2458-12-0

Basic information

• Product Name: 3-Amino-4-methylbenzoic acid
• Synonyms: 3-AMino-4-Methylbenzoic acid, 95+%;RARECHEM AL BO 1039;H-(3)ABZ(4-ME)-OH;H-(3)ATL(4)-OH;3-AMINO-P-TOLUIC ACID;3-AMINO-4-TOLUIC ACID;3-AMINO-4-METHYLBENZOIC ACID;Benzoic acid, 3-amino-4-methyl-
• CAS NO: 2458-12-0
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 219-543-1
• Product Categories: CARBOXYLICACID;Chemical intermediate for Nilotinib;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids
• Mol File: 2458-12-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 164-168 °C(lit.)
• Boiling Point: 273.17°C (rough estimate)
• Flash Point: 173.3 °C
• Appearance: Pink to grayish/Crystalline Powder
• Density: 1.2023 (rough estimate)
• Vapor Pressure: 6.64E-06mmHg at 25°C
• Refractive Index: 1.5810 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.61±0.10(Predicted)
• Water Solubility: Very soluble in water.
• Stability: Hygroscopic
• BRN: 2082449
• CAS DataBase Reference: 3-Amino-4-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4-methylbenzoic acid(2458-12-0)
• EPA Substance Registry System: 3-Amino-4-methylbenzoic acid(2458-12-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2458-12-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 2458-12-0 differently. You can refer to the following data:
1. 3-Amino-4-methylbenzoic acid is used as a starting material to synthesize cyclopropamitosene compounds, which have potential antitumour activity. 3-Amino-4-methylbenzoic acid also has some partial herbicidal activity.
2. 3-Amino-4-methylbenzoic acid, is a raw material used in synthesis. It is also used as an organic intermediate, Pharmaceutical intermediate.

Chemical Properties

white to light yellow crystal powder

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

Synthetic route

4-methyl-3-nitrobenzoic acid (96-98-0) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
With hydrogen; palladium In methanol for 5h;	48%
With hydrogenchloride; tin
With hydrogenchloride; tin(ll) chloride

3-acetylamino-4-methylbenzoic acid (6946-14-1) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
With hydrogenchloride at 110℃; im Rohr;

5-cyano-2-methylaniline (60710-80-7) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
With hydrogenchloride at 100℃; im Druckrohr;

2-bromo-4-methyl-5-nitro-benzoic acid → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
With sodium amalgam

hydrogenchloride (7647-01-0) + 4-methyl-3-nitrobenzoic acid (96-98-0) + tin dichloride → 3-amino-p-toluic acid (2458-12-0)

hydrogenchloride (7647-01-0) + 4-methyl-3-nitrobenzoic acid (96-98-0) + tin → 3-amino-p-toluic acid (2458-12-0)

2-bromo-4-methyl-5-nitro-benzoic acid + sodium amalgam → 3-amino-p-toluic acid (2458-12-0)

2-bromo-1-isopropyl-4-methyl-benzene (4478-10-8) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid / 12 - 15 °C 2: nitric acid 3: sodium amalgam View Scheme

1-bromo-2-isopropyl-5-methyl-4-nitro-benzene (859816-42-5) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid 2: sodium amalgam View Scheme

acetic acid-(5-chloroacetyl-2-methyl-anilide) (861525-09-9) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen peroxide; alkali 2: hydrochloric acid / 110 °C / im Rohr View Scheme

p-Toluic acid (99-94-5) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: fuming nitric acid 2: tin dichloride; hydrochloric acid View Scheme

4-(chloromethyl)-3-nitrobenzonitrile (90178-80-6) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin; fuming hydrochloric acid 2: fuming hydrochloric acid / 100 °C / im Druckrohr View Scheme

