2-(7-Methoxynaphthalen-1-yl)acetic acid Chemical Properties

Melting point:

153-154 ºC

Boiling point:

408.8±20.0 °C(Predicted)

Density 

1.235

storage temp. 

Sealed in dry,Room Temperature

solubility 

Dichloromethane (Slightly), Methanol (Slightly)

form 

Solid

pka

4.33±0.30(Predicted)

color 

White to Off-White

Safety Information

HS Code 

2916399090

2-(7-Methoxynaphthalen-1-yl)acetic acid Usage And Synthesis

Uses

7-Methyl-1-naphthyl acetic acid is a potent inhibitor of auxin action in plants. 7-Methyl-1-naphthyl acetic acid inhibits AUX1, PIN, and ABCB protein-mediated auxin transport expressed in yeast. 7-Methyl-1-naphthyl acetic acid can be used in auxin dependent development [1].

Synthesis

Step 3 Synthesis of (7-methoxy-1-naphthyl)acetic acid: To a solution of methanol (12 mL) containing ethyl 7-methoxy-1-naphthylacetate (2.38 g, 9.8 mmol), sodium hydroxide (0.62 g, 15.6 mmol) and water (6 mL) were added. The reaction mixture was heated at 40°C for about 2 hours with continuous stirring. Upon completion of the reaction, the mixture was concentrated under reduced pressure and the residue was diluted with 50 mL of water and extracted with ether (4 x 25 mL). The aqueous phase was acidified with concentrated hydrochloric acid to pH=2. After conventional extraction and post-treatment, the title compound 7-methoxy-1-naphthaleneacetic acid was obtained as an off-white solid (1.9 g, 90% yield). The product was confirmed by 1H NMR (300 MHz, CD3OD): δ 3.9 (s, 3H), 4.03 (s, 2H), 7.15 (dd, J = 9.0, 2.4 Hz, 1H), 7.27-7.41 (m, 4H), 7.76 (m, 2H); LC-MS showed the molecular ion peak as 215 (M + H)+.

References

[1] Tsuda E, et al. Alkoxy-auxins are selective inhibitors of auxin transport mediated by PIN, ABCB, and AUX1 transporters. J Biol Chem. 2011 Jan 21;286(3):2354-64. DOI:10.1074/jbc.M110.171165

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