108761-33-7

Basic information

• Product Name: 6-CHLOROINDOXYL-1,3-DIACETATE
• Synonyms: 1-acetyl-6-chloro-1H-indol-3-yl acetate;(1-acetyl-6-chloroindol-3-yl) acetate;6-Chloro indoxyl-1,3-diacetate≥ 98% (HPLC);6-CHLOROINDOXYL-1,3-DIACETATE;ACETIC ACID 1-ACETYL-6-CHLORO-1H-INDOL-3-YL ESTER;6-CHLOROINDOLYL-1,3-DIACETATE;6-Chloro-3-indolyl 1,3-diacetate
• CAS NO: 108761-33-7
• Molecular Formula: C₁₂H₁₀ClNO₃
• Molecular Weight: 251.67
• Product Categories: substrate
• Mol File: 108761-33-7.mol

Chemical Properties

• Melting Point: 111-113 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 376.951 °C at 760 mmHg
• Flash Point: 181.774 °C
• Appearance: /
• Density: 1.337 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Store at -20
• CAS DataBase Reference: 6-CHLOROINDOXYL-1,3-DIACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLOROINDOXYL-1,3-DIACETATE(108761-33-7)
• EPA Substance Registry System: 6-CHLOROINDOXYL-1,3-DIACETATE(108761-33-7)

Safety Data

• Hazardous Substances Data: 108761-33-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to yellowish brown powder

InChI:InChI=1/C12H10ClNO3/c1-7(15)14-6-12(17-8(2)16)10-4-3-9(13)5-11(10)14/h3-6H,1-2H3

Upstream product

• 108-24-7 acetic anhydride 
• 914221-22-0 2-(acetyl-carboxymethyl-amino)-4-chloro-benzoic acid 
• 99282-79-8 2-carboxymethylamino-4-chlorobenzoic acid 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 79-11-8 chloroacetic acid 
• 936-08-3 2-bromo-4-chlorobenzoic acid 
• 50-84-0 2,4 dichlorobenzoic acid 

Downstream Products

• 149231-54-9 1-acetyl-6-chloro-indol-3-ol 
• 114305-99-6 6-chloro-1H-indol-3-yl acetate 
• 133950-72-8 Nonanoic acid 6-chloro-1H-indol-3-yl ester 
• 68095-16-9 1-acetyl-6-chloro-1,2-dihydro-3H-indol-3-one 
• 700838-52-4 [2-(1-(2'-bromobenzenesulfonyl)-6-chloro-1H-indol-3-yloxy)ethyl]dimethylamine 
• 1629135-25-6 (S)-5-acetyl-7-chloro-4-phenyl-3,4-dihydropyrano[3,2-b]indol-2(5H)-one 
• 1629135-37-0 (R)-5-acetyl-7-chloro-4-phenyl-3,4-dihydropyrano[3,2-b]indol-2(5H)-one 

Relevant articles and documents

N-heterocyclic carbene-catalyzed enantioselective annulation of indolin-3-ones with bromoenals

N-Heterocyclic carbene-catalyzed reactions of indolin-3-ones with 2-bromoenals opened an asymmetric access to 3,4-dihydropyrano[3,2-b]indol-2(5 H)-ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented. More NHC-organocatalysis: N-Heterocyclic carbene-catalyzed reactions of indolin-3-ones with 2-bromoenals opened an asymmetric access to 3,4-dihydropyrano[3,2-b]indol-2(5 H)-ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented.

Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists

N1-Arylsulfonyl-3-piperazinyl indole derivatives were designed and identified as a novel class of 5-HT6 receptors ligands. All the compounds have high affinity and antagonist activity towards 5-HT6 receptor. The compound 7a (Ki = 3.4 nM, functional assay IC 50 = 310 nM) shows enhanced cognitive effect when tested in NORT and Morris water maze models. Synthesis, SAR and PK profile of these novel compounds constitute the subject matter of this Letter.

