Product Name

  • Name

    2-Aminonaphthalene

  • EINECS 202-080-4
  • CAS No. 91-59-8
  • Article Data220
  • CAS DataBase
  • Density 1.137 g/cm3
  • 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;
  • PSA 26.02000
  • LogP 3.00320

Synthetic route

2-nitronaphthalene
581-89-5

2-nitronaphthalene

naphthalen-2-ylamine
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%
2-acetylaminonaphthalene
581-97-5

2-acetylaminonaphthalene

naphthalen-2-ylamine
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%
N-2(hydroxybenzyl)-β-naphthylamine
95639-94-4

N-2(hydroxybenzyl)-β-naphthylamine

A

C21H18O3

C21H18O3

B

naphthalen-2-ylamine
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%
2-naphthyl triflate
3857-83-8

2-naphthyl triflate

naphthalen-2-ylamine
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%
2-bromonaphthalene
580-13-2

2-bromonaphthalene

naphthalen-2-ylamine
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

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

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

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

β-naphthol

naphthalen-2-ylamine
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%
2-chloronaphthalene
91-58-7

2-chloronaphthalene

naphthalen-2-ylamine
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%
naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

naphthalen-2-ylamine
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%
3-dicyanomethylene-3,4-dihydro-1H-naphth<2,1-d><1,3>oxazin-1-one
79894-40-9

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

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride In water for 55h; Heating;91%
2-hydrazinonaphthalene
2243-57-4

2-hydrazinonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With titanium(III) chloride; water In ethanol for 4h; Reflux; Inert atmosphere;91%
With titanium tetrachloride; magnesium In tetrahydrofuran at 20℃; Inert atmosphere;90%
With Molybdenum(III) Reagent In tetrahydrofuran; water for 3.5h; Heating;64%
2-iodonaphthalene
612-55-5

2-iodonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide In dimethyl sulfoxide at 130℃; for 12h; Sealed tube; Inert atmosphere;91%
Multi-step reaction with 2 steps
1: chlorotris(triphenylphosphine)cobalt(I); bis[2-(diphenylphosphino)phenyl] ether / toluene / 12 h / 100 °C
2: hydrogenchloride; water / methanol / 1 h / 20 °C
View Scheme
2-azidonaphthalene
20937-86-4

2-azidonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With dicobalt octacarbonyl In water at 20℃; for 3.5h;90%
With water for 5h; Inert atmosphere; UV-irradiation; Sealed tube; chemoselective reaction;48%
With (pyrolysis) In decalin at 122.1 - 152.5℃; Kinetics;
N-(diphenylmethylene)-2-naphthaleneamine
200712-40-9

N-(diphenylmethylene)-2-naphthaleneamine

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 20℃; Catalytic behavior; Reagent/catalyst; Solvent;89%
With hydrogenchloride In tetrahydrofuran; water at 20℃;25 mg
C13H13NO3S

C13H13NO3S

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid at 23℃; for 24h; Inert atmosphere;89%
methyl 2-naphthyl ketone
93-08-3

methyl 2-naphthyl ketone

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With methanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester In ethanol at 20℃; for 24h; Reagent/catalyst; Solvent;89%
With methanol; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid at 23℃; for 24h; Inert atmosphere;81%
2-naphthyl diethylcarbamate
61912-14-9

2-naphthyl diethylcarbamate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ammonium sulfate; C43H60ClFeNNiP2; sodium t-butanolate In o-xylene at 100℃; for 16h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave;87%
2,2'-azonaphthalene
582-08-1

2,2'-azonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ammonium acetate; zinc In methanol at 20℃; for 0.05h;86%
2-Vinylnaphthalene
827-54-3

2-Vinylnaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h;85%
2-nitronaphthalene
581-89-5

2-nitronaphthalene

A

naphthalene
91-20-3

naphthalene

B

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With formic acid In acetonitrile at 20℃; for 0.25h; Irradiation;A 17%
B 83%
naphthalen-2-yl tosylate
7385-85-5

naphthalen-2-yl tosylate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; for 20h; Inert atmosphere; chemoselective reaction;83%
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere;67%
2-(naphthalen-2-yloxy)propanamide
82162-90-1

2-(naphthalen-2-yloxy)propanamide

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 6h; Green chemistry;81%
With potassium hydroxide at 140℃;111.6 mg
naphthalene-2-carboxylate
93-09-4

naphthalene-2-carboxylate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydroxylamine hydrochloride Heating;80%
Stage #1: naphthalene-2-carboxylate With PPA; hydroxylamine hydrochloride at 20 - 160℃;
Stage #2: With potassium hydroxide In water		34%
With hydrogenchloride; PPA; hydroxylamine
1H-Naphtho<2,3-d><1,2,3>triazole
269-12-5

