3-AMINO-2-NAPHTHOIC ACID supplier

Name
3-Amino-2-naphthoic acid
EINECS 227-726-2
CAS No. 5959-52-4
Article Data21
CAS DataBase
Density 1.352 g/cm³
Solubility Soluble in alcohol and ether. Insoluble in water.
Melting Point 212-215 °C (dec.)(lit.)
Formula C₁₁H₉NO₂
Boiling Point 384.9 °C at 760 mmHg
Molecular Weight 187.198
Flash Point 186.6 °C
Transport Information
Appearance yellow-green to green powder
Safety 26-36
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Naphthoicacid, 3-amino- (6CI,7CI,8CI);2-Amino-3-carboxynaphthalene;2-Amino-3-naphthoicacid;2-Aminonaphthalene-3-carboxylic acid;3-Amino-2-naphthalenecarboxylicacid;3-Amino-2-naphthoic acid;NSC 37061;b-Naphthylamine-3-carboxylic acid;
PSA 63.32000
LogP 2.70140

Synthetic route

: 887242-59-3
3-(tert-butoxycarbonylamino)naphthalene-2-carboxylic acid

: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 24h;	99%

: 92-70-6
3-Hydroxy-2-naphthoic acid

: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
With ammonium hydroxide; zinc(II) chloride at 195℃; under 10351 - 20477 Torr; for 72h; Autoclave;	87.5%
With ammonium hydroxide; zinc(II) chloride at 30 - 195℃; under 15001.5 Torr; for 75h;	75%
With ammonium hydroxide; zinc(II) chloride In water at 190℃; for 108h; Inert atmosphere;	60%

: 5810-96-8
1H-benzo[f]indole-2,3-dione

: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
With potassium hydroxide; potassium chloride; dihydrogen peroxide at 20℃;

: 5580-64-3
N-(α-Oximino-acetyl)-β-naphthylamin

: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH3SO3H / 70 - 80 °C 2: KOH, KCl, 27percent H2O2 / 20 °C View Scheme

: 91-59-8
naphthalen-2-ylamine

: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Na2SO4, hydroxylamine sulfate, concd. HCl / H2O 2: CH3SO3H / 70 - 80 °C 3: KOH, KCl, 27percent H2O2 / 20 °C View Scheme

: nickel(II) sulphate

: 92-70-6
3-Hydroxy-2-naphthoic acid

A: {Ni(3-amino-2-naphthoate)2}

B: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
In ammonia 24 h, 210°C, 40 atm, in autoclave;
In ammonia aq. ammonia=NH3; 24 h, 210°C, 40 atm, in autoclave;
In ammonia 24 h, 210°C, 40 atm, in autoclave;

...Expand

: 13728-34-2
dimethyl 2,3-naphthalenedicarboxylate

: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium hydroxide; methanol / 24 h / 20 °C / Cooling with ice 2: diphenyl phosphoryl azide; triethylamine / 27 h / 20 °C / Reflux 3: potassium hydroxide; methanol / 12 h / 20 °C 4: trifluoroacetic acid / dichloromethane / 24 h / 20 °C View Scheme

: 35977-78-7
2,3-naphthalenedicarboxylic acid monomethyl ester

: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diphenyl phosphoryl azide; triethylamine / 27 h / 20 °C / Reflux 2: potassium hydroxide; methanol / 12 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 24 h / 20 °C View Scheme

: 643-79-8
o-phthalic dicarboxaldehyde

: 5959-52-4
2-Amino-3-naphthoic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: tributylphosphine / dichloromethane / 0 - 20 °C 1.2: 3 h / 20 °C / Cooling with ice 2.1: potassium hydroxide; methanol / 24 h / 20 °C / Cooling with ice 3.1: diphenyl phosphoryl azide; triethylamine / 27 h / 20 °C / Reflux 4.1: potassium hydroxide; methanol / 12 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C View Scheme

: 67-56-1
methanol

: 5959-52-4
2-Amino-3-naphthoic acid

: 21597-54-6
Methyl 3-amino-2-naphthoate

Conditions

Conditions	Yield
With sulfuric acid for 14h; Reflux;	100%
With sulfuric acid for 48h; Reflux;	96%
With sulfuric acid Reflux;	94%

