33626-98-1

Basic information

• Product Name: Methyl 6-bromo-2-naphthoate
• Synonyms: 6-BROMO-2-NAPHTHALENECARBOXYLIC ACID METHYL ESTER;6-BROMO-2-NAPHTHOIC ACID METHYL ESTER;METHYL 6-BROMO-2-NAPHTHALENECARBOXYLATE;METHYL 6-BROMO-2-NAPHTHOATE;6-Bromo-2-Naphtoic Acid Methyl Ester;2-Bromo-6-naphthoic acid methylester;Methyl-6-bromo-2-naphtoate;6-BROMO-2-NAPHTHOIC AICD
• CAS NO: 33626-98-1
• Molecular Formula: C₁₂H₉BrO₂
• Molecular Weight: 265.1
• EINECS: -0
• Product Categories: blocks;Bromides;Carboxes;Aromatic Esters;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;ADAPALENE;Intermediates of Adapalene;C12 to C63;Carbonyl Compounds;Esters;API;Others chemical reagents;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Naphthalene series
• Mol File: 33626-98-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 123-126 °C(lit.)
• Boiling Point: 357 °C at 760 mmHg
• Flash Point: 169.7 °C
• Appearance: Off-white to cream or light brown/Crystalline Powder
• Density: 1.492 g/cm³
• Vapor Pressure: 2.81E-05mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• BRN: 2578943
• CAS DataBase Reference: Methyl 6-bromo-2-naphthoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 6-bromo-2-naphthoate(33626-98-1)
• EPA Substance Registry System: Methyl 6-bromo-2-naphthoate(33626-98-1)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 24/25-45-36/37/39-27-26
• WGK Germany: 3
• Hazardous Substances Data: 33626-98-1(Hazardous Substances Data)

Usage

Description

Methyl 6-bromo-2-naphthoate is an organic compound that serves as an important intermediate in the synthesis of various retinoids, specifically Adapalene, which targets RARβ and RARγ receptors. It is characterized by its pale yellow or light brown powder appearance and undergoes an aromatic Finkelstein reaction followed by hydrolysis to produce 6-iodo-2-naphthoic acid.

Uses

Used in Pharmaceutical Industry:
Methyl 6-bromo-2-naphthoate is used as a key intermediate in the synthesis of Adapalene, a retinoid specific for RARβ and RARγ receptors, for the treatment of acne and other skin conditions. Its role in the synthesis process is crucial for the development of effective medications targeting specific retinoid receptors.
Additionally, Methyl 6-bromo-2-naphthoate may be used to synthesize various other compounds, such as:
1. 6-vinyl-2-naphthalencarbaldehyde
2. Methyl 6-(3-tert-butyl-4-methoxyphenyl)-2-naphthoate
3. Methyl 6-[3-tert-butyl-4-[(tert-butyldiethylsilyl)oxy]-phenyl]-2-naphthoate
4. Methyl 6-[3-(1-adamantyl)-4-[(tert-butyldimethylsilyl)-oxy]phenyl]-2-naphthoate
5. Methyl 6-[3-(1-adamantyl)-4-[[(2,3-dimethyl-1,3-dioxolan-4-yl)methylloxy]phenyl]-2-naphthoate
6. 2-bromo-6-(bromomethyl)naphthalene
These synthesized compounds can have potential applications in various fields, including pharmaceuticals, materials science, and chemical research.

InChI:InChI=1/C12H9BrO2/c1-15-12(14)10-3-2-9-7-11(13)5-4-8(9)6-10/h2-7H,1H3

Synthetic route

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%

methanol (67-56-1) + naphthalene-2-carboxylate (93-09-4) → methyl 6-bromo-2-naphthoate (33626-98-1)

Conditions	Yield
Stage #1: methanol; naphthalene-2-carboxylate at 150℃; under 4560.31 Torr; for 1h; Stage #2: With sodium hypobromite; benzenesulfonic acid; sodium bromide In water at 170℃; under 11400.8 Torr; for 6h; Pressure; Temperature;	98.3%

6-bromo-1-naphthoic acid (51934-38-4) + methyl iodide (74-88-4) → methyl 6-bromo-2-naphthoate (33626-98-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	98%

2-[1-(4-Bromo-phenyl)-meth-(Z)-ylidene]-3,3-dimethoxy-butyric acid methyl ester (123207-11-4) → methyl 6-bromo-2-naphthoate (33626-98-1)

