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Sigma-Aldrich

Methyl 6-bromo-2-naphthoate

98%

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About This Item

Linear Formula:
BrC10H6CO2CH3
CAS Number:
Molecular Weight:
265.10
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

123-126 °C (lit.)

SMILES string

COC(=O)c1ccc2cc(Br)ccc2c1

InChI

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

InChI key

JEUBRLPXJZOGPX-UHFFFAOYSA-N

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General description

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

Application

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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B Charpentier et al.
Journal of medicinal chemistry, 38(26), 4993-5006 (1995-12-22)
The retinoic acid receptors (RARs) transduce retinoid dependant gene regulation, and many biological effects of retinoids are mediated through binding and activation of three closely related receptor subtypes (RAR alpha, RAR beta, and RAR gamma). In order to investigate the
Carboxy-1, 4-phenylenevinylene-and carboxy-2, 6-naphthylene-vinylene unsymmetrical substituted zinc phthalocyanines for dye-sensitized solar cells.
Silvestri F, et al.
Journal of Porphyrins and Phthalocyanines, 13(03), 369-375 (2009)
Phil M Pithan et al.
Beilstein journal of organic chemistry, 12, 854-862 (2016-06-25)
Cationic biaryl derivatives were synthesized by Suzuki-Miyaura coupling of 3-bromonaphtho[1,2-b]quinolizinium bromide with arylboronic acids. The resulting cationic biaryl derivatives exhibit pronounced fluorosolvatochromic properties. First photophysical studies in different solvents showed that the emission energy of the biaryl derivatives decreases with
Mark W Irvine et al.
Journal of medicinal chemistry, 55(1), 327-341 (2011-11-25)
Competitive N-methyl-d-aspartate receptor (NMDAR) antagonists bind to the GluN2 subunit, of which there are four types (GluN2A-D). We report that some N(1)-substituted derivatives of cis-piperazine-2,3-dicarboxylic acid display improved relative affinity for GluN2C and GluN2D versus GluN2A and GluN2B. These derivatives

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