5773-80-8

Basic information

• Product Name: 6-Bromo-2-naphthoic acid
• Synonyms: 6-BROMO-2-NAPHTHALENE CARBOXYLIC ACID;6-BROMO-2-NAPHTHOIC ACID;6-BROMO-2-NAPHTHOLIC ACID;6-Bromo-2-naphtalenecarboxylicacid;6-BROMO-2-NAPHTHOLIC AICD;6-Bromo-2-naphthoicacid,96%;6-Bromonaphthalene-2-carboxylic acid;6-BROMO-2-NAPHTHOIC ACID 99%
• CAS NO: 5773-80-8
• Molecular Formula: C₁₁H₇BrO₂
• Molecular Weight: 251.08
• EINECS: 1308068-626-2
• Product Categories: blocks;Bromides;Carboxes;Naphthalene derivatives;Organic acids;Naphthalene series
• Mol File: 5773-80-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 294-295°C
• Boiling Point: 387.3 °C at 760 mmHg
• Flash Point: 188 °C
• Appearance: pale brown solid
• Density: 1.648 g/cm³
• Vapor Pressure: 1.08E-06mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.06±0.30(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 2328940
• CAS DataBase Reference: 6-Bromo-2-naphthoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2-naphthoic acid(5773-80-8)
• EPA Substance Registry System: 6-Bromo-2-naphthoic acid(5773-80-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36
• Hazardous Substances Data: 5773-80-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale brown solid

Uses

Benzimidazole derivatives has been prepared by using ortho-phenyl diamine and 6-bromo-2-naphthoic acid.

InChI:InChI=1/C11H7BrO2/c12-10-4-3-7-5-9(11(13)14)2-1-8(7)6-10/h1-6H,(H,13,14)

Synthetic route

methyl 6-bromo-2-naphthoate (33626-98-1) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
With water; lithium hydroxide In tetrahydrofuran at 20℃; for 5h;	96%
With lithium hydroxide In tetrahydrofuran; water at 20℃; for 5h;	96%
Stage #1: methyl 6-bromo-2-naphthoate With lithium hydroxide monohydrate In tetrahydrofuran; water Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=3;	92%

6-bromo-naphthalen-2-ol (15231-91-1) + acetic acid (64-19-7) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
for 1.5h; Large scale;	96%

Sodium; 6-bromo-naphthalene-2-carboxylate → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
With hydrogenchloride In water at 50℃; for 1h; Concentration; Inert atmosphere;	95.5%

methyl 6-bromo-2-naphthoate (33626-98-1) → 2-Naphthalenemethanol (1592-38-7) + 6-bromo-2-naphthoic acid (5773-80-8) + (6-bromo-2-naphthy)methanol (100751-63-1)

Conditions	Yield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium tert-butylate; hydrogen In 2-methyltetrahydrofuran at 45℃; under 3000.3 Torr; for 4h; Catalytic behavior; Pressure; Temperature; Autoclave;	A n/a B n/a C 82%

1-(6-bromonaphthalen-2-yl)ethanone (1590-25-6) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
With sodium hypochlorite; sodium hydroxide In 1,4-dioxane; water at 70℃; for 4h;	70%
With sodium hydroxide; sodium hypochlorite In 1,4-dioxane; water	3.54 g (88%)
With sodium hydroxide; sodium hypochlorite In 1,4-dioxane; sulfuric acid; water	3.54 g (88%)

carbon dioxide (124-38-9) + 6-bromo-2-naphthalenyl trifluoromethanesulfonate (151600-02-1) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine; DavePhos In dimethyl sulfoxide at 20℃; for 36h; Irradiation; Green chemistry; chemoselective reaction;	65%

1-(6-bromonaphthalen-2-yl)ethanone (1590-25-6) → 6-bromo-2-naphthoic acid (5773-80-8) + 1,1-bis(pyridinium)methane diiodide (32405-50-8)

Conditions	Yield
With pyridine; water; iodine In methanol at 30℃; Kinetics; Mechanism; Thermodynamic data; other temperatures; ΔH(excit.);

1-<6-bromo-naphthyl-(2)>-ethanone-(1) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
With alkaline aqueous sodium hypochlorite solution
With nitric acid

6-bromo-naphthonitrile-(2) → 6-bromo-2-naphthoic acid (5773-80-8)

2-bromonaphthalene (580-13-2) + 1-(6-bromonaphthalen-2-yl)ethanone (1590-25-6) + acetyl chloride (75-36-5) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
With hydrogenchloride; AlCl3 In hexane; nitrobenzene

sodium metabisulfite + 1-(6-bromonaphthalen-2-yl)ethanone (1590-25-6) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
With sodium hydroxide; sodium hypochlorite In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water

