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Basic Information

Molecular Structure:
CAS No.:	4389-45-1
Name:	3-Methylanthranilic acid
Article Data:	51

Formula:	C₈H₉NO₂
Molecular Weight:	151.165
Synonyms:	m-Toluicacid, 2-amino- (6CI,7CI,8CI);2-Amino-3-methylbenzoic acid;2-Amino-m-toluicacid;3-Methyl-2-aminobenzoic acid;
EINECS:	224-505-2
Density:	1.254 g/cm³
Melting Point:	174-177 °C(lit.)
Boiling Point:	315.1 °C at 760 mmHg
Flash Point:	144.4 °C
Appearance:	pink to grey-brown crystalline powder
Hazard Symbols:	Xn, Xi
Risk Codes:	22-36/37/38
Safety:	24/25-36-26
PSA:	63.32000
LogP:	1.85660

Synthetic route

: 5437-38-7
3-methyl-2-nitrobenzoic acid

: 4389-45-1
3-methylantranilic acid

Conditions

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%

: 15068-35-6
2-chloro-3-methylbenzoic acid

: 4389-45-1
3-methylantranilic acid

Conditions

Conditions	Yield
With ammonia; sodium carbonate; copper(l) chloride In dimethyl sulfoxide at 130 - 150℃; for 5h;	93.1%

: 1127-59-9
7-methyl-1H-indole-2,3-dione

: 4389-45-1
3-methylantranilic acid

Conditions

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%

: 50424-93-6
3-methyl-2-nitrobenzoyl chloride

: 83325-79-5
methyl 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilate

A: 4389-45-1
3-methylantranilic acid

B: 83334-85-4
methyl 3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilate

Conditions

Conditions	Yield
With lithium hydroxide In water; benzene	A n/a B 61%

...Expand

: 857203-66-8
8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione

: 4389-45-1
3-methylantranilic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 67-56-1
methanol

: 1127-59-9
7-methyl-1H-indole-2,3-dione

A: 22223-49-0
methyl 2-amino-3-methylbenzoate

B: 4389-45-1
3-methylantranilic acid

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium methylate 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;

...Expand

: 1127-59-9
7-methyl-1H-indole-2,3-dione

: 71-36-3
butan-1-ol

A: 4389-45-1
3-methylantranilic acid

B: 79101-84-1
3-Methylanthranilsaeure-n-butylester

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium hydride 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;

...Expand

: 1885-77-4
3-methyl-2-nitrobenzonitrile

: 4389-45-1
3-methylantranilic acid

Conditions

Conditions	Yield
(i) H2, Pd-C, (ii) aq. NaOH; Multistep reaction;

: 50424-93-6
3-methyl-2-nitrobenzoyl chloride

: 78877-00-6
3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilic acid

A: 4389-45-1
3-methylantranilic acid

B: 83325-80-8
3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilic acid

Conditions

Conditions	Yield
With lithium hydroxide In water; benzene Title compound not separated from byproducts;

...Expand

: 1127-59-9
7-methyl-1H-indole-2,3-dione

: 7722-84-1
dihydrogen peroxide

alkali: alkali

: 4389-45-1
3-methylantranilic acid

...Expand

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Chemistry

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

Uses

3-Methylanthranilic acid (CAS NO.4389-45-1) is used as intermediates in organic synthesis.

Safety Profile

Safety Information about 3-Methylanthranilic acid (CAS NO.4389-45-1):
Hazard Codes: Harmful 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

Specification

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.