3-Amino-4-methylbenzoic acid supplier

Name
3-Amino-4-methylbenzoic acid
EINECS 219-543-1
CAS No. 2458-12-0
Article Data13
CAS DataBase
Density 1.254 g/cm³
Solubility Very soluble in water.
Melting Point 164-168 °C(lit.)
Formula C₈H₉NO₂
Boiling Point 363 °C at 760 mmHg
Molecular Weight 151.165
Flash Point 173.3 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 3-amino-4-methyl-benzoate;3-Amino-p-toluic acid;4-Methyl-3-aminobenzoic acid;
PSA 63.32000
LogP 1.85660

Synthetic route

: 96-98-0
4-methyl-3-nitrobenzoic acid

: 2458-12-0
3-amino-p-toluic acid

Conditions

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

: 6946-14-1
3-acetylamino-4-methylbenzoic acid

: 2458-12-0
3-amino-p-toluic acid

Conditions

Conditions	Yield
With hydrogenchloride at 110℃; im Rohr;

: 60710-80-7
5-cyano-2-methylaniline

: 2458-12-0
3-amino-p-toluic acid

Conditions

Conditions	Yield
With hydrogenchloride at 100℃; im Druckrohr;

: 2-bromo-4-methyl-5-nitro-benzoic acid

: 2458-12-0
3-amino-p-toluic acid

Conditions

Conditions	Yield
With sodium amalgam

: 7647-01-0
hydrogenchloride

: 96-98-0
4-methyl-3-nitrobenzoic acid

tin dichloride: tin dichloride

: 2458-12-0
3-amino-p-toluic acid

...Expand

: 7647-01-0
hydrogenchloride

: 96-98-0
4-methyl-3-nitrobenzoic acid

tin: tin

: 2458-12-0
3-amino-p-toluic acid

...Expand

: 2-bromo-4-methyl-5-nitro-benzoic acid

sodium amalgam: sodium amalgam

: 2458-12-0
3-amino-p-toluic acid

: 4478-10-8
2-bromo-1-isopropyl-4-methyl-benzene

: 2458-12-0
3-amino-p-toluic acid

Conditions

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

: 859816-42-5
1-bromo-2-isopropyl-5-methyl-4-nitro-benzene

: 2458-12-0
3-amino-p-toluic acid

Conditions

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

: 861525-09-9
acetic acid-(5-chloroacetyl-2-methyl-anilide)

: 2458-12-0
3-amino-p-toluic acid

Conditions

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

: 99-94-5
p-Toluic acid

: 2458-12-0
3-amino-p-toluic acid

Conditions

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

: 90178-80-6
4-(chloromethyl)-3-nitrobenzonitrile

: 2458-12-0
3-amino-p-toluic acid

Conditions

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

: 874-86-2
4-cyanobenzyl chloride

: 2458-12-0
3-amino-p-toluic acid

Conditions

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

: 24424-99-5
di-tert-butyl dicarbonate

: 2458-12-0
3-amino-p-toluic acid

: 231958-04-6
3-[(tert-butyloxycarbonyl)amino]-4-methylbenzoic acid

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: 745048-63-9
5-amino-2-bromo-4-methylbenzoic acid

Conditions

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%

: 2458-12-0
3-amino-p-toluic acid

: 2592-95-2
benzotriazol-1-ol

: 765-30-0
Cyclopropylamine

: 623155-19-1
3-amino-N-cyclopropyl-4-methylbenzamide

Conditions

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%

...Expand

: 2458-12-0
3-amino-p-toluic acid

: 765-30-0
Cyclopropylamine

: 623155-19-1
3-amino-N-cyclopropyl-4-methylbenzamide

Conditions

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℃;

: 2458-12-0
3-amino-p-toluic acid

: 108-24-7
acetic anhydride

: 6946-14-1
3-acetylamino-4-methylbenzoic acid

Conditions

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%

: 64-17-5
ethanol

: 2458-12-0
3-amino-p-toluic acid

: 41191-92-8
3-amino-4-methylbenzoic acid ethyl ester

Conditions

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%

: 2458-12-0
3-amino-p-toluic acid

: 75-66-1
2-methylpropan-2-thiol

: 478169-77-6
3-(tert-butylthio)diazenyl-4-methylbenzoic acid

Conditions

Conditions	Yield
With hydrogenchloride for 1h;	96%

: 137-26-8
Thiram

: 2458-12-0
3-amino-p-toluic acid

: 242800-82-4
3-(N,N-dimethylthioureido)-4-methylbenzoic acid

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: 2592-95-2
benzotriazol-1-ol

: 54884-19-4
3-amino-4-methylbenzoic acid methylamide

Conditions

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%

: 67-56-1
methanol

: 2458-12-0
3-amino-p-toluic acid

: 18595-18-1
3-amino-4-methyl benzoic acid methyl ester

Conditions

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;

: 2458-12-0
3-amino-p-toluic acid

: 3682-12-0
diethyltin(IV) oxide

: 141368-92-5
diethyltin(IV) bis(3-amino-4-methylbenzoate)

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: C18H18N4O4

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: 532-55-8
Benzoyl isothiocyanate

: 461413-31-0
N-(benzoyl)-N'-(3-carboxy-6-methylphenyl)thiourea

Conditions

Conditions	Yield
In acetonitrile at 20℃;	92%

: 427878-41-9
4-chloro-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid ethyl ester