2-bromo-6-methylnaphthalene (37796-78-4) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate; acetic anhydride; acetic acid; potassium bromide at 110℃; for 4.5h; Concentration; Reagent/catalyst; Time; Temperature; Pressure;	8.29 g

β-naphthol (135-19-3) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: iron(II) bromide; acetic acid; dihydrogen peroxide / water / 8 h / 87 °C / 760.05 Torr / Large scale 2: / 0.58 h / 87 °C / 760.05 Torr / Inert atmosphere; Large scale 3: 1.5 h / Large scale View Scheme

2-bromonaphthalene (580-13-2) → 6-bromo-2-naphthoic acid (5773-80-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / nitrobenzene / 4 h / 100 °C 2: sodium hypochlorite; sodium hydroxide / water; 1,4-dioxane / 4 h / 70 °C View Scheme

6-bromo-2-naphthoic acid (5773-80-8) → 6-bromonaphthalene-2-carbonyl chloride (87700-60-5)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 3h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 18h;

6-bromo-2-naphthoic acid (5773-80-8) → 6-Bromonaphthalen-2-amine (7499-66-3)

Conditions	Yield
Stage #1: 6-bromo-2-naphthoic acid With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: With water In N,N-dimethyl-formamide at 100℃; for 1h;	100%
Stage #1: 6-bromo-2-naphthoic acid With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: With water In N,N-dimethyl-formamide at 100℃; for 1h;	100%
Stage #1: 6-bromo-2-naphthoic acid With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: With water In N,N-dimethyl-formamide at 100℃; for 1h;	100%

methanol (67-56-1) + 6-bromo-2-naphthoic acid (5773-80-8) → methyl 6-bromo-2-naphthoate (33626-98-1)

Conditions	Yield
With sulfuric acid; trimethyl orthoformate for 48h; Reflux;	100%
With sulfuric acid for 36h; Reflux;	100%
With sulfuric acid Reflux;	100%

4-aminotetrahydropyran (38041-19-9) + 6-bromo-2-naphthoic acid (5773-80-8) → 6-bromonaphthalene-2-carboxylic acid (tetrahydropyran-4-yl)amide (1350411-39-0)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice;	100%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 16h; Cooling with ice;	100%

Chloro-oxo-acetic acid (4732-69-8) + 6-bromo-2-naphthoic acid (5773-80-8) → 6-bromonaphthalene-2-carbonyl chloride (87700-60-5)

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide	100%

3-(1-adamantyl)-4-methoxyphenylboronic acid (459423-32-6) + 6-bromo-2-naphthoic acid (5773-80-8) → adapalene (106685-40-9)

Conditions	Yield
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium carbonate; palladium 10% on activated carbon In tetrahydrofuran; water for 8h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran for 1h; Product distribution / selectivity;	99%
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium hydroxide; 5%-palladium/activated carbon In tetrahydrofuran; water at 55℃; for 2h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃; pH=6 - 7; Product distribution / selectivity;	99%
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium carbonate; palladium diacetate; CyJohnPhos In tetrahydrofuran; water for 2 - 4h; Suzuki Coupling; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran for 1h; Product distribution / selectivity;	94.8%

6-bromo-2-naphthoic acid (5773-80-8) → naphthalene-2-carboxylate (93-09-4)

Conditions	Yield
With palladium 10% on activated carbon; potassium acetate; bis(pinacol)diborane In ethanol at 60℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;	98.8%

6-bromo-2-naphthoic acid (5773-80-8) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 6-bromo-N-methoxy-N-methyl-2-naphthamide (861880-64-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 12.25h;	98%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h;	90%

6-bromo-2-naphthoic acid (5773-80-8) + ethyl iodide (75-03-6) → ethyl 6-bromo-naphthalene-2-carboxylate (86471-14-9)

Conditions	Yield
With caesium carbonate In ethyl acetate; acetonitrile	97%

6-bromo-2-naphthoic acid (5773-80-8) → 6-bromo-naphthalene-2-carboxylic acid amide (1255871-55-6)

Conditions	Yield
Stage #1: 6-bromo-2-naphthoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With ammonium hydroxide In tetrahydrofuran at -10 - 20℃;	96%
Multi-step reaction with 2 steps 1: thionyl chloride / 16 h / 70 °C 2: ammonia / dichloromethane; methanol / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 16 h / 70 °C 2: ammonia / methanol / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride; triethylamine / 1 h / Reflux 2: ammonium hydroxide / water; dichloromethane / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere 2: ammonium hydroxide / water / 0.5 h / 0 - 20 °C View Scheme

