135-88-6

Basic information

• Product Name: N-(2-Naphthyl)aniline
• Synonyms: N-PHENYL-BETA-NAPHTHYLAMINE;N-2-NAPHTHYLANILINE;Phenylnaphthylamine,97%;N-Pheny-2-naphthylamine;N-Phenyl-2-Napthylamine;AGERATEPOWDER;N-Penyl-beta-baphthylamine;N-2-naphthylaniline N-phenyl-2-naphthylamine
• CAS NO: 135-88-6
• Molecular Formula: C₁₆H₁₃N
• Molecular Weight: 219.28
• EINECS: 205-223-9
• Product Categories: Industrial/Fine Chemicals
• Mol File: 135-88-6.mol
• Article Data: 103

Chemical Properties

• Melting Point: 105-108 °C(lit.)
• Boiling Point: 395-395.5 °C(lit.)
• Flash Point: 209.2 °C
• Appearance: light grey powder or crystals
• Density: 1.24
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.7020 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Methanol (Very Slightly)
• PKA: 0.78±0.30(Predicted)
• Water Solubility: Insoluble.
• Stability: Stable. Incompatible with oxidizing agents.
• BRN: 2211188
• CAS DataBase Reference: N-(2-Naphthyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Naphthyl)aniline(135-88-6)
• EPA Substance Registry System: N-(2-Naphthyl)aniline(135-88-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 36/38-40-43-51/53-53-51
• Safety Statements: 22-24/25-61-36/37-26
• RIDADR: 3077
• WGK Germany: 2
• RTECS: QM4550000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 135-88-6(Hazardous Substances Data)

Usage

Description

Phenyl-naphtylamine is an amine coumpound. Sensitization was reported in patients with hypersensitivity to rubber.

Chemical Properties

Different sources of media describe the Chemical Properties of 135-88-6 differently. You can refer to the following data:
1. light grey powder or crystals
2. Phenyl-β-naphthylamine is a light gray powder. A combustible solid.

Uses

Different sources of media describe the Uses of 135-88-6 differently. You can refer to the following data:
1. N-Phenyl-2-naphthylamine is used as an antioxidant in rubber processing; provides oxidation and flex-cracking resistance in natural rubber, synthetic rubbers, and latexes; stabilizer in electrical-insulating silicone enamels; antioxidant in otiJer polymers, greases, lubricating oils, and transformer oils; heat and light stabilizer; vulcanization accelerator; catalyst; polymerization inhibitor; component of rocket fuels, surgical plasters, and tin-electroplating batiJs; chemical intermediate; an inhibitor for butadiene; in the production of seven dyes; in rubber products made of natural rubber, styrene-butadiene, nitrile, butadiene, and chloroprene.
2. Formerly as an antioxidant in rubber processing to impart heat, oxidation, and flexcracking resistance in natural rubber, synthetic rubbers, and latexes; as a stabilizer in electricalinsulating silicone enamels
3. Formerly as an antioxidant in rubber processing to impart heat, oxidation, and flexcracking resistance in natural rubber, synthetic rubbers, and latexes; as a stabilizer in electricalinsulating silicone enamels

General Description

Light gray to gray powder. Solutions show blue fluorescence.

Air & Water Reactions

Insoluble in water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].

Reactivity Profile

N-(2-Naphthyl)aniline may react with strong oxidizing agents . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

N-phenyl-b-naphthylamine (PBNA) is carcinogenic to experimental animals in some studies.

Fire Hazard

Literature sources indicate that N-(2-Naphthyl)aniline is combustible.

Contact allergens

Phenyl-beta-naphthylamine is an amine compound. Sensitization was reported in patients with hypersensitivity from rubber.

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Moderately toxic by ingestion. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

Phenyl-β-naphthylamine is used as a rubber antioxidant; as an inhibitor for butadiene; a stabilizer in lubricants and an intermediate in chemical synthesis.

Carcinogenicity

The IARC has concluded that there is limited evidence for carcinogenicity to animals and inadequate evidence for humans.10 ACGIH considers PBNA to be a suspected human carcinogen because b-naphthylamine is both an impurity and a human metabolite of PBNA.

Purification Methods

Crystallise it from EtOH, MeOH, glacial acetic acid or *benzene/hexane. [Beilstein 12 H 1275, 12 I 535, 12 II 716, 12 III 2991.]

Incompatibilities

Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 24
48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.