: 5959-52-4
2-Amino-3-naphthoic acid

: 19411-56-4
3-chloro-2-naphthoic acid

Conditions

Conditions	Yield
Stage #1: 2-Amino-3-naphthoic acid With hydrogenchloride; sodium nitrite In water; acetonitrile at 0℃; for 1h; Stage #2: With copper(l) chloride In water; acetonitrile at 0 - 50℃; for 0.916667h;	100%
With hydrogenchloride; sodium nitrite Diazotization.Eintragen in eine aus Kupfer(II)-chlorid, Kupfer und wss. Salzsaeure hergestellte Loesung;
With hydrogenchloride; sulfuric acid; copper(l) chloride; sodium nitrite 1.) acetic acid, 40 deg C, 30 min, 2.) 80 deg C, 30 min; Yield given. Multistep reaction;
Stage #1: 2-Amino-3-naphthoic acid With sulfuric acid; sodium nitrite In acetic acid at 20 - 40℃; for 0.5h; Stage #2: With hydrogenchloride; copper(l) chloride In water; acetic acid at 0 - 80℃; for 0.5h;

: 5959-52-4
2-Amino-3-naphthoic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 21597-54-6
Methyl 3-amino-2-naphthoate

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at 20℃; for 24h;	100%
With acetic acid In methanol; hexane; toluene at 0 - 20℃;	83%
In diethyl ether; dichloromethane for 13h;	76.5%

: 5959-52-4
2-Amino-3-naphthoic acid

: 856071-79-9
3-amino-4,7-dibromonaphthalene-2-carbocylic acid

Conditions

Conditions	Yield
With bromine; acetic acid for 5h; Reflux;	100%
With bromine In acetic acid for 5h; Heating;	94%
Multi-step reaction with 4 steps 2: aqueous HNO3; NaNO2; acetic acid 3: acetic acid; bromine 4: aqueous HBr View Scheme

: 5959-52-4
2-Amino-3-naphthoic acid

: 5043-27-6
3-amino-4-bromo-2-naphthoic acid

Conditions

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	99%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2.75h;	99%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	98%

: 592-82-5
butyl isothiocyanate

: 5959-52-4
2-Amino-3-naphthoic acid

: 3-butyl-2,3-dihydro-2-thioxobenzo[g]quinazolin-4(1H)-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide Reflux;	98%
With triethylamine In N,N-dimethyl-formamide Reflux;

: 57-13-6
urea

: 5959-52-4
2-Amino-3-naphthoic acid

: 13898-60-7
naphtha[2',3':5,6]pyrimidine-2,4-[1H,3H]-dione

Conditions

Conditions	Yield
at 160℃; for 10h;	97%
In phenol at 180℃;	60%
With phenol
With phenol at 160 - 185℃; for 2h;
In neat (no solvent) at 150℃; for 12h;

: 6089-09-4
4-pentynoic acid

: 5959-52-4
2-Amino-3-naphthoic acid

: 1227624-64-7
3a-methyl-3,3a-dihydro-1H-naphtho[2,3-d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione

Conditions

Conditions	Yield
Stage #1: 4-pentynoic acid; 2-Amino-3-naphthoic acid With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride In water at 140℃; for 20h; Green chemistry; Stage #2: With trifluoroacetic acid In water at 140℃; for 4h; Green chemistry;	96%
Stage #1: 4-pentynoic acid; 2-Amino-3-naphthoic acid With (triphenylphosphine)gold(I) chloride In 1,2-dichloro-ethane at 140℃; for 20h; Sealed tube; Stage #2: With trifluoroacetic acid In 1,2-dichloro-ethane at 140℃; for 4h; regioselective reaction;	94%
With Echavarren's catalyst In 1,1-dichloroethane at 120℃; for 24h; Sealed vial;	90%

: 5959-52-4
2-Amino-3-naphthoic acid

: 141281-58-5
3-Amino-2-(hydroxymethyl)naphthalene

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;	95%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;	78%
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; Reflux;	42%

: 5959-52-4
2-Amino-3-naphthoic acid

: 56297-38-2
3-amino-4-chloro-2-naphthoic acid

Conditions

Conditions	Yield
With N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 20℃; for 18h; Inert atmosphere;	95%
With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 10h;
With N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 20℃; for 18h;

: 5959-52-4
2-Amino-3-naphthoic acid

: 57-06-7
N-allyl isothiocyanate

: 3-allyl-2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide Reflux;	95%
With triethylamine In ethanol for 4h; Reflux;	95%
With triethylamine In N,N-dimethyl-formamide Reflux;

: 28556-81-2
2,6-dimethylphenylisocyanate

: 5959-52-4
2-Amino-3-naphthoic acid

: 3-({[(2,6-dimethylphenyl)amino]carbonyl}amino)-2-naphthoic acid

Conditions

Conditions	Yield
Stage #1: 2-Amino-3-naphthoic acid With triethylamine In N,N-dimethyl-formamide for 0.5h; Stage #2: 2,6-dimethylphenylisocyanate In N,N-dimethyl-formamide at 75℃; for 2h;	94%

