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
• Article Data: 38

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

Chemical Properties

White powder

Uses

2-(4-Bromophenyl)naphthalene is used in the preparation of α-Phosphonosulfonate compounds which inhibit the enzyme squalene and thereby inhibit cholesterol biosynthesis.

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

• 1122-91-4 4-bromo-benzaldehyde 
• 96-09-3 styrene oxide 
• 32017-76-8 (+/-)-2-(4-bromophenyl)oxirane 
• 4482-01-3 o-benzenedisulfonimide 
• 32316-92-0 naphthalene-2-boronic acid 
• 106-40-1 4-bromo-aniline 
• 580-13-2 2-bromonaphthalene 
• 5467-74-3 4-Bromophenylboronic acid 
• 91-20-3 naphthalene 
• 589-87-7 1,4-bromoiodobenzene 
• 612-55-5 2-iodonaphthalene 
• 5419-55-6 Triisopropyl borate 
• 139139-81-4 bis(4-bromophenyl)iodonium triflate 
• 1241602-88-9 3-(4-bromophenyl)-1-(2-(2-methoxyvinyl)phenyl)prop-2-yn-1-ol 

Downstream Products

• 1446448-94-7 N,N-bis-(4-(2-naphthalenyl)phenyl)amine 
• 2135820-18-5 C₂₈H₂₁N 

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