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134-32-7

Basic Information
CAS No.: 134-32-7
Name: 1-Aminonaphthalene
Molecular Structure:
Molecular Structure of 134-32-7 (1-Aminonaphthalene)
Formula: C10H9N
Molecular Weight: 143.19
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%
92599-49-0

3-(Naphthalen-1-ylcarbamoyloxy)-cyclohex-1-enecarboxylic acid ethyl ester

A

55510-68-4, 200637-78-1

ethyl cyclohex-2-enyl-acetate

B

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With lithium di-n-butylcuprate In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether at -50 - -20℃; for 2h; in presence other reagents (Zn, CrCl2), too;A 97%
B n/a
90-14-2

1-Iodonaphthalene

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;97%
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;96%
Stage #1: 1-Iodonaphthalene With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h;
Stage #2: With ammonia In water; acetone at 90℃; for 24h;
95%
487-10-5

1,2-di(naphthalen-1-yl)diazene

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With zinc In methanol at 25℃; for 0.15h; Inert atmosphere;96%
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.666667h; pH=2; Inert atmosphere; Irradiation;92%
With formic acid; zinc In methanol at 20℃; for 0.266667h;85%
With ammonium formate; nickel In methanol at 20℃; for 0.266667h;85%
With ammonium acetate; zinc In methanol at 20℃; for 0.0833333h;85%
529-34-0

3,4-dihydronaphthalene-1(2H)-one

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
95%
With ethene; 5%-palladium/activated carbon; ammonium acetate In acetonitrile at 90℃; under 760.051 Torr; for 48h; Reagent/catalyst; Schlenk technique;89%
Multi-step reaction with 2 steps
2: hydrogen chloride; acetic acid; acetic acid anhydride
View Scheme
131775-94-5

2-[(naphthalen-1-ylamino)methylidene]malonic acid diethyl ester

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With ethylenediamine In ethanol at 20℃; for 5h;95%
6336-03-4

naphthalen-1-ylcarbamic acid benzyl ester

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction;94%
With methylmagnesium bromide; hydrogen; palladium diacetate; nickel diacetate In water at 45℃; for 18h;91%
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 1.5h;76%
118-44-5

1-N-ethylnaphthylamine

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With piperidine; dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In acetonitrile at -78℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation;94%
90-11-9

1-Bromonaphthalene

A

737-89-3

N,N-di(naphth-1-yl)amine

B

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
Stage #1: 1-Bromonaphthalene With ammonia; sodium t-butanolate; [(CyPF-tBu)PdCl2] In 1,2-dimethoxyethane at 90℃; under 4137.29 - 10343.2 Torr; for 20h;
Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 20℃; for 0.0833333h;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water Product distribution / selectivity;
A n/a
B 92%
Stage #1: 1-Bromonaphthalene With lithium amide; [(CyPF-tBu)PdCl2] In 1,2-dimethoxyethane at 80℃; for 20h; Sealed vial;
Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 20℃; for 0.0833333h;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water Product distribution / selectivity;
A n/a
B 89%
With C28H30Cl5N3Pd; ammonia; lithium isopropoxide; sodium t-butanolate In 1,4-dioxane at 100℃; for 2h; Reagent/catalyst; Inert atmosphere; Schlenk technique;A n/a
B 82%
13922-41-3

1-Naphthylboronic acid

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 16h;92%
With potassium carbonate; ammonium hydroxide In methanol at 60℃; for 17h;90%
With O-(2,4-dinitrophenyl)hydroxylamine In toluene at 50℃; for 24h; Inert atmosphere;84%
85630-39-3

1-naphthyl N,N-diethylcarbamate

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With ammonium sulfate; C43H60ClFeNNiP2; sodium t-butanolate In o-xylene at 100℃; for 16h; Reagent/catalyst; Inert atmosphere; Autoclave;91%
With (CyPFCy)Ni(o-tol)Cl; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 24h; Reagent/catalyst; Inert atmosphere; Sealed tube;60%
33555-03-2