1H-Naphtho<2,3-d><1,2,3>triazole

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 1h; Irradiation;80%
naphthalene
91-20-3

naphthalene

A

1-amino-naphthalene
134-32-7

1-amino-naphthalene

B

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 25℃; for 12h;A 77%
B 10%
With aluminium trichloride; hydroxylamine hydrochloride
Stage #1: naphthalene With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; N-(trifluoromethylsulfonyloxy)pyridinium trifluoromethanesulfonate In acetonitrile for 1.5h; Sealed tube; Inert atmosphere; Irradiation;
Stage #2: With piperidine In acetonitrile at 20℃; for 14h; Sealed tube; Inert atmosphere; Overall yield = 25 mg;
(NH4)2SO3

(NH4)2SO3

pyrographite
7440-44-0

pyrographite

β-naphthol
135-19-3

β-naphthol

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride; ammonium hydroxide In ethanol; water; toluene77%
...Expand
1,2,3,4-tetrahydronaphthalen-2-one
530-93-8

1,2,3,4-tetrahydronaphthalen-2-one

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ethene; 5%-palladium/activated carbon; ammonium acetate In acetonitrile at 90℃; under 760.051 Torr; for 3h; Reagent/catalyst; Schlenk technique;75%
potassium 2-naphthyltrifluoroborate

potassium 2-naphthyltrifluoroborate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With caesium carbonate; O-(2,4-dinitrophenyl)hydroxylamine In water; toluene at 50℃; for 30h;74%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile at 100℃; for 0.25h; Microwave irradiation;55%
2-(1-naphthyl)[1,3,2]dioxaborolane

2-(1-naphthyl)[1,3,2]dioxaborolane

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With caesium carbonate; O-(2,4-dinitrophenyl)hydroxylamine In 1,4-dioxane; water at 100℃; for 24h;73%
furfural
98-01-1

furfural

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

(E)-1-(furan-2-yl)-N-(naphthalen-2-yl)methanimine
6233-18-7

(E)-1-(furan-2-yl)-N-(naphthalen-2-yl)methanimine

Conditions
ConditionsYield
In diethyl ether at 20℃; Inert atmosphere; Molecular sieve; Darkness;100%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

ethyl (naphthalen-2-yl)carbamate
5255-69-6

ethyl (naphthalen-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1h;100%
With sodium carbonate; benzene
With diethyl ether
at 130℃; for 0.0833333h; microwave irradiation;
With sodium hydrogencarbonate In dichloromethane; chloroform; water
acrylonitrile
107-13-1

acrylonitrile

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

3-(2-naphthylamino)propionitrile
38266-46-5

3-(2-naphthylamino)propionitrile

Conditions
ConditionsYield
With silica-supported aluminum chloride at 60℃; for 20h; Michael addition; Neat (no solvent);100%
With acetic acid at 60℃; for 20h;62%
With acetic acid; copper(l) chloride
1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one
40657-29-2

1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

(E)-4-Ethoxy-1,1,1-trifluoro-4-(naphthalen-2-ylamino)-but-3-en-2-one
128648-68-0

(E)-4-Ethoxy-1,1,1-trifluoro-4-(naphthalen-2-ylamino)-but-3-en-2-one

Conditions
ConditionsYield
In acetonitrile for 18h; Ambient temperature;100%
N,N-diethylaminomethylene-1,1,1,5,5,5-hexafluoroacetylacetone
74888-65-6

N,N-diethylaminomethylene-1,1,1,5,5,5-hexafluoroacetylacetone

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1,1,1,5,5,5-Hexafluoro-3-(naphthalen-2-ylaminomethylene)-pentane-2,4-dione

1,1,1,5,5,5-Hexafluoro-3-(naphthalen-2-ylaminomethylene)-pentane-2,4-dione

Conditions
ConditionsYield
With iron(III) chloride100%
N-α-Tosyl-4-cyanphenylalaninchlorid
80852-48-8

N-α-Tosyl-4-cyanphenylalaninchlorid

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

3-(4-Cyano-phenyl)-N-naphthalen-2-yl-2-(toluene-4-sulfonylamino)-propionamide
80852-67-1

3-(4-Cyano-phenyl)-N-naphthalen-2-yl-2-(toluene-4-sulfonylamino)-propionamide

Conditions
ConditionsYield
In benzene for 1.5h; Ambient temperature;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

naphthalen-2-yl-carbamic acid tert-butyl ester
454713-45-2

naphthalen-2-yl-carbamic acid tert-butyl ester

Conditions
ConditionsYield
In methanol at 100℃; for 6h;100%
Stage #1: di-tert-butyl dicarbonate With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: naphthalen-2-ylamine In dichloromethane at 20℃; for 36h;		95%
With glycerol at 20℃; for 0.75h; Green chemistry; chemoselective reaction;94%
2-(2-nitroethenyl)thiophene
874-84-0, 34312-77-1

