5498-31-7

Usage

Uses

Used in Pharmaceutical Industry:
4-bromonaphthalen-2-ol is used as a reactant in the preparation of pyrazoles, which are inhibitors of the macrophage migration inhibitory factor (MIF). MIF is a key regulator of the immune system and has been implicated in various diseases, including autoimmune disorders, cancer, and inflammatory conditions. By inhibiting MIF, pyrazoles can potentially modulate the immune response and offer therapeutic benefits in treating these diseases.
In addition to its application in the pharmaceutical industry, 4-bromonaphthalen-2-ol may also find use in other areas, such as:
1. Chemical Synthesis:
As an intermediate in the synthesis of various organic compounds, including dyes, pigments, and other specialty chemicals.
2. Analytical Chemistry:
As a reference material or standard for the calibration of analytical instruments, such as gas chromatography and mass spectrometry, due to its well-defined chemical structure and properties.
3. Research and Development:
In academic and industrial research settings, 4-bromonaphthalen-2-ol can be used as a building block for the development of new compounds with potential applications in various fields, such as materials science, agrochemistry, and environmental science.

Synthetic route

4-bromo-1-diazonio-naphthalen-2-olate (33670-68-7) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0℃; for 3h;	98%
With sodium tetrahydroborate In ethanol at 0℃; for 3h;	98%
With ethanol; aluminium

5-bromonaphtho[1,2-d][1,2,3]oxadiazole → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Stage #1: 5-bromonaphtho[1,2-d][1,2,3]oxadiazole With sodium tetrahydroborate; ethanol for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In water for 1h;	78%
With sodium tetrahydroborate; ethanol for 12h; Inert atmosphere;	78%
Stage #1: 5-bromonaphtho[1,2-d][1,2,3]oxadiazole With sodium tetrahydroborate; ethanol for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In water for 1h;	78%
Stage #1: 5-bromonaphtho[1,2-d][1,2,3]oxadiazole With sodium tetrahydroborate; ethanol for 12h; Inert atmosphere; Stage #2: With hydrogenchloride; water for 1h;	78%
Stage #1: 5-bromonaphtho[1,2-d][1,2,3]oxadiazole With sodium tetrahydroborate In ethanol for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol; water for 1h; Inert atmosphere;	78%

4-bromo-2-hydroxynaphthalene-1-diazonium salt (53846-22-3) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 10℃;	75%

4-bromo-2-hydroxynaphthalene-1-diazonium bromide → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
With sodium tetrahydroborate; ethanol at 10 - 20℃; for 1.5h;	37%

4-bromonaphthalen-2-amine (74924-94-0) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
With sulfuric acid; Methamphetamin Diazotization.anschliessendes Erwaermen;
(i) NaNO2, (ii) aq. H2SO4; Multistep reaction;

4-bromo-2-nitro-1-naphthylamine (90767-01-4) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitrosylhydrogen sulfate 2: aluminium-powder; ethanol View Scheme
Multi-step reaction with 3 steps 1: (i) NaNO2, (ii) (deamination) 2: (reduction) 3: (i) NaNO2, (ii) aq. H2SO4 View Scheme

1-bromo-3-nitronaphthalene (7499-65-2) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: (reduction) 2: (i) NaNO2, (ii) aq. H2SO4 View Scheme

1-amino-naphthalene (134-32-7) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine; acetic acid / 1 h / 70 °C 2: acetic acid; propionic acid; sodium nitrite / 1 h / 5 - 8 °C 3: sodium tetrahydroborate / ethanol / 4 h / 13 - 18 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid; bromine / 0.33 h / 0 - 60 °C 2: acetic acid; sodium nitrite / propionic acid / 0.17 h / 0 °C 3: sodium tetrahydroborate / ethanol / 3 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: bromine; acetic acid / 1 h / 70 °C 2: propionic acid; acetic acid; sodium nitrite / 1 h / 5 - 8 °C 3: sodium tetrahydroborate; ethanol / 4 h / 13 - 18 °C View Scheme

2,4-dibromo-1-naphthylamine (20191-76-8) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; propionic acid; sodium nitrite / 1 h / 5 - 8 °C 2: sodium tetrahydroborate / ethanol / 4 h / 13 - 18 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; sodium nitrite / propionic acid / 0.17 h / 0 °C 2: sodium tetrahydroborate / ethanol / 3 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: propionic acid; acetic acid; sodium nitrite / 1 h / 5 - 8 °C 2: sodium tetrahydroborate; ethanol / 4 h / 13 - 18 °C View Scheme