InChI:InChI=1/C11H15NO/c1-11(2,3)12(13)9-10-7-5-4-6-8-10/h4-9H,1-3H3/b12-9-

Synthetic route

2-naphthalenesulfonic acid sodium salt (532-02-5) + sodium anilide (1865-45-8) → N-Phenyl-2-naphthylamine (135-88-6)

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%

2-naphthyl triflate (3857-83-8) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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

naphthalen-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (42096-34-4) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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%

sodium tetraphenyl borate (143-66-8) + naphthalen-2-ylamine (91-59-8) → N-Phenyl-2-naphthylamine (135-88-6)

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

chlorobenzene (108-90-7) + naphthalen-2-ylamine (91-59-8) → N-Phenyl-2-naphthylamine (135-88-6)

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%

tri(2-naphthyl) phosphate (7657-86-5) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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%

2-methylthionaphthalene (7433-79-6) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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%

naphthalen-2-yl tosylate (7385-85-5) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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%

β-naphthol (135-19-3) + phosphorous acid (10294-56-1) → N-Phenyl-2-naphthylamine (135-88-6)

Conditions	Yield
With aniline In water	94%

bromobenzene (108-86-1) + naphthalen-2-ylamine (91-59-8) → N-Phenyl-2-naphthylamine (135-88-6)

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%

nitrobenzene (98-95-3) + 1,2,3,4-tetrahydronaphthalen-2-one (530-93-8) → N-Phenyl-2-naphthylamine (135-88-6)

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%

1,2,3,4-tetrahydronaphthalen-2-one (530-93-8) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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.

N-(2-naphthyl)-N-phenyl-acetamide (74495-79-7) → N-Phenyl-2-naphthylamine (135-88-6)

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

2-naphthalenesulfonic acid sodium salt (532-02-5) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6) + β-naphthol (135-19-3)

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%

2-bromonaphthalene (580-13-2) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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%

2-chloronaphthalene (91-58-7) + 2,6-dimethylaniline (87-62-7) → N-Phenyl-2-naphthylamine (135-88-6)

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%

naphthalene-2-boronic acid (32316-92-0) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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%

aniline (62-53-3) + β-naphthol (135-19-3) → N-Phenyl-2-naphthylamine (135-88-6)

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%

chlorobenzene (108-90-7) + naphthalen-2-ylamine (91-59-8) → N-Phenyl-2-naphthylamine (135-88-6) + 1-phenyl-2-aminonaphthalene (29601-75-0)

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%

iodobenzene (591-50-4) + naphthalen-2-ylamine (91-59-8) → N-Phenyl-2-naphthylamine (135-88-6)

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%

aniline (62-53-3) + 4,4,5,5-tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane (256652-04-7) → N-Phenyl-2-naphthylamine (135-88-6)

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

2-Methoxynaphthalene (93-04-9) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6)

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

naphthalene-2-boronic acid (32316-92-0) + nitrobenzene (98-95-3) → N-Phenyl-2-naphthylamine (135-88-6)

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%

naphthalene-2-boronic acid (32316-92-0) + Phenyl azide (622-37-7) → N-Phenyl-2-naphthylamine (135-88-6)

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

naphthalen-2-yl N,N-dimethylsulfamic acid (1145-08-0) + anilinomagnesium bromide → N-Phenyl-2-naphthylamine (135-88-6)

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%

cyclohexenone (930-68-7) + naphthalen-2-ylamine (91-59-8) → N-Phenyl-2-naphthylamine (135-88-6)

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%

3-[(4-methylphenyl)sulfonyl]-1-phenyltriaz-1-ene (65739-06-2) + naphthalene-2-boronic acid (32316-92-0) → N-Phenyl-2-naphthylamine (135-88-6)

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%

phenylhydrazine (100-63-0) + naphthalen-2-ylamine (91-59-8) → N-Phenyl-2-naphthylamine (135-88-6) + N,1-diphenylnaphthalen-2-amine (1410783-23-1)

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

N-phenyl 2-naphthyl nitroxide (27067-31-8) → 2-(phenylamino)naphthoquinone (6628-97-3) + 2-(phenylamino)-4-(phenylimino)-1(4H)-naphthalenone (21720-68-3) + N-Phenyl-2-naphthylamine (135-88-6) + N,N'-diphenyl-(1,1'-binaphthyl)-2,2'-diamine (17704-02-8)

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

N-Phenyl-2-naphthylamine (135-88-6) → [2]naphthyl-nitroso-phenyl-amine (5488-73-3)