2-(naphthalen-1-ylamino)-1-phenylethan-1-one

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With magnesium; acetic acid In methanol at 20℃;90%
72594-62-8

naphthalen-1-yl-carbamic acid tert-butyl ester

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate In 1,4-dioxane; water at 70 - 72℃; for 2h;89%
With water at 150℃; for 8h; Subcritical conditions;88%
With methanol; oxalyl dichloride at 20℃; for 2h; Temperature;87%
1234464-24-4

1-tetralone pivaloyl oxime

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; tricyclopentylphosphine In toluene at 95℃; for 8h; Reagent/catalyst; Glovebox;87%
68716-52-9

1-naphthylboronic acid pinacol ester

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With potassium tert-butylate; 1-amino-1,4-diazabicyclo[2.2.2]octane-1,4-diium iodide In tetrahydrofuran at 100℃; for 1h; Sealed tube;87%
6141-93-1

(E)-di-[1]naphthyl-diazene

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With nickel; hydrazinium monoformate In methanol for 0.25h; Heating;85%
2298-07-9

4-Bromo-1-naphthylamine

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
Stage #1: 4-Bromo-1-naphthylamine With palladium dichloride In water at 20℃; for 0.0333333h;
Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 2.46667h;
85%

N,N-dimethyl-3-(naphthalen-1-ylamino)propionamide

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With Imidazole hydrochloride at 150℃; for 9h;85%
With Imidazole hydrochloride In neat (no solvent) at 150℃; for 9h; Schlenk technique;85%
703-55-9

1-naphthylmagnesiumbromide

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
Stage #1: 1-naphthylmagnesiumbromide With zinc(II) chloride In tetrahydrofuran at -3 - 20℃; Inert atmosphere;
Stage #2: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-diphenylaminobenzene; acetone oxime-o-p-benzenesulfonic ester; copper(l) chloride In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
84%
With hydrogenchloride; O-(diphenylphosphinyl)hydroxylamine In tetrahydrofuran for 12h; Ambient temperature;31%
Multi-step reaction with 2 steps
1.1: tetrahydrofuran / -5 - 20 °C / Inert atmosphere
2.1: triphenylphosphine; acetone oxime-o-p-benzenesulfonic ester / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
View Scheme
2216-68-4

N-methylnaphthalen-1-amine

134-32-7

1-amino-naphthalene

Conditions
ConditionsYield
With piperidine; dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In acetonitrile at -78℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation;84%
541-41-3

chloroformic acid ethyl ester

134-32-7

1-amino-naphthalene

5255-68-5

ethyl (naphthalen-1-yl)carbamate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 20℃; for 12h;100%
With triethylamine In tetrahydrofuran for 1h; Heating;99%
108-24-7

acetic anhydride

134-32-7

1-amino-naphthalene

575-36-0

1-acetamidonaphthalene

Conditions
ConditionsYield
In dichloromethane at 20℃; Inert atmosphere;100%
With silica gel for 0.05h; Microwave irradiation; neat (no solvent);98%
With rice husk ash at 20℃; Green chemistry;98%
1147550-11-5

ammonium thiocyanate

134-32-7

1-amino-naphthalene

86-88-4

naphthalen-1-yl-thiourea

Conditions
ConditionsYield
Stage #1: ammonium thiocyanate With benzoyl chloride In acetone for 0.333333h; Reflux;
Stage #2: 1-amino-naphthalene In acetone for 1h; Reflux;
Stage #3: With sodium hydroxide In water at 80℃; for 0.5h;
100%
With hydrogenchloride; water
With hydrogenchloride at 100℃;
134-32-7

1-amino-naphthalene

555-16-8

4-nitrobenzaldehdye

967-13-5

N-(napht-1-yl)-N-(p-nitrobenzylidene)amine

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
In ethanol85%
With ethanol
134-32-7

1-amino-naphthalene

100-52-7

benzaldehyde

890-51-7

N-benzylidenenaphthalen-1-amine

Conditions
ConditionsYield
With aluminum oxide for 5h; Milling;100%
In water at 20℃; for 2h;80%
In dichloromethane for 10h; Reflux;70%
134-32-7

1-amino-naphthalene

123-08-0

4-hydroxy-benzaldehyde

93324-84-6

(E)-4-((naphthalen-1-ylimino)methyl)phenol

Conditions
ConditionsYield
for 2h; Ambient temperature;100%
at 80℃; for 0.0833333h;78%
134-32-7

1-amino-naphthalene

121-33-5

vanillin

78174-01-3

2-methoxy-4-(1-naphthyliminomethyl)phenol

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
In ethanol at 20 - 23℃;92%
With ethanol
In ethanol
134-32-7

1-amino-naphthalene

98-59-9

p-toluenesulfonyl chloride

18271-17-5

N-tosyl-1-naphthylamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4℃;100%
With pyridine98%
at 20℃; for 0.166667h;94%
134-32-7

1-amino-naphthalene

87-13-8

diethyl 2-ethoxymethylenemalonate

131775-94-5

2-[(naphthalen-1-ylamino)methylidene]malonic acid diethyl ester

Conditions
ConditionsYield
High vacuum;100%
In ethanol at 28℃; for 6h;98%
at 130℃; for 2.75h; Substitution;91%
134-32-7

1-amino-naphthalene

6921-40-0

1-azidonaphthalene

Conditions
ConditionsYield
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 0 - 20℃; for 1h;100%
With dmap; 2-azido-1,3-dimethylimidazolin-1-ium hexafluorophosphate In dichloromethane at 50℃; for 1.5h; Inert atmosphere;92%
With dmap; 2-azido-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium hexafluorophosphate (V) In dichloromethane at 30℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere;92%
104-88-1

4-chlorobenzaldehyde

134-32-7

1-amino-naphthalene

135569-53-8

(E)-N-(4-chlorobenzylidene) naphthalen-1-amine

Conditions
ConditionsYield
for 2h; Ambient temperature;100%
In benzene for 4h; Heating;
In benzene Heating;
52225-57-7

2,2,2-trifluoro-N-{2,2,2-trifluoro-1-(trifluoromethyl) ethylidene}acetamide

134-32-7

1-amino-naphthalene

121825-80-7

N-(α-trifluoroacetylaminohexafluoroisopropyl)-α-naphthylamine

Conditions
ConditionsYield
In chloroform at -20℃;100%
40657-29-2

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

134-32-7

1-amino-naphthalene

128648-67-9

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

Conditions
ConditionsYield
In acetonitrile for 18h; Ambient temperature;100%
134-32-7

1-amino-naphthalene

74888-65-6

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

155495-74-2

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

Conditions
ConditionsYield
With iron(III) chloride100%
134-32-7

1-amino-naphthalene

80852-48-8

N-α-Tosyl-4-cyanphenylalaninchlorid

80852-66-0

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

Conditions
ConditionsYield
In benzene for 1.5h; Ambient temperature;100%
767-60-2

3-Methylindene

134-32-7

1-amino-naphthalene

100-52-7

benzaldehyde

(6S,6aR,11bR)-11b-Methyl-6-phenyl-6,6a,7,11b-tetrahydro-5H-benzo[h]indeno[1,2-c]quinoline

Conditions
ConditionsYield
With (polyallyl)scanduium trifylamide ditriflate In dichloromethane; acetonitrile at 40℃; for 15h;100%
134-32-7

1-amino-naphthalene

1122-91-4

4-bromo-benzaldehyde

116401-74-2

[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-naphthalen-1-yl-amine

Conditions
ConditionsYield
for 2h; Ambient temperature;100%
In benzene Reflux;
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

134-32-7

1-amino-naphthalene

92163-14-9

N-naphthylpyrrole

Conditions
ConditionsYield
With bismuth (III) nitrate pentahydrate at 75℃; for 0.0833333h; Microwave irradiation; neat (no solvent);100%
With bismuth (III) nitrate pentahydrate at 20℃; for 0.0833333h; Sonication; Neat (no solvent);95%
With scandium tris(trifluoromethanesulfonate) In 1,4-dioxane at 100℃; for 0.5h; Clauson-Kaas condensation;94%
24424-99-5

di-tert-butyl dicarbonate

134-32-7

1-amino-naphthalene

72594-62-8

naphthalen-1-yl-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 1-amino-naphthalene With triethylamine In tetrahydrofuran; water at 20℃; for 0.0833333h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 6h;
100%
In ethanol at 30℃; for 24h;99%
With iron oxide In ethanol at 20℃; for 3h; Green chemistry; chemoselective reaction;99%
134-32-7

1-amino-naphthalene

762-21-0

acetylenedicarboxylic acid diethyl ester

1148148-44-0

C18H19NO4

Conditions
ConditionsYield
In methanol Reflux;100%
In ethanol at 20℃; for 0.5h;
23391-99-3

4,4'-bicyclohexanone

134-32-7

1-amino-naphthalene

C32H36N2

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 16h; Cooling with ice;100%
124-64-1

tetrakis(hydroxymethyl)phosphonium chloride

134-32-7

1-amino-naphthalene

C44H40N4P(1+)*Cl(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;100%
305836-05-9

4-Butylaminomethyl-1,2-dimethoxy-naphthalene

134-32-7

1-amino-naphthalene

C19H25NO3

Conditions
ConditionsYield
With hydrogenchloride; sodium hydrogencarbonate; triethylamine; acetyl chloride In dichloromethane100%
134-32-7

1-amino-naphthalene

321-38-0

1-Fluoronaphthalene

Conditions
ConditionsYield
Stage #1: 1-amino-naphthalene With hydrogenchloride; sodium nitrite In water at 5 - 75℃;
Stage #2: With tetrafluoroboric acid In water for 0.25h;
Stage #3: at 85 - 90℃; Temperature;
99.8%
With potassium nitrite; hydrogen fluoride
With tert.-butylnitrite; silicon tetrafluoride 1.) CH2Cl2, room temp., 1 h, 2.) 130-140 deg C, 1 h; Yield given. Multistep reaction;
463-71-8

thiophosgene

134-32-7

1-amino-naphthalene

551-06-4

1-isothiocyanatonaphthalene

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h;99%
With triethylamine In dichloromethane at 20℃; for 1h;99%
With chloroform; water
134-32-7

1-amino-naphthalene

110-13-4

2,5-hexanedione

18494-86-5

2,5-dimethyl-1-(naphthyl)-pyrrole

Conditions
ConditionsYield
With amberlite IR 120 acidic resin at 20℃; for 0.666667h; Paal-Knorr pyrrole synthesis; Neat (no solvent);99%
With bentonite In neat (no solvent) at 20℃; for 0.05h; Reagent/catalyst; Paal-Knorr Pyrrole Synthesis; Milling; Green chemistry;97%
In neat (no solvent) at 20℃; for 0.383333h; Paal-Knorr Pyrrole Synthesis; Green chemistry;97%
75-15-0

carbon disulfide

134-32-7

1-amino-naphthalene

551-06-4

1-isothiocyanatonaphthalene

Conditions
ConditionsYield
Stage #1: carbon disulfide; 1-amino-naphthalene With triethylamine In tetrahydrofuran at 0 - 20℃;
Stage #2: With dmap; di-tert-butyl dicarbonate In tetrahydrofuran at 0 - 20℃; for 2h;
99%
With S,S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate; triethylamine In acetonitrile for 0.333333h;75%
With sodium hydroxide; diethyl chlorophosphate In toluene for 4h; Reflux;55%
134-32-7

1-amino-naphthalene

140160-24-3

5-(2-nitrophenyl)-2-furoyl isothiocyanate

1-naphthalen-1-yl-3-[5-(2-nitro-phenyl)-furan-2-carbonyl]-thiourea

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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.