28093-53-0

Usage

Type of compound

Synthetic auxin, or plant hormone.

Common uses

Promoting root formation and growth in cuttings, encouraging uniform and vigorous growth in crops, and aiding in the establishment of new plants in forestry and landscaping.

Mechanism of action

Acts as a plant growth regulator by stimulating the development of roots in plant cuttings, allowing for quicker and more successful propagation of desirable plant varieties.

Stability

Potent and stable form of the natural auxin indole-3-butyric acid (IBA).

Importance

Plays a crucial role in the successful propagation and growth of various plant species.

Upstream product

• 77758-51-1 methyl hex-5-ynoate 
• 615-43-0 2-iodophenylamine 
• 1172640-24-2 methyl 6-(2-nitrophenyl)-5-oxohexanoate 
• 1279093-35-4 methyl 6-(2-aminophenyl)hex-5-ynoate 
• 53293-00-8 hex-5-ynoic acid 
• 120-72-9 indole 
• 4897-84-1 Methyl 4-bromobutyrate 
• 81803-81-8 5-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-5-oxo-pentanoic acid methyl ester 
• 81803-83-0 6-(Hydroxy-phenyl-carbamoyl)-5-oxo-hexanoic acid methyl ester 

Downstream Products

• 29873-09-4 4-(1H-indol-2-yl)butanoic acid 

Relevant academic research and scientific papers

Palladium-Catalyzed Dearomatizing Difunctionalization of Indoles and Benzofurans

A palladium-catalyzed dearomatizing difunctionalization of N-Boc-indoles and benzofurans to give tricyclic indolines and 2,3-dihydrobenzofurans with a fully substituted carbon center is described. Product formation occurs under mild conditions at room temperature with commercially available aryl boronic acids and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as a mild oxidant in good yields. 2-Carboxyalkyl-substituted indoles and benzofurans react under Pd-catalysis with aryl boronic acids and TEMPO through dearomatizing arylation/cyclization to the corresponding indolines and dihydrobenzofurans containing a lactone moiety bearing a fully substituted carbon center.

Palladium-catalyzed direct 2-alkylation of indoles by norbornene-mediated regioselective cascade C-H activation

A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles has been developed. This reaction relies on a norbornene-mediated cascade C-H activation process at the indole ring, which features high regioselectivity and excellent functional group tolerance. The reaction represents the first example for a generally applicable, direct C-H alkylation of indole at the 2-position.

1, 2, 3, 9-tetrahydro-4H-carbazol-4-one and 8, 9-dihydropyrido- [1, 2-a]indol-6(7H)-one from 1H-indole-2-butanoic acid

Efficient syntheses of the title ring systems have been developed from 1H-indole-2-butanoic acid, which was easily prepared from 2-fluoro-1- nitrobenzene in four steps. Heating 1H-indole-2-butanoic acid in toluene containing p-toluenesulfonic acid at 110°

Heterogeneous palladium catalysts applied to the synthesis of 2- and 2,3-functionalised indoles

Heterogeneous palladium catalysts ([Pd(NH3)4] 2+/NaY and [Pd]/SBA-15) were applied to the synthesis of 2-functionalised indoles, giving generally high conversions and selectivities (>89% yield) using only 1 mol % [Pd]-catalyst under standard reaction conditions (polar solvent, 80°C). For the synthesis of 2,3-functionalised indoles by cross-coupling arylation, the [Pd]/SBA-15 catalyst was found to be particularly interesting, producing the expected compound with =35% yield after 12 days of reaction, which is comparable to the homogeneous catalyst, Pd(OAc)2 (= 48% yield). In the course of the study, the dual reactivity of the indole nucleus was demonstrated: aryl bromides gave clean C-C coupling while aryl iodides led to a clean C-N coupling.

MELDRUM'S ACID IN ORGANIC SYNTHESIS 3. SYNTHESIS OF 2-SUBSTITUTED INDOLES FROM PHENYLHYDROXYLAMINE

Treatment of phenylhydroxylamine oxalate with acyl Meldrum's acids in boiling acetonitrile readily gave N-acylacetylphenylhydroxylamines, which were converted to 2-substituted indoles by another treatment with acyl Meldrum's acids in refluxing toluene.N-B

Meldrum's Acid in Organic Synthesis. VI. Synthesis of 2-Substituted Indoles from Acyl Meldrum's Acids and Phenylhydroxylamine via Sigmatropic Rearrangement

Phenylhydroxylamine (13) oxalate was quite easily acylacetylated by heating with an equimolar amount of acyl Meldrum's acid (4) in acetonitrile to give an N-acylacetylphenylhydroxylamine (14) in high yield.When 14 was treated with another equimolar amount of the same 4 in refluxing toluene, a series of reactions, O-acylacetylation, 1-aza-1'-oxasigmatropic rearrangement, decarboxylation, dehydrative cyclization, and deacylation, occured consecutively to give a 2-substituted indole (16) in fair yield, though sometimes accompanied by the formation of a 5-substituted 4-isoxazolin-3-one (17).N-Benzoyl, N-acetyl, and N-benzyloxycarbonyl derivatives of phenylhydroxylamine (18) were treated with phenylacetyl Meldrum's acid (4i) in refluxing benzene containing copper powder to give readily rearranged ortho alkylation products (19), which were converted to the corresponding N-acyl-2-benzylindoles (20) by treatment with hydrochloric acid in boiling ethanol or with anhydrous p-toluenesulfonic acid in benzene at room temperature.Keywords - acyl Meldrum's acid; phenylhydroxylamine; N-acylacetylphenylhydroxylamine; 2-substituted indole; 1-aza-1'-oxasigmatropic rearrangement; acid-catalyzed cyclization