2-Amino-6-methylbenzoic acid supplier

Name
2-Amino-6-methylbenzoic acid
EINECS -0
CAS No. 4389-50-8
Article Data18
CAS DataBase
Density 1.254 g/cm³
Solubility
Melting Point 128-130 °C (dec.)(lit.)
Formula C₈H₉NO₂
Boiling Point 315.1 °C at 760 mmHg
Molecular Weight 151.165
Flash Point 144.4 °C
Transport Information
Appearance Pale yellow powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms o-Toluicacid, 6-amino- (6CI,8CI);6-Amino-o-toluic acid;6-Methyl-2-aminobenzoic acid;6-Methylanthranilic acid;ACR 1308;
PSA 63.32000
LogP 1.85660

Synthetic route

: 13506-76-8
2-methyl-6-nitrobenzoic acid

: 4389-50-8
2-amino-6-methylbenzoic acid

Conditions

Conditions	Yield
palladium	100%
With tin(ll) chloride In ethanol at 70℃; for 0.5h;	99%
With hydrazine hydrate; nickel In ethanol at 40℃;	67%

: 83-41-0
2,3-dimethylnitrobenzene

: 4389-50-8
2-amino-6-methylbenzoic acid

Conditions

Conditions	Yield
With selenium; nitrobenzene; lithium tert-butoxide In methanol; water; dimethyl sulfoxide at 90℃; for 5h; Inert atmosphere;	59%

: 40637-78-3
2-methyl-6-nitro-benzoic acid amide

: 4389-50-8
2-amino-6-methylbenzoic acid

Conditions

Conditions	Yield
With hydrogenchloride; tin
Multi-step reaction with 2 steps 1: potassium nitrite; sulfuric acid 2: ferrosulfate; ammonia View Scheme
Multi-step reaction with 2 steps 1: NaNO2, H2SO4 2: FeSO4, aq. NH3 View Scheme

: 1128-44-5
4-methyl-1H-indole-2,3-dione

: 7722-84-1
dihydrogen peroxide

: furan-2,3,5(4H)-trione pyridine (1:1)

: 4389-50-8
2-amino-6-methylbenzoic acid

...Expand

: 40637-78-3
2-methyl-6-nitro-benzoic acid amide

: 7664-41-7
ammonia

: iron(II) sulfate

: 4389-50-8
2-amino-6-methylbenzoic acid

...Expand

: 7647-01-0
hydrogenchloride

: 40637-78-3
2-methyl-6-nitro-benzoic acid amide

tin: tin

A: 4389-50-8
2-amino-6-methylbenzoic acid

B 4-methyl-β.γ-benzisoxazolone-(3): 4-methyl-β.γ-benzisoxazolone-(3)

...Expand

4-methyl-isatin: 4-methyl-isatin

: 4389-50-8
2-amino-6-methylbenzoic acid

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

: 13506-76-8
2-methyl-6-nitrobenzoic acid

A: 4389-50-8
2-amino-6-methylbenzoic acid

B 4-methyl-β.γ-benzisoxazolone-(3): 4-methyl-β.γ-benzisoxazolone-(3)

Conditions

Conditions	Yield
With ammonia; iron(II) sulfate

: 1885-76-3
2-cyano-3-nitrotoluene

: 4389-50-8
2-amino-6-methylbenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid 2: potassium nitrite; sulfuric acid 3: ferrosulfate; ammonia View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 3 steps 1: aq. H2SO4 2: NaNO2, H2SO4 3: FeSO4, aq. NH3 View Scheme

: 186581-53-3, 908094-01-9
diazomethane

: 4389-50-8
2-amino-6-methylbenzoic acid

: 18595-13-6
2-amino-6-methylbenzoic acid methyl ester

Conditions

Conditions	Yield
In diethyl ether for 1h; Inert atmosphere;	100%
In diethyl ether

: 4389-50-8
2-amino-6-methylbenzoic acid

: 79-04-9
chloroacetyl chloride

: 66232-40-4
2-[(chloroacetyl)amino]-6-methylbenzoic acid

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%
In benzene for 0.5h; Heating;	92%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 4 - 20℃;
In toluene at 100℃; for 6h;	30 g

: 4389-50-8
2-amino-6-methylbenzoic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 18595-13-6
2-amino-6-methylbenzoic acid methyl ester

Conditions

Conditions	Yield
In ethanol; hexane; ethyl acetate at 20℃; for 1.5h;	100%
In diethyl ether; ethanol; ethyl acetate at 20℃; for 4h; Cooling with ice;	16.5 g
In diethyl ether; ethanol; ethyl acetate at 20℃; for 4h;
In diethyl ether; ethanol; ethyl acetate at 20℃; for 4h;	16.5 g

: 75-44-5
phosgene

: 4389-50-8
2-amino-6-methylbenzoic acid

: 20877-81-0
5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

Conditions

Conditions	Yield
With sodium hydroxide In toluene for 1h; cyclocondensation;	98%
With sodium hydroxide In water	90%
With sodium carbonate In water; toluene for 8h;	75.4%