: 98-09-9
benzenesulfonyl chloride

: 5959-52-4
2-Amino-3-naphthoic acid

: 3-(phenylsulfonamido)-2-naphthoic acid

Conditions

Conditions	Yield
With sodium carbonate In water at 60 - 85℃; for 2.25h;	93%

: 32315-10-9
bis(trichloromethyl) carbonate

: 5959-52-4
2-Amino-3-naphthoic acid

: 29753-32-0
2H-naphth<2,3-d><3,1>oxazine-2,4(1H)-dione

Conditions

Conditions	Yield
With pyridine In dichloromethane; acetonitrile at 50 - 55℃; for 4h;	93%
With pyridine In dichloromethane; acetonitrile at 45℃;	77%

: 5959-52-4
2-Amino-3-naphthoic acid

: 27533-32-0
2-aminonaphthalene-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 2-Amino-3-naphthoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: With ammonia In tetrahydrofuran for 6h; Inert atmosphere; Schlenk technique;	93%
Stage #1: 2-Amino-3-naphthoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; for 22h; Inert atmosphere;	75%

: 51908-29-3
4-isothiocyanatobenzene sulfonamide

: 5959-52-4
2-Amino-3-naphthoic acid

: 4-(2-mercapto-4-oxobenzo[g]-quinazolin-3(4H)-yl)benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In ethanol for 2h; Reflux;	92%
With triethylamine In ethanol for 2h; Reflux;	92%
With triethylamine In ethanol
With TEA In ethanol

: 98-88-4
benzoyl chloride

: 5959-52-4
2-Amino-3-naphthoic acid

: 18600-63-0
2-phenyl-4H-naphthyl<2,3-d><1,3>oxazin-4-one

Conditions

Conditions	Yield
at 170℃; for 3h;	91%
In neat (no solvent) for 3h; Inert atmosphere; Reflux;	86.9%
In pyridine
at 130℃;

: 23489-36-3
1-(benzofuran-2-yl)-2-bromoethan-1-one

: 5959-52-4
2-Amino-3-naphthoic acid

: 2-(1-benzofuran-2-yl)-2-oxoethyl 3-amino-2-naphthoate

Conditions

Conditions	Yield
Stage #1: 2-Amino-3-naphthoic acid With potassium carbonate In N,N-dimethyl-formamide at 70℃; Stage #2: 1-(benzofuran-2-yl)-2-bromoethan-1-one In N,N-dimethyl-formamide at 20 - 50℃;	91%

: 6484-25-9
4-chloro-2-phenylquinazoline

: 5959-52-4
2-Amino-3-naphthoic acid

: 3-((2-phenylquinazolin-4-yl)amino)-2-naphthoic acid

Conditions

Conditions	Yield
In acetic acid for 1h; Reflux;	91%

: 103-72-0
phenyl isothiocyanate

: 5959-52-4
2-Amino-3-naphthoic acid

: 2,3-dihydro-3-phenyl-2-thioxobenzo[g]quinazolin-4(1H)-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide Reflux;	90%
With triethylamine In ethanol for 4h; Reflux;	79%

: 33578-00-6
(2-ethynyl)benzoic acid

: 5959-52-4
2-Amino-3-naphthoic acid

: 4b-methyl-4bH-naphtho[2’,3’:4,5][1,3]oxazino[2,3-a]isoindole-6,14-dione

Conditions

Conditions	Yield
Stage #1: (2-ethynyl)benzoic acid; 2-Amino-3-naphthoic acid With (triphenylphosphine)gold(I) chloride In 1,2-dichloro-ethane at 140℃; for 20h; Sealed tube; Stage #2: With trifluoroacetic acid In 1,2-dichloro-ethane at 140℃; for 4h; regioselective reaction;	90%
Stage #1: (2-ethynyl)benzoic acid; 2-Amino-3-naphthoic acid With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride In water at 140℃; for 20h; Green chemistry; Stage #2: With trifluoroacetic acid In water at 140℃; for 4h; Green chemistry;	72%

: 5959-52-4
2-Amino-3-naphthoic acid

: 63212-42-0
3-iodo-2-naphthoic acid

Conditions

Conditions	Yield
Stage #1: 2-Amino-3-naphthoic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 2h; Sandmeyer Reaction; Stage #2: With potassium iodide In water at 0 - 60℃; for 1.5h; Sandmeyer Reaction;	89%
Stage #1: 2-Amino-3-naphthoic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Sandmeyer Reaction; Stage #2: With potassium iodide In water at 0 - 90℃; for 1.08333h;	88%
Stage #1: 2-Amino-3-naphthoic acid With hydrogenchloride In water; acetonitrile at -5℃; for 0.5h; Reflux; Stage #2: With sodium nitrite In water; acetonitrile for 1h; Reflux; Stage #3: With potassium iodide In water; acetonitrile for 1.5h; Reflux;	88%

