Conditions | Yield |
---|---|
With graphitic carbon nitride; hydrazine hydrate In water at 70℃; for 36h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction; | 100% |
With palladium 10% on activated carbon; ammonium formate; silica gel In methanol for 1.5h; Milling; | 99% |
With hydrogen In ethanol; water at 18 - 20℃; under 760.051 Torr; for 10h; | 96.5% |
Conditions | Yield |
---|---|
With iron(III) oxide; hydrazine hydrate In water at 120℃; for 3h; Inert atmosphere; | 98% |
With ammonium hydroxide at 90℃; for 2h; | 89% |
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3; | 96% |
Conditions | Yield |
---|---|
With C26H30B10Cl2P2Pd In toluene at 60℃; under 760.051 Torr; for 10h; | 92% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 84% |
3-(benzylamino)benzoic acid
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With ammonium formate; zinc In ethylene glycol for 0.0583333h; microwave irradiation; | 80% |
Conditions | Yield |
---|---|
With phosphate buffer at 30℃; for 9.6h; rhodococcus rhodocrous AJ270, pH 7.0; | 79% |
With potassium phosphate buffer at 30℃; for 7h; Rhodococcus sp. AJ270 cells; | 78.5% |
With nitrilase from Gordonia terrae In aq. phosphate buffer at 35℃; for 1h; pH=8; Enzymatic reaction; |
Conditions | Yield |
---|---|
With urea-hydrogen peroxide at 160 - 162℃; for 0.0166667h; microwave irradiation; | 75% |
Conditions | Yield |
---|---|
With potassium hydroxide In 1,3,5-trimethyl-benzene at 160℃; for 24h; Inert atmosphere; | 72% |
3-Carboxyphenylboronic acid
meta-aminobenzoic acid
Conditions | Yield |
---|---|
Stage #1: 3-Carboxyphenylboronic acid With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 24h; Stage #2: With hydrogenchloride In methanol; water pH=1; | 65% |
Conditions | Yield |
---|---|
With hydrogenchloride |
3-amino-4-chloro-benzoic acid
2-chloro-5-aminobenzoic acid
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With sodium amalgam; water |
Conditions | Yield |
---|---|
With hydrogenchloride |
benzenediazonium
3-hydrazinobenzoic acid
A
3-azidobenzoic acid
B
meta-aminobenzoic acid
C
aniline
D
Phenyl azide
Conditions | Yield |
---|---|
beim Behandeln von Benzoldiazoniumnitrat; |
3-hydrazinobenzoic acid
A
3-azidobenzoic acid
B
meta-aminobenzoic acid
C
aniline
D
Phenyl azide
3-nitrobenzoic acid
A
3,3'-hydrazo-di-benzoic acid
B
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With sodium amalgam |
N,N'-bis(3-carboxy-phenyl)-triazene
phenol
A
3-[(4-hydroxyphenyl)diazenyl]benzoic acid
B
meta-aminobenzoic acid
(5S)-5-<(tert-butoxycarbonyl)amino>cyclohexadienecarboxylic acid
A
Gabaculine
B
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water Title compound not separated from byproducts; |
3-(3-nitro-benzylidenamino)-benzoic acid
A
3-nitro-benzaldehyde
B
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With borate buffer; water In methanol at 24.9℃; Rate constant; Thermodynamic data; ΔH (excit.), ΔS (excit.), further solv.; |
3-{[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid
A
4-nitrobenzaldehdye
B
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With borate buffer; water In methanol at 24.9℃; Rate constant; Thermodynamic data; ΔH (excit.), ΔS (excit.), further solv.; |
2-tert-butyl-5-hydroxy-1,4-benzoquinone
5-amino-1,3-cyclohexadiene-1-carboxylic acid
A
5-tert-butyl-1,2,4-trihydroxybenzene
B
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With tert-butylamine In dimethyl sulfoxide at 40℃; for 96h; |
Conditions | Yield |
---|---|
With sodium hydroxide Ambient temperature; | |
With alpha cyclodextrin In water Kinetics; Reagent/catalyst; Alkaline conditions; |
Conditions | Yield |
---|---|
at 150℃; |
Conditions | Yield |
---|---|
at 145 - 150℃; |
hydrogenchloride
5-amino-2,3-dihydrophthalazine-1,4-dione
meta-aminobenzoic acid
Conditions | Yield |
---|---|
at 145 - 150℃; |
hydrogenchloride
ethanol
3-(2,5-dioxopyrrolidin-1-yl)benzoic acid
A
meta-aminobenzoic acid
B
succinic acid diethyl ester
Conditions | Yield |
---|---|
beim Eindampfen der mit etwas Wasser versetzten Loesung; |
hydrogenchloride
2,4,6-tris(3-nitrophenyl)-1,3,5-triazine
A
meta-aminobenzoic acid
B
3-nitrobenzoic acid
Conditions | Yield |
---|---|
With thionyl chloride at 0℃; for 24h; Reflux; | 100% |
With thionyl chloride at 0 - 20℃; | 99% |
With thionyl chloride for 3h; Ambient temperature; | 96% |
Conditions | Yield |
---|---|
