5434-20-8

Basic information

• Product Name: 3-AMINOPHTHALIC ACID
• Synonyms: 3-amino-2-benzenedicarboxylicacid;3-AMINOPHTHALIC ACID;3-AMINO-1,2-BENZENEDICARBOXYLIC ACID;AKOS AUF2103;3-AMINOPHTHALIC ACID, TECH., 90%;3-Aminophthalic acid,95%;1,2-Benzenedicarboxylic acid, 3-amino-;3-AMinophthalic acid, 95% 1GR
• CAS NO: 5434-20-8
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• EINECS: 226-595-9
• Product Categories: Phthalic Acids, Esters and Derivatives;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 5434-20-8.mol
• Article Data: 36

Chemical Properties

• Melting Point: 180-185 °C(lit.)
• Boiling Point: 436.4 °C at 760 mmHg
• Flash Point: 217.7 °C
• Appearance: Yellow/Crystalline Powder
• Density: 1.551 g/cm³
• Vapor Pressure: 2.17E-08mmHg at 25°C
• Solubility: soluble in Methanol
• PKA: 3.41±0.10(Predicted)
• CAS DataBase Reference: 3-AMINOPHTHALIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINOPHTHALIC ACID(5434-20-8)
• EPA Substance Registry System: 3-AMINOPHTHALIC ACID(5434-20-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 5434-20-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystalline powder

Uses

3-Aminophthalic Acid is a reactant used in the preparation of local anesthetics. Also used as a precursor for a reagent in the synthesis of Apremilast (A729700).

InChI:InChI=1/C8H7NO4/c9-5-3-1-2-4(7(10)11)6(5)8(12)13/h1-3H,9H2,(H,10,11)(H,12,13)/p-2

Synthetic route

3-nitrophthalic acid (603-11-2) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃;	97%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant;	97%
With hydrogen; palladium-containing anion exchanger AB-17-8-Pd In ethanol at 20 - 40℃; under 750.06 Torr; Kinetics; Product distribution; Further Variations:; Catalysts;	97%

dimethyl 3-aminophthalate (34529-06-1) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
With sodium hydroxide In methanol for 2h; Reflux;	81%

3-nitrophthalic acid anhydride (641-70-3) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride
Multi-step reaction with 5 steps 1: 16 h / Reflux 2: thionyl chloride / 8 h / 40 °C 3: 2 h / Reflux 4: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 5: sodium hydroxide / methanol / 2 h / Reflux View Scheme

2-amino-6-methylbenzoic acid (4389-50-8) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
With sodium acetate; acetic anhydride nachfolgend Oxydation mit Permanganat in alkalischer Loesung und Verseifen des Reaktionsproduktes;

3-nitrophthalic acid (603-11-2) + iron(II) sulfate + aqueous barium hydroxide → 3-aminophthalic acid (5434-20-8)

3-nitrophthalic acid (603-11-2) + sodium sulfide → 3-aminophthalic acid (5434-20-8)

hydrogenchloride (7647-01-0) + 3-nitrophthalic acid (603-11-2) + tin dichloride → 3-aminophthalic acid (5434-20-8)

hydrogenchloride (7647-01-0) + 3-nitrophthalic acid (603-11-2) + tin → 3-aminophthalic acid (5434-20-8)

3-nitrophthalic acid (603-11-2) + acetic acid (64-19-7) + zinc dust → 3-aminophthalic acid (5434-20-8)

phthalic anhydride (85-44-9) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: durch Nitrierung 2: tin; hydrochloric acid / 20 °C View Scheme
Multi-step reaction with 2 steps 1: durch Nitrierung 2: tin (II)-chloride; hydrochloric acid / 22 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid 2: iron(II) sulfate; ammonia View Scheme

benzene-1,2-dicarboxylic acid (88-99-3) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; fuming nitric acid 2: tin dichloride; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: durch Nitrierung 2: tin; hydrochloric acid / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; fuming nitric acid 2: ammonia; ferrosulfate; aq. barium hydroxide solution View Scheme
Multi-step reaction with 2 steps 1: durch Nitrierung 2: tin (II)-chloride; hydrochloric acid / 22 °C View Scheme
Multi-step reaction with 2 steps 1: HNO3+H2SO4 2: tin dichloride; hydrochloric acid View Scheme

