6-Bromo-2-naphthoic acid Chemical Properties

Melting point:

294-295°C

Boiling point:

387.3±17.0 °C(Predicted)

Density 

1.648±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder to crystal

pka

4.06±0.30(Predicted)

color 

White to Light yellow

Water Solubility 

Insoluble in water.

BRN 

2328940

InChI

InChI=1S/C11H7BrO2/c12-10-4-3-7-5-9(11(13)14)2-1-8(7)6-10/h1-6H,(H,13,14)

InChIKey

NPMCAVBMOTZUPD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5773-80-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37/39-36

HS Code 

2916399090

MSDS

• Language:English Provider:ALFA

6-Bromo-2-naphthoic acid Usage And Synthesis

Chemical Properties

Pale brown solid

Uses

Benzimidazole derivatives has been prepared by using ortho-phenyl diamine and 6-bromo-2-naphthoic acid.

Synthesis

Methyl 6-bromo-2-naphthalenecarboxylate (3b) (2.7 g, 10.0 mmol) was used as a raw material to form a suspension with potassium hydroxide (1.1 g, 20.0 mmol) in methanol (50 mL) at 50 °C with vigorous stirring. At the beginning of the reaction, the suspension gradually changed to a homogeneous solution, indicating that the raw material was completely consumed. After the reaction lasted for 8 hours, about 2/3 of the volume of solvent was removed by evaporation under reduced pressure. Subsequently, water (1500 mL) was added to the residue and the unreacted esters were extracted with ethyl acetate. The aqueous phase was acidified to pH 3 with 10% H2SO4 and subsequently extracted with ethyl acetate (3 x 200 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give pure 6-bromo-2-naphthalenecarboxylic acid (3a) (2.1 g, 8.4 mmol, 84% yield). The melting point of the product was 290-294 °C (decomposition). High resolution mass spectrum (ESI+): m/z [M + 1]+ calculated value (C11H8BrO2) was 252.08591, measured value was 252.08582. 1H NMR (DMSO-d6) δ= 7.72 (1H, dd, J = 8.5 and 1.8 Hz, 7-naphthalenyl H), 7.99 (1H, d, J = 8.6 Hz, 4-naphthalenyl H) ), 8.02 (1H, dd, J = 8.6 and 1.4 Hz, 8-naphthalenyl H), 8.09 (1H, d, J = 8.8 Hz, 3-naphthalenyl H), 8.30 (1H, d, J = 1.6 Hz, 5-naphthalenyl H), 8.62 (1H, s, 1-naphthalenyl H), and 13.15 (1H, br.s, COOH).13C NMR ( 125.76 MHz, DMSO-d6) δ= 121.93, 126.50, 127.61, 128.81, 129.83, 130.01, 130.64, 130.90, 131.63, 136.11, 167.30.

References

[1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 27, p. 7477 - 7486
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 27, p. 7477 - 7486
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 4, p. 1557 - 1568
[4] Bioorganic Chemistry, 2011, vol. 39, # 4, p. 151 - 158
[5] Patent: US2012/88746, 2012, A1. Location in patent: Page/Page column 47-48

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