2-(2-nitroethenyl)thiophene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

C16H14N2O2S
1140448-29-8

C16H14N2O2S

Conditions
ConditionsYield
In water at 20℃; Michael condensation;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

2-naphthylisocyanate
2243-54-1

2-naphthylisocyanate

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane at 0℃; for 1.25h;100%
In dichloromethane at 0℃; Inert atmosphere;
In toluene at 95℃;
3,5-dichloro-[1,2,4]thiadiazole
2254-88-8

3,5-dichloro-[1,2,4]thiadiazole

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

C12H8ClN3S
1421694-69-0

C12H8ClN3S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In cyclohexanol at 20 - 80℃; Reagent/catalyst; Temperature; Solvent; regioselective reaction;100%
acetic anhydride
108-24-7

acetic anhydride

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

2-acetylaminonaphthalene
581-97-5

2-acetylaminonaphthalene

Conditions
ConditionsYield
With vanadyl triflate In dichloromethane at 20℃; for 8h;99%
Stage #1: acetic anhydride With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: naphthalen-2-ylamine In dichloromethane at 20℃; for 0.5h;		98%
With copper(II) ferrite In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry;95%
benzaldehyde
100-52-7

benzaldehyde

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

benzyl-2-naphthylamine
13672-18-9

benzyl-2-naphthylamine

Conditions
ConditionsYield
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 15201 Torr; for 6h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;99%
With hydrogenchloride; platinum Hydrogenation;
With hydrogen In water at 80℃; under 22502.3 Torr; for 8h; Inert atmosphere; Autoclave; Green chemistry;79 %Chromat.
naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1-bromo-2-naphthylamine
20191-75-7

1-bromo-2-naphthylamine

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfonic acid functionalized silica In diethyl ether; acetonitrile at 20℃; for 0.0166667h;99%
With N-Bromosuccinimide at 20℃; for 0.0333333h; regioselective reaction;99%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;98%
2-phenylsulfanyl-[1,4]benzoquinone
18232-03-6

2-phenylsulfanyl-[1,4]benzoquinone

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

A

2-(phenylthio)benzene-1,4-diol
18231-96-4

2-(phenylthio)benzene-1,4-diol

B

2-(Naphthalen-2-ylamino)-5-phenylsulfanyl-[1,4]benzoquinone
128920-14-9

2-(Naphthalen-2-ylamino)-5-phenylsulfanyl-[1,4]benzoquinone

Conditions
ConditionsYield
In ethanol for 12h; Ambient temperature;A n/a
B 99%
...Expand
2-chloroacenaphthylene-1-carbaldehyde
13152-84-6

2-chloroacenaphthylene-1-carbaldehyde

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

acenaphtho<1,2-b>benzoquinoline
238-05-1

acenaphtho<1,2-b>benzoquinoline

Conditions
ConditionsYield
With hydrogenchloride In ethanol Heating;99%
2,2-dimethylpropanoic anhydride
1538-75-6

2,2-dimethylpropanoic anhydride

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N-naphthalen-2-yl-2,2-dimethyl-propanamide
201015-17-0

N-naphthalen-2-yl-2,2-dimethyl-propanamide

Conditions
ConditionsYield
With vanadyl triflate In dichloromethane at 20℃; for 42h;99%
Stage #1: 2,2-dimethylpropanoic anhydride With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: naphthalen-2-ylamine In dichloromethane at 20℃; for 2.5h;		97%
With triethylamine In ethyl acetate at 80℃; Inert atmosphere; Sealed tube;40%
benzoic acid anhydride
93-97-0

benzoic acid anhydride

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N-(naphthalen-2-yl)benzamide
18271-22-2

N-(naphthalen-2-yl)benzamide

Conditions
ConditionsYield
Stage #1: benzoic acid anhydride With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: naphthalen-2-ylamine In dichloromethane at 20℃; for 50h;		99%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

niobium pentachloride
10026-12-7

niobium pentachloride

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Nb(N-2-naphthyl)Cl3(1,2-dimethoxyethane)
189813-51-2

Nb(N-2-naphthyl)Cl3(1,2-dimethoxyethane)

Conditions
ConditionsYield
With ZnCl2; pyridine In dichloromethane; toluene N2-atmosphere; addn. of 1 equiv. aniline and pyridine (in CH2Cl2) to mixt. of TaCl5 and DME with excess ZnCl2 (-40°C), stirring for 17 h; filtration, concn. (vac.), recrystn. (CH2Cl2/pentane); elem. anal.;99%
...Expand
6,8-dimethoxy-1,3-dimethyl-2-benzopyrilium tetrafluoroborate

6,8-dimethoxy-1,3-dimethyl-2-benzopyrilium tetrafluoroborate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N,2'-naphthyl-6,8-dimethoxy-1,3-dimethylisoquinolinium tetrafluoroborate