2-cyano-3-nitrotoluene (1885-76-3) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid 2: potassium nitrite; sulfuric acid 3: ferrosulfate; ammonia 4: acetic acid anhydride; sodium acetate / nachfolgend Oxydation mit Permanganat in alkalischer Loesung und Verseifen des Reaktionsproduktes View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid 2: tin; hydrochloric acid 3: acetic acid anhydride; sodium acetate / nachfolgend Oxydation mit Permanganat in alkalischer Loesung und Verseifen des Reaktionsproduktes View Scheme

2-methyl-6-nitrobenzoic acid (13506-76-8) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: ferrosulfate; ammonia 2: acetic acid anhydride; sodium acetate / nachfolgend Oxydation mit Permanganat in alkalischer Loesung und Verseifen des Reaktionsproduktes View Scheme

2-methyl-6-nitro-benzoic acid amide (40637-78-3) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium nitrite; sulfuric acid 2: ferrosulfate; ammonia 3: acetic acid anhydride; sodium acetate / nachfolgend Oxydation mit Permanganat in alkalischer Loesung und Verseifen des Reaktionsproduktes View Scheme
Multi-step reaction with 2 steps 1: tin; hydrochloric acid 2: acetic acid anhydride; sodium acetate / nachfolgend Oxydation mit Permanganat in alkalischer Loesung und Verseifen des Reaktionsproduktes View Scheme

phthalic anhydride (85-44-9) + activated aluminium → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: durch Nitrieren 2: zinc dust View Scheme

5-amino-2,3-dihydrophthalazine-1,4-dione (521-31-3) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
With GLUTATHIONE; Cu2(CH3COC(COCH3)CHNCH2CHOHCH2O)2; dihydrogen peroxide pH=10; aq. buffer;
With N-Bromosuccinimide; gold; 1-(2,3,4-trimethoxybenzyl)piperazine hydrochloride In water Concentration; Alkaline conditions;
With [Cu2(N,N'-dibenzylethylenediamine)2(tetraacetylethane)](ClO4)2; dihydrogen peroxide In methanol; aq. phosphate buffer; water pH=7.5; pH-value; Concentration;

2-(methoxycarbonyl)-3-nitrobenzoic acid (6744-85-0) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / 8 h / 40 °C 2: 2 h / Reflux 3: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 4: sodium hydroxide / methanol / 2 h / Reflux View Scheme

3-nitro-phthalic acid-1-chloride-2-methyl ester (22351-62-8) → 3-aminophthalic acid (5434-20-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2 h / Reflux 2: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C 3: sodium hydroxide / methanol / 2 h / Reflux View Scheme

reactive blue 19 (2580-78-1) → 3-aminophthalic acid (5434-20-8) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1) + 1,4-diamino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (4095-85-6) + 1-amino-9,10-anthracenedione (82-45-1) + benzene-1,2-dicarboxylic acid (88-99-3)

Conditions	Yield
With chitosan/polyaniline/CdS nanocomposite for 2h; pH=6; Catalytic behavior; Kinetics; pH-value; Irradiation;

3-aminophthalic acid (5434-20-8) + helional (1205-17-0) → 4-((3-(benzo[d][1,3]dioxol-5-yl)-2-methylpropyl)amino)isobenzofuran-1,3-dione

Conditions	Yield
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 60804.1 Torr; for 15h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;	99%

3-aminophthalic acid (5434-20-8) + N,N-dimethylethylenediamine (108-00-9) → 3-amino-N-[2-(dimethylamino)ethyl]phthalimide

Conditions	Yield
at 165℃; for 2.5h;	95%

3-aminophthalic acid (5434-20-8) + N,N-diethylethylenediamine (100-36-7) → 4-amino-2-(2-diethylaminoethyl)-1H-isoindole-1,3(2H)-dione (77763-82-7)

