90-11-9

Basic information

• Product Name: 11 -Bromonaphthalene
• Synonyms: 1-Naphthyl bromide;NSC 6551;Naphthalen-1-yl bromide;a-Bromonaphthalene;a-Naphthyl bromide
• CAS NO: 90-11-9
• Molecular Formula: C₁₀H₇Br
• Molecular Weight: 207.07
• EINECS: 201-965-2
• Mol File: 90-11-9.mol
• Article Data: 82

Chemical Properties

• Melting Point: -1℃
• Boiling Point: 282.677 °C at 760 mmHg
• Flash Point: 127.817 °C
• Appearance: clear yellow to yellow-brown liquid
• Density: 1.482 g/cm³
• Vapor Pressure: 0.00565mmHg at 25°C
• Refractive Index: 1.663
• Water Solubility: slightly soluble
• CAS DataBase Reference: 11 -Bromonaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 11 -Bromonaphthalene(90-11-9)
• EPA Substance Registry System: 11 -Bromonaphthalene(90-11-9)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 90-11-9(Hazardous Substances Data)

Usage

General Description

11-Bromonaphthalene is a chemical compound with the formula C10H7Br. It is a halogenated aromatic hydrocarbon, specifically a brominated derivative of naphthalene. It is a colorless to yellow liquid at room temperature and is insoluble in water but soluble in organic solvents. 11-Bromonaphthalene is primarily used as a chemical intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. It can also be used as a reagent in organic synthesis reactions, such as the preparation of other brominated organic compounds. Exposure to 11-bromonaphthalene should be limited, as it is considered to be a hazardous chemical, and proper precautions should be taken when handling and storing it.

InChI:InChI=1/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H

Synthetic route

triethyl(naphthalen-1-yl)germane → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h;	99%

naphthalene (91-20-3) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With aluminum oxide; copper(ll) bromide In tetrachloromethane at 80℃; for 1h;	98%
With ammonium cerium(IV) nitrate; lithium bromide In acetonitrile at 20℃; for 6h;	98%
With 1-dodecyl-3-methylimidazol-1-ium bromide at 50℃; for 2h;	98%

1-Naphthylboronic acid (13922-41-3) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 80℃; for 14h;	98%
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; Sealed tube;	87%

1-naphthylboronic acid pinacol ester (68716-52-9) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With copper(ll) bromide In methanol Heating;	95%

allylbenzene (300-57-2) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With carbon tetrabromide; iron In ethanol at 20℃; for 2h; Solvent; Reagent/catalyst; Irradiation;	94%

1-naphthyltrimethylsilane (18052-80-7) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With N-Bromosuccinimide In 1,2-dichloro-ethane; acetonitrile at 85℃; for 12h;	92%

6-Bromo-2,3-dihydro-naphtho[1,2-b][1,4]dithiine (135033-52-2) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With Ni(Ra)-W2 In acetic acid at 40℃; for 0.833333h;	90%

potassium trifluoro(naphth-1-yl)borate (166328-07-0) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With pyridinium hydrobromide perbromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;	90%
With acetic acid; lithium bromide In dimethyl sulfoxide at 100℃; for 8h; Schlenk technique;	42%

C10H7N2(1+)*C6H4NO4S2(1-) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;	87%
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;	81%

1-amino-naphthalene (134-32-7) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With trimethylsilyl bromide; N-benzyl-N,N,N-triethylammonium chloride; sodium nitrite In tetrachloromethane 1.) 0 deg C, 1.5 h, 2.) r.t., 17 h;	85%
With dinitrogen trioxide; hydrogen bromide; acetic acid at 5 - 10℃; anschliessendes Erhitzen bis auf Siedetemperatur;

1,8-diamino naphthaline bisdiazonium tetrafluoroborate → 1,8-dibromonaphthalene (17135-74-9) + 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With dibenzo-18-crown-6; potassium bromide; copper(ll) bromide; 1,10-Phenanthroline; copper(I) bromide In acetonitrile at 20℃; for 0.333333h; Sandmeyer bromination;	A 81% B 13%

4-bromo-1,2-dihydronaphthalene (3333-24-2) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 4h; Reflux;	72%

