2- Naphthaleneacetic acid

AIkyl-Ai,A/-diaLkyl-l-naphthalenecarboxamides are useful herbicides (86) and the 2,2-dimeth5lhydra2ide of 1-naphthalenecarboxyhc acid has been patented as a plant growth regulator (87). 2-Propynyl-2-naphthalenecarboxylate [53548-27-9] and similar esters are insecticides (88). 1-Naphthaleneacetic acid, the plant growth regulator, has been prepared from naphthalene, concentrated HCl, and paraformaldehyde without isolation of intermediate 1-chloromethylnaphthalene or l-naphthaleneacetonitnle (89). 

Naphthaleneacetic acid has also been prepared by the carbonyl-insertion reaction of 1-chloromethylnaphthalene cataly2ed by carbonyl cobalt cation (90,91). Carboxylation of 1-chloromethylnaphthalene in the presence of the catalyst Pd[P(CgH )2]2Cl2 under phase-transfer conditions gave 1-naphthaleneacetic acid in 78% yield (92). 

Hydroxy-1-naphthaleneacetic acid [10441-45-9] M 202.2, pK )-4.2, pKej,(2) -8.3. Treated with activated charcoal and crystd from EtOH/water (1 9, v/v). Dried under vacuum, over silica gel, in the dark. Stored in the dark at -20° [Gafni, Modlin and Brand J Phys Chem 80 898 1976. Forms a lactone (m 107°) readily. 

Naphthaleneacetic acid, a-fluoro-, ethyl ester [24021-14-5], 57, 73 1,4-Naphthalenedione [130-15-4], 56, 70... 

Ethyl 1-naphthylacetate 1-Naphthaleneacetic acid, ethyl ester (8,9) (2122-70-5) Lithium 2,2,6,6-tetramethylpiperidide Piperidine, 2,2,6,6-tetramethyl-, lithium salt (9) (38227-87-1)... 

The cuticular fraction (10-12%) of the cell walls has not received much attention, nor has the part (55-70%) which is usually called hemicellulose. Carlier and Buffel34 found nearly 50% more pentosan (measured as furfural) in potato tuber treated with 1-naphthaleneacetic acid at 10 mg. per liter in agar pectin increased in almost the same proportion, and in proportion to the increased intake of water starch decreased by 36%, apparently to provide the substrate for increased respiration. 

Indole-3-acetic acid is rather readily oxidized by peroxidases and is, in fact, probably not present in the plant in the free form to any appreciable extent. The nature of the complexing groups is not clear. The inherent instability of the compound in living tissue has made experimental observations difficult, and (the more stable) 1-naphthaleneacetic acid has often been used instead, although it is by no means certain that the biological activities are comparable. One view held is that auxin herbicides are effective either because they do not readily form conjugate systems, or because the conjugate retains the phytotoxic properties. 

Naphthaleneacetic acid A /J-Chlorophenylphthalamic acid 2,3,5-Triiodobenzoic acid 8, 12-14)... 

ETHYL 1 -NAPHTHYL ACETATE (1-Naphthaleneacetic acid, ethyl ester)... 

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