Conditions	Yield
at 170℃; for 1h;	92%

3-aminophthalic acid (5434-20-8) → 3-aminophthalic anhydride (17395-99-2)

Conditions	Yield
With dicyclohexyl-carbodiimide In acetone at 20℃; for 12h;	92%
With acetic anhydride for 3h; Reflux;	61%
With acetic anhydride for 3h; Reflux;	61%

4-Trifluoromethylbenzaldehyde (455-19-6) + 3-aminophthalic acid (5434-20-8) → 4-((4-(trifluoromethyl)benzyl)amino)isobenzofuran-1,3-dione

Conditions	Yield
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 60804.1 Torr; for 15h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;	92%

3-aminophthalic acid (5434-20-8) + o-carboxybenzaldehyde (119-67-5) → 2-(((1,3-dioxo-1,3-dihydroisobenzofuran-4-yl)amino)methyl)benzoic acid

Conditions	Yield
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 60804.1 Torr; for 15h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;	89%

3-aminophthalic acid (5434-20-8) + C13H15BrN2O3 → C34H35N5O10

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	87%

3-aminophthalic acid (5434-20-8) + 4-(bromoacetyl)toluene (619-41-0) → C26H23NO6

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	84%

3-aminophthalic acid (5434-20-8) + 2-bromo-4'-fluoroacetophenone (403-29-2) → C24H17F2NO6

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	82%

3-aminophthalic acid (5434-20-8) + 4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-fluoro-benzaldehyde (1609540-94-4) → 3-((4-(((tert-butyldimethylsilyl)oxy)methyl)-2-fluorobenzyl)amino)phthalic acid

Conditions	Yield
Stage #1: 3-aminophthalic acid; 4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-fluoro-benzaldehyde With acetic acid In methanol at 25℃; for 0.5h; Stage #2: With 2-picoline borane complex In methanol at 0 - 20℃; for 16h;	81.8%
Stage #1: 3-aminophthalic acid; 4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-fluoro-benzaldehyde In methanol; acetic acid at 25℃; for 0.5h; Stage #2: With methanol; 2-picoline borane complex In acetic acid at 0 - 20℃; for 16h;	81.8%
Stage #1: 3-aminophthalic acid; 4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-fluoro-benzaldehyde With acetic acid In methanol at 25℃; for 0.5h; Stage #2: With 2-picoline borane complex In methanol at 0 - 20℃; for 16h; Inert atmosphere;	81.8%
Stage #1: 3-aminophthalic acid; 4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-fluoro-benzaldehyde With acetic acid In methanol at 25℃; for 0.5h; Stage #2: With 2-picoline borane complex In methanol at 20℃; for 16h;	81.8%

3-aminophthalic acid (5434-20-8) + acetic anhydride (108-24-7) → 3-acetylaminophthalic anhydride (6296-53-3)

Conditions	Yield
for 4h; Concentration; Temperature; Reflux;	78.5%
at 0 - 5℃; for 4h; Heating / reflux;	61%
for 3h; Reflux;	61%

3-aminophthalic acid (5434-20-8) + 2,3'-dibromoacetophenone (18523-22-3) → C24H17Br2NO6

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	77%

3-aminophthalic acid (5434-20-8) + benzaldehyde (100-52-7) → 4-(benzylamino)isobenzofuran-1,3-dione

Conditions	Yield
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 60804.1 Torr; for 15h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;	77%

3-aminophthalic acid (5434-20-8) + α-bromoacetophenone (70-11-1) → bis(phenacyl) 3-aminophthalate

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	70%

3-aminophthalic acid (5434-20-8) + 2-bromo-1-(4-chloro-3-nitrophenyl)ethanone (22019-49-4) → C24H15Cl2N3O10

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	68%

3-aminophthalic acid (5434-20-8) + 1-(4-amino-3,5-dichlorophenyl)-2-bromoethan-1-one (37148-47-3) → C24H17Cl4N3O6

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	68%

3-aminophthalic acid (5434-20-8) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → C26H23NO8

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	65%

4,4'-bipyridine (553-26-4) + cobalt(II) nitrate hexahydrate + 3-aminophthalic acid (5434-20-8) → [Co(bpy)1.5(3adpa)]

