176242-83-4

Basic information

• Product Name: 1H-Indole, 3-(2-nitroethenyl)-1-(phenylmethyl)-, (E)-
• CAS NO: 176242-83-4
• Molecular Formula: C17H14N2O2
• Molecular Weight: 278.31
• Mol File: 176242-83-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 3-(2-nitroethenyl)-1-(phenylmethyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 3-(2-nitroethenyl)-1-(phenylmethyl)-, (E)-(176242-83-4)
• EPA Substance Registry System: 1H-Indole, 3-(2-nitroethenyl)-1-(phenylmethyl)-, (E)-(176242-83-4)

Safety Data

• Hazardous Substances Data: 176242-83-4(Hazardous Substances Data)

Usage

Molecular weight

308.36 g/mol

Structure

An indole ring with a nitroethenyl group at position 3 and a phenylmethyl group at position 1, with an E conformation of the double bond.

Appearance

Not provided in the material.

Physical properties

Not provided in the material.

Solubility

Not provided in the material.

Molar refractivity

Not provided in the material.

Polarity

Not provided in the material.

Uses

As a precursor for the synthesis of other organic compounds, or for research purposes in the fields of chemistry, pharmacology, or material science.

Purity

Not provided in the material.

Synthesis method

Not provided in the material.

Upstream product

• 75-52-5 nitromethane 
• 10511-51-0 1-Benzylindole-3-carboxaldehyde 
• 487-89-8 Indole-3-carboxaldehyde 
• 120-72-9 indole 
• 3377-71-7 N-benzylindole 
• 73430-27-0 1-dimethylamino-2-nitroethene 
• 100-44-7 benzyl chloride 

Downstream Products

• 1053700-69-8 (3aS,4S,6R,6aR)-6-{6-[2-(1-Benzyl-1H-indol-3-yl)-ethylamino]-purin-9-yl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid cyclopropylamide 
• 79670-27-2 12-(phenylmethyl)-12H-naphtho<2,3-a>carbazole-5,13-dione 
• 79670-29-4 9-benzyl-N'-phenylcarbazole-1,2-dicarboximide 
• 4307-98-6 N-benzyltryptamine 

Relevant articles and documents

Tryptamine derivatives disarm colistin resistance in polymyxin-resistant gram-negative bacteria

The last three decades have seen a dwindling number of novel antibiotic classes approved for clinical use and a concurrent increase in levels of antibiotic resistance, necessitating alternative methods to combat the rise of multi-drug resistant bacteria. A promising strategy employs antibiotic adjuvants, non-toxic molecules that disarm antibiotic resistance. When co-dosed with antibiotics, these compounds restore antibiotic efficacy in drug-resistant strains. Herein we identify derivatives of tryptamine, a ubiquitous biochemical scaffold containing an indole ring system, capable of disarming colistin resistance in the Gram-negative bacterial pathogens Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli while having no inherent bacterial toxicity. Resistance was overcome in strains carrying endogenous chromosomally-encoded colistin resistance machinery, as well as resistance conferred by the mobile colistin resistance-1 (mcr-1) plasmid-borne gene. These compounds restore a colistin minimum inhibitory concentration (MIC) below the Clinical & Laboratory Sciences Institute (CLSI) breakpoint in all resistant strains.

Rhodium-catalyzed asymmetric addition of arylboronic acids to indolylnitroalkenes

Indolylnitroethanes and their derivatives are key intermediates to many bioactive structures. Most approaches to access chiral indolylnitroethanes involve organocatalyzed or metal-catalyzed asymmetric Friedel-Crafts reaction of indoles with nitroalkenes.