6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine / ethanol / 16 h / 20 °C 2.1: acetic acid; palladium diacetate; N-Bromosuccinimide / 1 h / 80 °C 3.1: hydrogenchloride / 1,4-dioxane / 1 h / Reflux 4.1: sodium tetrahydroborate; ethanol / 16 h / 0 - 20 °C 5.1: toluene-4-sulfonic acid / toluene / 0.5 h / 0 °C / Reflux 5.2: 2 h / 40 °C 5.3: 16 h / 0 - 20 °C View Scheme

(N,6-dimethoxy-3,4-dihydro-2H-naphthalen-1-imine) (945830-92-2) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetic acid; palladium diacetate; N-Bromosuccinimide / 1 h / 80 °C 2.1: hydrogenchloride / 1,4-dioxane / 1 h / Reflux 3.1: sodium tetrahydroborate; ethanol / 16 h / 0 - 20 °C 4.1: toluene-4-sulfonic acid / toluene / 0.5 h / 0 °C / Reflux 4.2: 2 h / 40 °C 4.3: 16 h / 0 - 20 °C View Scheme

C12H14BrNO2 → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride / 1,4-dioxane / 1 h / Reflux 2.1: sodium tetrahydroborate; ethanol / 16 h / 0 - 20 °C 3.1: toluene-4-sulfonic acid / toluene / 0.5 h / 0 °C / Reflux 3.2: 2 h / 40 °C 3.3: 16 h / 0 - 20 °C View Scheme

C10H9BrO2 → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Stage #1: C10H9BrO2 With toluene-4-sulfonic acid In toluene at 0℃; for 0.5h; Reflux; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide In toluene at 40℃; for 2h; Stage #3: With boron tribromide In dichloromethane at 0 - 20℃; for 16h;

8-bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; ethanol / 16 h / 0 - 20 °C 2.1: toluene-4-sulfonic acid / toluene / 0.5 h / 0 °C / Reflux 2.2: 2 h / 40 °C 2.3: 16 h / 0 - 20 °C View Scheme

2,3-dibromonaphthalene-1-amine → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid; sodium nitrite; propionic acid / 0.5 h / 0 °C 2.1: sodium tetrahydroborate; ethanol / 12 h / Inert atmosphere 2.2: 1 h View Scheme
Multi-step reaction with 2 steps 1.1: acetic acid; sodium nitrite; propionic acid / 0.5 h / 0 °C 2.1: sodium tetrahydroborate; ethanol / 12 h / Inert atmosphere 2.2: 1 h View Scheme
Multi-step reaction with 2 steps 1.1: acetic acid; propionic acid / 0 °C 1.2: 0.5 h 2.1: sodium tetrahydroborate; ethanol / 12 h / Inert atmosphere 2.2: 1 h View Scheme

1-Nitronaphthalene (86-57-7) → 4-bromo-naphthalen-2-ol (5498-31-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylsilane; palladium dichloride / ethanol / 0.17 h / Inert atmosphere 2: bromine / acetic acid / 0.25 h / 0 - 60 °C 3: sodium nitrite; acetic acid; propionic acid / 0.17 h / 8 - 10 °C 4: sodium tetrahydroborate / ethanol / 0 - 10 °C View Scheme

4-bromo-naphthalen-2-ol (5498-31-7) → 4,4'-dibromo-[1,1'-binaphthalene]-2,2'-diol (178065-22-0, 178065-27-5, 178065-28-6)

Conditions	Yield
With di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride In dichloromethane at 20℃; for 16h;	100%
With oxygen In dichloromethane	90%
With N,N,N,N,-tetramethylethylenediamine; oxygen In dichloromethane at 25℃; for 4h;	90%

4-bromo-naphthalen-2-ol (5498-31-7) + methyl iodide (74-88-4) → 1-bromo-3-methoxy-naphthalene (5111-34-2)

Conditions	Yield
Stage #1: 4-bromo-naphthalen-2-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;	97%

triisopropylsilyl chloride (13154-24-0) + 4-bromo-naphthalen-2-ol (5498-31-7) → 4-Bromo-2-triisopropylsiloxynaphthalene (1186084-72-9)

Conditions	Yield
Stage #1: 4-bromo-naphthalen-2-ol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: triisopropylsilyl chloride In tetrahydrofuran at 0 - 20℃; for 2h;	96%