1,2-diethynylbenzene (21792-52-9) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With hydrogen bromide; platinum(II) chloride In water at 100℃; for 4h;	71%
Multi-step reaction with 2 steps 1: 98 percent / HBr / H2O; various solvent(s) / 1.5 h / 100 °C 2: PtCl2 / H2O; various solvent(s) / 12 h / 100 °C View Scheme

tetralin (119-64-2) → naphthalene (91-20-3) + 1-Bromonaphthalene (90-11-9) + 1,4-dibromo-1,2,3,4-tetrahydronaphthalene (6606-70-8) + trans-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (39834-40-7, 58679-98-4, 64245-04-1, 79465-07-9, 84275-50-3, 84275-51-4, 84275-52-5)

Conditions	Yield
With bromine In tetrachloromethane at 77℃; for 0.166667h; Further byproducts given;	A 14% B 10% C 63% D 8%

1-bromo-8-[(deuterio)dimethylsilyl]naphthalene → 1-Bromonaphthalene (90-11-9) + C12H12(2)HBrSi

Conditions	Yield
With iodine In benzene-d6 Inert atmosphere;	A 37% B 56%

1-bromo-8-[(deuterio)dimethylsilyl]naphthalene → 1-Bromonaphthalene (90-11-9) + C10H6(2)HBr

Conditions	Yield
With iodine In benzene-d6 Inert atmosphere;	A 43% B 52%

naphthalene (91-20-3) → 1-Bromonaphthalene (90-11-9) + C10H6Br2

Conditions	Yield
With oxygen; potassium bromide; sodium nitrite In water; trifluoroacetic acid at 20℃; for 5h; Product distribution;	A 49% B n/a

C11H9Br3O2 → 1-Bromonaphthalene (90-11-9) + 1-Chloronaphthalene (90-13-1)

Conditions	Yield
With 1,2-dichloro-ethane; copper(l) chloride; 1,3-bis(pyridin-2-ylmethyl)-1H-imidazolium chloride at 200℃; for 2h; Product distribution / selectivity; Microwave irradiation;	A 49% B n/a

1-Iodonaphthalene (90-14-2) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
In tetrahydrofuran at 25℃; for 60h;	40%
With bromobenzene; tetrabutylammomium bromide; o-CH3C6H4NiBr(PEt3)2 In benzene at 80℃; for 20h; sealed tube; Yield given. Yields of byproduct given;

naphthalene (91-20-3) → 1-Bromonaphthalene (90-11-9) + (1R,2S,3R,4S)-tetrabromo-1,2,3,4-tetrahydronaphthalene + 1,2,3,4-tetrabromo-1,2,3,4-tetrahydronaphthalene + (1S,2S,3S,4R)-tetrabromo-1,2,3,4-tetrahydronaphthalene

Conditions	Yield
With bromine In tetrachloromethane at 30℃; for 7h; Bromination; Irradiation;	A 25% B 3% C 35% D 6%

naphthalene (91-20-3) → 1-Bromonaphthalene (90-11-9) + 1,2,3,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (19922-78-2) + HBr

Conditions	Yield
With bromine In tetrachloromethane for 8h;	A 35% B n/a C n/a

naphthalene (91-20-3) + bromocyane (506-68-3) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
at 250℃;
at 250℃;

naphthalene (91-20-3) + carbon tetrabromide (558-13-4) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
at 150 - 180℃;

naphthalene (91-20-3) → 2-bromonaphthalene (580-13-2) + 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With bromine; iron(III) chloride at 150 - 200℃;
With bromine in der Gasphase bei 550-600grad in Gegenwart oder Abwesenheit von FeBr3;

tetrachloromethane (56-23-5) + naphthalene (91-20-3) + 1,3-dibromo-5-ethyl-5-methyl-imidazolidine-2,4-dione (82925-96-0) → 1-Bromonaphthalene (90-11-9)

2-bromonaphthalene (580-13-2) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
Isomerisierung;

1,4-dibromonaphthalene (83-53-4) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With diethyl ether; magnesium anschliessende Behandlung mit Wasser;
With magnesium; benzene anschliessende Behandlung mit Wasser;

1,6-dibromonaphthalene (19125-84-9) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With diethyl ether; magnesium anschliessende Behandlung mit Wasser;
With magnesium; benzene anschliessende Behandlung mit Wasser;

1-naphthalenesulfonic acid (85-47-2) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
With copper(ll) bromide

4-Bromo-1-naphthylamine (2298-07-9) → 1-Bromonaphthalene (90-11-9)

Conditions	Yield
durch Diazotieren des salpetersauren Salzes und Behandeln des Diazoniumnitrats mit Alkohol;

1-Bromonaphthalene (90-11-9) + cyclopentanone (120-92-3) → 1-Naphthylcyclopentanol (74709-98-1)

