147963-22-2

Basic information

• Product Name: 7-AMINO-4-CHLOROMETHYLCOUMARIN
• Synonyms: BLUE CMAC;CELLTRACKER(TM) BLUE CMAC;7-AMINO-4-CHLOROMETHYLCOUMARIN;CellHunt Blue CMAC [7-AMino-4-chloroMethylcouMarin];7-amino-4-(chloromethyl)-2H-chromen-2-one;2H-1-Benzopyran-2-one,7-amino-4-(chloromethyl)-;7-amino-4-(chloromethyl)chromen-2-one
• CAS NO: 147963-22-2
• Molecular Formula: C₁₀H₈ClNO₂
• Molecular Weight: 209.63
• Mol File: 147963-22-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 410.3 °C at 760 mmHg
• Flash Point: 201.9 °C
• Appearance: /
• Density: 1.399 g/cm³
• Vapor Pressure: 6.1E-07mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: 7-AMINO-4-CHLOROMETHYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 7-AMINO-4-CHLOROMETHYLCOUMARIN(147963-22-2)
• EPA Substance Registry System: 7-AMINO-4-CHLOROMETHYLCOUMARIN(147963-22-2)

Safety Data

• Hazardous Substances Data: 147963-22-2(Hazardous Substances Data)

Usage

General Description

7-Amino-4-Chloromethylcoumarin, also known as 4-Chloro-7-AminoMethylCoumarin, is a chemical compound that falls under the category of coumarins and derivatives. This chemical is used primarily in biological research, particularly as a precursor to fluorescent dyes that are used in various biological assessments. The substance has an appearance that ranges from light to dark yellow, and it contains a mixture of hazardous ingredients. The chemical requires precise handling and should be stored in a cool and well-ventilated place. It could cause harmful environmental effects if not disposed of properly.

InChI:InChI=1/C10H8ClNO2/c11-5-6-3-10(13)14-9-4-7(12)1-2-8(6)9/h1-4H,5,12H2

Upstream product

• 591-27-5 m-Hydroxyaniline 
• 62380-38-5 N(hydroxy-3 phenyl) carbamate de phenyle 
• 872167-09-4 7-N-(phenoxycarbonyl)amino-4-chloromethylcoumarin 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 447398-67-6 N-acetyl-7-amino-4-chloromethylcoumarin 
• 1210052-43-9 C₃₁H₄₀ClN₅O₁₂ 
• 7159-96-8 ethyl N-(3-hydroxyphenyl)carbamate 
• 147963-30-2 [4-(chloromethyl)-2-oxo-2H-1-benzopyran-7-yl]-carbamic acid ethyl ester 

Downstream Products

• 873950-20-0 (7-amino-2-oxo-2H-1-benzopyran-4-yl)-methyl acetate 
• 1461656-41-6 tert-butyl 4-((((1-((7-amino-2-oxo-2H-chromen-4-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)thio)carbonothioyl)piperazine-1-carboxylate 

Relevant articles and documents

Targeting of glut5 for transporter-mediated drug-delivery is contingent upon substrate hydrophilicity

Specific link between high fructose uptake and cancer development and progression highlighted fructose transporters as potential means to achieve GLUT-mediated discrimination between normal and cancer cells. The gained expression of fructose-specific transporter GLUT5 in various cancers offers a possibility for developing cancer-specific imaging and bioactive agents. Herein, we explore the feasibility of delivering a bioactive agent through cancer-relevant fructose-specific transporter GLUT5. We employed specific targeting of GLUT5 by 2,5-anhydro-D-mannitol and investigated several drug conjugates for their ability to induce cancer-specific cytotoxicity. The proof-of-concept analysis was carried out for conjugates of chlorambucil (CLB) in GLUT5-positive breast cancer cells and normal breast cells. The cytotoxicity of conjugates was assessed over 24 h and 48 h, and significant dependence between cancer-selectivity and conjugate size was observed. The differences were found to relate to the loss of GLUT5-mediated uptake upon increased conjugate size and hydrophobicity. The findings provide information on the substrate tolerance of GLUT5 and highlight the importance of maintaining appropriate hydrophilicity for GLUT-mediated delivery.

Novel coumarin-based pH sensitive fluorescent probes for the highly alkaline pH region

The design, synthesis and spectroscopic properties of novel polymerizable coumarin-based pH indicators are reported. They show a fluorescence response to pH in the highly alkaline pH region with calculated pKa values in the range of 12.2–12.5. Covalent immobilization of the indicators to polymer supports provides novel pH-sensitive materials that possess excellent photostability. The materials are sensitive to pH in a similar range and can be applied in optical pH sensors for measuring pH in various alkaline media.

Synthesis and biological evaluation of coumarin-1,2,3-triazole- dithiocarbamate hybrids as potent LSD1 inhibitors

Two series of coumarin-1,2,3-triazole-dithiocarbamate hybrids were designed, synthesized and evaluated for their inhibitory activity towards lysine specific demethylase 1 (LSD1). Compounds 8a, 8d-8f, 8i-8l presented potent activity against lysine specific demethylase 1. Among them, compound 8k showed potent and reversible inhibition against lysine specific demethylase 1 with an IC50 value of 0.39 μM, which was 74-fold more potent than that of tranylcypromine (2-PCPA). Besides, compound 8k displayed excellent selectivity against lysine specific demethylase 1 without inhibition against monoamine oxidases (MAOs) A and B. Further investigation revealed that compound 8k was active at both recombinant and cell levels by upregulating the expression of H3K4me1, H3K4me2 and H3K9me2. This journal is the Partner Organisations 2014.