6-bromo-2-naphthoic acid (5773-80-8) + 4-methoxyphenylboronic acid (5720-07-0) → 6-(4-methoxyphenyl)-2-naphthoic acid

Conditions	Yield
With palladium 10% on activated carbon; sodium carbonate In methanol; water at 78℃; Suzuki coupling; Inert atmosphere;	94%

rac-(2-ethynylcyclopropyl)methanol + 6-bromo-2-naphthoic acid (5773-80-8) → 6-(((trans)-2-(hydroxymethyl)cyclopropyl)ethynyl)-2-naphthoic acid

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran for 168h; Inert atmosphere;	94%

6-bromo-2-naphthoic acid (5773-80-8) → 6-chloronaphthalene-2-carboxylic acid (5042-97-7)

Conditions	Yield
With copper(l) iodide; copper(l) chloride In N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;	93%
With copper(l) iodide; copper(l) chloride In N,N-dimethyl-formamide for 4h; Inert atmosphere; Darkness; Reflux;	93%
With copper(l) iodide; copper(l) chloride In N,N-dimethyl-formamide for 4h; Reflux; Inert atmosphere; Darkness;	93%

6-bromo-2-naphthoic acid (5773-80-8) + tert-butyl alcohol (75-65-0) → 6-bromo-2-N-tert-butoxycarbonylaminonaphthalene (869114-68-1)

Conditions	Yield
With diphenylphosphoranyl azide; triethylamine In toluene at 100℃; for 4h;	93%
With diphenyl phosphoryl azide; triethylamine at 100℃;	85%
With diphenyl phosphoryl azide; triethylamine at 80℃; for 16h;

6-bromo-2-naphthoic acid (5773-80-8) + 3-adamantyl-4-methoxyphenyltriethoxysilane → adapalene (106685-40-9)

Conditions	Yield
With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Inert atmosphere;	93%

6-bromo-2-naphthoic acid (5773-80-8) → 6-bromo-2-aminonaphthalene hydrochloride (71590-31-3)

Conditions	Yield
Stage #1: 6-bromo-2-naphthoic acid With diphenyl phosphoryl azide; triethylamine In tert-butyl alcohol for 15h; Reflux; Stage #2: With hydrogenchloride In methanol at -78 - 20℃; for 15h;	91%
Stage #1: 6-bromo-2-naphthoic acid With diphenyl phosphoryl azide; triethylamine In tert-butyl alcohol for 15h; Reflux; Stage #2: With sodium hydrogencarbonate In tert-butyl methyl ether for 0.5h; Stage #3: With hydrogenchloride In methanol at -78 - 20℃; for 15h;	91%
Stage #1: 6-bromo-2-naphthoic acid With diphenyl phosphoryl azide; triethylamine In tert-butyl alcohol for 15h; Reflux; Stage #2: With hydrogenchloride In methanol at -78℃; for 15h;

6-bromo-2-naphthoic acid (5773-80-8) + trimethylaluminum (75-24-1) → 6-bromo-3-methyl-2-naphthoic acid

Conditions	Yield
Stage #1: 6-bromo-2-naphthoic acid; trimethylaluminum With iron(III)-acetylacetonate; 4-(bis(2-(diphenylphosphanyl)phenyl)phosphanyl)-N,N-dimethylaniline In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 20℃; Inert atmosphere; Schlenk technique; Stage #2: With 2,3-dichlorobutane In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;	91%

ethanol (64-17-5) + 6-bromo-2-naphthoic acid (5773-80-8) → ethyl 6-bromo-naphthalene-2-carboxylate (86471-14-9)

Conditions	Yield
With sulfuric acid at 90℃; for 16h;	91%

6-bromo-2-naphthoic acid (5773-80-8) → (6-bromo-2-naphthy)methanol (100751-63-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating;	90%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃;	89%
With borane-THF In tetrahydrofuran at 0 - 25℃;	85%

6-bromo-2-naphthoic acid (5773-80-8) + methylamine (74-89-5) → 6-bromo-N-methyl-2-naphthamide (426219-35-4)