: 2058-74-4
1-methyl-1H-indole-2,3-dione

: 4389-50-8
2-amino-6-methylbenzoic acid

: C17H14N2O3

Conditions

Conditions	Yield
for 0.05h; microwave irradiation;	98%
In ethanol at 20℃; for 3h;	94%

: 2058-72-2
5-bromo-1-methyl-1H-indole-2,3-dione

: 4389-50-8
2-amino-6-methylbenzoic acid

: C17H13BrN2O3

Conditions

Conditions	Yield
for 0.1h; microwave irradiation;	98%
In ethanol at 20℃; for 4h;	95%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 91-56-5
indole-2,3-dione

: 1,2-dihydro-5-methyl-spiro[4H-3,1-benzoxazine-2,3'[3H]indol]-4,2'-dione

Conditions

Conditions	Yield
for 0.05h; microwave irradiation;	98%
In ethanol at 20℃; for 3h;	95%

: 80-11-5
N-methyl-N-nitrosotoluene-p-sulfonamide

: 4389-50-8
2-amino-6-methylbenzoic acid

: 18595-13-6
2-amino-6-methylbenzoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: N-methyl-N-nitrosotoluene-p-sulfonamide With potassium hydroxide In diethyl ether; water Stage #2: 2-amino-6-methylbenzoic acid In diethyl ether for 1h;	98%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 1345444-50-9
6-amino-3-iodine-2-methylbenzoic acid

Conditions

Conditions	Yield
With Iodine monochloride; acetic acid for 3.5h;	98%
With Iodine monochloride; acetic acid for 2.5h;	95%
With Iodine monochloride; acetic acid at 25℃; for 3h;	95%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 79-30-1
isobutyryl chloride

: 2-isopropyl-5-methyl-4H-3,1-benzoxazin-4-one

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;	98%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 65658-16-4
2-amino-6-methylbenzyl alcohol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;	97%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	85%
With borane-THF In tetrahydrofuran at 0 - 30℃; for 1.66667h; Inert atmosphere;	83%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 87-48-9
5-Bromo-1H-indole-2,3-dione

: C16H11BrN2O3

Conditions

Conditions	Yield
for 0.0666667h; microwave irradiation;	97%
In ethanol at 20℃; for 3h;	96%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 2043-61-0
cyclohexanecarbaldehyde

: 2-cyclohexyl-5-methyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
With acetic acid In ethanol for 6h; Reflux;	97%

: 608-05-9
5-methyl-indole-2,3-dione

: 4389-50-8
2-amino-6-methylbenzoic acid

: C17H14N2O3

Conditions

Conditions	Yield
for 0.05h; microwave irradiation;	96%
In ethanol at 20℃; for 2h;	95%

: 443-69-6
5-fluoro-1H-indole-2,3-dione

: 4389-50-8
2-amino-6-methylbenzoic acid

: C16H11FN2O3

Conditions

Conditions	Yield
for 0.05h; microwave irradiation;	96%
In ethanol at 20℃; for 2h;	95%

: 653-37-2
perfluorobenzaldehyde

: 4389-50-8
2-amino-6-methylbenzoic acid

: 5-methyl-2-(perfluorophenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
With acetic acid In ethanol for 6h; Reflux;	96%

: 66440-60-6
1,5-dimethyl-1H-indole-2,3-dione

: 4389-50-8
2-amino-6-methylbenzoic acid

: C18H16N2O3

Conditions

Conditions	Yield
for 0.0666667h; microwave irradiation;	95%
In ethanol at 20℃; for 3h;	92%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 4755-77-5
Ethyl oxalyl chloride

: 1352572-07-6
ethyl 5-methyl-4-oxo-4H-benzo[d][1,3]oxazine-2-carboxylate

Conditions

Conditions	Yield
With triethylamine In chloroform for 1.16667h; Cooling with ice; Reflux;	95%

: 773-91-1
5-fluoro-1-methylisatin

: 4389-50-8
2-amino-6-methylbenzoic acid

: C17H13FN2O3

Conditions

Conditions	Yield
for 0.05h; microwave irradiation;	94%
In ethanol at 20℃; for 2h;	91%

: 4-chloro-5-fluoro-1-methyl-1H-indole-2,3-dione

: 4389-50-8
2-amino-6-methylbenzoic acid

: C17H12ClFN2O3

Conditions

Conditions	Yield
In ethanol at 20℃; for 4h;	93%
for 0.0833333h; microwave irradiation;	93%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 84378-94-9
4-chloro-5-fluoro-isatin

: C16H10ClFN2O3

Conditions

Conditions	Yield
for 0.0333333h; microwave irradiation;	92%
In ethanol at 20℃; for 2h;	90%