N,2'-naphthyl-6,8-dimethoxy-1,3-dimethylisoquinolinium tetrafluoroborate

Conditions
ConditionsYield
In acetic acid at 20℃; for 8h;99%
naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

acetone
67-64-1

acetone

N-isopropylnaphthalen-2-amine
53622-39-2

N-isopropylnaphthalen-2-amine

Conditions
ConditionsYield
With iridium bromide; formic acid; zinc In water at 30℃; for 20h;99%
With sodium tetrahydroborate; sodium acetate; acetic acid In ethanol; water at 0 - 25℃;
copper diacetate
142-71-2

copper diacetate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

2-acetylaminonaphthalene
581-97-5

2-acetylaminonaphthalene

Conditions
ConditionsYield
In acetic acid for 2.75h; Reflux; chemoselective reaction;99%
4-pentynoic acid
6089-09-4

4-pentynoic acid

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N-(2-naphthylmethyl)pent-4-ynamide
1415976-72-5

N-(2-naphthylmethyl)pent-4-ynamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;99%
naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

3,4-dimethoxy-N-(naphthalen-2-yl)benzamide
331270-79-2

3,4-dimethoxy-N-(naphthalen-2-yl)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;99%
p-chlorophenylsulfonyl hydrazide
2751-25-9

p-chlorophenylsulfonyl hydrazide

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1-((4-chlorophenyl)thio)naphthalen-2-amine

1-((4-chlorophenyl)thio)naphthalen-2-amine

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; propylene glycol dimethyl ether dimer at 100℃; for 12h; Schlenk technique;99%
With iodine; acetic acid In tetrahydrofuran at 100℃; for 5h;84%
p-bromophenylsulfonyl hydrazide
2297-64-5

p-bromophenylsulfonyl hydrazide

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1-((4-bromophenyl)thio)naphthalen-2-amine

1-((4-bromophenyl)thio)naphthalen-2-amine

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; propylene glycol dimethyl ether dimer at 100℃; for 12h; Schlenk technique;99%
With iodine; acetic acid In tetrahydrofuran at 100℃; for 5h;86%
diphenyl diselenide
1666-13-3

diphenyl diselenide

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1-(phenylselanyl)naphthalen-2-amine

1-(phenylselanyl)naphthalen-2-amine

Conditions
ConditionsYield
With iron(III) chloride; potassium iodide In dimethyl sulfoxide at 110℃; for 24h;99%
With iodine; dimethyl sulfoxide In neat (no solvent) at 80℃; for 24h; Sealed tube; Green chemistry; regioselective reaction;80%
With tert.-butylhydroperoxide; N-iodo-succinimide In water; N,N-dimethyl-formamide at 70℃; for 0.3h; regioselective reaction;65%
With Rose Bengal lactone In acetonitrile at 20℃; for 6h; Schlenk technique; Irradiation;43%
naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

diphenyldisulfane
882-33-7

diphenyldisulfane

1-(phenylsulfenyl)naphthalen-2-amine

1-(phenylsulfenyl)naphthalen-2-amine

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide In neat (no solvent) at 80℃; for 0.5h; Sealed tube; Microwave irradiation; Green chemistry; regioselective reaction;99%
With iron(III) chloride; potassium iodide In dimethyl sulfoxide at 110℃; for 24h;98%
With tetra-(n-butyl)ammonium iodide; propylene glycol dimethyl ether dimer at 100℃; for 12h; Schlenk technique;97%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

2-(3-methoxyphenyl)naphtho[2,1-d]thiazole

2-(3-methoxyphenyl)naphtho[2,1-d]thiazole

Conditions
ConditionsYield
With sulfur; ammonium iodide In dimethyl sulfoxide; chlorobenzene at 140℃; for 24h; Molecular sieve;99%
sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N-Phenyl-2-naphthylamine
135-88-6

N-Phenyl-2-naphthylamine

Conditions
ConditionsYield
With copper(II) acetate monohydrate; triethylamine In acetonitrile at 20℃; for 24h; Chan-Lam Coupling;99%
tert-butyl (1-benzyl-2-oxoindolin-3-ylidene)carbamate
1373942-84-7

tert-butyl (1-benzyl-2-oxoindolin-3-ylidene)carbamate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

(R)-tert-butyl (1-benzyl-3-(naphthalen-2-ylamino)-2-oxoindolin-3-yl)carbamate

(R)-tert-butyl (1-benzyl-3-(naphthalen-2-ylamino)-2-oxoindolin-3-yl)carbamate

Conditions
ConditionsYield
With C42H44N6O2 In dichloromethane at -20℃; for 2h; Temperature; enantioselective reaction;99%
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)urea In tert-butyl methyl ether at -30℃; for 6h; enantioselective reaction;97%

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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