Conditions	Yield
With iodine; magnesium In diethyl ether for 3h; Grignard reaction; Heating;	100%
With iodine; magnesium 1.) ether, reflux, 2.) ether, benzene, RT, 2 h; Yield given. Multistep reaction;
Stage #1: 1-Bromonaphthalene With magnesium In diethyl ether Stage #2: cyclopentanone In diethyl ether for 3h; Grignard reaction;
Stage #1: 1-Bromonaphthalene With magnesium In diethyl ether for 0.5h; Reflux; Stage #2: cyclopentanone In diethyl ether at 0℃; for 1h;

1-Bromonaphthalene (90-11-9) + phenylboronic acid (98-80-6) → 1-phenylnaphthalene (605-02-7)

Conditions	Yield
With C31H26N6O4Pd; potassium carbonate In water at 100℃; for 3h; Suzuki-Miyaura coupling;	100%
With potassium phosphate; 1,1'-bis(4-methoxyphenyl)-3,3'-methylene-diimidazoline-2,2'-diylidene-palladium(II)-dibromide In toluene at 40℃; for 2h; Reagent/catalyst; Temperature; Time; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With C16H21ClN2Pd; sodium carbonate In methanol at 85℃; for 1h; Reagent/catalyst; Suzuki-Miyaura Coupling;	100%

1-Bromonaphthalene (90-11-9) + 3CoCH3 → 1-Methylnaphthalene (90-12-0)

Conditions	Yield
In benzene at 10℃; for 24h;	100%

1-Bromonaphthalene (90-11-9) + dimethyl zinc(II) (544-97-8) → 1-Methylnaphthalene (90-12-0)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 2h; Heating;	100%
Stage #1: 1-Bromonaphthalene; dimethyl zinc(II) With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.5h; Substitution; Stage #2: With oxovanadium(V) ethoxydichloride In tetrahydrofuran; diethyl ether; hexane at 20℃; for 3h; Oxidation; Alkylation; Further stages.;	73%

cyclopentadecanone (502-72-7) + 1-Bromonaphthalene (90-11-9) → 1-Naphthylcyclopentadecanol

Conditions	Yield
Stage #1: 1-Bromonaphthalene With iodine; magnesium In diethyl ether Grignard reaction; Stage #2: cyclopentadecanone In diethyl ether Grignard reaction;	100%

1-Bromonaphthalene (90-11-9) + 1-Naphthylboronic acid (13922-41-3) → 1,1'-bisnaphthalene (604-53-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate In tetrahydrofuran at 20℃; for 6h; Suzuki coupling; Inert atmosphere;	100%
With C64H76Br2N4O2Pd; potassium carbonate In N,N-dimethyl acetamide at 20 - 140℃; for 24h; Suzuki coupling; Inert atmosphere;	99%
With potassium fluoride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 48h; Suzuki coupling;	97%

1-Bromonaphthalene (90-11-9) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → Methyl 1-naphthylphosphinate (145051-67-8)

Conditions	Yield
With anilinium hypophosphorous salt; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In acetonitrile Heating;	100%

2-Acetylthiophene (88-15-3) + 1-Bromonaphthalene (90-11-9) → 1-(5-(naphthalen-1-yl)thiophen-2-yl)ethan-1-one (5866-23-9)

Conditions	Yield
With dichloro[1-(β-methallyl)-3-(2,4,6-trimethyl)benzylbenzimidazole-2-ylidene]pyridine palladium(II); potassium acetate In N,N-dimethyl acetamide at 130℃; for 1h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	100%
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;	82%
With sodium acetate; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl acetamide at 150℃; for 20h;	77%
With sodium carbonate; silver(l) oxide; Trimethylacetic acid In N,N-dimethyl-formamide at 120℃; for 18h; Quantum yield; Green chemistry;	52%

1-Bromonaphthalene (90-11-9) + potassium ferrocyanide → 1-Cyanonaphthalene (86-53-3)

Conditions	Yield
With sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one; Hexadecane at 140℃; for 16h;	100%
With 1-methyl-pyrrolidin-2-one; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate at 120℃; for 12h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;	95%
With dichlorobis(dibenzyl diisopropylphosphoramidite)palladium(II); sodium fluoride In N,N-dimethyl-formamide at 130℃; for 16h;	94%

(4R,5R)-4-(tert-butyldimethylsiloxy)-5-[(tert-butyldimethylsiloxy)methyl]-5-methyldihydrofuran-2(3H)-one (869210-37-7) + 1-Bromonaphthalene (90-11-9) → (3R,4R)-3,5-bis(tert-butyldimethylsiloxy)-4-hydroxy-4-methyl-1-(1-naphthyl)pentan-1-one (869210-43-5)