4-cyanobenzyl chloride (874-86-2) → 3-amino-p-toluic acid (2458-12-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated sulfuric acid; KNO3 / Giessen in Eiswasser 2: tin; fuming hydrochloric acid 3: fuming hydrochloric acid / 100 °C / im Druckrohr View Scheme

di-tert-butyl dicarbonate (24424-99-5) + 3-amino-p-toluic acid (2458-12-0) → 3-[(tert-butyloxycarbonyl)amino]-4-methylbenzoic acid (231958-04-6)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 18h;	100%
In tetrahydrofuran at 50℃;	91%
In tetrahydrofuran at 50℃;	88%

3-amino-p-toluic acid (2458-12-0) → 5-amino-2-bromo-4-methylbenzoic acid (745048-63-9)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 5 - 15℃; for 1.08h; Inert atmosphere;	100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 1.16667h; Inert atmosphere;	89%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;	89%

3-amino-p-toluic acid (2458-12-0) + benzotriazol-1-ol (2592-95-2) + Cyclopropylamine (765-30-0) → 3-amino-N-cyclopropyl-4-methylbenzamide (623155-19-1)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 54℃; for 1.83333h;	100%

3-amino-p-toluic acid (2458-12-0) + Cyclopropylamine (765-30-0) → 3-amino-N-cyclopropyl-4-methylbenzamide (623155-19-1)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In N,N-dimethyl-formamide at 0 - 20℃;	100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃;	100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃;	72%
With dmap In water; ethyl acetate; N,N-dimethyl-formamide	72%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃;

3-amino-p-toluic acid (2458-12-0) + acetic anhydride (108-24-7) → 3-acetylamino-4-methylbenzoic acid (6946-14-1)

Conditions	Yield
In acetic acid Acetylation;	98%
In acetic acid at 20℃; for 1h;	96.2%
With acetic acid at 20℃; for 16h;	90%
In acetic acid at 20℃;	87.6%

ethanol (64-17-5) + 3-amino-p-toluic acid (2458-12-0) → 3-amino-4-methylbenzoic acid ethyl ester (41191-92-8)

Conditions	Yield
With thionyl chloride Heating;	98%
With sulfuric acid for 12h; Reflux; Inert atmosphere;	98%
With thionyl chloride	98%
With sulfuric acid at 75℃; for 31h;	90%

3-amino-p-toluic acid (2458-12-0) + 2-methylpropan-2-thiol (75-66-1) → 3-(tert-butylthio)diazenyl-4-methylbenzoic acid (478169-77-6)

Conditions	Yield
With hydrogenchloride for 1h;	96%

Thiram (137-26-8) + 3-amino-p-toluic acid (2458-12-0) → 3-(N,N-dimethylthioureido)-4-methylbenzoic acid (242800-82-4)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; thiocarbamoylation;	95%

3-amino-p-toluic acid (2458-12-0) + benzotriazol-1-ol (2592-95-2) → 3-amino-4-methylbenzoic acid methylamide (54884-19-4)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; methylamine In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 54℃; for 2h;	95%

methanol (67-56-1) + 3-amino-p-toluic acid (2458-12-0) → 3-amino-4-methyl benzoic acid methyl ester (18595-18-1)

Conditions	Yield
With thionyl chloride at 5℃; for 6h; Reflux;	94.9%
With thionyl chloride at 5℃; for 6h; Reflux;	94.9%
With thionyl chloride at 5℃; for 6h; Reflux;	94.9%
With sulfuric acid Heating;
With thionyl chloride at 0℃; for 1h; Reflux;

3-amino-p-toluic acid (2458-12-0) + diethyltin(IV) oxide (3682-12-0) → diethyltin(IV) bis(3-amino-4-methylbenzoate) (141368-92-5)

Conditions	Yield
In ethanol; toluene according to: M. Boualam et al., Appl. Organomet. Chem. 4 (1990) 335; addn. of diorganotin oxide to soln. (toluene/ethanol 4:1) of 3-amino-4-methylbenzoic acid (molar ratio 2:1), refluxing (4 h), azeotrop distn.; evapn. (red. pressure), recrystn. (chloroform/petroleum ether);	93%

