22272-32-8

Basic information

• Product Name: 2-(sec-Butylamino)-3-chloro-1,4-naphthoquinone
• Synonyms: 2-(sec-Butylamino)-3-chloro-1,4-naphthoquinone
• CAS NO: 22272-32-8
• Molecular Formula: C14H14 Cl N O2
• Molecular Weight: 0
• Mol File: 22272-32-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 359.5°C at 760 mmHg
• Flash Point: 171.2°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 2.37E-05mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 2-(sec-Butylamino)-3-chloro-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(sec-Butylamino)-3-chloro-1,4-naphthoquinone(22272-32-8)
• EPA Substance Registry System: 2-(sec-Butylamino)-3-chloro-1,4-naphthoquinone(22272-32-8)

Safety Data

• Hazardous Substances Data: 22272-32-8(Hazardous Substances Data)

Usage

General Description

2-(sec-Butylamino)-3-chloro-1,4-naphthoquinone, also known as Chloranil Red, is a chemical compound commonly used in the production of dyes and pigments. It is a red-brown crystalline powder with a molecular formula of C14H11ClO2N and a molecular weight of 261.69 g/mol. 2-(sec-Butylamino)-3-chloro-1,4-naphthoquinone is known for its ability to undergo oxidation-reduction reactions and is often used as an oxidizing agent in organic synthesis. It is also used as a dye in various applications, such as coloring textiles and inks. However, 2-(sec-Butylamino)-3-chloro-1,4-naphthoquinone is known to be a skin and eye irritant, and exposure to high levels can cause respiratory irritation and damage to the central nervous system. Therefore, proper safety precautions must be taken when handling this chemical.

InChI:InChI=1/C14H14ClNO2/c1-3-8(2)16-12-11(15)13(17)9-6-4-5-7-10(9)14(12)18/h4-8,16H,3H2,1-2H3

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 33966-50-6 SEC-BUTYLAMINE 

Relevant articles and documents

Functionalized Dioxonaphthoimidazoliums: A Redox Cycling Chemotype with Potent Bactericidal Activities against Mycobacterium tuberculosis

Disruption of redox homeostasis in mycobacteria causes irreversible stress induction and cell death. Here, we report the dioxonaphthoimidazolium scaffold as a novel redox cycling antituberculosis chemotype with potent bactericidal activity against growing and nutrient-starved phenotypically drug-resistant nongrowing bacteria. Maximal potency was dependent on the activation of the redox cycling quinone by the positively charged scaffold and accessibility to the mycobacterial cell membrane as directed by the lipophilicity and conformational characteristics of the N-substituted side chains. Evidence from microbiological, biochemical, and genetic investigations implicates a redox-driven mode of action that is reliant on the reduction of the quinone by type II NADH dehydrogenase (NDH2) for the generation of bactericidal levels of the reactive oxygen species (ROS). The bactericidal profile of a potent water-soluble analogue 32 revealed good activity against nutrient-starved organisms in the Loebel model of dormancy, low spontaneous resistance mutation frequency, and synergy with isoniazid in the checkerboard assay.