22082-99-1

Basic information

• Product Name: 2-(4-Bromophenyl)naphthalene
• Synonyms: 2-(4-Bromophenyl)naphthalene;2-(4-BroMophenyl)-naphthlene;Naphthalene, 2-(4-bromophenyl)-
• CAS NO: 22082-99-1
• Molecular Formula: C₁₆H₁₁Br
• Molecular Weight: 283.16254
• Mol File: 22082-99-1.mol

Chemical Properties

• Melting Point: 131.0 to 135.0 °C
• Boiling Point: 394.251 °C at 760 mmHg
• Flash Point: 190.425 °C
• Appearance: /
• Density: 1.381 g/cm³
• Vapor Pressure: 4.56E-06mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(4-Bromophenyl)naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Bromophenyl)naphthalene(22082-99-1)
• EPA Substance Registry System: 2-(4-Bromophenyl)naphthalene(22082-99-1)

Safety Data

• Hazardous Substances Data: 22082-99-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Bromophenyl)naphthalene is used as a key intermediate in the synthesis of α-Phosphonosulfonate compounds. These compounds serve as inhibitors of the enzyme squalene, which plays a crucial role in cholesterol biosynthesis. By inhibiting this enzyme, 2-(4-Bromophenyl)naphthalene contributes to the development of drugs that can help in managing and treating conditions related to high cholesterol levels.

InChI:InChI=1/C16H11Br/c17-16-9-7-13(8-10-16)15-6-5-12-3-1-2-4-14(12)11-15/h1-11H

Synthetic route

1,4-bromoiodobenzene (589-87-7) + naphthalene-2-boronic acid (32316-92-0) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 84 - 88℃; for 9h; Inert atmosphere;	91.11%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 7h; Suzuki Coupling; Heating / reflux;	85%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Inert atmosphere; Reflux;	84%

3-(4-bromophenyl)-1-(2-(2-methoxyvinyl)phenyl)prop-2-yn-1-ol (1241602-88-9) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With Echavarren's catalyst In dichloromethane at 23℃; for 0.0833333h; Inert atmosphere;	91%

o-benzenedisulfonimide (4482-01-3) + naphthalene-2-boronic acid (32316-92-0) + 4-bromo-aniline (106-40-1) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions

Yield

Stage #1: o-benzenedisulfonimide; 4-bromo-aniline With acetic acid at 0 - 5℃; for 0.166667h; Inert atmosphere; Stage #2: With isopentyl nitrite for 0.166667h; Inert atmosphere; Stage #3: naphthalene-2-boronic acid With bis[(trifluoromethanesulfonyl)imidate]-2-(dicyclohexyl(2’,6’-dimethoxybiphenyl))phosphine gold(I); caesium carbonate In tetrahydrofuran at 20℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; chemoselective reaction;

81%

1,4-bromoiodobenzene (589-87-7) + 2-naphthylboronic acid → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In water	77%

1.4-dibromobenzene (106-37-6) + naphthalene-2-boronic acid (32316-92-0) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 65℃; for 18h;	70%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Reflux; Inert atmosphere;	65%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 24h; Suzuki Coupling; Heating / reflux;	47%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 3h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 3h; Inert atmosphere;	10 g

2-((4-bromophenyl)sulfinyl)naphthalene → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With 2-(trimethylsilyl)phenyl trifluoromethanesulfonate; cesium fluoride In acetonitrile at 20℃; for 72h; Inert atmosphere; Glovebox;	69%

1,4-bromoiodobenzene (589-87-7) + 1,3-dihydro-1,1,3,3-tetramethylnaphth[2,3-c][1,2,5]oxadisilole (442912-20-1) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran at 35℃; for 24h; Inert atmosphere;	68%

bis(4-bromophenyl)iodonium trifluoroacetate + naphthalene (91-20-3) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With sodium tetrachloroplatinate(II) hydrate; tetrabutylammonium trifluoromethylsulfonate at 100℃; for 72h;	57%

2-iodonaphthalene (612-55-5) + C12H8Br2Zn → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
In tetrahydrofuran at 110℃; for 24h; Inert atmosphere;	53%

