| Identification | Back Directory | [Name]
2-(7-Methoxynaphthalen-1-yl)acetic acid | [CAS]
6836-22-2 | [Synonyms]
(7-Methoxy-1-naphthyl)acetic acid
7-Methoxy-1-naphthaleneacetic acid
7-Methoxy-1-napthalene acetic acid
2-(7-Methoxy-1-naphthyl)acetic Acid
1-Naphthaleneacetic acid, 7-Methoxy-
2-(7-Methoxyphthalen-1-yl)acetic acid
2-(7-Methoxynaphthalen-1-yl)acetic acid | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C13H12O3 | [MDL Number]
MFCD12756806 | [MOL File]
6836-22-2.mol | [Molecular Weight]
216.23 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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