Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr; | 99% |
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 25857.4 Torr; | 99% |
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr; | 99% |
2-chloro-3-methylbenzoic acid
3-methylantranilic acid
Conditions | Yield |
---|---|
With ammonia; sodium carbonate; copper(l) chloride In dimethyl sulfoxide at 130 - 150℃; for 5h; | 93.1% |
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide | 90% |
With potassium chloride; dihydrogen peroxide; sodium hydroxide In water at 0 - 20℃; for 2.25h; | 80% |
60% |
3-methyl-2-nitrobenzoyl chloride
methyl 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilate
A
3-methylantranilic acid
B
methyl 3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilate
Conditions | Yield |
---|---|
With lithium hydroxide In water; benzene | A n/a B 61% |
8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione
3-methylantranilic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
methanol
7-methyl-1H-indole-2,3-dione
A
methyl 2-amino-3-methylbenzoate
B
3-methylantranilic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium methylate 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction; |
7-methyl-1H-indole-2,3-dione
butan-1-ol
A
3-methylantranilic acid
B
3-Methylanthranilsaeure-n-butylester
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium hydride 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
(i) H2, Pd-C, (ii) aq. NaOH; Multistep reaction; |
3-methyl-2-nitrobenzoyl chloride
3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilic acid
A
3-methylantranilic acid
B
3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilic acid
Conditions | Yield |
---|---|
With lithium hydroxide In water; benzene Title compound not separated from byproducts; |
7-methyl-1H-indole-2,3-dione
dihydrogen peroxide
3-methylantranilic acid
8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione
A
3-methylantranilic acid
B
o-toluidine
hydrogenchloride
3-methyl-2-nitrobenzoic acid
A
3-methylantranilic acid
B
o-toluidine
Conditions | Yield |
---|---|
at 100℃; im Rohr; |
(2-amino-3-methyl-phenyl)-glyoxylic acid
dihydrogen peroxide
3-methylantranilic acid
(2-amino-3-methyl-phenyl)-glyoxylic acid
3-methylantranilic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 46 percent / HNO3 / 1 h / -10 °C 2: 99 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr View Scheme | |
Multi-step reaction with 2 steps 1: fuming nitric acid 2: tin; hydrochloric acid View Scheme | |
Multi-step reaction with 2 steps 1: fuming nitric acid 2: tin; hydrochloric acid View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid / -10 - -5 °C 2: palladium 10% on activated carbon; hydrogen / methanol View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid / 1 h / -10 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 49 percent / fuming nitric acid / 1 h / -10 °C 2: 89 percent / tin, hydrochloric acid / ethanol / 1.5 h / 70 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86percent H2SO4 / 1) 55 deg C, 10 min, 2) 75 deg C, 30 min 2: H2O2, NaOH View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / 0.33 h / 80 °C 2: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sulfuric acid / 60 - 80 °C 2.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C 2.2: pH 4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: concentrated hydrochloric acid / im Druckrohr 2: fuming nitric acid 3: tin; hydrochloric acid View Scheme |
3-Methyl-2-nitrobenzenecarboxamide
3-methylantranilic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: POCl3 2: (i) H2, Pd-C, (ii) aq. NaOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium sulfate / water / 40 °C 1.2: Reflux 2.1: sulfuric acid / 0.33 h / 80 °C 3.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium sulfate / water / 40 °C 1.2: 0.17 h / Reflux 2.1: sulfuric acid / 60 - 80 °C 3.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C 3.2: pH 4 View Scheme | |