: 79791-29-0
2-(3-(2,5-dimethylphenoxy)propyl)-2-methylpropionyl chloride

: 4389-50-8
2-amino-6-methylbenzoic acid

: 2-(5-(2,5-dimethylphenoxy)-2,2-dimethylpentanamido)-6-methylbenzoic acid

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 0℃; for 10.5h;	91.4%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 95-53-4
o-toluidine

: 371244-06-3
2-amino-6-methyl-N-o-tolylbenzamide

Conditions

Conditions	Yield
Stage #1: 2-amino-6-methylbenzoic acid With thionyl chloride In toluene for 1h; Heating; Stage #2: o-toluidine In tetrahydrofuran for 18h; Heating; Further stages.;	91%
With thionyl chloride In chloroform; benzene

: 3132-99-8
m-bromobenzoic aldehyde

: 4389-50-8
2-amino-6-methylbenzoic acid

: 2-(3-bromophenyl)-5-methyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
With acetic acid In ethanol for 6h; Reflux;	91%

: 506-68-3
bromocyane

: 4389-50-8
2-amino-6-methylbenzoic acid

: 93701-53-2
2-Amino-5-methyl-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
With sodium hydroxide In water for 16h;	90%

: 100-43-6
4-vinylpyridine

: 75-44-5
phosgene

: 4389-50-8
2-amino-6-methylbenzoic acid

: 541-41-3
chloroformic acid ethyl ester

: 123101-59-7
5-Methyl-4H-3, 1-Benzoxazin-4-One

Conditions

Conditions	Yield
In diethyl ether; toluene	90%
In diethyl ether; dichloromethane; toluene	67%

...Expand

: 75-44-5
phosgene

: 62563-03-5
1-vinyl-1,2-dihydro-pyridine

: 4389-50-8
2-amino-6-methylbenzoic acid

: 541-41-3
chloroformic acid ethyl ester

: 123101-59-7
5-Methyl-4H-3, 1-Benzoxazin-4-One

Conditions

Conditions	Yield
In diethyl ether; toluene	90%
In diethyl ether; dichloromethane; toluene	67%

...Expand

: 4389-50-8
2-amino-6-methylbenzoic acid

: 1609-47-8
diethyl dicarbonate

: 2-ethoxycarbonylamino-6-methylbenzoic acid

Conditions

Conditions	Yield
In PEG-400 at 20℃; for 0.5h;	90%
With polyethylene glycol PEG-400 at 20℃; for 0.5h; Green chemistry;	90%

: 4389-50-8
2-amino-6-methylbenzoic acid

: 57-06-7
N-allyl isothiocyanate

: 3-allyl-2,3-dihydro-5-methyl-2-thioxoquinazolin-4(1H)-one

Conditions

Conditions	Yield
With triethylamine In ethanol for 1h; Reflux;	90%

2-Amino-6-methylbenzoic acid Specification

This chemical is called Benzoic acid, 2-amino-6-methyl-, and it can also be named as 6-Methylanthranilic acid. With the molecular formula of C₈H₉NO₂, its product categories are Carboxylicacid; Fine Chemical & Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic Acid. The CAS registry number of this chemical is 4389-50-8. In addition, this chemical should be sealed in the cool and dry place.

Other characteristics of the Benzoic acid, 2-amino-6-methyl- can be summarised as followings: (1)ACD/LogP: 1.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.34; (4)ACD/LogD (pH 7.4): -1.21; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 8.96; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 29.54 Å²; (13)Index of Refraction: 1.618; (14)Molar Refractivity: 42.24 cm³; (15)Molar Volume: 120.5 cm³; (16)Polarizability: 16.74×10^-24cm³; (17)Surface Tension: 58.2 dyne/cm; (18)Density: 1.254 g/cm³; (19)Flash Point: 144.4 °C; (20)Enthalpy of Vaporization: 58.74 kJ/mol; (21)Boiling Point: 315.1 °C at 760 mmHg; (22)Vapour Pressure: 0.000189 mmHg at 25 °C.

Production method of this chemical: The Benzoic acid, 2-amino-6-methyl- could be obtained by the reactant of 2-methyl-6-nitro-benzoic acid. This reaction needs the reagent of FeSO₄, aq. NH_3.

Uses of this chemical: The Benzoic acid, 2-amino-6-methyl- could react with cyanogen bromide, and obtain the 2-amino-5-methyl-benzo[d][1,3]oxazin-4-one. This reaction needs the reagent of NaOH, and the solvent of H₂O. The yield is 90 %. In addition, this reaction should be taken for 16 hours.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing to avoid contacting with skin and eyes. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(O)c1c(cccc1N)C
2.InChI: InChI=1/C8H9NO2/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4H,9H2,1H3,(H,10,11)
3.InChIKey: XHYVBIXKORFHFM-UHFFFAOYAU

Product Name

2-Amino-6-methylbenzoic acid

Synthetic route

2-Amino-6-methylbenzoic acid Specification

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