4-bromo-naphthalen-2-ol (5498-31-7) + benzyl bromide (100-39-0) → 3-(benzyloxy)-1-bromonaphthalene (611235-22-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 1h;	95%
With potassium carbonate In acetonitrile at 80℃; for 1h;	95%
Stage #1: 4-bromo-naphthalen-2-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 50℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide at 20℃; for 16h; Inert atmosphere;	93%

4-bromo-naphthalen-2-ol (5498-31-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (4-bromo-2-naphthyl)oxy-tert-butyldimethyl-silane

Conditions	Yield
With 1H-imidazole In dichloromethane at 25℃; for 1h;	90.7%

4-bromo-naphthalen-2-ol (5498-31-7) + diphenylamine (122-39-4) → 4-(diphenylamino)naphthalen-2-ol

Conditions	Yield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium t-butanolate In toluene for 4h; Inert atmosphere; Reflux;	89.5%

4-bromo-naphthalen-2-ol (5498-31-7) + Diphenylphosphinic chloride (1499-21-4) → diphenyl-phosphinic acid 4-bromo-naphthalen-2-yl ester (864423-16-5)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 18h;	88%

trifluoromethylsulfonic anhydride (358-23-6) + 4-bromo-naphthalen-2-ol (5498-31-7) → 4-bromonaphthalen-2-yl trifluoromethanesulfonate

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	86.7%
With pyridine In dichloromethane at 0 - 20℃;	86.7%
With pyridine In dichloromethane at 0 - 20℃;	86.7%
With pyridine In dichloromethane at 0 - 20℃;	86.7%

4-bromo-naphthalen-2-ol (5498-31-7) + (3-(chloro(3,5-dimethylphenyl)phosphoryl)-5-methylphenyl)methylium (137219-83-1) → C26H24BrO2P (1198163-29-9)

Conditions	Yield
With dmap; triethylamine In dichloromethane	85%

4-bromo-naphthalen-2-ol (5498-31-7) + 2-bromo-1-(triisopropylsilyloxy)ethane (425638-79-5) → [2-(4-bromonaphthalen-2-yloxy)ethoxy]triisopropylsilane (1191399-68-4)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 5h;	84%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N-methyl-acetamide

4-bromo-naphthalen-2-ol (5498-31-7) + acetyl chloride (75-36-5) → 1-(4-bromo-2-hydroxynapthalen-1-yl)ethanone (838855-57-5)

Conditions	Yield
With aluminum (III) chloride In dichloromethane for 2h; Heating / reflux;	83%

4-bromo-naphthalen-2-ol (5498-31-7) + chloromethyl methyl ether (107-30-2) → 1-bromo-3-(methoxymethoxy)naphthalene

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 14h;	81%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 14h;	81%
Stage #1: 4-bromo-naphthalen-2-ol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: chloromethyl methyl ether In tetrahydrofuran; mineral oil at 20℃; for 3h;	72%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	43%

4-bromo-naphthalen-2-ol (5498-31-7) → C10H6BrIO

Conditions	Yield
Stage #1: 4-bromo-naphthalen-2-ol With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: With iodine In tetrahydrofuran at 20℃;	75%

4-bromo-naphthalen-2-ol (5498-31-7) + phenylboronic acid (98-80-6) → 4-phenylnaphthalen-2-ol (36159-74-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 65℃; for 18h;	73%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 65℃; for 18h;	73%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 65℃; for 18h;	73%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 65℃; for 18h;	73%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 65℃; for 18h;	72%

2-pyrazylcarboxylic acid (98-97-5) + 4-bromo-naphthalen-2-ol (5498-31-7) → C15H9BrN2O2

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbamide; 4-<3-(dimethylamino)propyl>pyridine In tetrahydrofuran at 20℃; for 24h;	72%

4-bromo-naphthalen-2-ol (5498-31-7) + 2,4-diphenyl-6-(4-(4,4',5,5'-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine → C31H21N3O

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Inert atmosphere; Reflux;	71%

4-bromo-naphthalen-2-ol (5498-31-7) + 1,1-diphenyl-2-propyn-1-ol (3923-52-2) → 6-bromo-3,3-diphenyl-<3H>-naphtho<2,1-b>pyran (227471-77-4)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane Ambient temperature;	67%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 12h;	67%

4-bromo-naphthalen-2-ol (5498-31-7) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl)naphthalen-2-ol

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 5h; Inert atmosphere;	67%

4-bromo-naphthalen-2-ol (5498-31-7) + pivaloyl chloride (3282-30-2) → (4-bromo-2-naphthyl) 2,2-dimethylpropanoate

