21299-80-9

Upstream product

• 338744-37-9 α-methyl-1-methoxycarbonyl-3-indoleacetic acid methyl ester 
• 174319-54-1 methyl 3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate 
• 338744-40-4 (R)-1-phenylethyl (-)-2-(3-indolyl)propionate 
• 2597-26-4 2-(1H-Indol-3-yl)-propionic acid 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 87-51-4 indole-3-acetic acid 

Relevant academic research and scientific papers

Synthesis, absolute configuration and biological activity of both enantiomers of 2-(5,6-dichloro-3-indolyl)propionic acid: New dichloroindole auxins

Racemic 2-(5,6-dichloro-3-indolyl)propionic acid (5,6-Cl2-2-IPA) was synthesized from 5,6-dichloroindole-3-acetic acid (5,6-Cl2-IAA) by successive esterification, methoxycarbonylation, methylation, and double hydrolysis. The racemate was converted to the diastereomeric esters of (S)-(-)-1-phenylethyl alcohol. These were separated by HPLC into two optically active diastereomers and then hydrolyzed with p-TsOH to the optically active enantiomers of 5,6-Cl2-Z-IPA. The absolute configurations of both the 5,6-CI2-Z-IPA enantiomers were determined by comparing the 1H-NMR spectra of their diastereomeric (S)-(-)-1-phenylethyl esters with those of the diastereomeric (S)-(-)-1-phenylethyl esters of 2-(3-indolyl)propionic acid (2-IPA) whose absolute configurations are already known. There was no essential difference between (S)-(+)- and (R)-(-)-5,6-Cl2-2-IPA in hypocotyl growth-inhibiting activity toward Chinese cabbage, but their inhibitory activities were stronger than that of the potent mother auxin, 5,6-Cl2-IAA. No essential difference in the coleoptile elongating activity of Avena sativa was apparent for the enantiomers, this activity being about one-third that of 5,6-Cl2-IAA.