C10H12ClN3O2 + 3-amino-p-toluic acid (2458-12-0) → C18H18N4O4

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;	92%

3-amino-p-toluic acid (2458-12-0) + Benzoyl isothiocyanate (532-55-8) → N-(benzoyl)-N'-(3-carboxy-6-methylphenyl)thiourea (461413-31-0)

Conditions	Yield
In acetonitrile at 20℃;	92%

4-chloro-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid ethyl ester (427878-41-9) + 3-amino-p-toluic acid (2458-12-0) → C18H18N4O4

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 16h;	92%

4-((4-fluorobenzyl)oxy)benzaldehyde (56442-17-2) + 3-amino-p-toluic acid (2458-12-0) → 3-((4-((4-fluorobenzyl)oxy)benzyl)amino)-4-methylbenzoic acid

Conditions	Yield
Stage #1: 4-((4-fluorobenzyl)oxy)benzaldehyde; 3-amino-p-toluic acid In toluene for 2h; Reflux; Dean-Stark; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 25℃; for 12h;	92%

3-amino-p-toluic acid (2458-12-0) + diethyltin(IV) oxide (3682-12-0) → bis{diethyl(3-amino-4-methylbenzoato)tin(IV)} oxide

Conditions	Yield
In ethanol; toluene according to: M. Boualam et al., Appl. Organomet. Chem. 4 (1990) 335; addn. of diorganotin oxide to soln. (toluene/ethanol 4:1) of 3-amino-4-methylbenzoic acid (molar ratio 1:1), refluxing (4 h), azeotrop distn.; evapn. (red. pressure), recrystn. (toluene/ethanol);	91%

carbon disulfide (75-15-0) + 3-amino-p-toluic acid (2458-12-0) → 3-isothiocyanato-4-methylbenzoic acid (114379-99-6)

Conditions	Yield
Stage #1: carbon disulfide; 3-amino-p-toluic acid With triethylamine In tetrahydrofuran; water at 20℃; for 26h; Stage #2: With iodine In tetrahydrofuran; water at 0℃; for 2.03333h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	91%

3-amino-p-toluic acid (2458-12-0) + di(n-butyl)tin oxide (818-08-6) → di-n-butyltin(IV) bis(3-amino-4-methylbenzoate) (141368-91-4)

Conditions	Yield
In ethanol; toluene according to: M. Boualam et al., Appl. Organomet. Chem. 4 (1990) 335; addn. of diorganotin oxide to soln. (toluene/ethanol 4:1) of 3-amino-4-methylbenzoic acid (molar ratio 2:1), refluxing (4 h), azeotrop distn.; evapn. (red. pressure), recrystn. (chloroform/ethanol);	89%

3-amino-p-toluic acid (2458-12-0) → 3-azido-4-methyl-benzoic acid (98555-09-0)

Conditions	Yield
Stage #1: 3-amino-p-toluic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Acidic aqueous solution; Stage #2: With sodium azide In water at 0℃; Acidic aqueous solution;	88%
With hydrogenchloride; sodium azide; sodium nitrite In water	88%
Stage #1: 3-amino-p-toluic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water for 0.5h;

C14H12ClN3O + 3-amino-p-toluic acid (2458-12-0) → C22H20N4O3

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 60℃; for 3h;	88%

3-amino-p-toluic acid (2458-12-0) → 3-(Formylamino)-4-methylbenzoic Acid

Conditions	Yield
With formic acid In water for 2h; Heating / reflux;	88%

C14H10ClN3O (621685-57-2) + 3-amino-p-toluic acid (2458-12-0) → C22H18N4O3

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 3h;	88%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60 - 100℃;

3-amino-p-toluic acid (2458-12-0) + pyrazolo[1,5-a]pyridine-3-carbonyl chloride (78933-24-1) → 4-methyl-3-(pyrazolo[1,5-a]pyridine-3-carboxamido)benzoic acid

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	87%

3-Aminomethylpyridine (3731-52-0) + 3-amino-p-toluic acid (2458-12-0) → 3-amino-4-methyl-N-(pyridin-3-ylmethyl)benzamide

