2486-70-6

Basic information

• Product Name: 4-Amino-3-methylbenzoic acid
• Synonyms: Benzoic acid, 4-amino-3-methyl-;RARECHEM AL BO 2396;4-AMINO-M-TOLUIC ACID;4-AMINO-3-METHYL BENZOATE;4-AMINO-3-METHYLBENZOIC ACID;4-AMINO-3-METHYLBENZENECARBOXYLIC ACID;3-METHYL-4-AMINOBENZOIC ACID;4-Amino-3-Methylhenzoic Acid
• CAS NO: 2486-70-6
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 219-629-9
• Product Categories: CARBOXYLICACID;FINE Chemical & INTERMEDIATES;Amines;blocks;Carboxes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;pharmacetical;Organic acids;Acids & Esters;Anilines, Amides & Amines;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 2486-70-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 169-171 °C(lit.)
• Boiling Point: 273.17°C (rough estimate)
• Flash Point: 159.1 °C
• Appearance: Yellowish or brown powder
• Density: 1.2023 (rough estimate)
• Vapor Pressure: 3.55E-05mmHg at 25°C
• Refractive Index: 1.5810 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.93±0.10(Predicted)
• Stability: Light Sensitive
• BRN: 2802615
• CAS DataBase Reference: 4-Amino-3-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-3-methylbenzoic acid(2486-70-6)
• EPA Substance Registry System: 4-Amino-3-methylbenzoic acid(2486-70-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2486-70-6(Hazardous Substances Data)

Usage

Chemical Properties

beige or light buff to orange

Uses

4-Amino-3-methylbenzoic Acid is used in preparation of Amide-substituted Benzo[d]imidazole compounds as selective inhibitors of indoleamine-2,3-dioxygenases.

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

Synthetic route

3-methyl-4-nitrobenzoic acid (3113-71-1) → 4-amino 3-methylbenzoic acid (2486-70-6)

Conditions	Yield
With hydrogenchloride; sulfuric acid In water; acetonitrile at 40℃; for 4h; Solvent; Reagent/catalyst; Temperature; Electrolysis;	99%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 1875.19 Torr; for 2h;	98%
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 24h;	96%

4-(4,6-dimethyl-benzothiazol-2-yl)-2-methyl-aniline (5855-93-6) → 4-amino 3-methylbenzoic acid (2486-70-6) + 3,5-dimethyl-2-aminobenzenethiol (56536-88-0)

Conditions	Yield
bei der Alkalischmelze;

hydrogenchloride (7647-01-0) + 3-methyl-4-nitrobenzoic acid (3113-71-1) + tin → 4-amino 3-methylbenzoic acid (2486-70-6)

m-Toluic acid (99-04-7) → 4-amino 3-methylbenzoic acid (2486-70-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated nitric acid 2: iron sulfate(II) hydrate; ammonia View Scheme
Multi-step reaction with 2 steps 1: fuming nitric acid 2: iron sulfate(II) hydrate; ammonia View Scheme
Multi-step reaction with 2 steps 1: fuming nitric acid 2: iron sulfate(II) hydrate; ammonia View Scheme

o-toluidine (95-53-4) → 4-amino 3-methylbenzoic acid (2486-70-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / 36 °C / Inert atmosphere 2: triethylamine / methanol; isopropyl alcohol / 22.67 h / 116 - 140 °C / 5168.35 - 8360.56 Torr View Scheme

N-(tert-butoxycarbonyl)-o-toluidine (74965-31-4) + methyl chloroformate (79-22-1) → 4-amino 3-methylbenzoic acid (2486-70-6)

Conditions	Yield
With triethylamine In methanol; isopropyl alcohol at 116 - 140℃; under 5168.35 - 8360.56 Torr; for 22.67h; Pressure; Temperature;

chloroformic acid ethyl ester (541-41-3) + N-(tert-butoxycarbonyl)-o-toluidine (74965-31-4) → 4-amino 3-methylbenzoic acid (2486-70-6)

Conditions	Yield
With ethylenediamine In propan-1-ol; ethanol at 110 - 130℃; under 4560.31 - 6080.41 Torr; for 11.5h;

