic acid / 3 h / 100 °C 3: water; sodium hydroxide / ethylene glycol / 6 h / 100 °C View Scheme

4-amino-2-methylbenzoic acid (2486-75-1) + ortho-toluoyl chloride (933-88-0) → 2-methyl-4-(2-methylbenzoylamino)benzoic acid (317374-08-6)

Conditions	Yield
With pyridine In chloroform at 0 - 40℃; for 8h; Reagent/catalyst; Solvent; Temperature;	95.6%

methanol (67-56-1) + 4-amino-2-methylbenzoic acid (2486-75-1) → methyl 4-amino-2-methylbenzoate (6933-47-7)

Conditions	Yield
With hydrogenchloride In water Reflux;	85%

4-amino-2-methylbenzoic acid (2486-75-1) + 2-(4-(8-chloroimidazo[1,2-a]pyrazin-3-yl)-2,3-difluorophenoxyl)propanenitrile → 4-((3-(4-(1-cyanoethoxyl)-2,3-difluorophenyl)imidazo[1,2-a]pyrazin-8-yl)amino)-2-methylbenzoic acid

Conditions	Yield
With acetic acid In acetonitrile at 90℃; for 15h;	80.2%
With acetic acid In acetonitrile at 90℃; for 15h; Inert atmosphere;	80.2%
With acetic acid In acetonitrile at 90℃; for 15h;	80.2%
With acetic acid In acetonitrile at 90℃; for 15h; Inert atmosphere;	560 mg
With acetic acid In acetonitrile at 90℃; for 15h;	560 mg

4-amino-2-methylbenzoic acid (2486-75-1) + N,N-dimethylammonium chloride (506-59-2) → 4-amino-N,N,2-trimethylbenzamide (862470-14-2)

Conditions	Yield
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h; Inert atmosphere;	78%
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h;	78%
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h;	78%
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h;	78%
Stage #1: 4-amino-2-methylbenzoic acid; N,N-dimethylammonium chloride With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 10h; Inert atmosphere;

di-tert-butyl dicarbonate (24424-99-5) + 4-amino-2-methylbenzoic acid (2486-75-1) → 4-[(tert-butoxycarbonyl)amino]-2-methylbenzoic acid (1303931-49-8)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water for 2h;	73%

4-amino-2-methylbenzoic acid (2486-75-1) + 8-chloro-3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazine → 4-((3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl)amino)-2-ethylbenzoic acid

Conditions	Yield
With acetic acid In acetonitrile at 65℃; for 12h;	72.64%

4-amino-2-methylbenzoic acid (2486-75-1) + benzyl alcohol (100-51-6) → 4-(1,2-diphenylethylamino)-2-methylbenzoic acid (1347032-87-4)

Conditions	Yield
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; sealed tube;	70%

ethanol (64-17-5) + 2-(4-hexylphenyl)-2-oxoacetaldehyde (14333-88-1) + 4-amino-2-methylbenzoic acid (2486-75-1) → 4-((1-ethoxy-2-(4-octylphenyl)-2-oxoethyl)amino)-2-methylbenzoic acid

Conditions	Yield
at 20℃;	26%

4-amino-2-methylbenzoic acid (2486-75-1) + benzyl bromide (100-39-0) → 4-Amino-2-methyl-benzoesaeure-benzylester

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	19%

ethanol (64-17-5) + 2-oxo-2-[4-(1-piperidinyl)phenyl]acetaldehyde monohydrate (1171309-72-0) + 4-amino-2-methylbenzoic acid (2486-75-1) → 4-((1-ethoxy-2-oxo-2-(4-(piperidin-1-yl)phenyl)ethyl)amino)-2-methylbenzoic acid

Conditions	Yield
at 20℃;	15%
at 20℃;

ethanol (64-17-5) + 2-(4-hexylphenyl)-2-oxoacetaldehyde (14333-88-1) + 4-amino-2-methylbenzoic acid (2486-75-1) → 4-((1-ethoxy-2-(4-hexylphenyl)-2-oxoethyl)amino)-2-methylbenzoic acid