Conditions	Yield
at 475 - 500℃; vapor-phase pyrolysis; Yield given;

methanol (67-56-1) + carbon monoxide (201230-82-2) + 6-bromo-2-naphthalenyl trifluoromethanesulfonate (151600-02-1) → methyl 6-bromo-2-naphthoate (33626-98-1)

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate

diazomethane (186581-53-3, 908094-01-9) + 6-bromo-naphthoic acid-(2) → methyl 6-bromo-2-naphthoate (33626-98-1)

Conditions	Yield
With diethyl ether

6-bromo-naphthalen-2-ol (15231-91-1) → methyl 6-bromo-2-naphthoate (33626-98-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: DIEA 2: dppp / Pd(OAc)2 View Scheme

C16H23BrO4 → methyl 6-bromo-2-naphthoate (33626-98-1)

Conditions	Yield
With sulfuric acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In methanol; water at 0 - 20℃; for 1h;

4-((2,2,2-trifluoroacetamido)methyl)phenylboronic acid (528894-31-7) + methyl 6-bromo-2-naphthoate (33626-98-1) → methyl 6-[4-(N-trifluoroacetylamino)methylphenyl]-2-naphthalenecarboxylate (869748-83-4)

Conditions	Yield
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 20h; Suzuki-Miyaura cross-coupling reaction; Heating;	100%

methyl 6-bromo-2-naphthoate (33626-98-1) → (6-bromo-2-naphthy)methanol (100751-63-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -10 - -5℃; for 1.33333h;	99%
With diisobutylaluminium hydride In tetrahydrofuran; hexane at 20℃; for 40h; Inert atmosphere;	99%
With diisobutylaluminium hydride In tetrahydrofuran; n-heptane at -78 - 20℃; for 14h; Inert atmosphere;	98%

methyl 6-bromo-2-naphthoate (33626-98-1) + phenylboronic acid (98-80-6) → 6-(phenyl)-2-naphthoic acid methyl ester (904688-59-1)

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 2h; Catalytic behavior; Suzuki Coupling; Inert atmosphere; Irradiation;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 18h; Suzuki coupling; Inert atmosphere;	73%
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane; water at 80℃; for 3.5h;

4-Phenyl-1-butene (768-56-9) + methyl 6-bromo-2-naphthoate (33626-98-1) → (E)-methyl 6-(4-phenylbut-1-en-1-yl)-2-naphthoate

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 18h; Heck Reaction; Inert atmosphere;	98%

methyl 6-bromo-2-naphthoate (33626-98-1) + 4-tert-butylphenylboronic acid (123324-71-0) → C22H22O2

Conditions	Yield
With potassium phosphate monohydrate; C50H60F3NO6PPdS In water at 55℃; for 7h; Suzuki-Miyaura Coupling;	97%
With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In water at 45℃; for 21h; Suzuki-Miyaura Coupling;	96%

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%

methyl 6-bromo-2-naphthoate (33626-98-1) + Dimethyl phosphite (868-85-9) → methyl 6-(dimethoxyphosphoryl)-2-naphthoate (1402577-09-6)

Conditions	Yield
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100℃; Inert atmosphere;	96%

methyl 6-bromo-2-naphthoate (33626-98-1) + 2,4-dimethylbenzeneboronic acid (55499-44-0) → methyl 6-(2,4-dimethylphenyl)-2-naphthoate

Conditions	Yield
With potassium phosphate monohydrate; C66H84O10P2Pd In water; ethyl acetate; toluene at 45℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;	96%
With potassium phosphate monohydrate; palladium diacetate; N2Phos In water; toluene at 45℃; for 1.5h; Suzuki-Miyaura Coupling;	96%

allylcyclopentane (3524-75-2) + methyl 6-bromo-2-naphthoate (33626-98-1) → (E)-methyl 6-(3-cyclopentylprop-1-en-1-yl)naphthalene-2-carboxylate

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 18h; Heck Reaction; Inert atmosphere;	96%

methyl 6-bromo-2-naphthoate (33626-98-1) → 6-bromo-naphthalene-2-carboxaldehyde (170737-46-9)