Conditions	Yield
Stage #1: 6-bromo-2-naphthoic acid With thionyl chloride; N,N-dimethyl-formamide In toluene at 45 - 50℃; for 1h; Stage #2: methylamine With triethylamine In methanol; toluene at 10 - 25℃; for 1h;	89%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 18h; Inert atmosphere;	82%
Stage #1: 6-bromo-2-naphthoic acid With thionyl chloride In DMF (N,N-dimethyl-formamide); ethyl acetate at 30 - 65℃; for 0.5h; Stage #2: methylamine With triethylamine In methanol; DMF (N,N-dimethyl-formamide); water; ethyl acetate at 25℃; for 3h;	80%

6-bromo-2-naphthoic acid (5773-80-8) + N-Boc-1,3-diaminopropane (75178-96-0) → tert-butyl 3-(6-bromo-2-naphthamido)propylcarbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h;	85%

6-bromo-2-naphthoic acid (5773-80-8) + (trifluoromethyl)trimethylsilane (81290-20-2) → 1-(6-bromonaphthalen-2-yl)-2,2,2-trifluoroethan-1-one

Conditions	Yield
With dmap; cesium fluoride; trifluoroacetic anhydride at 120℃; for 15h; Schlenk technique; Inert atmosphere;	84%

N-(2-phenylquinazolin-4-yl)-benzene-1,4-diamine + 6-bromo-2-naphthoic acid (5773-80-8) → 6-bromo-N-(3-((2-phenylquinazolin-4-yl)amino)phenyl)-2-naphthamide

Conditions	Yield
Stage #1: 6-bromo-2-naphthoic acid With HATU In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: N-(2-phenylquinazolin-4-yl)-benzene-1,4-diamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.333333h; Inert atmosphere;	81%

6-bromo-2-naphthoic acid (5773-80-8) + bis(pinacol)diborane (73183-34-3) → 6-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-naphthalen-2-carboxylic acid (1426082-97-4)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃;	80%

6-bromo-2-naphthoic acid (5773-80-8) + N-phenyl-1,2-benzenediamine (534-85-0) → 2-(6-bromonaphthalen-2-yl)-1-phenyl-1H-benzimidazole (935472-87-0)

Conditions	Yield
Stage #1: 6-bromo-2-naphthoic acid With thionyl chloride; N,N-dimethyl-formamide for 4h; Heating; Stage #2: N-phenyl-1,2-benzenediamine In 1-methyl-pyrrolidin-2-one at 160℃; for 12h;	78%
Stage #1: 6-bromo-2-naphthoic acid With thionyl chloride In N,N-dimethyl-formamide for 4h; Reflux; Stage #2: N-phenyl-1,2-benzenediamine In 1-Methylpyrrolidine; N,N-dimethyl-formamide at 160℃; for 12h;	78%
Stage #1: 6-bromo-2-naphthoic acid With thionyl chloride; N,N-dimethyl-formamide for 4h; Heating; Stage #2: N-phenyl-1,2-benzenediamine In 1-methyl-pyrrolidin-2-one at 160℃; for 12h;	78%

Upstream product

• 580-13-2 2-bromonaphthalene 
• 1590-25-6 1-(6-bromonaphthalen-2-yl)ethanone 
• 75-36-5 acetyl chloride 
• 135-19-3 β-naphthol 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 64-19-7 acetic acid 
• 33626-98-1 methyl 6-bromo-2-naphthoate 
• 124-38-9 carbon dioxide 
• 151600-02-1 6-bromo-2-naphthalenyl trifluoromethanesulfonate 
• 37796-78-4 2-bromo-6-methylnaphthalene 

Downstream Products

• 100751-63-1 (6-bromo-2-naphthy)methanol 
• 33626-98-1 methyl 6-bromo-2-naphthoate 
• 91065-17-7 6-bromo-naphthalene-2-carbonitrile 
• 1255871-55-6 6-bromonaphthalene-2-carboxamide 
• 1255871-58-9 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthonitrile 
• 1256387-44-6 1-(6-bromo-naphthalen-2-yl)-2-diazo-ethanone 
• 87700-60-5 6-bromonaphthalene-2-carbonyl chloride 
• 1609552-91-1 6-bromonaphthalene-2-carboxylic acid benzyloxyamide 
• 1609552-93-3 C₃₄H₃₃NO₃ 
• 935472-87-0 2-(6-bromonaphthalen-2-yl)-1-phenyl-1H-benzimidazole 
• 736989-93-8 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-2-carboxylic acid methyl ester 
• 940968-13-8 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-6-yl)-1-phenyl-1H-benzo[d]imidazole 
• 259199-34-3 6-[2-(4-methoxy-phenyl)-vinyl]-naphthalene-2-carbonitrile 

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