Conditions	Yield
at 20℃;	12.6%

4-amino-2-methylbenzoic acid (2486-75-1) → 4-hydroxy-2-methylbenzoic acid (578-39-2)

Conditions	Yield
With cis-nitrous acid

4-amino-2-methylbenzoic acid (2486-75-1) → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + 1-amino-3-methylbenzene (108-44-1)

Conditions	Yield
at 200℃;

4-amino-2-methylbenzoic acid (2486-75-1) + acetic anhydride (108-24-7) → 4-acetylamino-2-methylbenzoic acid (103204-69-9)

4-amino-2-methylbenzoic acid (2486-75-1) + N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide (159005-71-7) → 4-Amino-N-{(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-2-methyl-benzamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

4-amino-2-methylbenzoic acid (2486-75-1) + cis-nitrous acid (7782-77-6) → 4-hydroxy-2-methylbenzoic acid (578-39-2)

4-amino-2-methylbenzoic acid (2486-75-1) → 2-methyl-4-nitrobenzoic acid (1975-51-5)

Conditions	Yield
With Streptomyces thioluteus para-aminobenzoate N-oxygenase

C13H13N5O3S (840537-53-3) + 4-amino-2-methylbenzoic acid (2486-75-1) → C20H18N6O3

Conditions	Yield
With 2,6-dimethylpyridine In DMF (N,N-dimethyl-formamide) at 60℃; for 20h;

4-amino-2-methylbenzoic acid (2486-75-1) + 2-amino-benzenethiol (137-07-5) → 4-(benzo[d]thiazol-2-yl)-3-methylaniline

Conditions	Yield
With PPA at 185℃; for 5h;
With polyphosphoric acid at 125℃; for 0.583333h; Microwave irradiation;

N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (1124212-41-4) + 4-amino-2-methylbenzoic acid (2486-75-1) → 3-((4-(4-amino-2-methylbenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (1124213-60-0)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 20℃;
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 20℃; for 2h;

4-amino-2-methylbenzoic acid (2486-75-1) → C16H13NO3 (1314003-50-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C 2: sodium hydrogencarbonate / dichloromethane; toluene; water / 0.75 h / 5 - 20 °C View Scheme

4-amino-2-methylbenzoic acid (2486-75-1) → C31H36N2O4 (1314003-51-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C 2.1: sodium hydrogencarbonate / dichloromethane; toluene; water / 0.75 h / 5 - 20 °C 3.1: sodium hydrogencarbonate / chloroform; water 3.2: 20 h / 58 °C View Scheme

Upstream product

• 67081-02-1 5-nitro-3H-isobenzofuran-1-one 
• 72115-06-1 4-amino-2-methylbenzonitrile 
• 61594-81-8 4-amino-2-methylbenzaldehyde 
• 108-44-1 1-amino-3-methylbenzene 
• 99-51-4 4-nitro-o-xylene 
• 95-47-6 o-xylene 
• 7647-01-0 hydrogenchloride 
• 103204-69-9 4-acetylamino-2-methylbenzoic acid 
• 1975-51-5 2-methyl-4-nitrobenzoic acid 

Downstream Products

• 103204-69-9 4-acetylamino-2-methylbenzoic acid 
• 1124213-58-6 N-tert-butyl-3-((4-(2-methyl-4-(3-neopentylureido)benzoyl)piperazin-1-yl)methyl)benzamide 
• 317374-08-6 2-methyl-4-(2-methylbenzoylamino)benzoic acid 
• 578-39-2 4-hydroxy-2-methylbenzoic acid 
• 15719-64-9 methylammonium carbonate 
• 108-44-1 1-amino-3-methylbenzene 
• 1303931-49-8 4-[(tert-butoxycarbonyl)amino]-2-methylbenzoic acid 

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