Multi-step reaction with 3 steps 1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 55 °C 2: sulfuric acid / neat (no solvent) / 55 - 80 °C 3: sodium hydroxide; dihydrogen peroxide; potassium chloride / water / 2.25 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 0.17 h / Reflux 2: sulfuric acid / 0.83 h / 70 - 80 °C 3: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium sulfate; hydrogenchloride / water / 12 h / 55 °C / Inert atmosphere 2: sulfuric acid / 0.67 h / Heating; Inert atmosphere 3: dihydrogen peroxide; sodium hydroxide / water / 5.5 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With Pseudomonas fluorescens kynureninase In aq. phosphate buffer at 37℃; pH=8; Kinetics; Enzymatic reaction; |
ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate
3-methylantranilic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sulfuric acid / water / 2 h / 55 - 60 °C 2: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice 3: hydrogenchloride / water / 4 h / Reflux 4: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme |
3-methylantranilic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice 2: hydrogenchloride / water / 4 h / Reflux 3: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme |
ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(2-formamido-3-methylphenyl)pentanoate
3-methylantranilic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 4 h / Reflux 2: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme |
methyl 2-amino-3-methylbenzoate
3-methylantranilic acid
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; ethanol; water at 50℃; for 3h; Inert atmosphere; |
3-methylantranilic acid
2-amino-3-methylbenzyl alcohol
Conditions | Yield |
---|---|
Stage #1: 3-methylantranilic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: With water; sodium hydroxide In tetrahydrofuran | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h; | 97% |
3-methylantranilic acid
2-amino-5-bromo-3-methylbenzoic acid
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
With bromine; acetic acid at 20 - 25℃; | 97% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 70 - 80℃; for 0.5h; | 95.6% |
Conditions | Yield |
---|---|
Stage #1: 3-methylantranilic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; | 100% |
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 18.5h; | 92% |
Stage #1: 3-methylantranilic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 24h; | 77% |
Stage #1: 3-methylantranilic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 24h; | |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; |
3-carboxyphthalic anhydride
3-methylantranilic acid
C17H11NO6
Conditions | Yield |
---|---|
at 150℃; for 12h; | 100% |
6-[(R)-5-(3-amino-propyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one
3-methylantranilic acid
Conditions | Yield |
---|---|
100% |
3-methylantranilic acid
2-amino-5-chloro-3-methylbenzoic acid
Conditions | Yield |
---|---|
With chlorine In 1,2-dichloro-ethane at 50℃; for 3h; Solvent; | 98.1% |
With N-chloro-succinimide In N,N-dimethyl-formamide at 70 - 80℃; for 0.5h; | 97.8% |
With N-chloro-succinimide In N,N-dimethyl-formamide at 75℃; | 91% |
3-methylantranilic acid
ortho-chlorobenzoic acid
2-<(2-carboxyphenyl)amino>-3-methylbenzoic acid
Conditions | Yield |
---|---|
With copper; potassium carbonate; copper(I) bromide In various solvent(s) at 160℃; for 0.5h; | 98% |
Conditions | Yield |
---|---|
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 16h; | 98% |
Conditions | Yield |
---|---|
98% |
3-methylantranilic acid
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
C17H15NO4
Conditions | Yield |
---|---|
at 110℃; for 16h; Inert atmosphere; neat (no solvent); | 98% |
Conditions | Yield |
---|---|
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide | 98% |
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 16h; Inert atmosphere; | 98% |
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 16h; Inert atmosphere; | 98% |
p-chlorophenyl isoselenocyanate
3-methylantranilic acid
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 40℃; for 4.5h; | 98% |
3-methylantranilic acid
2-amino-5-iodo-3-methylbenzoic acid
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; iodine In tetrachloromethane at 77℃; for 6h; | 97.7% |
With N-iodo-succinimide In N,N-dimethyl-formamide at 20 - 80℃; for 2h; | 97% |
With N-iodo-succinimide In N,N-dimethyl-formamide at 75℃; for 1h; Inert atmosphere; | 96% |
3-methylantranilic acid
6,6'-dimethyl-1,1'-biphenyl-2,2'-dicarboxylic acid
Conditions | Yield |
---|---|