2-bromonaphthalene (580-13-2) + 4-Bu3Sn,2Cl-C6H3CONH-Rink resin → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Mg; I2 / tetrahydrofuran / 14 h / Heating 1.2: tetrahydrofuran / -78 - 20 °C 2.1: 6.2 g / aq. HCl / tetrahydrofuran / 2 h / 20 °C 3.1: 79 percent / Pd(PPh3)4; Ba(OH)2*8H2O / H2O; dioxane / 24 h / Heating View Scheme

C10H7BH2O2C4H8 → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 6.2 g / aq. HCl / tetrahydrofuran / 2 h / 20 °C 2: 79 percent / Pd(PPh3)4; Ba(OH)2*8H2O / H2O; dioxane / 24 h / Heating View Scheme

thrice-fused zinc chloride + 2-bromonaphthalene (580-13-2) + 1,4-bromoiodobenzene (589-87-7) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With hydrogenchloride; tert.-butyl lithium; sodium thiosulfate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; pentane	4.05 g (72%)

naphthalene (91-20-3) + bis(4-bromophenyl)iodonium triflate (139139-81-4) → 2-(4-bromophenyl)naphthalene (22082-99-1) + 1-(4-bromo-phenyl)-naphthalene (204530-94-9)

Conditions	Yield
In neat (no solvent) at 150℃; for 1h; Inert atmosphere; Microwave irradiation; Overall yield = 69 %; Overall yield = 98 mg;

Triisopropyl borate (5419-55-6) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane; water; toluene
With n-butyllithium In tetrahydrofuran; hexane; water; toluene

1,4-bromoiodobenzene (589-87-7) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere 1.2: -78 - 0 °C 2.1: tetrahydrofuran / 24 h / 110 °C / Inert atmosphere View Scheme

4-Bromophenylboronic acid (5467-74-3) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate / diethyl ether; dichloromethane 2: sodium 2,2,2-trifluoroacetate / water; dichloromethane 3: sodium tetrachloroplatinate(II) hydrate; tetrabutylammonium trifluoromethylsulfonate / 72 h / 100 °C View Scheme

bis(4-bromophenyl)iodonium tetrafluoroborate → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium 2,2,2-trifluoroacetate / water; dichloromethane 2: sodium tetrachloroplatinate(II) hydrate; tetrabutylammonium trifluoromethylsulfonate / 72 h / 100 °C View Scheme

2-bromonaphthalene (580-13-2) → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 1.2: 12 h / -78 - 20 °C / Inert atmosphere 1.3: 0.5 h / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene / 24 h / Inert atmosphere; Reflux View Scheme

(4-bromophenyl)(naphthalen-2-yl)sulfane → 2-(4-bromophenyl)naphthalene (22082-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C / Inert atmosphere 2: 2-(trimethylsilyl)phenyl trifluoromethanesulfonate; cesium fluoride / acetonitrile / 72 h / 20 °C / Inert atmosphere; Glovebox View Scheme

2-(4-bromophenyl)naphthalene (22082-99-1) + bis(biphenyl-4-yl)amine (102113-98-4) → C40H29N

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 60 - 120℃; for 7h; Inert atmosphere;	93%

2-(4-bromophenyl)naphthalene (22082-99-1) + (R)-3,3'-bis(dihydroxyborane)-2,2'-dimethoxy-1,1'-binaphthyl → 2,2'-dimethoxy-3,3'-bis-(4-naphthalen-2-yl-phenyl)-[1,1']binaphthalenyl

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water Inert atmosphere; Reflux;	89%
With barium dihydroxide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water for 24h; Suzuki reaction; Heating;

((10-(naphthalen-1-yl)anthracen-9-yl)boronic acid) (400607-46-7) + 2-(4-bromophenyl)naphthalene (22082-99-1) → 9-(naphthalene-1-yl)-10-(4-(naphthalene-2-yl)phenyl)anthracene

Conditions	Yield
With potassium carbonate In ethanol; water at 70 - 76℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;	88.92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Inert atmosphere; Reflux;	82%

2-(4-bromophenyl)naphthalene (22082-99-1) + anthracene-9-boronic acid (100622-34-2) → 9-(4-(naphthalen-2-yl)phenyl)anthracene (866611-28-1)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 5h; Suzuki Coupling; Heating / reflux;	87%