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.0166667h;	65.4%
With triethylamine In dichloromethane at 0℃; for 0.166667h;	65.4%
With triethylamine In dichloromethane at 0℃; for 0.166667h;	65.4%
With triethylamine In dichloromethane at 0℃; for 0.166667h;	64.4%

10-phenylanthracene-9-boronic acid + 4-bromo-naphthalen-2-ol (5498-31-7) → C30H20O

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene at 110℃;	64.7%

4-bromo-naphthalen-2-ol (5498-31-7) + 5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane (355408-55-8) → 4-(thien-2-yl)naphth-2-ol

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 20h;	54%

4-bromo-naphthalen-2-ol (5498-31-7) + 5,5-dimethyl-2-(2,2'-bithien-5-yl)[1,3,2]dioxoborinane (320381-92-8) → 4-(2,2'-bithien-5-yl)naphth-2-ol (583886-91-3)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 20h;	49%

4-bromo-naphthalen-2-ol (5498-31-7) + dimethyl sulfate (77-78-1) → 1-bromo-3-methoxy-naphthalene (5111-34-2)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 24h;	41%
With sodium hydroxide In water for 24h;	41%
With hydroxide

benzenediazonium (2684-02-8) + 4-bromo-naphthalen-2-ol (5498-31-7) → 4-bromo-1-phenylazo-[2]naphthol

p-nitrobenzenediazonium (14368-49-1) + 4-bromo-naphthalen-2-ol (5498-31-7) → 4-bromo-1-(4-nitro-phenylazo)-[2]naphthol

4-bromo-naphthalen-2-ol (5498-31-7) + 2-hydroxy-2-phenylacetophenone (119-53-9) → 5-bromo-1,2-diphenyl-naphtho[2,1-b]furan (873965-31-2)

Conditions	Yield
With sulfuric acid

Upstream product

• 86-57-7 1-Nitronaphthalene 
• 53846-22-3 4-bromo-2-hydroxynaphthalene-1-diazonium salt 
• 172943-00-9 5-bromonaphtho[1,2-d][1,2,3]oxadiazole 
• 945830-92-2 (N,6-dimethoxy-3,4-dihydro-2H-naphthalen-1-imine) 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 20191-76-8 2,4-dibromo-1-naphthylamine 
• 134-32-7 1-amino-naphthalene 
• 7499-65-2 4-bromo-2-nitronaphthalene 
• 90767-01-4 4-bromo-2-nitro-1-naphthylamine 
• 74924-94-0 4-bromonaphthalene-2-amine 
• 33670-68-7 4-bromo-1-diazonio-naphthalen-2-olate 

Downstream Products

• 873965-31-2 5-bromo-1,2-diphenyl-naphtho[2,1-b]furan 
• 227471-77-4 6-bromo-3,3-diphenyl-<3H>-naphtho<2,1-b>pyran 
• 864423-16-5 diphenyl-phosphinic acid 4-bromo-naphthalen-2-yl ester 
• 611235-22-4 3-(benzyloxy)-1-bromonaphthalene 
• 2374831-10-2 ethyl 3-(3-methoxy-1-naphthylamino)benzoate 

Relevant academic research and scientific papers

Kras-G12C inhibitor heterocyclic compounds

The invention relates to Kras-G12C inhibitor heterocyclic compounds represented by formula I, a preparation method thereof, and application of the Kras-G12C inhibitor heterocyclic compounds in prevention and treatment of tumor diseases such as lung cancer, colorectal cancer and pancreatic cancer. In the preparation process, the compounds of the general formula I are obtained through a series of reactions such as SN2 reaction, protection, coupling reaction, deprotection, condensation reaction and the like.

KRAS G12C INHIBITORS

The present invention relates to compounds that, inhibit KRas G12C, In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.

KRAS G12C INHIBITORS

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Anthracene derivatives compounds and organic electroluminescent devices comprising the same

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Discovery of Novel Naphthylphenylketone and Naphthylphenylamine Derivatives as Cell Division Cycle 25B (CDC25B) Phosphatase Inhibitors: Design, Synthesis, Inhibition Mechanism, and in Vitro Efficacy against Melanoma Cell Lines

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Antracene derivatives having heteroaryl substituted naphthyl group and organic light-emitting diode including the same

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Asymmetric antracene derivatives having two naphthyl groups and organic light-emitting diode including the same

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Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion

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PYRAZOLE-CONTAINING MACROPHAGE MIGRATION INHIBITORY FACTOR INHIBITORS

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