Stage #1: meta-aminobenzoic acid With sulfuric acid; sodium nitrite In water at 0℃; for 1.5h; Inert atmosphere; Stage #2: With sodium azide In water at 0 - 20℃; for 16.5h; Inert atmosphere; | 100% |
Stage #1: meta-aminobenzoic acid With sulfuric acid; sodium nitrite In water at 0℃; for 1.5h; Stage #2: With sodium azide In water at 0 - 20℃; for 16.5h; | 100% |
With tert.-butylnitrite; trimethylsilylazide In acetonitrile Inert atmosphere; | 99% |
di-tert-butyl dicarbonate
meta-aminobenzoic acid
3-((tert-butoxycarbonyl)amino)benzoic acid
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water at 20℃; for 24h; | 100% |
With triethylamine In 1,4-dioxane; water at 20℃; for 18h; | 100% |
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; | 98% |
Conditions | Yield |
---|---|
In butan-1-ol at 180℃; for 1h; Under nitrogen atmosphere; | 100% |
di(n-butyl)tin oxide
meta-aminobenzoic acid
bis(m-aminobenzoato-O,O') di-n-butyltin(IV)
Conditions | Yield |
---|---|
In acetonitrile Reflux; | 100% |
In benzene byproducts: H2O; boiling 10mmol di-n-butyltin(IV) oxide and 20mmol amino benzoic acid in 50ml C6H6 for 4h (continuous removal of H2O), evapn., extractn. of residue with light petroleum ether (b.p. 40-60°C), evapn.;; recrystn. from a mixture of ether and petroleum ether (b.p. 40-60°C); elem. anal., mass spectroscopy;; |
meta-aminobenzoic acid
malonoyl dichloride
3,3'-malonyldiamino-di-benzoic acid
Conditions | Yield |
---|---|
In 1,4-dioxane at 20℃; for 0.25h; | 100% |
Conditions | Yield |
---|---|
Stage #1: meta-aminobenzoic acid With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 1h; Stage #2: acetylacetone With sodium acetate In ethanol; water at 20℃; for 1h; | 100% |
Stage #1: meta-aminobenzoic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: acetylacetone With sodium acetate In water at 20℃; for 1h; | 78% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 100% |
dichloromaleic acid anhydride
meta-aminobenzoic acid
dichloromaleic acid N-m-carboxyphenylimide
Conditions | Yield |
---|---|
In acetic acid for 1h; Heating; | 99% |
Conditions | Yield |
---|---|
In tetrahydrofuran Ambient temperature; | 99% |
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With Nitrogen dioxide In 1,4-dioxane at 10 - 40℃; | 99% |
With tributyl phosphate-NO2 In various solvent(s) at 10 - 15℃; | 95% |
With Nitrogen dioxide; N,N-dimethyl-formamide In N,N-dimethyl-formamide for 0.0833333h; | 93% |
With polyethylene glycol - NO2 In various solvent(s) | 91% |
meta-aminobenzoic acid
Conditions | Yield |
---|---|
Stage #1: meta-aminobenzoic acid With sodium nitrite In water at 30℃; Acidic conditions; Flow reactor; Stage #2: With sodium sulfite In water at 100 - 120℃; Stage #3: With sulfuric acid In water at 125℃; | 98.2% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 98% |
Stage #1: meta-aminobenzoic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere; Reflux; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 91% |
With lithium aluminium tetrahydride |
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide; sodium bromide In water at 15℃; for 2h; | 98% |
With bromine In tetrachloromethane at 20 - 40℃; | 97% |
With N-Bromosuccinimide In water at 20℃; for 0.166667h; | 95% |
Conditions | Yield |
---|---|
Stage #1: meta-aminobenzoic acid With sulfuric acid; sodium nitrite at 5 - 20℃; for 1h; Stage #2: With water Reflux; | 98% |
With mixture of gaseous nitrogen oxides; water |
maleic anhydride
meta-aminobenzoic acid
3-[[(2Z)-3-carboxy-1-oxo-2-propen-1-yl]amino]benzoic acid
Conditions | Yield |
---|---|
In acetic acid for 0.166667h; Heating; | 98% |
In tetrahydrofuran at 25℃; for 1h; | 92% |
at 20℃; | 92% |
meta-aminobenzoic acid
benzyl chloroformate
3-(benzyloxycarbonylamino)benzoic acid
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran for 2.5h; Ambient temperature; | 98% |
With sodium hydrogencarbonate In 1,4-dioxane; water-d2 at 20℃; for 7h; | 87% |
With potassium carbonate |
meta-aminobenzoic acid
p-trifluoromethyl-phenylisocyanate
3-[3-(4-trifluoromethyl-phenyl)-ureido]-benzoic acid
Conditions | Yield |
---|---|
In tetrahydrofuran Ambient temperature; | 98% |
Stage #1: meta-aminobenzoic acid; p-trifluoromethyl-phenylisocyanate In N,N-dimethyl-formamide at 70℃; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 0 - 20℃; for 1h; | 51% |
In tetrahydrofuran at 20℃; for 60h; |
5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
meta-aminobenzoic acid
Conditions | Yield |
---|---|
In ethanol at 20℃; | 98% |
methanol
meta-aminobenzoic acid
