Methyl 6-bromo-2-naphthoate Chemical Properties

Melting point:

123-126 °C (lit.)

Boiling point:

357.0±15.0 °C(Predicted)

Density 

1.492±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Crystalline Powder

color 

Off-white to cream or light brown

BRN 

2578943

InChI

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

InChIKey

JEUBRLPXJZOGPX-UHFFFAOYSA-N

SMILES

C1=C2C(C=C(Br)C=C2)=CC=C1C(OC)=O

CAS DataBase Reference

33626-98-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

20/21/22-34

Safety Statements 

24/25-45-36/37/39-27-26

WGK Germany 

3

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl 6-bromo-2-naphthoate Usage And Synthesis

Chemical Properties

Pale yellow or light brown powder

Uses

Methyl 6-Bromo-2-napthoate (Adapalene USP Related Compound A) is used in the synthesis of Adapalene, a retinoid specific for RARβ and RARγ receptors.

Uses

Methyl 6-bromo-2-naphthoate may be used to synthesize:

• 6-vinyl-2-naphthalencarbaldehyde
• methyl 6-(3-tert-butyl-4-methoxyphenyl)-2-naphthoate
• methyl 6-[3-tert-butyl-4-[(tert-butyldiethylsilyl)oxy]-phenyl]-2-naphthoate
• methyl 6-[3-(1-adamantyl)-4-[(tert-butyldimethylsilyl)-oxy]phenyl]-2-naphthoate
• methyl 6-[3-(1-adamantyl)-4-[[(2,3-dimethyl-1,3-dioxolan-4-yl)methylloxy]phenyl]-2-naphthoate
• 2-bromo-6-(bromomethyl)naphthalene

Uses

Methyl 6-Bromo-2-napthoate is used in the synthesis of Adapalene, a retinoid specific for RARβ and RARγ receptors.

General Description

Methyl 6-bromo-2-naphthoate undergoes aromatic Finkelstein reaction followed by hydrolysis to afford 6-iodo-2-naphthoic acid.

Synthesis

To a 60 mL dry egg-shaped flask was added 6-bromo-2-naphthalenecarboxylic acid (2.4996 g, 10.0 mmol) followed by 20 mL of anhydrous methanol to dissolve it. Slowly 1 mL of concentrated sulfuric acid was added dropwise to the reaction system and then the mixture was refluxed overnight. The progress of the reaction was monitored by TLC until complete conversion of the feedstock. After completion of the reaction, the heating was stopped and the system was allowed to cool to room temperature. The reaction was quenched with saturated aqueous sodium carbonate and the reaction system was adjusted to neutral. The reaction mixture was extracted with ethyl acetate and the organic phase was washed with saturated aqueous sodium carbonate, water and saturated aqueous sodium chloride, respectively. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give methyl 6-bromo-2-naphthalenecarboxylate (S7, 2.63 g, 100% yield) as a white solid.

References

[1] Tetrahedron, 2009, vol. 65, # 7, p. 1349 - 1360
[2] Journal of the American Chemical Society, 2008, vol. 130, # 50, p. 16836 - 16837
[3] Patent: CN107286150, 2017, A. Location in patent: Paragraph 0153; 0154; 0155; 0156; 0157
[4] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 277 - 287
[5] Patent: JP2016/37458, 2016, A. Location in patent: Paragraph 0172; 0173

Methyl 6-bromo-2-naphthoate(33626-98-1)Related Product Information

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