Conditions	Yield
With sodium hydroxide In water at 150℃; for 48h; Autoclave;	64%

3-aminophthalic acid (5434-20-8) → 3-iodophthalic acid (6937-34-4)

Conditions	Yield
Stage #1: 3-aminophthalic acid With hydrogenchloride; sodium nitrate In water for 3.33333h; Cooling; Stage #2: With urea; potassium iodide In water at 20℃; for 20h;	62%
Diazotization.Eintragen von Jodwasserstoffsaeure in die schwefelsaure Diazoniumsalzloesung;
Diazotization.Umsetzen der Diazoniumsalz-Loesung mit Kaliumjodid;
Stage #1: 3-aminophthalic acid With sulfuric acid; sodium nitrite In water at -10℃; Stage #2: With urea; potassium iodide at 70℃;

3-aminophthalic acid (5434-20-8) + 4-Carboxybenzaldehyde (619-66-9) → 4-(((1,3-dioxo-1,3-dihydroisobenzofuran-4-yl)amino)methyl)benzoic acid

Conditions	Yield
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 60804.1 Torr; for 15h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;	62%

3-aminophthalic acid (5434-20-8) + 7-chloro-6-fluoro-1-(4-fluoro-phenyl)-8-nitro-4-oxo-1, 4-dihydro-quinoline-3-carboxylic acid → 2-[(3-carboxy-1-(4-fluorophenyl)-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinolin-7-yl)amino]phthalic acid

Conditions	Yield
With pyridine In dimethyl sulfoxide at 70℃; for 240h;	60%

3-aminopiperidin-2-one (1892-22-4, 4077-38-7, 34294-79-6, 88763-76-2) + 3-aminophthalic acid (5434-20-8) → 4-amino-2-(2-oxopiperidin-3-yl)isoindoline-1,3-dione

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere;	35%

3-aminophthalic acid (5434-20-8) + pyridoxal 5'-phosphate (54-47-7) → 6-(2,3-Dicarboxyphenylazo)-pyridoxal-5-phosphate (608523-87-1)

Conditions	Yield
	30%

methanol (67-56-1) + 3-aminophthalic acid (5434-20-8) → 3-Methoxybenzoic acid (586-38-9)

Conditions	Yield
With sulfuric acid; sodium nitrite

3-aminophthalic acid (5434-20-8) → 3-azido-phthalic acid

Conditions	Yield
With cis-nitrous acid anschliessendes Umsetzen mit NaN3;

3-aminophthalic acid (5434-20-8) → 3-hydroxyphthalic acid (601-97-8)

Conditions	Yield
With sulfuric acid Diazotization;

3-aminophthalic acid (5434-20-8) → 3-benzoylamino-phthalic acid (16524-16-6)

Conditions	Yield
durch Benzoylieren;

3-aminophthalic acid (5434-20-8) → meta-aminobenzoic acid (99-05-8)

Conditions	Yield
With hydrogenchloride

Upstream product

• 641-70-3 3-nitrophthalic acid anhydride 
• 603-11-2 3-nitrophthalic acid 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 2580-78-1 reactive blue 19 
• 34529-06-1 dimethyl 3-aminophthalate 
• 22351-62-8 3-nitro-phthalic acid-1-chloride-2-methyl ester 
• 6744-85-0 2-(methoxycarbonyl)-3-nitrobenzoic acid 
• 521-31-3 5-amino-2,3-dihydrophthalazine-1,4-dione 
• 13506-76-8 2-methyl-6-nitrobenzoic acid 
• 1885-76-3 2-cyano-3-nitrotoluene 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 85-44-9 phthalic anhydride 
• 4389-50-8 2-amino-6-methylbenzoic acid 

Downstream Products

• 20579-79-7 3-amino-N-phenylphthalimide 
• 32360-48-8 2-Amino-5-carboxy-4-oxo-3,1,4-benzoxazin 
• 92792-46-6 3-(amino-1,3-dioxoisoindolin-2-yl)-phthalic acid 

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