3-amino-benzoic acid methyl ester hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride for 16h; | 98% |
With chloro-trimethyl-silane at 20℃; for 24h; | 90% |
With thionyl chloride for 2h; Heating; |
Conditions | Yield |
---|---|
In propan-1-ol at 70℃; for 4h; Temperature; Solvent; | 98% |
2,6-difluorobenzylamine
meta-aminobenzoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 15h; | 98% |
Conditions | Yield |
---|---|
In methanol at 85℃; for 2h; Catalytic behavior; Temperature; Solvent; Ugi Condensation; Sealed tube; Microwave irradiation; | 98% |
Conditions | Yield |
---|---|
Stage #1: meta-aminobenzoic acid With hydrogenchloride; sodium nitrite In water for 1h; Stage #2: 3'-nitroacetoacetanilide With sodium acetate In methanol; water for 1.5h; | 97.2% |
Conditions | Yield |
---|---|
Stage #1: meta-aminobenzoic acid With hydrogenchloride; sodium nitrite In water at 5℃; for 1h; Cooling with ice; Stage #2: 3'-nitroacetoacetanilide With sodium acetate In methanol; water at 5℃; for 1.5h; Cooling with ice; | 97.2% |
meta-aminobenzoic acid
2,5-hexanedione
3-(2,5-dimethylpyrrol-1-yl)benzoic acid
Conditions | Yield |
---|---|
With amberlite IR 120 acidic resin at 20℃; for 0.6h; Paal-Knorr pyrrole synthesis; Neat (no solvent); | 97% |
With zirconyl chloride octahydrate; urea at 20℃; for 0.5h; Paal-Knorr Pyrrole Synthesis; Green chemistry; | 85% |
With acetic acid at 150℃; for 4h; Cooling with ice; | 61% |
Conditions | Yield |
---|---|
With sodium tungstate; phosphoric acid; dihydrogen peroxide In ethanol at 60 - 65℃; | 97% |
terephthalaldehyde,
meta-aminobenzoic acid
N,N'-terephthalylidenebis(m-aminobenzoic acid)
Conditions | Yield |
---|---|
In benzene at 20℃; for 24h; | 97% |
In methanol for 2.5h; | |
In acetonitrile Reflux; |
The IUPAC name of this product is 3-aminobenzoic acid. With the CAS registry number 99-05-8, it is also named as 3-Carboxyaniline; 4-14-00-01092 (Beilstein Handbook Reference); AI3-04707; Aniline-3-carboxylic acid; BRN 0471603; MABA; NSC 15012; m-Carboxyaniline; Benzoic acid, 3-amino-. The product's categories are fine chemical & intermediates, aromatic carboxylic acids, amides, anilides, anhydrides & salts, organic acids, peptide synthesis and unnatural amino acid derivatives.
The 3-Aminobenzoic Acid is white to off white crystalline powder which is soluble in acetone, boiling water, hot alcohol, hot chloroform and ether, slightly soluble in cold water, cold alcohol and cold chloroform, insoluble in benzene and gasoline. It is used as medicine and dye intermediate in the manufacture of azo dyes, medicine, bile acid and B-iodobenzene shadow acids, reagents.
The 3-Aminobenzoic Acid is toxic. It is flammable and it can produce toxic nitrogen oxide fumes when buring. So the storage environment should be ventilate, low-temperature and dry. So this product is harmful if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and gloves and eye/face protection.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.78 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -0.38 ; (4)ACD/LogD (pH 7.4): -1.97 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 4.33 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 3 ; (10)#H bond donors: 3 ; (11)#Freely Rotating Bonds: 2 ; (12)Index of Refraction: 1.637 ; (13)Molar Refractivity: 37.41 cm3 ; (14)Molar Volume: 104.2 cm3 ; (15)Polarizability: 14.83×10-24 cm3 ; (16)Surface Tension: 64.3 dyne/cm ; (17)Enthalpy of Vaporization: 63.04 kJ/mol ; (18)Vapour Pressure: 1.41E-05 mmHg at 25°C ; (19)Rotatable Bond Count: 1 ; (20)Exact Mass: 137.047678 ; (21)MonoIsotopic Mass: 137.047678 ; (22)Topological Polar Surface Area: 63.3 ; (23)Heavy Atom Count: 10 ; (24)Complexity: 136.
People can use the following data to convert to the molecule structure. SMILES: O=C(O)c1cc(N)ccc1; InChI: InChI=1/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10); InChIKey: XFDUHJPVQKIXHO-UHFFFAOYAM. 3-Aminobenzoic Acid has many suppliers, such as Changzhou Sunlight Pharmaceutical Co., Ltd..
The following is the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 750mg/kg (750mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
mouse | LD50 | oral | 6300mg/kg (6300mg/kg) | Quarterly Journal of Pharmacy & Pharmacology. Vol. 19, Pg. 483, 1946. | |
mouse | LDLo | intraperitoneal | 500mg/kg (500mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 53, 1954. |
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