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%

N-Phenyl-2-naphthylamine (135-88-6) + methyl iodide (74-88-4) → N-methyl-N-phenylnaphthalen-2-amine (6364-05-2)

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%

N-Phenyl-2-naphthylamine (135-88-6) + 6,12-dibromochrysene (131222-99-6) → C50H34N2

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

1-ferrocenylmethanol (1273-86-5) + N-Phenyl-2-naphthylamine (135-88-6) → C5H5FeC5H4CH2N(C6H5)(C10H7) (93122-40-8)

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%

1,8-dibromopyrene (38303-35-4) + N-Phenyl-2-naphthylamine (135-88-6) → 1,8-bis[N-(2-naphthyl)-N-phenylamino]pyrene

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%

2,2′-dibromo-9,9′-spirobi[9H-fluorene] (67665-47-8) + N-Phenyl-2-naphthylamine (135-88-6) → C57H38N2

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

N-Phenyl-2-naphthylamine (135-88-6) → N-phenyl-1,2,3,4-tetrahydronaphthalen-2-amine (33816-55-6)

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;

1-Bromonaphthalene (90-11-9) + N-Phenyl-2-naphthylamine (135-88-6) → N-(naphthalen-2-yl)-N-phenylnaphthalen-1-amine (1400899-20-8)

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%

N-Phenyl-2-naphthylamine (135-88-6) + 2,3-bis(4-bromophenyl)benzo[g]quinoxaline → 2,3-bis[4-(N-phenyl-2-naphthylamino)phenyl]benzo[g]quinoxaline

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%

N-Phenyl-2-naphthylamine (135-88-6) + C13H13BrN2O3 (1467758-59-3) → (S)-tert-butyl (5-bromo-3-(4-(naphthalen-2-ylamino)phenyl)-2-oxoindolin-3-yl)carbamate

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%

1-ferrocenylethanol (1277-49-2) + N-Phenyl-2-naphthylamine (135-88-6) → C5H5FeC5H4CH(CH3)N(C6H5)(C10H7) (93122-45-3)

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 + N-Phenyl-2-naphthylamine (135-88-6) → C5H5FeC5H4CH(C6H5)N(C6H5)(C10H7) (93122-48-6)

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%

N-Phenyl-2-naphthylamine (135-88-6) + tert-butyl 2-oxoindolin-3-ylidenecarbamate (1373942-82-5) → (S)-tert-butyl (3-(4-(naphthalen-2-ylamino)phenyl)-2-oxoindolin-3-yl)carbamate

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%

C30H23BrSi (1022211-28-4) + N-Phenyl-2-naphthylamine (135-88-6) → C46H35NSi (1022211-18-2)

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

Upstream product

• 118-92-3 anthranilic acid 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 5488-73-3 [2]naphthyl-nitroso-phenyl-amine 
• 64-19-7 acetic acid 
• 62-53-3 aniline 
• 142-04-1 aniline hydrochloride 
• 93-01-6 2-naphthol-6-sulfonic acid 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 135-19-3 β-naphthol 
• 64-10-8 phenyl carbamate 
• 603-54-3 N,N-diphenylurea 
• 3898-08-6 1,1-diphenylthiourea 
• 36611-02-6 naphthalen-2-yl-phenyl-aminyl 
• 7553-56-2 iodine 

Downstream Products

• 10525-17-4 furfuryl acrylate 
• 55566-61-5 2-(2-anilino-[1]naphthylazo)-benzoic acid 
• 38455-57-1 9-anilino-7-phenyl-benzo[a]phenazinium; chloride 
• 17704-04-0 o-semidine 
• 412312-73-3 N-[2]naphthyl-N-phenyl-thiourea 
• 21784-66-7 2-anilinonaphthalene-8-sulfonic acid 
• 83662-03-7 6-anilino-naphthalene-1-sulfonic acid 
• 225-11-6 benz[a]acridine 
• 3340-93-0 9-methylbenz[a]acridine 
• 818-67-7 acrylic acid methallyl ester 
• 52529-64-3 3-methyl-4-phenylbenzoquinolinium iodide 
• 1487-18-9 (furan-2-yl)ethylene 
• 21720-66-1 9-phenyldibenzocarbazole 
• 17704-02-8 N,N'-diphenyl-(1,1'-binaphthyl)-2,2'-diamine 

Relevant articles and documents

Nucleophilic ipso-Substitution of Aryl Methyl Ethers through Aryl C-OMe Bond Cleavage; Access to Functionalized Bisthiophenes

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