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3665-51-8

Basic Information
CAS No.: 3665-51-8
Name: 2-Hydroxy-3-naphtoamide
Article Data: 16
Molecular Structure:
Molecular Structure of 3665-51-8 (2-Hydroxy-3-naphtoamide)
Formula: C11H9 N O2
Molecular Weight: 187.198
Synonyms: 2-Naphthamide,3-hydroxy- (6CI,7CI,8CI); 2-Hydroxy-3-naphthalenecarboxamide;2-Hydroxy-3-naphthamide; 2-Hydroxy-3-naphthoamide; 2-Hydroxy-3-naphthoic acidamide; 3-Hydroxy-2-naphthalenecarboxamide; 3-Hydroxy-2-naphthamide; NSC 37060
EINECS: 222-926-6
Density: 1.33g/cm3
Melting Point: 211-216 ºC
Boiling Point: 426.4°Cat760mmHg
Flash Point: 211.7°C
Hazard Symbols:
Risk Codes: R36/37/38   
Safety: Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.
PSA: 63.32000
LogP: 2.34460
Synthetic route
53855-64-4

3-acetoxy-2-naphthoyl chloride

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
With ammonium hydroxide In dichloromethane for 24h; Ambient temperature;95%
92-70-6

3-Hydroxy-2-naphthoic acid

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
With phosphoric acid; urea at 180℃; for 2h;90%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 1h;72%
Multi-step reaction with 2 steps
1: HCl
2: alcoholic ammonia / 170 °C / im geschlossenen Rohr
View Scheme
Multi-step reaction with 5 steps
1: concentrated sulfuric acid
2: thionyl chloride; benzene / Einleiten von Ammoniak in das Reaktionsgemisch
3: thionyl chloride
4: methanolic KOH-solution
5: concentrated sulfuric acid / 0 °C
View Scheme
52449-77-1

3-hydroxy-2-naphthonitrile

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
With sulfuric acid at 0℃;
7163-25-9

ethyl 3-hydroxy-2-naphthanoate

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
With ammonia at 170℃; im geschlossenen Rohr;
With ammonium sulfite; ammonia at 125℃; im geschlossenen Rohr;
1734-00-5

3-hydroxy-2-naphthoyl chloride

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
With ammonia; benzene
13042-06-3

3-methoxy-[2]naphthoic acid amide

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid
92616-44-9

3-methoxy-2-naphthonitrile

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid
92-70-6

3-Hydroxy-2-naphthoic acid

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
With phosphoric acid
5464-07-3

3-acetoxy-2-naphthoic acid

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / oxalyl chloride, DMF / toluene / 1 h / Ambient temperature
2: 95 percent / conc. NH4OH / CH2Cl2 / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: thionyl chloride; benzene / Einleiten von Ammoniak in das Reaktionsgemisch
2: thionyl chloride
3: methanolic KOH-solution
4: concentrated sulfuric acid / 0 °C
View Scheme
92-70-6

3-Hydroxy-2-naphthoic acid

disulfite

disulfite

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 82 percent / conc. H2SO4 / 0.08 h / Heating
2: 97 percent / oxalyl chloride, DMF / toluene / 1 h / Ambient temperature
3: 95 percent / conc. NH4OH / CH2Cl2 / 24 h / Ambient temperature
View Scheme
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Chemistry

Molecular Formula: C11H9NO2
Molecular Weight: 187.20
EINECS: 222-926-6
Density: 1.33 g/cm
Flash Point: 211.7 °C
Melting Point: 211-216 °C 
Index of Refraction: 1.708 
Appearance: ochre powder
CAS Registry Number: 3665-51-8  
Enthalpy of Vaporization: 70.75 kJ/mol 
Boiling Point: 426.4 °C at 760 mmHg 
Vapour Pressure: 7.16E-08 mmHg at 25°C 
IUPAC Name: 3-hydroxynaphthalene-2-carboxamide
Synonyms: 3-Hydroxy-2-Naphthalenecarboxamide ; 3-Hydroxy-2-naphthamid ; 3-Hydroxy-2-Naphtoamide ; 2-Hydroxy-3-naphthalenecarboxamide ; 3-Hydroxy-2-naphthoylamide ; 3-hydroxynaphthalene-2-carboxamide |
Following is the molecular structure of 3-Hydroxy-2-Naphtoamide (CAS NO.3665-51-8):

Uses

 3-Hydroxy-2-Naphtoamide (CAS NO.3665-51-8) is used as a medicine, high-grade organic pigments, automotive paints, as well as dedicated an important intermediate of dye.

Toxicity Data With Reference

1.    

ipr-rat LD50:2000 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 108 (1953),450.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.
Safety Information of 3-Hydroxy-2-Naphtoamide (CAS NO.3665-51-8):
Hazard Codes: Xi Irritant
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 37/39-26
S37/39: Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.