2-(4-bromophenyl)naphthalene (22082-99-1) + C32H21NS → C48H31NS

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Inert atmosphere; Reflux;	87%

2-(4-bromophenyl)naphthalene (22082-99-1) + C38H25NO → C54H35NO

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Inert atmosphere; Reflux;	86%

2-(4-bromophenyl)naphthalene (22082-99-1) + 7,17-dimethyl-7,17-divinyl-1,3,5,9,11,13,15,1-octaphenylhexacyclo[9.13.11,9 .13,15 .15,13 .111,19 ]decasiloxane → C86H72O14Si10

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In toluene at 100℃; Inert atmosphere;	85%

2-(4-bromophenyl)naphthalene (22082-99-1) + C29H24BN5O2 → C39H23N5

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 6h; Inert atmosphere; Reflux;	85%

2-(4-bromophenyl)naphthalene (22082-99-1) → 4-(naphthalene-2-yl)phenylboronic acid pinacol ester (918655-03-5)

Conditions	Yield
Stage #1: 2-(4-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran; hexane at -60℃; for 1h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -60 - 20℃; for 18h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; for 1h;	84%
Stage #1: 2-(4-bromophenyl)naphthalene With n-butyllithium In diethyl ether; hexane; toluene at -64℃; for 2.5h; Stage #2: With Trimethyl borate In diethyl ether; hexane; toluene at 20℃; for 12.25h; Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene at 0 - 10℃;
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride / tetrahydrofuran / 0.5 h / Inert atmosphere View Scheme

Triisopropyl borate (5419-55-6) + 2-(4-bromophenyl)naphthalene (22082-99-1) → 4-(naphthalene-2-yl)phenylboronic acid pinacol ester (918655-03-5)

Conditions	Yield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; toluene	84%
Stage #1: 2-(4-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran; hexane at -60℃; for 0.5h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -60 - 20℃; Inert atmosphere; Stage #3: With water In tetrahydrofuran; hexane Inert atmosphere;

2-(4-bromophenyl)naphthalene (22082-99-1) + C32H21NO → C48H31NO

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Inert atmosphere; Reflux;	84%

2-(4-bromophenyl)naphthalene (22082-99-1) + C36H23NOS → C52H33NOS

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Reflux; Inert atmosphere;	83%

2-(4-bromophenyl)naphthalene (22082-99-1) + N-([1,1'-biphenyl]-4-yl)-4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine → C52H36N2

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	82.9%

2-(4-bromophenyl)naphthalene (22082-99-1) + C36H26N2 → C52H36N2

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	82.5%

2-(4-bromophenyl)naphthalene (22082-99-1) + C36H26N2 → C52H36N2

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	82.3%

2-(4-bromophenyl)naphthalene (22082-99-1) + C38H24N2OS → C53H33N3OS

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Inert atmosphere; Reflux;	82%

2-(4-bromophenyl)naphthalene (22082-99-1) + 7-phenyl-7,9-dihydrobenzofuro[2,3-g]indolo[2,3-b]carbazole → C46H28N2O

Conditions	Yield
With potassium phosphate; copper(l) iodide; ethylenediamine In toluene at 140℃; for 6h;	81%

4-tert-Butylaniline (769-92-6) + 2-(4-bromophenyl)naphthalene (22082-99-1) → C26H25N

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 3h; Reflux;	80%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 3h; Reflux;	80%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 3h; Reflux;	80%

9,9-dimethyl-9H-fluoren-2-ylamine (108714-73-4) + 1-(4-bromophenyl)adamantane (2245-43-4) + 2-(4-bromophenyl)naphthalene (22082-99-1) → C47H43N

Conditions	Yield
Stage #1: 9,9-dimethyl-9H-fluoren-2-ylamine; 4-(1-Adamantyl)bromobenzene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 70 - 105℃; for 2h; Inert atmosphere; Stage #2: 2-(4-bromophenyl)naphthalene In toluene at 70 - 105℃; for 12h;	80%

2-(4-bromophenyl)naphthalene (22082-99-1) + C38H28BNO2 → C54H37N

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Reflux; Inert atmosphere;	80%

