61220-51-7

Basic information

• Product Name: 5-CHLOROTRYPTOPHOL
• Synonyms: 2-(5-CHLORO-1H-INDOL-3-YL)ETHANOL;5-CHLOROTRYPTOPHOL;5-CHLOROTRYPTOPHOL, 98+%;5-Chloro-1H-indole-3-ethanol;1H-Indole-3-ethanol,5-chloro-
• CAS NO: 61220-51-7
• Molecular Formula: C₁₀H₁₀ClNO
• Molecular Weight: 195.65
• Mol File: 61220-51-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 390.7 °C at 760 mmHg
• Flash Point: 190.1 °C
• Appearance: /
• Density: 1.357 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLOROTRYPTOPHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROTRYPTOPHOL(61220-51-7)
• EPA Substance Registry System: 5-CHLOROTRYPTOPHOL(61220-51-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 61220-51-7(Hazardous Substances Data)

Usage

General Description

5-CHLOROTRYPTOPHOL is a chemical compound that belongs to the class of tryptophol derivatives. It is a chlorinated indole derivative containing a hydroxyl group and is known for its sedative and hypnotic effects. 5-CHLOROTRYPTOPHOL has been studied for its potential in treating insomnia and anxiety-related disorders. It is also being investigated for its potential use in the development of new pharmaceuticals. However,

Upstream product

• 13436-46-9 2-ethoxytetrahydrofuran 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 163160-58-5 (5-chloro-1H-indol-3-yl)-oxo-acetic acid ethyl ester 
• 163160-55-2 (5-chloro-1H-indol-3-yl)oxoacetic acid methylester 
• 17422-32-1 5-chloro-1H-indole 
• 883-55-6 2-(5-chloro-1H-indol-3-yl)-2-oxoacetyl chloride 
• 1191-99-7 2,3-dihydro-2H-furan 
• 526-55-6 2-(3-indole)-ethanol 

Downstream Products

• 325773-39-5 3-(2-bromo-ethyl)-5-chloro-1H-indole 
• 1025906-94-8 5-chloro-3-(p-toluenesulfonyloxyethyl)-1-(p-toluenesulfonyl)indole 
• 936252-63-0 5-chloro-3-(2-iodoethyl)-1-(p-toluenesulfonyl)indole 
• 936252-81-2 6-chloro-2-(3''-(5''-chloro-1''-(p-toluenesulfonyl)indolyl)ethyloxy)-3',4',5'-triacetyladenosine 
• 936252-95-8 2-(3-(5-chloro-1-(p-toluenesulfonyl)indolyl)ethyloxy)adenosine 
• 872674-45-8 methyl 4-[2-(5-chloro-1H-indol-3-yl)ethoxy]benzoate 
• 1026938-90-8 C₁₈H₁₅BrClNO₃ 
• 934284-90-9 methyl 4-{2-[2-bromo-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy}benzoate 
• 934284-92-1 4-{2-[2-bromo-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy}benzoic acid 
• 872674-46-9 methyl 4-[2-[5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy]benzoate 
• 850406-55-2 2-(5-chloro-1-methyl-1H-indol-3-yl)-ethanol 
• 1487273-59-5 5-chloro-3-(2-(4-((2,3-dihydro-2-phenylbenzo[b][1,4]dioxin-3-yl)methyl)piperazin-1-yl)ethyl)-1H-indole 
• 898746-66-2 tert-butyl 5-chloro-3-(2-hydroxyethyl)-1H-indole-1-carboxylate 

Relevant articles and documents

Enantioselective Construction of Spirooxindole-Fused Cyclopentanes

The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.

Directed evolution of RebH for catalyst-controlled halogenation of indole C-H bonds

RebH variants capable of chlorinating substituted indoles ortho-, meta-, and para-to the indole nitrogen were evolved by directly screening for altered selectivity on deuterium-substituted probe substrates using mass spectrometry. This systematic approach allowed for rapid accumulation of beneficial mutations using simple adaptive walks and should prove generally useful for altering and optimizing the selectivity of C-H functionalization catalysts. Analysis of the beneficial mutations showed that structure-guided selection of active site residues for targeted mutagenesis can be complicated either by activity/selectivity tradeoffs that reduce the possibility of detecting such mutations or by epistatic effects that actually eliminate the benefits of a mutation in certain contexts. As a corollary to this finding, the precise manner in which the beneficial mutations identified led to the observed changes in RebH selectivity is not clear. Docking simulations suggest that tryptamine binds to these variants as tryptophan does to native halogenases, but structural studies will be required to confirm these models and shed light on how particular mutations impact tryptamine binding. Similar directed evolution efforts on other enzymes or artificial metalloenzymes could enable a wide range of C-H functionalization reactions.

A2 ADENOSINE RECEPTOR AGONISTS

Disclosed are AZB adenosine receptor (AR) agonists of formula (I), in which R1, R2, R3, R4, Z, and n are defined herein. The invention also provides compositions comprising at least one compound of formula I and methods of use thereof, for example, in the treatment of septic shock, cystic fibrosis, restenosis, erectile dysfunction, inflammation, myocardial ischemia, and reperfusion injury.