Conditions	Yield
Stage #1: 1-Bromonaphthalene With tert.-butyl lithium In tetrahydrofuran at -78℃; Stage #2: With cerium chloride In tetrahydrofuran; pentane for 2h; Cooling; Stage #3: (4R,5R)-4-(tert-butyldimethylsiloxy)-5-[(tert-butyldimethylsiloxy)methyl]-5-methyldihydrofuran-2(3H)-one In tetrahydrofuran; pentane at -100℃; for 0.5h;	100%

(4S,5S)-4-(tert-butyldimethylsiloxy)-5-[(tert-butyldimethylsiloxy)methyl]-5-methyldihydrofuran-2(3H)-one (1041189-10-9) + 1-Bromonaphthalene (90-11-9) → (3S,4S)-3,5-bis(tert-butyldimethylsiloxy)-4-hydroxy-4-methyl-1-(1-naphthyl)pentan-1-one (1041189-20-1)

Conditions	Yield
Stage #1: 1-Bromonaphthalene With tert.-butyl lithium In tetrahydrofuran at -78℃; Stage #2: With cerium chloride In tetrahydrofuran; pentane for 2h; Cooling; Stage #3: (4S,5S)-4-(tert-butyldimethylsiloxy)-5-[(tert-butyldimethylsiloxy)methyl]-5-methyldihydrofuran-2(3H)-one In tetrahydrofuran; pentane at -100℃; for 0.5h;	100%

1-Bromonaphthalene (90-11-9) + phenylmethanethiol (100-53-8) → 1-(benzylsulfanyl)naphthalene (5023-64-3)

Conditions	Yield
Stage #1: phenylmethanethiol With sodium t-butanolate In tetrahydrofuran at 23℃; for 0.166667h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran for 0.166667h; Inert atmosphere; Stage #3: 1-Bromonaphthalene With di-μ-bromobis(tri-tert-butylphosphino)dipalladium(I); lithium iodide In tetrahydrofuran at 90℃; for 2h; Inert atmosphere;	100%

2-(n-propyl)-thiazole (17626-75-4) + 1-Bromonaphthalene (90-11-9) → 5-(naphthalen-1-yl)-2-propylthiazole (1109226-36-9)

Conditions	Yield
With dichloro[1-(β-methallyl)-3-(2,3,5,6-tetramethyl)benzylbenzimidazole-2-ylidene]pyridine palladium(II); potassium acetate In N,N-dimethyl acetamide at 130℃; for 1h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	100%

carbon monoxide (201230-82-2) + 1-Bromonaphthalene (90-11-9) → 1-naphthalenecarboxylic acid (86-55-5)

Conditions	Yield
With sodium hydroxide; cobalt(II) acetate In ethanol at 65℃; under 1520 Torr; for 4h; Irradiation;	99.3%
With sodium hydroxide; tetrabutylammomium bromide; dicobalt octacarbonyl In water; benzene at 65℃; under 760 Torr; for 5h; Irradiation;	96%
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 4.5h; Irradiation;	95%
With tributyl-amine; water; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride at 110 - 130℃; under 3 Torr; for 24h;	48%
With water; sodium acetate; triethylamine; Pd-bis(1-methylbenzothiazole-2-carbene) In N,N-dimethyl acetamide at 130℃; for 7h;	55 % Chromat.

n-butyllithium (109-72-8, 29786-93-4) + 1-Bromonaphthalene (90-11-9) → 1-butylnaphthalene (1634-09-9)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In cyclohexane at 20℃; for 0.00555556h; pH=6; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique;	99%
Stage #1: 1-Bromonaphthalene With bis(tri-tert-butylphosphine)palladium(0); sodium chloride In water at 20℃; for 0.166667h; Negishi Coupling; Schlenk technique; Stage #2: n-butyllithium With zinc(II) chloride In 2-methyltetrahydrofuran; water at 10℃; for 0.00555556h; Schlenk technique; chemoselective reaction;	98%
Stage #1: n-butyllithium With zinc(II) chloride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 1-Bromonaphthalene; dichloro bis(acetonitrile) palladium(II) In toluene at 60℃; for 3h; Negishi coupling; Further stages.;	96%

1-Bromonaphthalene (90-11-9) → naphthalene (91-20-3)

