CAS No.91-59-8,2-Aminonaphthalene Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	91-59-8
Name:	2-Aminonaphthalene
Article Data:	220

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

Synthetic route

: 581-89-5
2-nitronaphthalene

: 91-59-8
naphthalen-2-ylamine

Conditions

Conditions	Yield
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

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%

: 95639-94-4
N-2(hydroxybenzyl)-β-naphthylamine

A: C21H18O3

B: 91-59-8
naphthalen-2-ylamine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

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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.

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

Analytical Methods

For occupational chemical analysis use NIOSH: Naphthylamines, 5518.

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.