Design, synthesis and pharmacological evaluation of conformationally restricted N-arylsulfonyl-3-aminoalkoxy indoles as a potential 5-HT6 receptor ligands

A series of novel conformationally restricted N1-arylsulfonyl-3-aminoalkoxy indoles were designed and synthesized as 5-HT6 receptor (5-HT6R) ligands. Many of the synthesized compounds have moderate in vitro-binding affinities at 5-HT6R. The lead compound 8b (% inhibition=97.2 at 1 μM) from this series has good pharmacokinetic profile in male Wister rats and is active in animal model of cognition like Morris water maze. The details of chemistry, SAR, pharmacokinetics and pharmacological data constitute the subject matter of this report.

BENZYL-SUBSTITUTED TETRACYCLIC HETEROCYCLIC COMPOUNDS AS PDE5 INHIBITORS

The present invention pertains to Benzyl-substituted tetracyclic heterocyclic compounds, as well as the resulting pharmaceutical compositions, and their use in the treatment or prophylaxis of diseases alleviated by inhibition of type 5 phosphodiesterases. Furthermore, the present invention pertains to the methods of manufacturing these Benzyl-substituted tetracyclic heterocyclic compounds.

An improved synthesis of 1-acetyl-1H-indol-3-yl acetates

(Chemical Equation Presented) An efficient two steps procedure for the synthesis of 1-acetyl-1H-indol-3-yl acetates, starting from 2-chlorobenzoic acids, was developed and in general, moderate to good yields were obtained.

Synthesis of some cryptolepine analogues, assessment of their antimalarial and cytotoxic activities, and consideration of their antimalarial mode of action

A series of analogues of cryptolepine (1) have been synthesized and evaluated for their in vitro antiplasmodial and cytotoxic properties. The IC50 values of several compounds (11a, 11k-m, 11o, 13) against Plasmodium falciparum (strain K1) were 90% at doses of 25 mg kg-1 day -1 with no apparent toxicity to the mice. 2,7-Dibromocryptolepine (15) was evaluated at several dose levels, and a dose-dependent suppression of parasitemia was seen (ED90 = 21.6 mg kg-1 day -1). The antimalarial mode of action of 1 appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation. A number of analogues were assessed for their effects on the inhibition of β-hematin (hemozoin) formation, and the results were compared with their antiplasmodial activities having taken account of their predicted accumulation into the acidic parasite food vacuole. No correlation was seen (r2 = 0.0781) suggesting that the potent antimalarial activity of compounds such as 15 involves other mechanisms in addition to the inhibition of hemozoin formation.

Method, test media and chromogenic compounds for identifying and differentiating general coliforms and Escherichia coli bacteria

A chromogenic β-galactosidase substrate producing an insoluble precipitate of a first color when reacted upon by β-galactosidase and a chromogenic β-glucuronidase substrate producing an insoluble precipitate of a second, contrasting color when reacted upon by β-glucuronidase are combined in test medium for quantitatively identifying and differentiating general coliforms and E. coli. The β-galactosidase substrate 5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside which produces an indigo blue precipitate when reacted upon by β-galactosidase may be used with one of the novel compounds 6-chloroindolyl-β-D-glucuronide, 4,6-dichloroindolyl-β-D-glucuronide, 6,7-dichloroindolyl-β-D-glucuronide, and 4,6,7-trichloroindolyl-β-D-glucuronide, which produce mauve or magenta precipitates when reacted upon by β-glucuronidase. The β-glucuronidase substrate 5-bromo-4-chloro-3-indolyl-β-D-glucuronide, which produces an indigo blue precipitate when reacted upon by β-glucuronidase may be used with one of the novel compounds 6-chloroindolyl-β-D-galactoside, 4,6-dichloroindolyl-β-D-galactoside, 6,7-dichloroindolyl-β-D-galactoside, and 4,6,7-trichloroindolyl-β-D-galactoside which produce mauve or magenta precipitates when reacted upon by β-galactosidase.