4-amino 3-methylbenzoic acid (2486-70-6) + Benzoyl isothiocyanate (532-55-8) → 4-[(benzoylcarbamothioyl)amino]-3-methylbenzoic acid

Conditions	Yield
In acetone at 60℃; for 0.666667h;	100%

ethanol (64-17-5) + 4-amino 3-methylbenzoic acid (2486-70-6) → 1-amino-2-methylbenzene-4-carboxylic acid ethyl ester (40800-65-5)

Conditions	Yield
With sulfuric acid for 3h; Reflux;	99%

diazomethane (186581-53-3, 908094-01-9) + 4-amino 3-methylbenzoic acid (2486-70-6) → methyl 4-amino-3-methylbenzoate (18595-14-7)

Conditions	Yield
In diethyl ether	96%

4-amino 3-methylbenzoic acid (2486-70-6) + 1-tert-butoxycarbonyl-4,4'-bipiperidine (171049-35-7) → tert butyl 1'-(4-amino-3-methylbenzoyl)-4,4'-bipiperidine-1-carboxylate

Conditions	Yield
With (diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one In dichloromethane at 20℃; for 20h;	96%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 4-amino 3-methylbenzoic acid (2486-70-6) → 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbenzoic acid (892878-63-6)

Conditions	Yield
In tetrahydrofuran Inert atmosphere; Reflux;	96%

4-amino 3-methylbenzoic acid (2486-70-6) → C8H8N2O3

Conditions	Yield
With tartaric acid; sodium nitrite In ethanol; water at 35℃; for 2h; Solvent; Reagent/catalyst;	95.7%

methanol (67-56-1) + 4-amino 3-methylbenzoic acid (2486-70-6) → methyl 4-amino-3-methylbenzoate (18595-14-7)

Conditions	Yield
With sulfuric acid Reflux; Inert atmosphere;	95%
With thionyl chloride In dichloromethane at 80℃; for 3h;	95%
With thionyl chloride at 20℃; for 12h;	95%

4-amino 3-methylbenzoic acid (2486-70-6) + butyryl chloride (141-75-3) → N-butyryl-4-amino-3-methylbenzoic acid (1016696-74-4)

Conditions	Yield
Stage #1: 4-amino 3-methylbenzoic acid; butyryl chloride With pyridine In chloroform for 12h; Reflux; Stage #2: With hydrogenchloride In water at 20℃;	94%
With sodium carbonate In dichloromethane at 40℃; for 4h; Temperature; Solvent; Reagent/catalyst;	84.9%

4-amino 3-methylbenzoic acid (2486-70-6) + acetic anhydride (108-24-7) → 4-acetamido-3-methylbenzoic acid (37901-92-1)

Conditions	Yield
Stage #1: 4-amino 3-methylbenzoic acid With triethylamine In dichloromethane for 0.5h; Stage #2: acetic anhydride In dichloromethane at 20℃; for 72h;	93%
With triethylamine In dichloromethane Inert atmosphere;	10 g
With triethylamine In dichloromethane at 0 - 20℃;	10 g

4-amino 3-methylbenzoic acid (2486-70-6) + N,N-dimethylammonium chloride (506-59-2) → 4-amino-N,N,3-trimethylbenzamide (953739-92-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	92%

4-amino 3-methylbenzoic acid (2486-70-6) + Allyl chloroformate (2937-50-0) → 4-(((allyloxy)carbonyl)amino)-3-methylbenzoic acid

Conditions	Yield
With sodium carbonate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; water at 0℃; for 16h;	91%

4-amino 3-methylbenzoic acid (2486-70-6) → 4-bromo-3-methylbenzoic acid (7697-28-1)

Conditions	Yield
Stage #1: 4-amino 3-methylbenzoic acid With hydrogen bromide In water at 25℃; for 1h; Stage #2: With sodium nitrate In water at -2 - -1℃; for 1.75h; Stage #3: With hydrogen bromide; copper(I) bromide In water at -2 - 70℃; for 2h;	90%
Diazotization.Kochen der Diazoverbindung mit Bromwasserstoffsaeure;
With hydrogen bromide; sodium nitrite; copper(I) chloride In water

4-amino 3-methylbenzoic acid (2486-70-6) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → (E)-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)-3-methylbenzoic acid

