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3-AMINO-2-NAPHTHOIC ACID

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Name

3-AMINO-2-NAPHTHOIC ACID

EINECS 227-726-2
CAS No. 5959-52-4 Density 1.352 g/cm3
PSA 63.32000 LogP 2.70140
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 N/A Appearance yellow-green to green powder
Safety 26-36 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 5959-52-4 (3-Amino-2-naphthoic acid) Hazard Symbols IrritantXi
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;

Article Data 21

3-AMINO-2-NAPHTHOIC ACID Synthetic route

887242-59-3

3-(tert-butoxycarbonylamino)naphthalene-2-carboxylic acid

5959-52-4

2-Amino-3-naphthoic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;
13728-34-2

dimethyl 2,3-naphthalenedicarboxylate

5959-52-4

2-Amino-3-naphthoic acid

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

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

1.    

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 NOx. 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

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