7-Amino-4-methylcoumarin

Base Information

• Chemical Name: 7-Amino-4-methylcoumarin
• CAS No.: 26093-31-2
• Deprecated CAS: 53095-32-2,54576-76-0,79818-52-3
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 32049000
• European Community (EC) Number: 247-454-8
• NSC Number: 45796
• UNII: OCY3JCT44X
• DSSTox Substance ID: DTXSID40885333
• Nikkaji Number: J150.531I
• Wikidata: Q27097396
• Metabolomics Workbench ID: 73965
• ChEMBL ID: CHEMBL270672
• Mol file: 26093-31-2.mol

Synonyms:4-methyl-7-aminocoumarin;7-amino-4-methylcoumarin;7-amino-4-methylcoumarin, conjugate monoacid;coumarin 120;coumarin C440;coumarin, 7-amino-4-methyl-

Chemical Property of 7-Amino-4-methylcoumarin

Chemical Property:

• Appearance/Colour: Yellow powder.
• Vapor Pressure: 6.37E-06mmHg at 25°C
• Melting Point: 223-226 °C(lit.)
• Refractive Index: 1.627
• Boiling Point: 378.3 °C at 760 mmHg
• PKA: 1.89 ± 0.20, most basic, temperature: 25 °C
• Flash Point: 216.9 °C
• PSA: 56.23000
• Density: 1.275 g/cm³
• LogP: 2.26480
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in acetone (10 mg/ml) dimethyl sulfoxide (10 mg/ml) and
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 260

Purity/Quality:

99% ^*data from raw suppliers

7-Amino-4-methylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Coumarin Dyes
• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)N
• Uses: Coumarin 120 is widely used fluorophore, well-known for preparing fluorogenic substrates for cystine aminopeptidase and other hydrolases. Used as reference compound in enzyme assays. suitable for determining polygalacturonase activity λ max 354 nm in EthanolSuitable as laser dye and used as a fluorescent labeling reagent for trace determination of enzymes.

Technology Process of 7-Amino-4-methylcoumarin

There total 130 articles about 7-Amino-4-methylcoumarin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl acetoacetate (141-97-9) + m-Hydroxyaniline (591-27-5) → 7-amino-4-methylcoumarin. (26093-31-2)

Guidance literature:

With zirconium(IV) phosphate; at 110 ℃; for 0.166667h; chemoselective reaction; Microwave irradiation;

DOI:10.1016/j.apcata.2010.12.027

Reference yield: 99.0%

(4-methyl-2-oxo-2H-1-benzopyran-7-yl)carbamic acid ethyl ester (58632-48-7) → 7-amino-4-methylcoumarin. (26093-31-2)

Guidance literature:

With sulfuric acid; In acetic acid; at 120 ℃; for 4h; Reflux;

Reference yield: 93.0%

7-azido-4-methyl-2H-chromen-2-one → 7-amino-4-methylcoumarin. (26093-31-2)

Guidance literature:

7-azido-4-methyl-2H-chromen-2-one; With 9-phenyl-9-phosphafluorene; phenylsilane; In 1,4-dioxane; at 101 ℃; for 16h; Inert atmosphere;

With water; In 1,4-dioxane; at 20 ℃; Inert atmosphere;

DOI:10.1002/adsc.201100967

upstream raw materials:

N-(4-methyl-2-oxo-2H-chromen-7-yl)acetamide

ethyl acetoacetate

m-Hydroxyaniline

-butyl vinyl ether

Downstream raw materials:

C₃₇H₄₁N₅O₉

N-(4-methyl-7-coumarinyl)-N-α-(tert-butyloxycarbonyl)-lysinamide

4-methylcoumarin-7-phenylcarbamate

7-[ethyl-(4-methanesulfonylphenyl)amino]-4-methylcoumarin

Refernces

• 1、 Knuettel, Torsten,Meyer, Hartmut,Scheper, Thomas. "Application of 2D-fluorescence spectroscopy for on-line monitoring of pseudoenantiomeric transformations in supercritical carbon dioxide systems". . p. 6184 - 6189. Retrieved 2005.
• 2、 Kiani, Mahtab,Karami, Bahador. "Synthesis of Novel and Thermally Stable Water Insoluble Coumarin-based Azo Dyes via a Mild and Green Procedure". . p. 756 - 760. Retrieved 2015.
• 3、 Zeng,Pan,Tan,Xiong,Zhang. "Natural biflavones as?novel inhibitors of?cathepsin B and?K". . p. 1247 - 1252. Retrieved 2006.
• 4、 Zhu, Bei-Wei,Zhao, Lu-Lu,Sun, Li-Ming,Li, Dong-Mei,Murata, Yoshiyuki,Yu, Lei,Zhang, Lei. "Purification and characterization of a cathepsin L-like enzyme from the body wall of the sea cucumber Stichopus japonicus". . p. 1430 - 1437. Retrieved 2008.
• 5、 Peyret, Ariane,Ibarboure, Emmanuel,Tron, Arnaud,Beauté, Louis,Rust, Ruben,Sandre, Olivier,McClenaghan, Nathan D.,Lecommandoux, Sebastien. "Polymersome Popping by Light-Induced Osmotic Shock under Temporal, Spatial, and Spectral Control". . p. 1566 - 1570. Retrieved 2017.
• 6、 Fan, Long. "Synthesis of Two Coumarin-Derived Schiff Bases and Investigation of theirs Selectivity for Zn2+". . p. 1331 - 1337. Retrieved 2017.
• 7、 Karami, Bahador,Kiani, Mahtab. "Application of 7-amino coumarins for the synthesis of novel and thermally stable water-insoluble azo-coumarin dyes". . p. 111 - 116. Retrieved 2016.
• 8、 Yamamoto, Shuhei,Otsuka, Yuichi,Borjigin, Gerelt,Masuda, Kanna,Ikeuchi, Yoshihide,Nishiumi, Tadayuki,Suzuki, Atsushi. "Effects of a high-pressure treatment on the activity and structure of rabbit muscle proteasome". . p. 1239 - 1247. Retrieved 2005.
• 9、 Henthorn, Hillary A.,Pluth, Michael D.. "Mechanistic Insights into the H2S-Mediated Reduction of Aryl Azides Commonly Used in H2S Detection". . p. 15330 - 15336. Retrieved 2015.
• 10、 Hosta-Rigau, Leticia,Chung, Shiow Fong,Postma, Almar,Chandrawati, Rona,Staedler, Brigitte,Caruso, Frank. "Capsosomes with "free-Floating" Liposomal Subcompartments". . p. 4082 - 4087. Retrieved 2011.