116230-30-9

Basic information

• Product Name: 2-Bromo-7-hydroxynaphthalene
• Synonyms: 2-BROMO-7-HYDROXYNAPHTHALENE;7-BROMONAPHTHALEN-2-OL;7-Bromonaphthalene-2-ol;7-Bromo-2-naphthol;2-Bomo-7-Hydroxynaphthalene;2-Naphthalenol,7-broMo-;2-hydroxy-7-BROMONAPHTHALENE;BroMonaphthalen-2-ol
• CAS NO: 116230-30-9
• Molecular Formula: C₁₀H₇BrO
• Molecular Weight: 223.07
• EINECS: 1312995-182-4
• Product Categories: Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 116230-30-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 133-138 °C
• Boiling Point: 353.8 °C at 760 mmHg
• Flash Point: 167.8 °C
• Appearance: /
• Density: 1.614 g/cm³
• Vapor Pressure: 1.71E-05mmHg at 25°C
• Refractive Index: 1.704
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.17±0.40(Predicted)
• CAS DataBase Reference: 2-Bromo-7-hydroxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-7-hydroxynaphthalene(116230-30-9)
• EPA Substance Registry System: 2-Bromo-7-hydroxynaphthalene(116230-30-9)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 116230-30-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C10H7BrO/c11-9-3-1-7-2-4-10(12)6-8(7)5-9/h1-6,12H

Synthetic route

2,7-Dihydroxynaphthalene (582-17-2) → 7-bromonaphthalen-2-ol (116230-30-9)

Conditions	Yield
With bromine; triphenylphosphine In acetonitrile at 70 - 250℃; for 1.25h;	84%
With bromine; triphenylphosphine In acetonitrile at 0 - 250℃; for 1.5h;	84%
With bromine; triphenylphosphine In acetonitrile at 70℃; for 1h; Schlenk technique;	66%

7-methoxy-2-naphthol (5060-82-2) → 7-bromonaphthalen-2-ol (116230-30-9)

Conditions	Yield
Stage #1: 7-methoxy-2-naphthol With bromine; triphenylphosphine In acetonitrile for 2h; Reflux; Stage #2: at 250℃; Sealed tube;	19%

3,7-dibromo-[2]naphthol (709667-62-9) → 7-bromonaphthalen-2-ol (116230-30-9)

Conditions	Yield
With sodium amalgam

7-Hydrazino-[2]naphthol (861072-57-3) → 7-bromonaphthalen-2-ol (116230-30-9)

Conditions	Yield
With hydrogen bromide; copper(ll) bromide

7-Hydrazino-[2]naphthol (861072-57-3) + diluted hydrobromic acid + copper (II)-bromide → 7-bromonaphthalen-2-ol (116230-30-9)

3,7-dibromo-[2]naphthol (709667-62-9) + sodium amalgam → 7-bromonaphthalen-2-ol (116230-30-9)

7-bromonaphthalen-2-ol (116230-30-9) → C10H6Br2O

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20℃; for 3h;	100%
With pyridinium perbromide hydrobromide In acetonitrile at 0℃;

7-bromonaphthalen-2-ol (116230-30-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-bromo-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthalene (1314130-89-6)

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 0.5h;	99%
With 1H-imidazole In dichloromethane at 20℃; for 4h;	88%
With 1H-imidazole In dichloromethane at 0 - 20℃;
With 1H-imidazole In dichloromethane at 0 - 20℃;

7-bromonaphthalen-2-ol (116230-30-9) + methylmagnesium bromide (75-16-1) → 7-methylnaphthalen-2-ol (26593-50-0)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 90℃; Inert atmosphere;	99%

(E)-2-oxo-3-(2,2,2-trifluoroethylidene)indoline-1-carboxylic acid tert-butyl ester + 7-bromonaphthalen-2-ol (116230-30-9) → tert-butyl (2-((1S,2R)-9-bromo-3-oxo-1-(trifluoromethyl)-2,3-dihydro-1H-benzo[f]chromen-2-yl)phenyl)carbamate

Conditions	Yield
With C33H36N4O5 In dichloromethane at -30℃; for 18h; Molecular sieve; stereoselective reaction;	98%

7-bromonaphthalen-2-ol (116230-30-9) + N,N-diethylcarbamyl chloride (88-10-8) → 7-bromonaphthalen-2-yl diethylcarbamate

Conditions	Yield
Stage #1: 7-bromonaphthalen-2-ol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 0.166667h; Stage #2: N,N-diethylcarbamyl chloride With dmap In 1,2-dimethoxyethane; mineral oil at 20℃; for 2h;	98%

