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2-Aminonaphthalene

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Name

2-Aminonaphthalene

EINECS 202-080-4
CAS No. 91-59-8 Density 1.137 g/cm3
PSA 26.02000 LogP 3.00320
Solubility Slightly soluble in hot water Melting Point 111-113 °C(lit.)
Formula C10H9N Boiling Point 307.5 °C at 760 mmHg
Molecular Weight 143.188 Flash Point 157.1 °C
Transport Information UN 1650 6.1/PG 2 Appearance Light brown sSolid
Safety 53-45-61 Risk Codes 45-22-51/53
Molecular Structure Molecular Structure of 91-59-8 (2-Aminonaphthalene) Hazard Symbols ToxicT; DangerousN
Synonyms

2-Naphthylamine(8CI);2-Naphthalenamine;C.I. 37270;Fast Scarlet Base B;Naphthalen-2-ylamine;o-Aminonaphthalene;b-Aminonaphthalene;b-Naphthylamine;naphthalen-2-amine;β-Naphthylamine;

Article Data 220

2-Aminonaphthalene Synthetic route

581-89-5

2-nitronaphthalene

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With LaCu0.67Si1.33; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 96h; Autoclave;96%
With hydrazine hydrate; zinc In methanol at 20℃; for 0.0833333h;94%
With borane-ammonia complex; copper(II) oxide In methanol at 50℃; for 0.333333h;94%
581-97-5

2-acetylaminonaphthalene

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water Inert atmosphere; Reflux;96%
With hydrogenchloride; water In ethanol for 7h; Reflux;96%
With hydrogenchloride; water In ethanol for 1h; Reflux;92%
95639-94-4

N-2(hydroxybenzyl)-β-naphthylamine

A

C21H18O3

B

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
at 230℃; under 10 Torr; for 0.0833333h; Product distribution; pyrolysis without solvent;A n/a
B 95%
3857-83-8

2-naphthyl triflate

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
Stage #1: 2-naphthyl triflate With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; tetrabutylammomium bromide; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 9h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
95%
580-13-2

2-bromonaphthalene

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In toluene at 100℃; for 2h; Glovebox; Sealed tube;95%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 12h; Reagent/catalyst; Sealed tube; Inert atmosphere;89%
Stage #1: 2-bromonaphthalene With magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Reagent/catalyst; Inert atmosphere;
89%

1,1,1,3,3,3-hexamethyl-2-naphthalen-2-yl-disilazane

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; for 1h;94%
With hydrogenchloride In diethyl ether
135-19-3

β-naphthol

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With sulfur dioxide; ammonia In water for 0.5h; Bucherer reaction; Irradiation;93%
With ammonium hydroxide; ammonium sulfite monohydrate In water at 180℃;93%
With sodium tetrahydroborate; 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere;85%
91-58-7

2-chloronaphthalene

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
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;93%
With ammonium sulfate; C39H45FeNNiP2; sodium t-butanolate In 2-methyltetrahydrofuran at 100℃; for 7h; Reagent/catalyst; Solvent; Inert atmosphere; Glovebox; Autoclave;86%
32316-92-0

naphthalene-2-boronic acid

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;92%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile at 100℃; for 0.25h; Microwave irradiation;87%
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 16h;86%
With caesium carbonate; O-(2,4-dinitrophenyl)hydroxylamine In toluene at 25℃; for 24h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;84%
With N-Bromosuccinimide; N-methoxylamine hydrochloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃;74%
79894-40-9

3-dicyanomethylene-3,4-dihydro-1H-naphth<2,1-d><1,3>oxazin-1-one

91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride In water for 55h; Heating;91%

2-Aminonaphthalene Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 261.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 ,1974,p. 97.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 ,1974,p. 97.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Community Right-To-Know List. EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

2-Aminonaphthalene Standards and Recommendations

OSHA PEL: Cancer Suspect Agent
ACGIH TLV: Confirmed Human Carcinogen
DFG MAK: Human Carcinogen
NIOSH REL: (β-Naphthylamine) TWA use 29 CFR 1910.1009
DOT Classification:  6.1; Label: Poison

2-Aminonaphthalene Analytical Methods

For occupational chemical analysis use NIOSH: Naphthylamines, 5518.

2-Aminonaphthalene Specification

The 2-Naphthalenamine, with the CAS registry number 91-59-8 and EINECS registry number 202-080-4, has the systematic name and IUPAC name of naphthalen-2-amine. And the molecular formula of this chemical is C10H9N. It is a kind of light brown solid, and belongs to the following product categories: Intermediates of Dyes and Pigments; Naphthylamine; 13C & 2H Sugars; Amines; Aromatics.

The 2-Naphthalenamine is an aromatic amine which is slightly soluble in hot water and denser than water. It is listed as a known human carcinogen, and can be found in cigarette smoke and suspected to contribute to the development of bladder cancer. It is activated in the liver but quickly deactivated by conjugation to glucuronic acid. In the bladder, glucuronidase re-activates it by deconjugation, which leads to the development of bladder cancer. What's more, it is used to make azo dyes.

The physical properties of 2-Naphthalenamine are as following: (1)ACD/LogP: 2.17; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.15; (4)ACD/LogD (pH 7.4): 2.17; (5)ACD/BCF (pH 5.5): 24.87; (6)ACD/BCF (pH 7.4): 26.1; (7)ACD/KOC (pH 5.5): 342.49; (8)ACD/KOC (pH 7.4): 359.38; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 3.24 Å2; (13)Index of Refraction: 1.694; (14)Molar Refractivity: 48.33 cm3; (15)Molar Volume: 125.8 cm3; (16)Polarizability: 19.16×10-24cm3; (17)Surface Tension: 51.4 dyne/cm; (18)Density: 1.137 g/cm3; (19)Flash Point: 157.1 °C; (20)Enthalpy of Vaporization: 54.81 kJ/mol; (21)Boiling Point: 307.5 °C at 760 mmHg; (22)Vapour Pressure: 0.000722 mmHg at 25°C.

Preparation and use of 2-Naphthylamine: It can be prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by heating 2-naphthol with ammonium acetate to 270-280 °C. And it is used to make azo dyes. What' more, it is also used to product various naphthalene derivatives.

You should be cautious while dealing with this chemical. It is harmful if swallowed, and may also cause cancer. What's more, it is toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic environment. Therefore, you had better take the following instructions: Avoid exposure - obtain special instruction before use; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); Avoid release to the environment. Refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: c12ccccc1ccc(N)c2
(2)InChI: InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
(3)InChIKey: JBIJLHTVPXGSAM-UHFFFAOYAA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo unreported 500mg/kg (500mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

KIDNEY, URETER, AND BLADDER: HEMATURIA

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 176, 1941.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,
rat LD50 oral 727mg/kg (727mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 466, 1986.

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