1912-45-4

Basic information

• Product Name: 5-CHLOROINDOLE-3-ACETIC ACID
• Synonyms: RARECHEM AH BS 0086;2-(5-CHLOROINDOL-1H-3-YL)ACETIC ACID;5-CHLORO-IAA;5-CHLOROINDOLE-3-ACETIC ACID;5-CHLOROINDOLE-3-ACETIC ACID 98% (HPLC);5-Cl-IAA;5-CHLOROINDOLE-3-ACETIC ACID (5ClIAA);2-(5-chloro-1H-indol-3-yl)acetic acid
• CAS NO: 1912-45-4
• Molecular Formula: C₁₀H₈ClNO₂
• Molecular Weight: 209.63
• Product Categories: Indoles and derivatives
• Mol File: 1912-45-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 445.6 °C at 760 mmHg
• Flash Point: 223.3 °C
• Appearance: /
• Density: 1.483 g/cm³
• Vapor Pressure: 1.01E-08mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 5-CHLOROINDOLE-3-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROINDOLE-3-ACETIC ACID(1912-45-4)
• EPA Substance Registry System: 5-CHLOROINDOLE-3-ACETIC ACID(1912-45-4)

Safety Data

• Hazardous Substances Data: 1912-45-4(Hazardous Substances Data)

Usage

Uses

5-Chloroindole-3-acetic Acid can be used in biological study for defining the selectivity of processes along the auxin response chain: a study using auxin analogs.

InChI:InChI=1/C10H8ClNO2/c11-7-1-2-9-8(4-7)6(5-12-9)3-10(13)14/h1-2,4-5,12H,3H2,(H,13,14)

Upstream product

• 328-50-7 α-ketoglutaric acid 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 81630-83-3 2-(5-chloro-1H-indol-3-yl)acetonitrile 
• 17422-32-1 5-chloro-1H-indole 
• 221188-28-9 (5-chloro-1H-indol-3-yl)acetic acid ethyl ester 
• 106-47-8 4-chloro-aniline 
• 72963-97-4 (2-ethoxycarbonyl-5-chloro-indol-3-yl)-acetic acid ethyl ester 
• 120716-95-2 (2-carboxy-5-chloro-indol-3-yl)-acetic acid 

Downstream Products

• 738608-59-8 1-(2-benzoyl-5-chloro-1H-indol-3-yl)-butan-2-one 
• 924633-70-5 benzyl 3-(3-acetoxy-2-oxopropyl)-5-chloro-1H-indole-1-carboxylate 
• 924634-99-1 benzyl 5-chloro-3-(3-chloro-2-oxopropyl)-1H-indole-1-carboxylate 
• 924634-97-9 2-(1-(benzyloxycarbonyl)-5-chloro-1H-indol-3-yl)acetic acid 
• 215998-11-1 5-chloroindole-3-methanol 
• 442883-74-1 5-chloro-3-methylene-2-oxindole 
• 74339-45-0 methyl 2-(5-chloro-1H-indol-3-yl)acetate 

Relevant articles and documents

Cyclizations of unsymmetrical bis-1,2-(3-indolyl)ethanes: Synthesis of (-)-tjipanazole F1

The inter- and intramolecular dimerization of 3-substituted indoles was studied. The rate and extent of dimerization depends on the indole substituents. The intramolecular dimerization of unsymmetrical bis-1,2-(3-indolyl)ethanes could be controlled using either thermodynamic reaction conditions (neat trifluoroacetic acid) or kinetic conditions (2 equiv acid/chloroform). This control of regiochemistry has been applied to an efficient synthesis of (-)- tjipanazole F1.

A substituted indole -3 - acetic acid synthesis method (by machine translation)

The present invention provides a substituted indole - 3 - acetic acid synthesis method, comprises the following steps: (1) in order to replace the indole as the starting material, with the acylation reagent under the action of catalyst through the tutor - acylation to obtain the 1, 3 - diacetyl substituted indole; (2) intermediate 1, 3 - diacetyl substituted indole does not need refining, directly with the morpholine and sulfur by the Willgerodt - Kindler rearrangement reaction, the inorganic under the catalysis of alkali hydrolysis, acidified to obtain substituted indole - 3 - acetic acid. (by machine translation)

Use of indole-3-acetic acid derivatives in medicine

Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R′3 are independently selected from II or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups lower alkoxy groups, aryl groups or aryloxy groups, wherein it least one of R4, R5, R6, and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT