N-Phenyl-2-naphthylamine supplier

Name
N-(2-Naphthyl)aniline
EINECS 205-223-9
CAS No. 135-88-6
Article Data136
CAS DataBase
Density 1.156 g/cm³
Solubility <0.1 g/100 mL at 19 °C in water
Melting Point 105-108 °C(lit.)
Formula C₁₆H₁₃N
Boiling Point 395.5 °C at 760 mmHg
Molecular Weight 219.286
Flash Point 209.2 °C
Transport Information
Appearance light grey powder or crystals
Safety 22-24/25-61-36/37-26
Risk Codes 36/38-40-43-51/53-53-51
Molecular Structure
Hazard Symbols Xn,N
Synonyms 2-Naphthylamine,N-phenyl- (7CI,8CI);2-Anilinonaphthalene;2-Naphthylphenylamine;Aceto PBN;AgeRite Powder;Antioxidant 116;Antioxidant D;Antioxidant PBN;N-(2-Naphthyl)aniline;N-Phenyl-b-naphthylamine;Naftam 2;Neozon D;Neozone;Neozone D;Phenyl-2-naphthylamine;N-Phenyl-2-naphthylamine;
PSA 12.03000
LogP 4.65640

Synthetic route

: 532-02-5
2-naphthalenesulfonic acid sodium salt

: 1865-45-8
sodium anilide

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

Conditions

Conditions	Yield
With aniline at 290℃; for 0.25h;	99%
With aniline at 290℃; for 0.25h; Product distribution; other temp.: 190 to 270 deg. C; other reaction time: 0.5 to 12 h;	99%

: 3857-83-8
2-naphthyl triflate

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 85℃; for 8h;	99%

: 42096-34-4
naphthalen-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); 2,4,6-(i-Pr)3-[2-P(t-Bu)2-phenyl]benzene; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 150℃; for 0.5h; microwave irradiation;	99%

: 143-66-8
sodium tetraphenyl borate

: 91-59-8
naphthalen-2-ylamine

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

Conditions

Conditions	Yield
With copper(II) acetate monohydrate; triethylamine In acetonitrile at 20℃; for 24h; Chan-Lam Coupling;	99%

: 108-90-7
chlorobenzene

: 91-59-8
naphthalen-2-ylamine

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

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1.5h; Inert atmosphere;	98%

: 7657-86-5
tri(2-naphthyl) phosphate

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; potassium carbonate at 130℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube;	98%
With N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; [Pd(π-cinnamyl)Cl]2 at 130℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube;	98%
With NiCl(1-naphthyl)(PPh3)2; sodium hydride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 110℃; Inert atmosphere;	75%

: 7433-79-6
2-methylthionaphthalene

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); lithium hexamethyldisilazane; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 100℃; for 12h; Buchwald-Hartwig Coupling;	97%

: 7385-85-5
naphthalen-2-yl tosylate

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; potassium phosphate; palladium diacetate; phenylboronic acid In butan-1-ol at 110℃; for 15h; Inert atmosphere;	96%
With (1,3-bis(2,6-diisopropylphenyl)imidazolidene)Ni(styrene)2; lithium tert-butoxide In 1,4-dioxane for 10h; Inert atmosphere; Heating; Schlenk technique;	93%
With sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; chlorobis(triphenylphosphine)(1-naphthyl)nickel(II) In 1,4-dioxane at 110℃; for 0.5h;	92%

: 135-19-3
β-naphthol

: 10294-56-1
phosphorous acid

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

Conditions

Conditions	Yield
With aniline In water	94%

: 108-86-1
bromobenzene

: 91-59-8
naphthalen-2-ylamine

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

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; sodium t-butanolate; 1,3-diisopropyl-1H-imidazol-3-ium chloride In 1,2-dimethoxyethane at 80℃; for 12h; Inert atmosphere;	94%
With [Cu(N,N'-bis(diisopropylphosphino)-N,N'-dimethyl-2,6-diaminopyridine)Br]; potassium tert-butylate In tetrahydrofuran at 110℃; for 16h; Inert atmosphere; Sealed tube;	86%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 40℃;	82%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 40℃;	82%

: 98-95-3
nitrobenzene

: 530-93-8
1,2,3,4-tetrahydronaphthalen-2-one

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

Conditions

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere; Sealed vessel;	94%

: 530-93-8
1,2,3,4-tetrahydronaphthalen-2-one

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With ethene; 5%-palladium/activated carbon In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; under 760.051 Torr; for 24h; Molecular sieve; Autoclave;	94%
With sulfur; oxygen In pyridine; cyclohexane at 110℃; for 24h; Sealed tube;	63%
With gold-palladium bimetallic nanoparticles supported on TiO2 In 1,3,5-trimethyl-benzene at 160℃; under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique;	66 %Chromat.

: 74495-79-7
N-(2-naphthyl)-N-phenyl-acetamide

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

Conditions

Conditions	Yield
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	92%
Stage #1: N-(2-naphthyl)-N-phenyl-acetamide With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	89%
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

: 532-02-5
2-naphthalenesulfonic acid sodium salt

: 62-53-3
aniline

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

B: 135-19-3
β-naphthol

Conditions

Conditions	Yield
With potassium hydroxide at 230℃; for 6h; Product distribution; other bases: NaOH + K2CO3, NaOH + Na2CO3, NaOH + KCl, NaOH + KF, NaOH; other temp.: 230 to 310 deg. C, other reaction time: 2 to 12 h;	A 90% B 3%
With sodium hydroxide; potassium carbonate at 310℃; for 4h;	A 34% B 65%

...Expand

: 580-13-2
2-bromonaphthalene

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 5.5h; Inert atmosphere;	90%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; Buchwald-Hartwig Coupling;	83%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃;	80%

: 91-58-7
2-chloronaphthalene

: 87-62-7
2,6-dimethylaniline

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

Conditions

Conditions	Yield
With PdCl2(N,N’-bis-(2,6-di(iso-propyl)phenyl)imidazolidin-2-ylidene)(AsPh3); potassium tert-butylate In 1,4-dioxane at 110℃; for 4h; Buchwald-Hartwig Coupling;	88%

: 32316-92-0
naphthalene-2-boronic acid

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane at 0 - 5℃; for 4h; Sonication; Green chemistry;	87%
With N-(pyrid-2-yl)benzamide; nickel(II) acetate tetrahydrate; N,N,N',N'-tetramethylguanidine In toluene at 60℃; for 24h; Chan-Lam Coupling;	80%
With [Cu(4-(dimethylamino)pyridine)4I]I In methanol at 20℃; for 0.25h; Chan-Lam Coupling;	70%

: 62-53-3
aniline

: 135-19-3
β-naphthol

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

Conditions

Conditions	Yield
Stage #1: β-naphthol With potassium hydroxide In water; toluene at 20℃; Flow reactor; Stage #2: aniline With methanesulfonato(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II) In water; toluene at 120℃; Flow reactor;	85%
With p-toluene sulfonic acid - choline chloride covalently immobilized on polymeric microspheres coated iron oxide magnetic nanoparticles In neat (no solvent) at 120℃; for 12h; chemoselective reaction;	81%
With boron trifluoride diethyl etherate at 80℃; for 15h; Inert atmosphere;	77%

: 108-90-7
chlorobenzene

: 91-59-8
naphthalen-2-ylamine

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

B: 29601-75-0
1-phenyl-2-aminonaphthalene

Conditions

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In diethyl ether; cyclohexane at 25℃; for 24h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;	A n/a B 84%

...Expand

: 591-50-4
iodobenzene

: 91-59-8
naphthalen-2-ylamine

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

Conditions

Conditions	Yield
With copper(I) thiophene-2-carboxylate; sodium t-butanolate In dimethyl sulfoxide at 100℃; for 6h; Inert atmosphere;	83%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In toluene at 120℃; Inert atmosphere;	43%

: 62-53-3
aniline

: 256652-04-7
4,4,5,5-tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane

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

Conditions

Conditions	Yield
With copper diacetate; triethylamine In methanol; acetonitrile at 80℃; for 24h; Chan-Lam Coupling; Molecular sieve; Sealed tube;	77%

: 93-04-9
2-Methoxynaphthalene

: 62-53-3
aniline

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

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In neat (no solvent) at 120℃; for 48h; Inert atmosphere; Sealed tube;	75%

: 32316-92-0
naphthalene-2-boronic acid

: 98-95-3
nitrobenzene

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

Conditions

Conditions	Yield
Stage #1: nitrobenzene With [2,2]bipyridinyl; [MoO2Cl2(dmf)2] In toluene for 0.0333333h; Stage #2: naphthalene-2-boronic acid With triphenylphosphine In toluene at 100℃; for 20h;	74%

: 32316-92-0
naphthalene-2-boronic acid

: 622-37-7
Phenyl azide

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

Conditions

Conditions	Yield
With indium; copper diacetate In methanol at 70℃; for 3h;	70%

: 1145-08-0
naphthalen-2-yl N,N-dimethylsulfamic acid

: anilinomagnesium bromide

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

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In tetrahydrofuran; 1,4-dioxane at 150℃; for 24h; Kumada Cross-Coupling; Inert atmosphere;	70%

: 930-68-7
cyclohexenone

: 91-59-8
naphthalen-2-ylamine

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

Conditions

Conditions	Yield
With hydrogenchloride; iodine; dimethyl sulfoxide In N,N,N,N,N,N-hexamethylphosphoric triamide; water at 110℃; for 20h; Schlenk technique; Sealed tube; Green chemistry;	69%

: 65739-06-2
3-[(4-methylphenyl)sulfonyl]-1-phenyltriaz-1-ene

: 32316-92-0
naphthalene-2-boronic acid

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

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique;	65%

: 100-63-0
phenylhydrazine

: 91-59-8
naphthalen-2-ylamine

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

B: 1410783-23-1
N,1-diphenylnaphthalen-2-amine

Conditions

Conditions	Yield
With tetrabenzoporphyrinatocobalt(II); copper diacetate In acetonitrile at 0℃; for 13h; chemoselective reaction;	A 57% B 25%

...Expand

: 27067-31-8
N-phenyl 2-naphthyl nitroxide

A: 6628-97-3
2-(phenylamino)naphthoquinone

B: 21720-68-3
2-(phenylamino)-4-(phenylimino)-1(4H)-naphthalenone

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

D: 17704-02-8
N,N'-diphenyl-(1,1'-binaphthyl)-2,2'-diamine

Conditions

Conditions	Yield
In benzene for 336h; Ambient temperature; in the dark; Further byproducts given;	A 47% B 2.5% C 40% D 0.5%

...Expand

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

: 5488-73-3
[2]naphthyl-nitroso-phenyl-amine

Conditions

Conditions	Yield
With sulfuric acid; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.25h;	99%
With trichloromelamine; silica gel; sodium nitrite In dichloromethane; water at 20℃; for 0.416667h;	92%
With Nafion-H(R); silica gel; sodium nitrite In dichloromethane at 20℃; for 0.5h;	75%

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

: 74-88-4
methyl iodide

: 6364-05-2
N-methyl-N-phenylnaphthalen-2-amine

Conditions

Conditions	Yield
Stage #1: N-Phenyl-2-naphthylamine With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃;	99%

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

: 131222-99-6
6,12-dibromochrysene

: C50H34N2

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;	98%

: 1273-86-5
1-ferrocenylmethanol

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

: 93122-40-8
C5H5FeC5H4CH2N(C6H5)(C10H7)

Conditions

Conditions	Yield
With HClO4 or HBF4 In dichloromethane byproducts: H2O; aq. HClO4 (70 %) or HBF4 (45 %) added (vigorous stirring) to the Fe-complex and the amine; soln. stirred (30 min, room temp.), addn. of ether; ethereal soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.), recrystn. (ethyl acetate); elem. anal.;	98%

: 38303-35-4
1,8-dibromopyrene

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

: 1,8-bis[N-(2-naphthyl)-N-phenylamino]pyrene

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In o-xylene at 125 - 130℃; for 3.5h; Buchwald-Hartwig Coupling; Inert atmosphere;	98%

: 67665-47-8
2,2′-dibromo-9,9′-spirobi[9H-fluorene]

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

: C57H38N2

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene at 110℃; for 20h; Inert atmosphere;	96%

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

: 33816-55-6
N-phenyl-1,2,3,4-tetrahydronaphthalen-2-amine

Conditions

Conditions	Yield
With tris(pentafluorophenyl)borate; hydrogen In toluene at 60℃; under 15001.5 Torr; for 6h; Pressure; Solvent; Temperature; Inert atmosphere; Autoclave;	94%
With nickel at 100 - 150℃; under 147102 Torr; Hydrogenation;
With copper oxide-chromium oxide at 250 - 300℃; under 147102 Torr; Hydrogenation;

: 90-11-9
1-Bromonaphthalene

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

: 1400899-20-8
N-(naphthalen-2-yl)-N-phenylnaphthalen-1-amine

Conditions

Conditions	Yield
Stage #1: 1-Bromonaphthalene; N-Phenyl-2-naphthylamine With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In toluene Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube; Stage #2: With n-hexyllithium In hexane; toluene at 105℃; for 2h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;	94%
With 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl; n-hexyllithium; palladium diacetate In hexane; toluene at 105℃; for 2h; Buchwald-Hartwig Coupling; Inert atmosphere;	94%

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

: 2,3-bis(4-bromophenyl)benzo[g]quinoxaline

: 2,3-bis[4-(N-phenyl-2-naphthylamino)phenyl]benzo[g]quinoxaline

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 100℃; for 5h; Buchwald-Hartwig Coupling; Inert atmosphere;	94%

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

: 1467758-59-3
C13H13BrN2O3

: (S)-tert-butyl (5-bromo-3-(4-(naphthalen-2-ylamino)phenyl)-2-oxoindolin-3-yl)carbamate

Conditions

Conditions	Yield
With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at -60℃; for 35h; Schlenk technique; Inert atmosphere; enantioselective reaction;	94%

: 1277-49-2
1-ferrocenylethanol

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

: 93122-45-3
C5H5FeC5H4CH(CH3)N(C6H5)(C10H7)

Conditions

Conditions	Yield
With HClO4 or HBF4 In dichloromethane byproducts: H2O; aq. HClO4 (70 %) or HBF4 (45 %) added (vigorous stirring) to the Fe-complex and the amine; soln. stirred (30 min, room temp.), addn. of ether; ether soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.); elem. anal.;	93%

: 1-ferrocenylphenylmethanol

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

: 93122-48-6
C5H5FeC5H4CH(C6H5)N(C6H5)(C10H7)

Conditions

Conditions	Yield
With HBF4 or HClO4 In dichloromethane byproducts: H2O; aq. HBF4 (45 %) or HClO4 (70 %) added (vigorous stirring) to the Fe-complex and the amine; soln. stirred (30 min, room temp.), addn. of ether; ethereal soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.), recrystn. (heptane); elem. anal.;	91%

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

: 1373942-82-5
tert-butyl 2-oxoindolin-3-ylidenecarbamate

: (S)-tert-butyl (3-(4-(naphthalen-2-ylamino)phenyl)-2-oxoindolin-3-yl)carbamate

Conditions

Conditions	Yield
With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at -60℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;	91%

: 1022211-28-4
C30H23BrSi

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

: 1022211-18-2
C46H35NSi

Conditions

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 90℃; for 3h;	90%

N-Phenyl-2-naphthylamine Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 318.(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 Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 16 ,1978,p. 325.(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 Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 16 ,1978,p. 325.(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) . Reported in EPA TSCA Inventory.