Conditions	Yield
With acetic acid In ethanol at 50℃; for 1h;	88%

4-amino 3-methylbenzoic acid (2486-70-6) + 2-amino-5-methoxy-thiophenol (6274-29-9) → 4-(6-methoxybenzothiazol-2-yl)-2-methylphenylamine (247080-26-8)

Conditions	Yield
With melamine formaldehyde resin supported sulfuric acid Microwave irradiation;	87%

2-ethoxy-1-ethanamine (110-76-9) + 4-amino 3-methylbenzoic acid (2486-70-6) → 4-amino-N-[2-(ethyloxy)ethyl]-3-methylbenzamide (1150617-11-0)

Conditions	Yield
With triethylamine; HATU at 20℃; for 4h;	86%

4-amino 3-methylbenzoic acid (2486-70-6) + 2-amino-benzenethiol (137-07-5) → 2-(4'-amino-3'-methylphenyl)-benzothiazole (178804-04-1)

Conditions	Yield
With melamine formaldehyde resin supported sulfuric acid Microwave irradiation;	85%
With PPA at 220℃; for 4h;	58%
With PPA at 220℃;

4-amino 3-methylbenzoic acid (2486-70-6) + 1,1′-bis(2,4-dinitrophenyl)-[4,4′-bipyridine]-1,1′-diium chloride (41168-79-0) → 2Cl(1-)*C26H22N2O4(2+)

Conditions	Yield
In ethanol Reflux;	82%

4-amino 3-methylbenzoic acid (2486-70-6) + 2-amino-5-ethylbenzothiazole (90382-10-8) → 4-(6-ethylbenzothiazol-2-yl)-2-methylphenylamine (1237737-89-1)

Conditions	Yield
With melamine formaldehyde resin supported sulfuric acid Microwave irradiation;	81%

ethyl 2-phenyldiazoacetate (22065-57-2) + 4-amino 3-methylbenzoic acid (2486-70-6) → 4-((2-ethoxy-2-oxo-1-phenylethyl)amino)-3-methylbenzoic acid

Conditions	Yield
With C43H37Br2CuN3P2(1+)*ClO4(1-) In methanol at 0 - 20℃; for 6h; Schlenk technique; Inert atmosphere; chemoselective reaction;	81%

4-amino 3-methylbenzoic acid (2486-70-6) + acryloyl chloride (814-68-6) → 4-acrylamido-3-methylbenzoic acid

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Temperature;	81%
With pyridine In N,N-dimethyl-formamide at 20℃; for 3h; Temperature;	6%

Pyromellitic dianhydride (89-32-7) + 4-amino 3-methylbenzoic acid (2486-70-6) → N,N′-bis(4-carboxy-2-methylphenyl)pyromellitic di-imide

Conditions	Yield
In acetic acid at 120℃; for 24h;	79%

4-amino 3-methylbenzoic acid (2486-70-6) → 4-amino-3-bromo-5-methylbenzoic acid

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 100℃; for 1h;	78.3%
With bromine In methanol at 0 - 10℃;	117 g

4-amino 3-methylbenzoic acid (2486-70-6) + biotin (58-85-5) → C18H23N3O4S

Conditions	Yield
Stage #1: biotin With tributyl-amine; isobutyl chloroformate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 4-amino 3-methylbenzoic acid In N,N-dimethyl-formamide at 0℃; for 2h;	77.6%

di-tert-butyl dicarbonate (24424-99-5) + 4-amino 3-methylbenzoic acid (2486-70-6) → 4-tert-butoxyamino-3-methyl-benzoic acid

Conditions	Yield
Stage #1: di-tert-butyl dicarbonate; 4-amino 3-methylbenzoic acid With sodium hydroxide In 1,4-dioxane; water at 20℃; for 90h; Stage #2: With hydrogenchloride In 1,4-dioxane; water	77%

4-amino 3-methylbenzoic acid (2486-70-6) + 1H-benzo[d][1,2,3]triazol-1-yl ethyl carbonate (42014-43-7) → 1H-1,2,3-benzotriazol-1-yl 4-amino-3-methylbenzoate