Conditions	Yield
Stage #1: methyl 6-bromo-2-naphthoate With diisobutylaluminium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With pyridinium chlorochromate In dichloromethane at 60℃; for 6h; Inert atmosphere;	95%
Stage #1: methyl 6-bromo-2-naphthoate With diisobutylaluminium hydride In tetrahydrofuran at 0 - 20℃; for 12h; Stage #2: With pyridinium chlorochromate In dichloromethane for 5h; Reflux;	95%
With manganese dioxide; dibal In methanol; dichloromethane; toluene	61%

methyl 6-bromo-2-naphthoate (33626-98-1) + Diphenylphosphine oxide (4559-70-0) → methyl 6-(diphenylphosphoryl)-2-naphthoate (1378042-98-8)

Conditions	Yield
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100℃; Inert atmosphere;	95%

methyl 6-bromo-2-naphthoate (33626-98-1) → 6-bromonaphthalene-2-carbohydrazide (948859-96-9)

Conditions	Yield
With hydrazine In methanol at 20 - 80℃; for 22h;	94%
With hydrazine hydrate In ethanol for 3h; Reflux;	81%
With hydrazine hydrate In methanol at 60 - 65℃; for 2h; Time;
With hydrazine hydrate In methanol at 60℃;

methyl 6-bromo-2-naphthoate (33626-98-1) + allylmagnesium bromide (1730-25-2) → 4-(6-bromonaphth-2-yl)hepta-1,6-dien-4-ol (1126524-60-4)

Conditions	Yield
In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere;	94%

methyl 6-bromo-2-naphthoate (33626-98-1) + 6-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-1,4,4-trimethyl-1,2,3,4-tetrahydroquinoline → 6-(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)-naphthalene-2-carboxylic acid methyl ester

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; tripotassium phosphate dihydrate In water; dimethyl sulfoxide at 80℃; for 18h; Inert atmosphere; Glovebox;	94%

4-methylpentyne (7154-75-8) + methyl 6-bromo-2-naphthoate (33626-98-1) → methyl 6-(4-methylpent-1-yn-1-yl)-2-naphthoate

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;	94%

methyl 6-bromo-2-naphthoate (33626-98-1) + 2,2-difluoroethenyl 4-methylbenzene-1-sulfonate (185739-14-4) → C14H10F2O2

Conditions	Yield
With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;	94%

methyl 6-bromo-2-naphthoate (33626-98-1) → methyl 6-iodonaphthalene-2-carboxylate (5042-98-8)

Conditions	Yield
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 65h; Finkelstein reaction; Inert atmosphere;	93%
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 65h; Inert atmosphere;	90%

methyl 6-bromo-2-naphthoate (33626-98-1) + trimethylsilylacetylene (1066-54-2) → methyl 6-((trimethylsilyl)ethynyl)-2-naphthoate

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dichloromethane at 90℃; for 16h; Inert atmosphere; Schlenk technique;	93%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 90℃; for 16h; Inert atmosphere; Schlenk technique;	93%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 80℃; for 16h; Inert atmosphere;	83%

2,2,2-trifluoroethanol (75-89-8) + methyl 6-bromo-2-naphthoate (33626-98-1) → methyl 6-(2,2,2-trifluoroethoxy)-2-naphthoate

Conditions	Yield
With C43H59NO2PPd(1+)*CH3O3S(1-); caesium carbonate In toluene at 80℃; Schlenk technique; Inert atmosphere;	93%

3-(1-adamantyl)-4-methoxyphenylboronic acid (459423-32-6) + methyl 6-bromo-2-naphthoate (33626-98-1) → 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester (106685-41-0)

Conditions	Yield
With sodium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	92%
Suzuki-Miyaura coupling;

n-octyne (629-05-0) + methyl 6-bromo-2-naphthoate (33626-98-1) → methyl 6-(octynyl)-2-naphthoate (1242239-82-2)

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide; toluene at 20℃; for 31.5h; Inert atmosphere;	92%

methyl 6-bromo-2-naphthoate (33626-98-1) + bis(pinacol)diborane (73183-34-3) → 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalene-2-carboxylic acid methyl ester (736989-93-8)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere;	91%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate In dimethyl sulfoxide for 24h; Schlenk technique; Inert atmosphere; Reflux;	87%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate In dimethyl sulfoxide for 24h; Schlenk technique; Inert atmosphere; Reflux;	87%

methyl 6-bromo-2-naphthoate (33626-98-1) + 4-butoxyphenylboronic acid (105365-51-3) → methyl 6-(4-butoxyphenyl)-2-naphthoate

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; methylmagnesium chloride at 45℃; for 24h; Suzuki-Miyaura Coupling;	91%