Conditions	Yield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 6h; ultrasonic acceleration of reduction;	99%
With 2,2'-azobis(isobutyronitrile); tert-butyl(2,6-dimethoxy-1-methylcyclohexa-2,5-dien-1-yl)dimethylsilane In hexane for 18h; Heating;	99%
With 2,2'-azobis(isobutyronitrile); tert-butyl(2,6-dimethoxy-1-methylcyclohexa-2,5-dien-1-yl)dimethylsilane In hexane for 18h; Heating;	99%

1-Bromonaphthalene (90-11-9) → 1,1'-bisnaphthalene (604-53-5)

Conditions	Yield
Stage #1: 1-Bromonaphthalene With tert.-butyl lithium In diethyl ether at -78℃; Stage #2: In diethyl ether Stage #3: With Duroquinone In diethyl ether	99%
With DPEPhos; potassium tert-butylate; palladium diacetate; bis(pinacol)diborane for 12h; Heating;	99%
With chromium dichloride; manganese; nickel dichloride; bipyridyl-type ligand In tetrahydrofuran at 20℃; for 17h; Arylation; Homocoupling reaction;	98%

carbon monoxide (201230-82-2) + 1-Bromonaphthalene (90-11-9) + butan-1-ol (71-36-3) → naphthalene-1-carboxylic acid butyl ester (3007-95-2)

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; palladium dichloride at 120℃; under 760.051 Torr; for 12h;	99%
With tributyl-amine; triphenylphosphine; silica-supported poly<3-(2-cyanoethylsulfanyl)propylsiloxane palladium> at 100℃; under 760 Torr; for 72h;	34%
With bis(triphenylphosphine)palladium dibromide; tributyl-amine

1-Bromonaphthalene (90-11-9) → 1-deuteronaphthalene (875-62-7)

Conditions	Yield
With potassium phosphate; d(4)-methanol; palladium diacetate; catacxium A In toluene at 80℃; for 16h;	99%
With sodium amalgam; deuteromethanol for 2h; Heating;	95%
With tetrahydrofuran-d8; 2,2'-azobis-(2,4-dimethylvaleronitrile); tri-n-butyl-tin hydride for 5h; Reflux; regioselective reaction;	68%
With water-d2; magnesium 1.) Grignard; Multistep reaction;
With water-d2; potassium carbonate In acetonitrile at 20℃; pH=12.15; Electrochemical reaction;

1-Bromonaphthalene (90-11-9) + (3-dimethylaminopropyl)dimethylgallium → 1-Methylnaphthalene (90-12-0)

Conditions	Yield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 15h;	99%

1-Bromonaphthalene (90-11-9) + 4-methylphenylboronic acid (5720-05-8) → 1-(4-methylphenyl)naphthalene (27331-34-6)

Conditions	Yield
With potassium phosphate; N-[(4-diphenylphosphinophenyl)methyl] D-gluconamide; PdCl2(GLCAphos)2 In water at 80℃; for 16h;	99%
With 3,5-di-tert-butyl-2-hydroxybenzaldehyde; potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 2h; Suzuki-Miyaura Coupling;	99%
With potassium carbonate; palladium diacetate In various solvent(s) at 110℃; for 15h; Suzuki reaction;	97%

1-Bromonaphthalene (90-11-9) + formic acid ethyl ester (109-94-4) → bis(1-naphthyl)methanol (62784-66-1)

Conditions	Yield
With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 1h;	99%
Stage #1: 1-Bromonaphthalene With iodine; magnesium In tetrahydrofuran at 65℃; for 2h; Inert atmosphere; Stage #2: formic acid ethyl ester In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Heating;	93%
Stage #1: 1-Bromonaphthalene With iodine; magnesium In tetrahydrofuran at 20℃; for 2.15h; Stage #2: formic acid ethyl ester In tetrahydrofuran at 20℃; for 2h;	90%

1-Bromonaphthalene (90-11-9) + Cyclopropylamine (765-30-0) → N-cyclopropylnaphthalen-1-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 24h;	99%
With tris-(dibenzylideneacetone)dipalladium(0); sodium tert-pentoxide; (R)-tol-BINAP In toluene at 80℃; for 18h; Inert atmosphere;	99%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 4h; Inert atmosphere;	92%
With C37H55O2PPd(1+)*CF3O3S(1-); sodium t-butanolate In toluene at 90℃; for 6h; Schlenk technique; Inert atmosphere;	75%
With [Pd(allyl)(BrettPhos)]OTf; sodium t-butanolate In toluene at 90℃; Schlenk technique; Inert atmosphere;	72%

acrylic acid n-butyl ester (141-32-2) + 1-Bromonaphthalene (90-11-9) → butyl (E)-3-(naphthalen-1-yl)acrylate (123230-71-7)

