35308-87-3

Basic information

• Product Name: 4-(oxiranylmethoxy)-1H-indole
• Synonyms: 4-(Oxiranylmethoxy)indole;1,2-epoxy-3-(indol-4-yloxy)propane;4-(oxiran-2-ylmethoxy)-1H-indole;4-(oxiranylmethoxy)-1H-indole;4-(2,3-EPOXYPROPOXY)INDOLE
• CAS NO: 35308-87-3
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21054
• EINECS: 252-506-8
• Mol File: 35308-87-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: 64-66 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 381.2°Cat760mmHg
• Flash Point: 138.6°C
• Appearance: /
• Density: 1.294g/cm³
• Vapor Pressure: 1.13E-05mmHg at 25°C
• Refractive Index: 1.661
• PKA: 17.10±0.30(Predicted)
• CAS DataBase Reference: 4-(oxiranylmethoxy)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(oxiranylmethoxy)-1H-indole(35308-87-3)
• EPA Substance Registry System: 4-(oxiranylmethoxy)-1H-indole(35308-87-3)

Safety Data

• Hazardous Substances Data: 35308-87-3(Hazardous Substances Data)

Usage

General Description

4-(oxiranylmethoxy)-1H-indole is a chemical compound consisting of an oxiranylmethoxy group attached to a 1H-indole ring. It is commonly referred to as an indole derivative and is often used in pharmaceutical and chemical research due to its potential therapeutic applications. The oxiranylmethoxy group, also known as the epoxy group, has a cyclic three-membered ring containing one oxygen atom and is often utilized in organic synthesis and as a reactive functional group in various chemical reactions. The presence of the oxiranylmethoxy group in 4-(oxiranylmethoxy)-1H-indole suggests possible reactivity and biological activity, making this compound a subject of interest for further study and exploration.

InChI:InChI=1/C11H11NO2/c1-2-10-9(4-5-12-10)11(3-1)14-7-8-6-13-8/h1-5,8,12H,6-7H2

Upstream product

• 2380-94-1 1H-indol-4-ol 
• 106-89-8 epichlorohydrin 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 67843-74-7 (S)-epichlorohydrin 
• 3132-64-7 1,2-Epoxy-3-bromopropane 

Downstream Products

• 102573-77-3 carvedilol 
• 102573-82-0 1-(4-Fluoro-benzylamino)-3-(1H-indol-4-yloxy)-propan-2-ol 
• 39731-09-4 4-benzyloxylindole-2-carboxylic acid 
• 73907-82-1 4-(2,3-epoxypropoxy)-1H-indol-2-carbonitrile 
• 26328-11-0 (S)-pindolol 
• 1335302-85-6 (+/-)-benzyl 2-(2-(2-(3-(1H-indol-4-yloxy)-2-hydroxypropylamino)ethoxy)ethoxy)ethylcarbamate 
• 1335302-83-4 (+/-)-benzyl 2-(2-hydroxy-3-(1H-indol-4-yloxy)propylamino)ethylcarbamate 
• 946845-13-2 (2RS)-1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol 
• 111794-59-3 3-[2-Hydroxy-3-(1H-indol-4-yloxy)-propylamino]-N-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-propionamide 
• 674774-67-5 N-Boc-wrenchnolol 
• 674774-66-4 [3-([1'-(adamantane-1-carbonyl)-[4,4']bipiperidinyl-1-carbonyl]-{2-hydroxy-3-[1-(toluene-4-sulfonyl)-1H-indol-4-yloxy]-propyl}-amino)-propyl]-carbamic acid tert-butyl ester 
• 674774-63-1 N-[3-(N-tosyl-4-indolyloxy)-2-hydroxypropyl]-N'-Boc-1,5-pentanediamine 
• 674774-62-0 N-[3-(N-tosyl-4-indolyloxy)-2-hydroxypropyl]-N'-Boc-1,3-propanediamine 
• 127414-58-8 1-(4-indolyloxy)-3-cyclohexylamino-2-propanol 

Relevant articles and documents

Chemoenzymatic synthesis of (S)-Pindolol using lipases

A straightforward chemoenzymatic synthesis of (S)-Pindolol has been developed. The key step involved the enzymatic kinetic resolution of rac-2-acetoxy-1-(1H-indol-4-yloxy)-3-chloropropane with lipase from Pseudomonas fluorescens via hydrolytic process to obtain enantiomerically enriched halohydrin (2S)-1-(1H-indol-4-yloxy)-3-chloro-2-propanol (96% ee) and (2R)-2-acetoxy-1-(1H-indol-4-yloxy)-3-chloropropane (97% ee). The latter was subjected to a hydrolysis reaction catalyzed by Candida rugosa leading to (2R)-1-(1H-indol-4-yloxy)-3-chloro-2-propanol (97% ee), followed by a reaction with isopropylamine, producing (S)-Pindolol (97% ee) in quantitative yield.

STORE OVERLOAD-INDUCED CALCIUM RELEASE INHIBITORS AND METHODS FOR PRODUCING AND USING THE SAME

The present invention provides compounds having store overload-induced Ca2+ release (SOICR) inhibitory activity and methods for producing and using the same. In particular, compounds of the invention is of the formula: R1-X1-L-X2-R2, wherein R1, X1, L, X2, and R2 are those defined herein.

Synthesis and characterization of high-affinity 4,4-difluoro-4-bora-3a,4a- diaza-s-indacene-labeled fluorescent ligands for human β-adrenoceptors

The growing practice of exploiting noninvasive fluorescence-based techniques to study G protein-coupled receptor pharmacology at the single cell and single molecule level demands the availability of high-quality fluorescent ligands. To this end, this study evaluated a new series of red-emitting ligands for the human β-adrenoceptor family. Upon the basis of the orthosteric ligands propranolol, alprenolol, and pindolol, the synthesized linker-modified congeners were coupled to the commercially available fluorophore BODIPY 630/650-X. This yielded high-affinity β-adrenoceptor fluorescent ligands for both the propranolol and alprenolol derivatives; however, the pindolol-based products displayed lower affinity. A fluorescent diethylene glycol linked propranolol derivative (18a) had the highest affinity (log KD of -9.53 and -8.46 as an antagonist of functional β2- and β1-mediated responses, respectively). Imaging studies with this compound further confirmed that it can be employed to selectively label the human β2-adrenoceptor in single living cells, with receptor-associated binding prevented by preincubation with the nonfluorescent β2-selective antagonist 3-(isopropylamino)-1-[(7- methyl-4-indanyl)oxy]butan-2-ol (ICI 118551) (J. Cardiovasc. Pharmacol.1983, 5, 430-437.)