: 5959-52-4
2-Amino-3-naphthoic acid

A benzo[g]-3H-quinazol-4-one: benzo[g]-3H-quinazol-4-one

B: 4-(3-bromoanilino)benzo[g]quinazoline hydrochloride

Conditions

Conditions	Yield
With sodium hydroxide In formamide	A 89% B n/a

: 7-chloro-9-phenyl-2,3-dihydro-1H-acridin-4-one

: 5959-52-4
2-Amino-3-naphthoic acid

: 3,8-dichloro-5-phenylbenzo[b]naphtho[j][1,10]phenanthroline

Conditions

Conditions	Yield
With trichlorophosphate at 130℃; for 5h;	89%

: 2284-20-0
4-Methoxyphenyl isothiocyanate

: 5959-52-4
2-Amino-3-naphthoic acid

: 3-(4-methoxyphenyl)-2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-one

Conditions

Conditions	Yield
With triethylamine In ethanol for 4h; Reflux;	89%

: 108-73-6
3,5-dihydroxyphenol

: 5959-52-4
2-Amino-3-naphthoic acid

: 284671-56-3
1,3-Dihydroxy-5,12-dihydro-benzo[b]acridin-12-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In n-heptan1ol for 48h; Cyclization; Heating;	88%
With toluene-4-sulfonic acid In n-heptan1ol for 19h; Inert atmosphere; Reflux;	59%

: 5959-52-4
2-Amino-3-naphthoic acid

: 521973-02-4
5-((Z)-4-hydroxybenzylidene)-2-methylmercapto-4-thiazolidinone

: 521973-36-4
3-(5-(2-hydroxy-3-methoxybenzylidene)-4-oxo-thiazolidin-2-ylideneamino)naphthalene-2-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 24h; Heating;	88%

: 556-61-6
methyl thioisocyanate

: 5959-52-4
2-Amino-3-naphthoic acid

: 3-methyl-2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-one

Conditions

Conditions	Yield
With triethylamine In ethanol for 4h; Reflux;	88%
With triethylamine In N,N-dimethyl-formamide Reflux;	86%
With triethylamine In N,N-dimethyl-formamide Reflux;

3-AMINO-2-NAPHTHOIC ACID Chemical Properties

IUPAC Name: 3-Amino-2-naphthoic acid
The MF of 3-Amino-2-naphthoic acid (5959-52-4) is C₁₁H₉NO₂.

The MW of 3-Amino-2-naphthoic acid (5959-52-4) is 187.19.
Synonyms of 3-Amino-2-naphthoic acid (5959-52-4): 2-Naphthalenecarboxylic acid, 3-amino- ; 3-Amino-2-naphthoic acid ; 2-Amino-3-carboxynaphthalene ; 2-Amino-3-naphthoic acid ; 2-Naphthoic acid, 3-amino- ; 3-Aminoisonaphthoic acid
Product Categories: Intermediates of Dyes and Pigments;Naphthalene derivatives;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
Form: yellow-green to green powder
Index of Refraction: 1.73
EINECS: 227-726-2
Density: 1.352 g/ml
Flash Point: 186.6 °C
Boiling Point: 384.9 °C
Melting Point: 212-215 °C
Merck: 14,452
BRN: 744099

3-AMINO-2-NAPHTHOIC ACID Uses

3-Amino-2-naphthoic acid (5959-52-4) is used as organic synthesis, dyes intermediates.

3-AMINO-2-NAPHTHOIC ACID Toxicity Data With Reference

orl-mus LD50:1600 mg/kg

14CYAT Industrial Hygiene and Toxicology. 2 (1963),1840.

3-AMINO-2-NAPHTHOIC ACID Consensus Reports

Reported in EPA TSCA Inventory.

3-AMINO-2-NAPHTHOIC ACID Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NO_x. See also AROMATIC AMINES.
Safety information of 3-Amino-2-naphthoic acid (5959-52-4):
Hazard Codes Xn
Risk Statements
22 Harmful if swallowed
36/37/38 Irritating to eyes, respiratory system and skin
Safety Statements
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36 Wear suitable protective clothing
WGK Germany 3
RTECS QL1400000

Product Name

3-Amino-2-naphthoic acid

Synthetic route

3-AMINO-2-NAPHTHOIC ACID Chemical Properties

3-AMINO-2-NAPHTHOIC ACID Uses

3-AMINO-2-NAPHTHOIC ACID Toxicity Data With Reference

3-AMINO-2-NAPHTHOIC ACID Consensus Reports

3-AMINO-2-NAPHTHOIC ACID Safety Profile

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