2-(4-bromophenyl)naphthalene (22082-99-1) + C49H29NO2 → C65H39NO2

Conditions	Yield
With bis[tris( 1,1-dimethylethyl)phosphine]-palladium; sodium t-butanolate In toluene at 100℃; for 2h; Sealed tube;	80%

2-(4-bromophenyl)naphthalene (22082-99-1) + C38H25NO → C54H35NO

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Inert atmosphere; Reflux;	80%

2-(4-bromophenyl)naphthalene (22082-99-1) + C36H23NS2 → C52H33NS2

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Reflux; Inert atmosphere;	80%

2-(4-bromophenyl)naphthalene (22082-99-1) + C36H23NOS → C52H33NOS

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Reflux; Inert atmosphere;	80%

2-(4-bromophenyl)naphthalene (22082-99-1) + C36H23NS2 → C52H33NS2

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Reflux; Inert atmosphere;	77%

2-(9,10-di(naphthalene-2-yl)anthracene-2-yl)4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (624744-67-8) + 2-(4-bromophenyl)naphthalene (22082-99-1) → C50H32

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Suzuki Coupling; Heating / reflux;	76%

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 32316-92-0 naphthalene-2-boronic acid 
• 580-13-2 2-bromonaphthalene 
• 106-37-6 1.4-dibromobenzene 
• 442912-20-1 1,3-dihydro-1,1,3,3-tetramethylnaphth[2,3-c][1,2,5]oxadisilole 
• 1241602-88-9 3-(4-bromophenyl)-1-(2-(2-methoxyvinyl)phenyl)prop-2-yn-1-ol 
• 91-20-3 naphthalene 
• 139139-81-4 bis(4-bromophenyl)iodonium triflate 
• 612-55-5 2-iodonaphthalene 
• 5467-74-3 4-Bromophenylboronic acid 
• 4482-01-3 o-benzenedisulfonimide 
• 106-40-1 4-bromo-aniline 
• 96-09-3 styrene oxide 
• 32017-76-8 (+/-)-2-(4-bromophenyl)oxirane 

Downstream Products

• 179821-46-6 3-Hydroxy-3-(4-naphth-2-yl-phenyl)piperidine 
• 866611-28-1 9-(4-(naphthalen-2-yl)phenyl)anthracene 
• 918655-03-5 4-(naphthalene-2-yl)phenylboronic acid pinacol ester 
• 1337916-16-1 3,5-dimethyl-2-(4-naphthalen-2-yl-phenyl)pyrazine 
• 1398394-32-5 C₅₄H₃₄N₄ 
• 1398395-50-0 C₆₀H₃₈N₄ 
• 897671-79-3 {4-(naphthalen-2-yl)phenyl}-phenylamine 
• 209848-36-2 2-(4-aminophenyl)naphthalene 
• 1446448-94-7 N,N-bis-(4-(2-naphthalenyl)phenyl)amine 

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The present invention refers to one or more layers including a light emitting layer between anode and cathode is interposed as above wherein at least one of an organic electroluminescent device, comprising of a luminescent layer for organic thin film layer contains said formula 1, formula 2 characterized in that said hole transport material to the light emitting layer employed in conjunction with an organic electroluminescence device number under public affairs substrate. The organic electroluminescence device of the present invention exhibits high efficiency and long lifetime properties. [Formula 1][Formula 2] (by machine translation)

Iron Phosphate Catalyzed Asymmetric Cross-Dehydrogenative Coupling of 2-Naphthols with β-Ketoesters

Chiral iron phosphate complexes were successfully exploited for asymmetric cross-dehydrogenative coupling reactions between 2-naphthols and β-ketoester derivatives. On the basis of kinetic studies, it is suggested that iron monophosphate complexes constitute the active catalysts that induce stereoselectivity during the carbon-carbon bond-formation step.

An electroluminescent compound and an electroluminescent device comprising the same

The present invention relates to an organic light emitting compound adopted to an organic electroluminescent device. The organic light emitting compound is represented by chemical formula 1 or chemical formula 2. In the case of adopting the organic light emitting compound as a phosphorescence host compound in a hole transport functional layer or a luminous layer, an organic electroluminescent device having excellent luminous characteristics such as operating voltage, brightness, long lifespan, etc.