Stage #1: 3-methylantranilic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With copper(I) In water | 97% |
With Cu(I)-salt; sodium nitrite | 78% |
Stage #1: 3-methylantranilic acid With sodium hydroxide; sodium nitrite at 0℃; for 0.5h; Stage #2: With hydroxyammonium sulfate; copper(II) sulfate In water | 72% |
3-methylantranilic acid
[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; sodium carbonate In 1,4-dioxane at 95℃; for 17h; Molecular sieve; Green chemistry; | 97% |
Conditions | Yield |
---|---|
In 1,4-dioxane; benzene Ambient temperature; | 96% |
With sodium hydrogencarbonate In toluene at 0 - 20℃; for 0.25h; | 86% |
3-methylantranilic acid
α,α-diphenylsuccinic acid anhydride
2-(2,5-dioxo-3,3-diphenylpyrrolidin-1-yl)-3-methylbenzoic acid
Conditions | Yield |
---|---|
at 150℃; for 12h; Condensation; | 96% |
at 150℃; neat (no solvent, solid phase); |
Conditions | Yield |
---|---|
In formamide at 160℃; for 12h; | 96% |
With formamide at 160℃; | 96% |
3-methylantranilic acid
1-fluoro-4-isoselenocyanatobenzene
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 40℃; for 4.5h; | 96% |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 6h; Reflux; | 96% |
bis(trichloromethyl) carbonate
3-methylantranilic acid
6-methylisatoic anhydride
Conditions | Yield |
---|---|
In 1,4-dioxane for 6.5h; Reflux; | 95% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane | 94% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane | 94% |
3-methylantranilic acid
1,2-cis-cyclohexanedicarboxylic anhydride
C16H17NO4
Conditions | Yield |
---|---|
at 110℃; for 10h; Inert atmosphere; neat (no solvent); | 95% |
3-methylantranilic acid
4-bromophenyl isoselenocyanate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 40℃; for 4.5h; | 95% |
3-methylantranilic acid
Conditions | Yield |
---|---|
With bromine; acetic acid In dichloromethane at 20℃; for 1h; | 95% |
3-methylantranilic acid
acetic anhydride
2-acetylamino-3-methylbenzoic acid
Conditions | Yield |
---|---|
for 2h; Reflux; | 94% |
for 2h; Heating; | 87% |
for 1h; Acetylation; Heating; | 85% |
at 60℃; Reflux; |
3-methylantranilic acid
6-methylisatoic anhydride
Conditions | Yield |
---|---|
With bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 16.5h; | 94% |
Multi-step reaction with 2 steps 1: triethylamine; dmap / acetonitrile / 2 h / 20 °C 2: 2-chloro-1-methyl-pyridinium iodide / acetonitrile / 0.17 h / 20 °C View Scheme |
3-methylantranilic acid
formamidine acetic acid
formamide
8-methylquinazolin-4(3H)-one
Conditions | Yield |
---|---|
at 180℃; for 3h; | 94% |
4-pentynoic acid
3-methylantranilic acid
3a,9-dimethyl-3,3a-dihydro-1H-benzo[d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione
Conditions | Yield |
---|---|
With Echavarren's catalyst In 1,1-dichloroethane at 120℃; for 12h; Sealed vial; | 93% |
IUPAC Name: 2-Amino-3-methylbenzoic acid
Synonyms of 3-Methylanthranilic acid (CAS NO.4389-45-1): 2-Amino-3-methylbenzoic acid ; 3-Methyl-2-aminobenzoic acid ; Benzoic acid, 2-amino-3-methyl- (9CI) ; m-Toluic acid, 2-amino- (8CI)
CAS NO: 4389-45-1
Molecular Formula: C8H9NO2
Molecular Weight: 151.16
Molecular Structure:
H bond acceptors: 3
H bond donors: 3
Freely Rotating Bonds: 2
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.618
Molar Refractivity: 42.24 cm3
Molar Volume: 120.5 cm3
Surface Tension: 58.2 dyne/cm
Density: 1.254 g/cm3
Flash Point: 144.4 °C
Enthalpy of Vaporization: 58.74 kJ/mol
Boiling Point: 315.1 °C at 760 mmHg
Vapour Pressure: 0.000188 mmHg at 25°C
Melting Point: 174-177 °C(lit.)
Appearance: pink to grey-brown crystalline powder
Product Categories of 3-Methylanthranilic acid (CAS NO.4389-45-1): CARBOXYLICACID;FINE Chemical & INTERMEDIATES;Amines;blocks;Carboxes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Benzoic acid;Organic acids;Carboxylic Acids;Phenyls & Phenyl-Het
3-Methylanthranilic acid (CAS NO.4389-45-1) is used as intermediates in organic synthesis.
Safety Information about 3-Methylanthranilic acid (CAS NO.4389-45-1):
Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25: Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 3
F: 10
Hazard Note: Irritant
HazardClass: IRRITANT
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Keep container closed when not in use.
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