: 2458-12-0
3-amino-p-toluic acid

: C18H18N4O4

Conditions

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

: 56442-17-2
4-((4-fluorobenzyl)oxy)benzaldehyde

: 2458-12-0
3-amino-p-toluic acid

: 3-((4-((4-fluorobenzyl)oxy)benzyl)amino)-4-methylbenzoic acid

Conditions

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%

: 2458-12-0
3-amino-p-toluic acid

: 3682-12-0
diethyltin(IV) oxide

: bis{diethyl(3-amino-4-methylbenzoato)tin(IV)} oxide

Conditions

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%

: 75-15-0
carbon disulfide

: 2458-12-0
3-amino-p-toluic acid

: 114379-99-6
3-isothiocyanato-4-methylbenzoic acid

Conditions

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%

: 2458-12-0
3-amino-p-toluic acid

: 818-08-6
di(n-butyl)tin oxide

: 141368-91-4
di-n-butyltin(IV) bis(3-amino-4-methylbenzoate)

Conditions

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%

: 2458-12-0
3-amino-p-toluic acid

: 98555-09-0
3-azido-4-methyl-benzoic acid

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: C22H20N4O3

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: 3-(Formylamino)-4-methylbenzoic Acid

Conditions

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

: 621685-57-2
C14H10ClN3O

: 2458-12-0
3-amino-p-toluic acid

: C22H18N4O3

Conditions

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℃;

: 2458-12-0
3-amino-p-toluic acid

: 78933-24-1
pyrazolo[1,5-a]pyridine-3-carbonyl chloride

: 4-methyl-3-(pyrazolo[1,5-a]pyridine-3-carboxamido)benzoic acid

Conditions

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

: 3731-52-0
3-Aminomethylpyridine

: 2458-12-0
3-amino-p-toluic acid

: 3-amino-4-methyl-N-(pyridin-3-ylmethyl)benzamide

Conditions

Conditions	Yield
With triethylamine; HATU In dichloromethane	83%

: 919084-99-4
6-(2-chloro-benzoimidazol-1-yl)-pyrimidin-4-ylamine

: 2458-12-0
3-amino-p-toluic acid

: 3-[1-(6-amino-pyrimidin-4-yl)-1H-benzoimidazol-2-ylamino]-4-methyl-benzoic acid

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: 56-81-5
glycerol

: 74316-52-2
8-methyl-5-quinolinecarboxylic acid

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: 6946-14-1
3-acetylamino-4-methylbenzoic acid

Conditions

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%

: 2458-12-0
3-amino-p-toluic acid

: 818-08-6
di(n-butyl)tin oxide

: bis{di-n-butyl(3-amino-4-methylbenzoato)tin(IV)} oxide

Conditions

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%

: 870221-17-3
4-(2-chloropyridin-3-yl)pyrimidine

: 2458-12-0
3-amino-p-toluic acid

: 870221-16-2
4-methyl-3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)benzoic acid

Conditions

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

: 2458-12-0
3-amino-p-toluic acid

: 129694-52-6
ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formamidate

: 931424-02-1
3-{[(Z)-2-amino-1,2-dicyanovinyl]amino}methyleneamino-4-methylbenzoic acid

Conditions

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

3-Amino-4-methylbenzoic acid Chemical Properties

Product Name: 3-Amino-4-methylbenzoic acid (CAS NO.2458-12-0)

Molecular Formula: C₈H₉NO₂
Molecular Weight: 151.16g/mol
Mol File: 2458-12-0.mol
EINECS: 219-543-1
Melting Point: 164-168 °C(lit.)
Boiling point: 363 °C at 760 mmHg
Flash Point: 173.3 °C
Density: 1.254 g/cm³
Index of Refraction: 1.618
Molar Refractivity: 42.24 cm³
Molar Volume: 120.5 cm³
Surface Tension: 58.2 dyne/cm
Enthalpy of Vaporization: 64.25 kJ/mol
Vapour Pressure: 6.64E-06 mmHg at 25°C
XLogP3-AA: 0.3
H-Bond Donor: 2
H-Bond Acceptor: 3
Structure Descriptors of 3-Amino-4-methylbenzoic acid (CAS NO.2458-12-0):
IUPAC Name: 3-amino-4-methylbenzoic acid
Canonical SMILES: CC1=C(C=C(C=C1)C(=O)O)N
InChI: InChI=1S/C8H9NO2/c1-5-2-3-6(8(10)11)4-7(5)9/h2-4H,9H2,1H3,(H,10,11)
InChIKey: XKFIFYROMAAUDL-UHFFFAOYSA-N
Product Categories: CARBOXYLICACID; Chemical intermediate for Nilotinib; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic acid; Organic acids

3-Amino-4-methylbenzoic acid Safety Profile

Safety Information about 3-Amino-4-methylbenzoic acid (CAS NO.2458-12-0):
Hazard Codes Xi Irritant
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
FIRST AID MEASURES
   Eyes:Flush eyes with plenty of water for at least 15 minutes,occasionally lifting the upper and lower eyelids. Get medical aid immediately.
    Skin:Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
    Ingestion:If victim is conscious and alert, give 2-4 cupfuls of milk or water.Never give anything by mouth to an unconscious person. Get medical aid.
    Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult,give oxygen. Get medical aid.

3-Amino-4-methylbenzoic acid Specification

3-Amino-4-methylbenzoic acid , its CAS NO. is 2458-12-0, the synonym is 3-Amino-p-toluic acid .

Product Name

3-Amino-4-methylbenzoic acid

Synthetic route

3-Amino-4-methylbenzoic acid Chemical Properties

3-Amino-4-methylbenzoic acid Safety Profile

3-Amino-4-methylbenzoic acid Specification

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