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CAS No.: | 91-59-8 |
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Name: | 2-Aminonaphthalene |
Article Data: | 220 |
Molecular Structure: | |
Formula: | C10H9N |
Molecular Weight: | 143.188 |
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; |
EINECS: | 202-080-4 |
Density: | 1.137 g/cm3 |
Melting Point: | 111-113 °C(lit.) |
Boiling Point: | 307.5 °C at 760 mmHg |
Flash Point: | 157.1 °C |
Solubility: | Slightly soluble in hot water |
Appearance: | Light brown sSolid |
Hazard Symbols: | T; N |
Risk Codes: | 45-22-51/53 |
Safety: | 53-45-61 |
Transport Information: | UN 1650 6.1/PG 2 |
PSA: | 26.02000 |
LogP: | 3.00320 |
Conditions | Yield |
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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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
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at 230℃; under 10 Torr; for 0.0833333h; Product distribution; pyrolysis without solvent; | A n/a B 95% |
Conditions | Yield |
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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% |
Conditions | Yield |
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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% |
naphthalen-2-ylamine
Conditions | Yield |
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With hydrogenchloride; water In methanol at 20℃; for 1h; | 94% |
With hydrogenchloride In diethyl ether |
Conditions | Yield |
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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% |
Conditions | Yield |
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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% |
naphthalene-2-boronic acid
naphthalen-2-ylamine
Conditions | Yield |
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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% |
3-dicyanomethylene-3,4-dihydro-1H-naphth<2,1-d><1,3>oxazin-1-one
naphthalen-2-ylamine
Conditions | Yield |
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With hydrogenchloride In water for 55h; Heating; | 91% |
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. |