7-bromonaphthalen-2-ol (116230-30-9) + dimethyl sulfate (77-78-1) → 2-bromo-7-methoxy-naphthalene

Conditions	Yield
With sodium hydroxide In water at 20℃; for 24h;	98%

7-bromonaphthalen-2-ol (116230-30-9) → (rac)‐7,7'‐dibromo‐[1,1'‐binaphthalene]‐2,2'‐diol (196081-12-6, 196406-40-3, 196406-43-6)

Conditions	Yield
With iron(III) chloride In water at 100℃; for 3h;	97%
With air In dichloromethane for 12h;	96%
With tert-butylamine; copper dichloride In methanol at 20℃; for 24h; Dimerization; Oxidation;	94%

(Z)-2-bromo-2-nitro-1-phenylethene (18315-81-6) + 7-bromonaphthalen-2-ol (116230-30-9) → 8-bromo-2-nitro-1-phenyl-1,2-dihydronaphtho[2,1-b]furan

Conditions	Yield
With potassium carbonate In water at 5℃; for 72h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	97%

7-bromonaphthalen-2-ol (116230-30-9) + N-(4-(1-hydroxy-1,3-diphenylprop-2-yn-1-yl)phenyl)pivalamide → C36H30BrNO2

Conditions	Yield
With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at 20℃; for 3h;	97%

7-bromonaphthalen-2-ol (116230-30-9) + methyl iodide (74-88-4) → 2-bromo-7-methoxy-naphthalene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 72h;	96%
Stage #1: 7-bromonaphthalen-2-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; Cooling with ice;	95.4%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	95%

7-bromonaphthalen-2-ol (116230-30-9) + isopropyl magnesium halide → 7-isopropylnaphthalen-2-ol (760179-65-5)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran at 0℃; for 3h; Kumada Cross-Coupling; Reflux;	96%

7-bromonaphthalen-2-ol (116230-30-9) → 6-bromo-1,1-difluoro-2(1H)-naphthalenone (382136-90-5)

Conditions	Yield
With 1-Chloromethyl-4-methyl-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) In acetonitrile at 20℃; for 72h;	96%

C12H9BrN2O2 + 7-bromonaphthalen-2-ol (116230-30-9) → C22H16Br2N2O3

Conditions	Yield
With nickel(II) triflate; C43H46N2O2; sodium hydrogencarbonate In chloroform at 15℃; for 6h; Green chemistry; enantioselective reaction;	96%

1-Naphthylboronic acid (13922-41-3) + 7-bromonaphthalen-2-ol (116230-30-9) → [1,2'-binaphthalen]-7'-ol

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 6h; Reflux;	96%

2-phenyl-3-(phenyl(tosyl)methyl)-1H-indole (1099592-76-3) + 7-bromonaphthalen-2-ol (116230-30-9) → C31H22BrNO (1443383-19-4)

Conditions	Yield
With potassium phosphate; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)thiourea In toluene at 30℃; for 24h; Michael Addition; enantioselective reaction;	95%

1,1-Diphenylmethanol (91-01-0) + 7-bromonaphthalen-2-ol (116230-30-9) → 1-benzhydryl-7-bromonaphthalen-2-ol

Conditions	Yield
With phosphomolybdic acid In acetonitrile at 20℃; for 0.5h;	95%
With stannic bromide In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation; Inert atmosphere;	90%

7-bromonaphthalen-2-ol (116230-30-9) + o-hydroxy-α-(p-anisyl)benzyl alcohol (340732-72-1) → (R)-7-bromo-1-((2-hydroxyphenyl)(4-methoxyphenyl)methyl)naphthalen-2-ol

Conditions	Yield
With C45H47O3P In dichloromethane at 20℃; Friedel-Crafts Alkylation; Inert atmosphere; enantioselective reaction;	94%

4-methoxyphenylboronic acid (5720-07-0) + 7-bromonaphthalen-2-ol (116230-30-9) → 7-(4-methoxyphenyl)naphthalen-2-ol

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 6h; Reflux;	94%

7-bromonaphthalen-2-ol (116230-30-9) + 2-chloro-benzaldehyde (89-98-5) + malononitrile (109-77-3) → 3-amino-9-bromo-1-(2-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	94%

2-chlorocyclopentanone (694-28-0) + 7-bromonaphthalen-2-ol (116230-30-9) → 2-bromo-8,9,10,10a-tetrahydro-7aH-cyclopenta[b]naphtha[1,2-d]furan-7a-ol (1574664-87-1)

Conditions	Yield
With sodium carbonate In 2,2,2-trifluoroethanol at 20℃; chemoselective reaction;	93%