Conditions	Yield
With triethylamine; HATU In dichloromethane	83%

6-(2-chloro-benzoimidazol-1-yl)-pyrimidin-4-ylamine (919084-99-4) + 3-amino-p-toluic acid (2458-12-0) → 3-[1-(6-amino-pyrimidin-4-yl)-1H-benzoimidazol-2-ylamino]-4-methyl-benzoic acid

Conditions	Yield
With methanesulfonic acid In 1,3-dimethyl-2-imidazolinone at 80℃; for 12h;	82%

3-amino-p-toluic acid (2458-12-0) + glycerol (56-81-5) → 8-methyl-5-quinolinecarboxylic acid (74316-52-2)

Conditions	Yield
With Fe(SO3C6H4NO2)3*4.5H2O In sulfuric acid at 140℃; for 4h;	80%

3-amino-p-toluic acid (2458-12-0) → 3-acetylamino-4-methylbenzoic acid (6946-14-1)

Conditions	Yield
Stage #1: 3-amino-p-toluic acid With acetic anhydride; acetic acid at 60℃; for 0.75h; Stage #2: 3-amino-p-toluic acid With 3-acetylamino-4-methyl-2-nitrobenzoic acid; acetic anhydride for 0.5h; Heating / reflux;	76%

3-amino-p-toluic acid (2458-12-0) + di(n-butyl)tin oxide (818-08-6) → bis{di-n-butyl(3-amino-4-methylbenzoato)tin(IV)} oxide

Conditions	Yield
In ethanol; toluene according to: M. Boualam et al., Appl. Organomet. Chem. 4 (1990) 335; addn. of diorganotin oxide to soln. (toluene/ethanol 4:1) of 3-amino-4-methylbenzoic acid (molar ratio 1:1), refluxing (4 h), azeotrop distn.; evapn. (red. pressure), recrystn. (chloroform/ethanol);	76%

4-(2-chloropyridin-3-yl)pyrimidine (870221-17-3) + 3-amino-p-toluic acid (2458-12-0) → 4-methyl-3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)benzoic acid (870221-16-2)

Conditions	Yield
With triethylamine triflouroacetate In dimethyl sulfoxide at 95℃; for 65h;	71%
With triethylamine triflouroacetate In dimethyl sulfoxide at 95℃; for 65h;

3-amino-p-toluic acid (2458-12-0) + ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formamidate (129694-52-6) → 3-{[(Z)-2-amino-1,2-dicyanovinyl]amino}methyleneamino-4-methylbenzoic acid (931424-02-1)

Conditions	Yield
1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; for 24h;	70%

Upstream product

• 6946-14-1 3-acetylamino-4-methylbenzoic acid 
• 874-86-2 4-cyanobenzyl chloride 
• 90178-80-6 4-(chloromethyl)-3-nitrobenzonitrile 
• 99-94-5 p-Toluic acid 
• 861525-09-9 acetic acid-(5-chloroacetyl-2-methyl-anilide) 
• 859816-42-5 1-bromo-2-isopropyl-5-methyl-4-nitro-benzene 
• 4478-10-8 2-bromo-1-isopropyl-4-methyl-benzene 
• 7647-01-0 hydrogenchloride 
• 96-98-0 4-methyl-3-nitrobenzoic acid 
• 60710-80-7 5-cyano-2-methylaniline 

Downstream Products

• 137093-29-9 C₂₆H₁₉NO₄ 
• 74316-52-2 8-methyl-5-quinolinecarboxylic acid 
• 242800-82-4 3-(N,N-dimethylthioureido)-4-methylbenzoic acid 
• 623155-19-1 3-amino-N-cyclopropyl-4-methylbenzamide 
• 478169-77-6 3-(tert-butylthio)diazenyl-4-methylbenzoic acid 
• 704-91-6 1H-indazole-6-carboxylic acid 
• 7697-26-9 3-bromo-4-methylbenzoic acid 
• 1148050-93-4 3-(1-(2,4-difluorophenyl)-7-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-4-ylamino)-4-methylbenzoic acid 

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