N-Phenyl-2-naphthylamine Standards and Recommendations

ACGIH TLV: Not Classifiable as a Human Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans

N-Phenyl-2-naphthylamine Specification

The N-Phenyl-beta-naphthylamine is an organic compound with the formula C₁₆H₁₃N. The IUPAC name of this chemical is N-phenylnaphthalen-2-amine. With the CAS registry number 135-88-6 and EINECS 205-223-9, it is also named as 2-Naphthylamine, N-phenyl-. The product's category is Industrial / Fine Chemicals. It is light grey powder or crystal which is insoluble in water, soluble in alcohol, carbon tetrachloride, benzene and acetone. Moverover, this chemical may gradually change into deep red when exposed to air or sunlight. Additionally, it should be stored in the cool and dry place.

Physical properties about N-Phenyl-beta-naphthylamine are: (1)ACD/LogP: 4.54; (2)ACD/LogD (pH 5.5): 4.54; (3)ACD/LogD (pH 7.4): 4.54; (4)ACD/BCF (pH 5.5): 1662.33; (5)ACD/BCF (pH 7.4): 1662.36; (6)ACD/KOC (pH 5.5): 7030.47; (7)ACD/KOC (pH 7.4): 7030.61; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.702; (12)Molar Refractivity: 73.47 cm³; (13)Molar Volume: 189.59 cm³; (14)Polarizability: 29.126 10-24cm³; (15)Surface Tension: 50.1209983825684 dyne/cm; (16)Density: 1.157 g/cm³; (17)Flash Point: 209.226 °C; (18)Enthalpy of Vaporization: 64.567 kJ/mol; (19)Boiling Point: 395.498 °C at 760 mmHg

Preparation of N-Phenyl-beta-naphthylamine: It can be obtained by condensation of 2-naphthol and aniline in the presence of aniline hydrochloride at 250 °C. Add 2-naphthol and aniline in melting pot for fusion and add aniline hydrochloride for condensation. After the reaction finishing, add sodium carbonate for neutralization. Then steam out the excess aniline. Finally, after dehydration and dried under vacuum, we can get the product.

N-Phenyl-beta-naphthylamine can be obtained by condensation of 2-naphthol and aniline in the presence of aniline hydrochloride

Uses of N-Phenyl-beta-naphthylamine: It is used for natural rubber, synthetic rubber and latex. And this material is universal antioxidant in natural rubber, diene synthetic rubber, chloroprene rubber and latex. What's more, it can react with acrylonitrile to get N-(b-naphthyl)-N-(phenyl)-b-aminopropionitrile. This reaction needs reagent gl. acetic acid. The yield is 85%.

N-Phenyl-beta-naphthylamine can react with acrylonitrile to get N-(b-naphthyl)-N-(phenyl)-b-aminopropionitrile

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes and skin. And it has limited evidence of a carcinogenic effect. What;s more, it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. So people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and gloves. Avoid release to the environment. Refer to special instructions / safety data sheets.

You can still convert the following datas into molecular structure:
1. SMILES:c3c(Nc1ccccc1)cc2ccccc2c3
2. InChI:InChI=1/C16H13N/c1-2-8-15(9-3-1)17-16-11-10-13-6-4-5-7-14(13)12-16/h1-12,17H
3. InChIKey:KEQFTVQCIQJIQW-UHFFFAOYAL

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	1450mg/kg (1450mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Hygiene and Sanitation Vol. 31(1-3), Pg. 183, 1966.
rat	LD50	oral	8730mg/kg (8730mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Hygiene and Sanitation Vol. 31(1-3), Pg. 183, 1966.
rat	LD50	unreported	8700mg/kg (8700mg/kg)	LIVER: OTHER CHANGES BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	Tijdschrift Voor Sociale Geneeskunde. Vol. 53, Pg. 415, 1975.

Product Name

N-(2-Naphthyl)aniline

Synthetic route

N-Phenyl-2-naphthylamine Consensus Reports

N-Phenyl-2-naphthylamine Standards and Recommendations

N-Phenyl-2-naphthylamine Specification

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