87-01-4

Basic information

• Product Name: 7-Dimethylamino-4-methylcoumarin
• Synonyms: 2H-1-Benzopyran-2-one, 7-(dimethylamino)-4-methyl-;7-(DIMETHYLAMINO)-4-METHYLCOUMARIN, 95.0+%(GC)(T);7-(N,N-Dimethylamino)-4-methyl-2H-1-benzopyran-2-one;Calcofluor White LD;7-(dimethylamino)-4-methyl-2h-1-benzopyran-2-on;7-(dimethylamino)-4-methyl-2H-1-Benzopyran-2-one;7-(Dimethylamino)-4-methyl-2H-chromen-2-one;7-dimethylamino-4-methyl-coumari
• CAS NO: 87-01-4
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• EINECS: 201-717-3
• Mol File: 87-01-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 144-146°C
• Boiling Point: 341.55°C (rough estimate)
• Flash Point: 153.2oC
• Appearance: /
• Density: 1.1255 (rough estimate)
• Vapor Pressure: 1.24E-05mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.91±0.20(Predicted)
• CAS DataBase Reference: 7-Dimethylamino-4-methylcoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Dimethylamino-4-methylcoumarin(87-01-4)
• EPA Substance Registry System: 7-Dimethylamino-4-methylcoumarin(87-01-4)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-36/37/39-36-26
• RTECS: GN6650000
• Hazardous Substances Data: 87-01-4(Hazardous Substances Data)

Usage

General Description

7-Dimethylamino-4-methylcoumarin, also known as DMMC, is a bright yellow fluorescent dye commonly used as a tracer in biochemical assays and as a fluorogenic substrate for proteases. It is a synthetic compound that belongs to the coumarin family and contains a dimethylamino group as well as a methyl group which contribute to its fluorescent properties. DMMC has been used in various applications such as DNA sequencing, enzyme activity assays, and organic synthesis. Its fluorescent properties make it a valuable tool for studying biological processes and detecting specific molecules in biological systems. Due to its versatility and sensitivity, DMMC is widely utilized in research and diagnostic settings.

InChI:InChI=1/C12H13NO2/c1-8-6-12(14)15-11-7-9(13(2)3)4-5-10(8)11/h4-7H,1-3H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 99-07-0 3-Dimethylaminophenol 
• 141-78-6 ethyl acetate 
• 506-59-2 N,N-dimethylammonium chloride 
• 878672-65-2 4-methyl-2-oxo-2H-benzopyran-7-yltrifluoromethanesulfonate 
• 26093-31-2 7-amino-4-methylcoumarin. 
• 74-88-4 methyl iodide 

Downstream Products

• 107070-69-9 1-(4-(dimethylamino)-2-hydroxyphenyl)ethanone 
• 99-07-0 3-Dimethylaminophenol 

Relevant articles and documents

Enantioselective Synthesis and Application of Small and Environmentally Sensitive Fluorescent Amino Acids for Probing Biological Interactions

Environmentally sensitive fluorescent amino acids (FlAAs) have been used extensively to probe biological interactions. However, most of these amino acids are large and do not resemble amino acid side chains. Here, we report the enantioselective synthesis of two small and environmentally sensitive fluorescent amino acids bearing 7-dialkylaminocoumarin side chains by alkylation of a Ni(II) glycine Schiff base complex. These amino acids exhibit a large increase in fluorescence as environment polarity decreases. One of these FLAAs was incorporated into a highly active analog of the cyclic lipopeptide antibiotic paenibacterin by Fmoc solid-phase peptide synthesis via a new and very efficient route. This peptide was used to probe the interaction of the antibiotic with model liposomes, lipopolysaccharides, and live bacteria.

A General Strategy to Enhance Donor-Acceptor Molecules Using Solvent-Excluding Substituents

While organic donor-acceptor (D-A) molecules are widely employed in multiple areas, the application of more D-A molecules could be limited because of an inherent polarity sensitivity that inhibits photochemical processes. Presented here is a facile chemical modification to attenuate solvent-dependent mechanisms of excited-state quenching through addition of a β-carbonyl-based polar substituent. The results reveal a mechanism wherein the β-carbonyl substituent creates a structural buffer between the donor and the surrounding solvent. Through computational and experimental analyses, it is demonstrated that the β-carbonyl simultaneously attenuates two distinct solvent-dependent quenching mechanisms. Using the β-carbonyl substituent, improvements in the photophysical properties of commonly used D-A fluorophores and their enhanced performance in biological imaging are shown.

A novel fluorescent thiol reagent: syntheses and electronic spectra of N-(7-dimethylamino-4-methyl-3-coumarinyl)-maleimide (DACM-3) and the related compounds

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