C22H22O3 + 7-bromonaphthalen-2-ol (116230-30-9) → 7-bromo-1-[(R)-{2-[(S)-2-methoxy-1-phenylethoxy]phenyl}-(phenyl)methyl]naphthalen-2-ol

Conditions	Yield
With stannic bromide In nitromethane at 20℃; for 2h; Friedel-Crafts Alkylation; Inert atmosphere; diastereoselective reaction;	93%

4,4'-dichlorobenzophenone (90-97-1) + 7-bromonaphthalen-2-ol (116230-30-9) → C23H15BrCl2O

Conditions	Yield
With phosphomolybdic acid In acetonitrile at 20℃; for 0.5h;	93%

7-bromonaphthalen-2-ol (116230-30-9) + 4-chlorobenzaldehyde (104-88-1) + malononitrile (109-77-3) → 3-amino-9-bromo-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	93%

trifluoromethylsulfonic anhydride (358-23-6) + 1,1'-sulfinylbisbenzene (945-51-7) + 7-bromonaphthalen-2-ol (116230-30-9) → C22H16BrOS(1+)*CF3O3S(1-)

Conditions	Yield
In acetonitrile at 0℃; for 3h; Green chemistry;	92%

7-bromonaphthalen-2-ol (116230-30-9) + 4-bromo-benzaldehyde (1122-91-4) + malononitrile (109-77-3) → 3-amino-9-bromo-1-(4-bromophenyl)-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	92%

C27H22N2O2S (1443382-87-3) + 7-bromonaphthalen-2-ol (116230-30-9) → C30H21BrN2O (1443383-32-1)

Conditions	Yield
With potassium phosphate; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)thiourea In toluene at 30℃; for 24h; Michael Addition; enantioselective reaction;	91%

2-methylbenzhydrol (5472-13-9) + 7-bromonaphthalen-2-ol (116230-30-9) → C24H19BrO

Conditions	Yield
With phosphomolybdic acid In acetonitrile at 20℃; for 0.5h;	91%

7-bromonaphthalen-2-ol (116230-30-9) + benzo[b]thiophen-3-yl-3-boronic acid (113893-08-6) → 7-(benzo[b]thiophen-3-yl)naphthalen-2-ol

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 6h; Reflux;	91%

7-bromonaphthalen-2-ol (116230-30-9) + 4-fluorobenzaldehyde (459-57-4) + malononitrile (109-77-3) → 3-amino-9-bromo-1-(4-fluorophenyl)-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	91%

7-bromonaphthalen-2-ol (116230-30-9) + 3-Chlorobenzaldehyde (587-04-2) + malononitrile (109-77-3) → 3-amino-9-bromo-1-(3-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile

Conditions	Yield
With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	91%

Upstream product

• 5060-82-2 7-methoxy-2-naphthol 
• 861072-57-3 7-Hydrazino-[2]naphthol 
• 709667-62-9 3,7-dibromo-[2]naphthol 
• 582-17-2 2,7-Dihydroxynaphthalene 

Downstream Products

• 221018-05-9 7-phenylnaphthalen-2-ol 
• 2848-16-0 diphenyldiboronic acid 
• 1426082-25-8 C₂₈H₂₆N₄O₂ 
• 1574190-63-8 8-bromo-2-hydroxy-2-phenylnaphtho[2,1-b]furan-1(2H)-one 
• 1544009-73-5 8-chloro-7-((cis-4-(trifluoromethyl)cyclohexyl)oxy)-2-naphthaldehyde 
• 1544009-72-4 7-((cis-4-(trifluoromethyl)cyclohexyl)oxy)-2-naphthaldehyde 
• 1544010-13-0 ethyl 1-((8-chloro-7-((cis-4-ethylcyclohexyl)oxy)naphthalen-2-yl)methyl)piperidine-4-carboxylate 
• 1544010-10-7 8-chloro-7-((cis-4-ethylcyclohexyl)oxy)-2-naphthaldehyde 
• 1544010-07-2 7-((cis-4-ethylcyclohexyl)oxy)-2-naphthaldehyde 
• 1544009-98-4 8-iodo-7-((cis-4-(trifluoromethyl)cyclohexyl)oxy)-2-naphthaldehyde 
• 1544009-89-3 7-bromo-1-(difluoromethyl)-2-((cis-4-(trifluoromethyl)cyclohexyl)oxy)naphthalene 
• 1544009-84-8 7-bromo-2-((cis-4-(trifluoromethyl)cyclohexyl)oxy)-1-naphthaldehyde 
• 1543999-84-3 4-[7-(cis-4-methylcyclohexyloxy)-8-trifluoromethyl-naphthalen-2-ylmethyl]morpholine 

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