Conditions	Yield
With C68H96Br2N2O8P2Pd2; triethylamine; 3,3'-di-tert-butyl-5,5'-dimethoxybiphenyl-2,2'-diyl diisopropylphosphoramidite In 1-methyl-pyrrolidin-2-one at 80℃; for 16h; Mizoroki-Heck reaction; Inert atmosphere; regioselective reaction;	99%
With phenyl carbamate; potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 130℃; for 2h; Heck-type reaction;	98%
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Heck Reaction; Inert atmosphere; Schlenk technique;	97%

1-Bromonaphthalene (90-11-9) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyano-2-(naphthalen-1-yl)acetate (13234-71-4)

Conditions	Yield
With P(i-BuNCH2CH2)3N; potassium tert-butylate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 90℃; for 5h;	99%
With tri-tert-butyl phosphine; sodium phosphate; bis(dibenzylideneacetone)-palladium(0) In toluene at 70℃; for 4h;	83%

1-Bromonaphthalene (90-11-9) + Na(1+)*(NCC3H6CC)4Al(1-) → 6-(1-naphthyl)hex-5-ynenitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane for 16h; Heating;	99%

1-Bromonaphthalene (90-11-9) + 4-methoxyphenylboronic acid (5720-07-0) → 1-(4-methoxyphenyl)naphthalene (27331-33-5)

Conditions	Yield
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	99%
With tetraamminepalladium(II) chloride; tetra(n-butyl)ammonium hydroxide In water at 45℃; for 2h; Suzuki-Miyaura Coupling; Green chemistry;	99%
With Ti0.97Pd0.03O1.97; potassium carbonate In water at 100℃; for 6h; Suzuki-Miyaura Coupling;	99%

Upstream product

• 91-20-3 naphthalene 
• 123-91-1 1,4-dioxane 
• 7726-95-6 bromine 
• 56-23-5 tetrachloromethane 
• 7732-18-5 water 
• 124-38-9 carbon dioxide 
• 7705-08-0 iron(III) chloride 
• 64-19-7 acetic acid 
• 7727-15-3 aluminium bromide 
• 5438-13-1 1,2-dibromonaphthalene 
• 10035-10-6 hydrogen bromide 
• 19922-78-2 1,2,3,4-tetrabromo-1,2,3,4-tetrahydronaphthalene 
• 21792-52-9 1,2-diethynylbenzene 
• 19125-84-9 1,6-dibromonaphthalene 

Downstream Products

• 1634-09-9 1-butylnaphthalene 
• 91-20-3 naphthalene 
• 630-95-5 1-naphthyldiphenylmethanol 
• 612-78-2 2,2'-binaphthalene 
• 188-72-7 terrylene 
• 7461-72-5 2,5,2',5'-Tetraacetoxy-4,4'-dimethoxy-biphenyl 
• 86-55-5 1-naphthalenecarboxylic acid 
• 86-87-3 naphth-1-yl acetic acid 
• 604-53-5 1,1'-bisnaphthalene 
• 62062-39-9 1-naphthalen-1-yl-piperidine 
• 5465-85-0 N-(2-naphthyl)piperidine 
• 90-15-3 α-naphthol 
• 580-13-2 2-bromonaphthalene 
• 83-53-4 1,4-dibromonaphthalene 

Relevant articles and documents

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Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons

A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).

Direct bromodeboronation of arylboronic acids with CuBr2 in water

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.

Electrocatalytic Deuteration of Halides with D2O as the Deuterium Source over a Copper Nanowire Arrays Cathode

Precise deuterium incorporation with controllable deuterated sites is extremely desirable. Here, a facile and efficient electrocatalytic deuterodehalogenation of halides using D2O as the deuteration reagent and copper nanowire arrays (Cu NWAs) electrochemically formed in situ as the cathode was demonstrated. A cross-coupling of carbon and deuterium free radicals might be involved for this ipso-selective deuteration. This method exhibited excellent chemoselectivity and high compatibility with the easily reducible functional groups (C=C, C≡C, C=O, C=N, C≡N). The C?H to C?D transformations were achieved with high yields and deuterium ratios through a one-pot halogenation–deuterodehalogenation process. Efficient deuteration of less-active bromide substrates, specific deuterium incorporation into top-selling pharmaceuticals, and oxidant-free paired anodic synthesis of high-value chemicals with low energy input highlighted the potential practicality.