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

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Basic Information

Molecular Structure:
CAS No.:	5959-52-4
Name:	3-Amino-2-naphthoic acid
Article Data:	21

Formula:	C₁₁H₉NO₂
Molecular Weight:	187.198
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;
EINECS:	227-726-2
Density:	1.352 g/cm³
Melting Point:	212-215 °C (dec.)(lit.)
Boiling Point:	384.9 °C at 760 mmHg
Flash Point:	186.6 °C
Solubility:	Soluble in alcohol and ether. Insoluble in water.
Appearance:	yellow-green to green powder
Hazard Symbols:	Xi
Risk Codes:	22-36/37/38
Safety:	26-36
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%

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Chemistry

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

Uses

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

Toxicity Data With Reference

orl-mus LD50:1600 mg/kg

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

Consensus Reports

Reported in EPA TSCA Inventory.

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