7-Amino-4-(trifluoromethyl)coumarin

Base Information

• Chemical Name: 7-Amino-4-(trifluoromethyl)coumarin
• CAS No.: 53518-15-3
• Molecular Formula: C10H6F3NO2
• Molecular Weight: 229.158
• Hs Code.: 29322090
• European Community (EC) Number: 258-599-1
• NSC Number: 337981
• UNII: P5QQ8K4F5Q
• DSSTox Substance ID: DTXSID0068862
• Nikkaji Number: J236.240F
• Wikidata: Q27122739
• ChEMBL ID: CHEMBL1301731
• Mol file: 53518-15-3.mol

Synonyms:7-amino-4-trifluoromethylcoumarin;7-ATFMC;ATFMC cpd

Chemical Property of 7-Amino-4-(trifluoromethyl)coumarin

Chemical Property:

• Appearance/Colour: yellow powder
• Melting Point: 221-222 ºC
• Boiling Point: 314.6°Cat760mmHg
• PKA: 1.12±0.20(Predicted)
• Flash Point: 144.1°C
• PSA: 56.23000
• Density: 1.523g/cm³
• LogP: 2.97520
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility.: Soluble in dimethyl sulfoxide (25 mg/ml), dimethyl formamide (25 mg/ml), and methanol (25 mg/ml). Insoluble in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 229.03506292
• Heavy Atom Count: 16
• Complexity: 337

Purity/Quality:

99% ^*data from raw suppliers

7-Amino-4-(trifluoromethyl)coumarin ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Coumarin Dyes
• Canonical SMILES: C1=CC2=C(C=C1N)OC(=O)C=C2C(F)(F)F
• Uses: Coumarin 151 is used to prepare peptidase substrates and for the synthesis of substrates for the fluorometric assay of proteolytic enzymes in biological fluids. 7-Amino-4-(trifluoromethyl)coumarin is used in the synthesis of substrates for the fluorometric assay of proteolytic enzymes in biological fluids. It is suitable as laser dye.

Technology Process of 7-Amino-4-(trifluoromethyl)coumarin

There total 27 articles about 7-Amino-4-(trifluoromethyl)coumarin 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: 98.0%

ethyl 4,4,4-trifluoroacetoacetate (372-31-6) + m-Hydroxyaniline (591-27-5) → Coumarin 151 (53518-15-3)

Guidance literature:

With magnesium bis(trifluoromethane solfonyl)imide; In neat (no solvent); at 80 ℃; for 0.416667h;

DOI:10.1007/s00706-012-0823-4

Reference yield: 85.0%

ethyl 4,4,4-trifluoroacetoacetate (372-31-6) + m-Hydroxyaniline (591-27-5) → 7-hydroxy-4-(trifluoromethyl)-2(1H)-quinolinone (73496-29-4) + Coumarin 151 (53518-15-3)

Guidance literature:

indium(III) chloride; at 65 ℃; for 0.5h;

DOI:10.1016/S0040-4039(02)02266-9

Reference yield: 46.0%

7-(Carbethoxyamido)-4-(trifluoromethylcoumarin) (63450-46-4) → Coumarin 151 (53518-15-3)

Guidance literature:

7-(Carbethoxyamido)-4-(trifluoromethylcoumarin); With sulfuric acid; acetic acid; for 4h; Reflux;

With sodium hydroxide; In water; Cooling;

DOI:10.1016/j.bmc.2011.11.016

upstream raw materials:

ethyl 4,4,4-trifluoroacetoacetate

m-Hydroxyaniline

C₃₁H₃₈F₃N₅O₁₂

7-(Carbethoxyamido)-4-(trifluoromethylcoumarin)

Downstream raw materials:

7-(N^α-Boc-N^ε-Z-L-lysinamido)-4-(trifluoromethyl)-coumarin

7-(N^α-Z-L-Argininamido)-4-(trifluoromethyl)-coumarin Hydrochloride

7-(N^α-Z-L-Argininamido)-4-(trifluoromethyl)coumarin Hydrobromide

7-(N^α-Z-N^ε-Boc-L-Lysinamido)-4-(trifluoromethyl)-coumarin

Refernces

• 1、 Wang, Xin,Li, Ping,Ding, Qi,Wu, Chuanchen,Zhang, Wen,Tang, Bo. "Illuminating the Function of the Hydroxyl Radical in the Brains of Mice with Depression Phenotypes by Two-Photon Fluorescence Imaging". . p. 4674 - 4678. Retrieved 2019.
• 2、 -. "Benzopyrone or quinolinone compound and application thereof". Paragraph 0163-0165. . Retrieved 2020/08/25.