1-penten (109-67-1) + methyl 6-bromo-2-naphthoate (33626-98-1) → (E)-methyl 6-(pent-1-en-1-yl)-2-naphthoate

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 18h; Heck Reaction; Inert atmosphere;	91%

ethyl 2-methyl-4-pentenoate (53399-81-8) + methyl 6-bromo-2-naphthoate (33626-98-1) → C20H22O4

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 18h; Heck Reaction; Inert atmosphere;	91%

methyl 6-bromo-2-naphthoate (33626-98-1) → methyl 6-<3-(1-adamantyl)-4-<<(2,3-dimethyl-1,3-dioxolan-4-yl)methyl>oxy>phenyl>-2-naphthoate (146966-02-1)

Conditions	Yield
Stage #1: 3-(1-adamantyl)-4-<<(2,3-dimethyl-1,3-dioxolan-4-yl)methyl>oxy>bromobenzene With magnesium; ethylene dibromide In tetrahydrofuran for 1.5h; Heating / reflux; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; for 1.5h; Stage #3: methyl 6-bromo-2-naphthoate; cis-[NiCl2(1,2-bis(diphenylphosphino)ethane)] In tetrahydrofuran at 20℃; for 15h;	89%

4-Methyl-1-pentene (691-37-2) + methyl 6-bromo-2-naphthoate (33626-98-1) → (E)-methyl 6-(4-methylpent-1-en-1-yl)-2-naphthoate

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 18h; Heck Reaction; Inert atmosphere;	89%

Upstream product

• 67-56-1 methanol 
• 5773-80-8 6-bromo-2-naphthoic acid 
• 93-09-4 naphthalene-2-carboxylate 
• 51934-38-4 6-bromo-1-naphthoic acid 
• 74-88-4 methyl iodide 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 186581-53-3 diazomethane 
• 201230-82-2 carbon monoxide 
• 151600-02-1 6-bromo-2-naphthalenyl trifluoromethanesulfonate 
• 123207-11-4 2-[1-(4-Bromo-phenyl)-meth-(Z)-ylidene]-3,3-dimethoxy-butyric acid methyl ester 

Downstream Products

• 869748-83-4 methyl 6-[4-(N-trifluoroacetylamino)methylphenyl]-2-naphthalenecarboxylate 
• 958328-29-5 6-Bromo-naphthalene-2-carboxylic acid [(R)-1-(4-methanesulfonylamino-3-methyl-phenyl)-ethyl]amide 
• 958328-39-7 6-PYRROLIDIN-1-YL-NAPHTHALENE-2-CARBOXYLIC ACID [(R)-1-(4-METHANESULFONYL-AMINO-3-METHYLPHENYL)ETHYL]AMIDE 
• 958328-42-2 6-cyclopropylnaphthalene-2-carboxylic acid [(R)-1-(4-methane-sulfonyl-amino-3-methylphenyl)ethyl]amide 
• 958328-47-7 6-AZETIDIN-1-YL-NAPHTHALENE-2-CARBOXYLIC ACID [(R)-1-(4-METHANE-SULFONYLAMINO-3-METHYLPHENYL)ETHYL]AMIDE 
• 958328-50-2 6-PIPERIDIN-1-YL-NAPHTHALENE-2-CARBOXYLIC ACID [(R)-1-(4-METHANE-SULFONYL-AMINO-3-METHYLPHENYL)ETHYL]AMIDE 
• 958329-21-0 (R)-N-(1-(2-FLUORO-5-METHYL-4-(METHYLSULFONAMIDO)PHENYL)ETHYL)-6-CYCLOPROPYL-2-NAPHTHAMIDE 
• 958329-41-4 (R)-N-(1-(2-CHLORO-5-METHYL-4-(METHYLSULFONAMIDO)PHENYL)ETHYL)-6-CYCLOPROPYL-2-NAPHTHAMIDE 
• 958328-46-6 6-morpholin-4-yl-naphthalene-2-carboxylic acid [(R)-1-(4-methane-sulfonylamino-3-methylphenyl)ethyl]amide 
• 1424035-58-4 (R)-methyl 6-(1-phenylethyl)-2-naphthoate 
• 1467041-37-7 C₂₀H₁₉NO₂ 
• 129667-70-5 6-amino-2-naphthalenecarbonitrile 
• 91065-17-7 6-bromo-naphthalene-2-carbonitrile 
• 1269935-87-6 C₄₃H₃₅NO₂ 

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