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Basic Information
CAS No.: 134-32-7
Name: 1-Aminonaphthalene
Article Data: 349
Molecular Structure:
Molecular Structure of 134-32-7 (1-Aminonaphthalene)
Formula: C10H9N
Molecular Weight: 143.188
Synonyms: 1-Naphthylamine(8CI);1-Naphthalamine;C.I. 37265;C.I. Azoic DiazoComponent 114;Fast Garnet Base B;Naphthalen-1-ylamine;Naphthalidam;Naphthalidine;a-Aminonaphthalene;alfa-Naftyloamina;
EINECS: 205-138-7
Density: 1.137 g/cm3
Melting Point: 47-50 °C
Boiling Point: 301 °C at 760 mmHg
Flash Point: 152.1 °C
Solubility: 0.1698 g/100 mL in water
Appearance: light tan to purple crystalline solid
Hazard Symbols: HarmfulXn,CorrosiveC,DangerousN
Risk Codes: 34-51/53-22
Safety: 26-36/37/39-45-61-24
Transport Information: UN 2790 8/PG 3
PSA: 26.02000
LogP: 3.00320
Synthetic route
86-57-7

1-Nitronaphthalene

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.166667h; Inert atmosphere;100%
With hydrazine hydrate at 90℃; for 1h; chemoselective reaction;100%
With Zr12(μ3-O)5[(μ3-O)CoCl]8[(μ2-O)2(μ3-O)CoCl]3Li3(triphenyldicarboxylate)9; hydrogen; sodium triethylborohydride In toluene at 110℃; under 30003 Torr; for 42h; Catalytic behavior; Inert atmosphere; Schlenk technique;100%
91-20-3

naphthalene

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
Stage #1: naphthalene With pyridine; trifluorormethanesulfonic acid; tetrabutylammonium tetrafluoroborate In acetonitrile at 25℃; Electrochemical reaction;
Stage #2: With piperidine In acetonitrile at 80℃; for 12h; Electrochemical reaction;
99%
With oxygen; potassium carbonate; ammonium chloride In acetonitrile at 20℃; for 48h; pH=8 - 10; UV-irradiation;53%
With boron carbon nitride; ammonia; oxygen In dimethyl sulfoxide under 760.051 Torr; Irradiation;53%
25216-21-1

N-(2-naphthyl) allylcarbamate

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With chloro-trimethyl-silane; cyclopentadienyl titanium(IV) trichloride; magnesium; triethylamine In tetrahydrofuran at 50℃; for 24h;99%
134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With Pd(OH)x/LDH In N,N-dimethyl acetamide at 150℃; for 6h; Schlenk technique; Inert atmosphere;99%

C29H23NO2

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With palladium 10% on activated carbon In tetrahydrofuran; water at 45℃; for 6h;99%
6921-40-0

1-azidonaphthalene

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With D-glucose; potassium hydroxide In water at 85℃; for 0.166667h; Green chemistry; chemoselective reaction;98%
With methanol; sodium tetrahydroborate In tetrahydrofuran for 1h; Heating;94%
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane for 1.5h; Ambient temperature;94%
90-11-9

1-Bromonaphthalene

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;98%
With ammonia; triethylamine In water at 20℃; for 10h;97%
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;95%
32566-86-2

benzhydrylidene-[1]naphthyl-amine

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water Ambient temperature;98%
With hydrogenchloride In tetrahydrofuran at 20℃;80%
With hydrogenchloride In tetrahydrofuran; water at 20℃;18.1 mg
941-98-0

1'-naphthacetophenone

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With methanol; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid at 23℃; for 24h; Inert atmosphere;98%
With O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid In ethanol at 20℃; for 24h;62%
90-13-1

1-Chloronaphthalene

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;97%
With ammonium sulfate; (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(tri-ortho-tolylphosphine)palladium(0); sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; Glovebox;97%
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;90%
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Consensus Reports

EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: Cancer Suspect Agent
NIOSH REL: (α-Naphthylamine) TWA use 29 CFR 1910.1004
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

Analytical Methods

For occupational chemical analysis use NIOSH: Naphthylamines, 5518.

Specification

The IUPAC name of 1-Naphthylamine is naphthalen-1-amine. With the CAS registry number 134-32-7, it is also named as 1-Aminonaphthalene. The product's categories are Intermediates of Dyes and Pigments; Anilines, Aromatic Amines and Nitro Compounds; Chemistry, and the other registry number is 12262-09-8. Besides, it is light tan to purple crystalline solid, which should be stored in sealed, cool, dark and dry place at 2-8 °C. In addition, its molecular formula is C10H9N and molecular weight is 143.19.

The other characteristics of this product can be summarized as: (1)EINECS: 205-138-7; (2)ACD/LogP: 2.17; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.16; (5)ACD/LogD (pH 7.4): 2.17; (6)ACD/BCF (pH 5.5): 25.42; (7)ACD/BCF (pH 7.4): 26.11; (8)ACD/KOC (pH 5.5): 350.06; (9)ACD/KOC (pH 7.4): 359.48; (10)#H bond acceptors: 1; (11)#H bond donors: 2; (12)#Freely Rotating Bonds: 1; (13)Index of Refraction: 1.694; (14)Molar Refractivity: 48.33 cm3; (15)Molar Volume: 125.8 cm3; (16)Surface Tension: 51.4 dyne/cm; (17)Density: 1.137 g/cm3; (18)Flash Point: 152.1 °C; (19)Melting point: 47-50 °C; (20)Water solubility: 0.1698 g/100 mL; (21)Enthalpy of Vaporization: 54.11 kJ/mol; (22)Boiling Point: 301 °C at 760 mmHg; (23)Vapour Pressure: 0.00108 mmHg at 25 °C.

Preparation of 1-Naphthylamine: this chemical can be prepared by reducing 1-Nitronaphthalene with iron and Hydrochloric acid at about 70 °C.



The reaction mixture should be neutralized with milk of lime, and the naphthylamine steam-distilled.

Uses of 1-Naphthylamine: this chemical is an intermediate of multiple dyes. It is also the main raw material of rubber antioxidants. Additionally, it can be used as an reagent to test nitro compounds for thin layer chromatography. It is also used as UV-derived reagent of aldehyde ketone, and used as acid-base fluorescence indicator. It can be used to produce 1-Naphthol that is an intermediate of Sevin. Similarly, it can react with Succinic acid anhydride to get N-[1]Naphthyl-succinamic acid.



This reaction needs Toluene by heating. The yield is 92 %.

When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. It also may cause burns. Moreover, it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin. Furthermore, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Please avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure.
(1)SMILES: c1cccc2cccc(N)c12
(2)InChI: InChI=1/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2
(3)InChIKey: RUFPHBVGCFYCNW-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2
(5)Std. InChIKey: RUFPHBVGCFYCNW-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LDLo oral 4gm/kg (4000mg/kg)   Journal of Industrial Hygiene. Vol. 13, Pg. 87, 1931.
mouse LD50 intraperitoneal 96mg/kg (96mg/kg)   Progress in Mutation Research. Vol. 1, Pg. 682, 1981.
rabbit LDLo subcutaneous 300mg/kg (300mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS
U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 174, 1941.