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 10℃; for 2h;	74%

4-amino 3-methylbenzoic acid (2486-70-6) + triethylamine (121-44-8) + mono-4-methoxytrityl chloride (14470-28-1) → C6H15N*C28H25NO3 (1471099-03-2)

Conditions	Yield
Stage #1: 4-amino 3-methylbenzoic acid; triethylamine With chloro-trimethyl-silane In dichloromethane at 70℃; for 2h; Stage #2: mono-4-methoxytrityl chloride In dichloromethane for 16h; Reflux;	73%

4-amino 3-methylbenzoic acid (2486-70-6) + 2-amino-phenol (95-55-6) → 4-(benzo[d]oxazol-2-yl)-2-methylaniline

Conditions	Yield
With polyphosphoric acid at 220℃; for 4h;	72%
With polyphosphoric acid at 160℃; for 5h;

bis(trichloromethyl) carbonate (32315-10-9) + 4-amino 3-methylbenzoic acid (2486-70-6) → 4,4'-(carbonylbis(azanediyl))bis(3-methylbenzoic acid)

Conditions	Yield
With boric acid; sodium hydroxide In tetrahydrofuran; water for 0.666667h; pH=Ca. 9;	70%

4-amino 3-methylbenzoic acid (2486-70-6) → 4-amino-3-chloro-5-methylbenzoic acid

Conditions	Yield
With N-chloro-succinimide In N,N-dimethyl-formamide at 100℃; for 1h;	69.6%

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 74965-31-4 N-(tert-butoxycarbonyl)-o-toluidine 
• 79-22-1 methyl chloroformate 
• 3113-71-1 3-methyl-4-nitrobenzoic acid 
• 7647-01-0 hydrogenchloride 
• 95-53-4 o-toluidine 
• 5855-93-6 4-(4,6-dimethyl-benzothiazol-2-yl)-2-methyl-aniline 
• 99-04-7 m-Toluic acid 

Downstream Products

• 37653-90-0 4-Methoxycarbonylamino-3-methyl-benzoic acid 
• 83560-89-8 3-methyl-4-(methylmaleimido)benzoic acid 
• 40800-65-5 1-amino-2-methylbenzene-4-carboxylic acid ethyl ester 
• 178804-04-1 2-(4'-amino-3'-methylphenyl)-benzothiazole 
• 81364-42-3 4-(n-hexadecanamido)-3-methylbenzoic acid 
• 926195-66-6 (4-amino-3-methylphenyl)(4-methylpiperazin-1-yl)methanone 
• 1124213-96-2 3-((4-(4-amino-3-methylbenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide 
• 926198-86-9 4-benzenesulfonylamino-3-methylbenzoic acid 
• 1157172-46-7 4-(octylamino)-3-methylbenzoic acid 
• 1344028-96-1 2-(dimethylamino)ethyl 4-(octylamino)-3-methylbenzoate 
• 1344028-75-6 2-(dimethylamino)ethyl 4-(butylamino)-3-methylbenzoate 
• 1157344-43-8 4-(butylamino)-3-methylbenzoic acid 
• 1346608-90-9 3-methyl-4-(methylsulfamoyl)benzoic acid 
• 808745-05-3 ethyl 4-acetamido-3-methylbenzoate 

Relevant articles and documents

Novel preparation method of antihypertensive drug telmisartan intermediate

The invention relates to an electric reduction preparation method of aminobenzoic acid represented by formula I and ester thereof. The preparation reaction of the method is shown in the description; and in the reaction formula, R is selected from hydrogen, a methyl group, an ethyl group, a benzyl group, a C3 or C4 straight-chain alkyl or branched-chain alkyl group, -NO2 is selected from 4-NO2 or 5-NO2, and Y is selected from H or 4-NHCOC3H7-n. The electroreduction preparation method of aminobenzoic acid and ester I thereof is characterized in that in a separated electrolytic cell, an acidic solution of nthe itrobenzoic acid and ester III thereof is taken as a catholyte; the voltage of a cathode working electrode relative to a reference electrode is 1.00-2.50 V; and an anolyte is an acidicsolution, the current density is 25.0-250.0 mA/cm, and the electrolysis temperature is 15-90 DEG C.

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