6,8-Difluoro-7-hydroxy-4-methylcoumarin

Base Information

• Chemical Name: 6,8-Difluoro-7-hydroxy-4-methylcoumarin
• CAS No.: 215868-23-8
• Molecular Formula: C10H6F2O3
• Molecular Weight: 212.153
• DSSTox Substance ID: DTXSID901318263
• Nikkaji Number: J1.656.590C
• Wikidata: Q27122705
• Metabolomics Workbench ID: 57829
• ChEMBL ID: CHEMBL107323
• Mol file: 215868-23-8.mol

Synonyms:6,8-difluoro-4-methylumbelliferone;6,8-difluoro-4-methylumbelliferyl sulfate;DiFMUS

Chemical Property of 6,8-Difluoro-7-hydroxy-4-methylcoumarin

Chemical Property:

• Melting Point: 213-215°C
• Boiling Point: 332.3±42.0 °C(Predicted)
• PKA: 4.7, (at 22℃) (calcd.) 5.50 ± 0.20, most acidic, temperature: 25 °C
• PSA: 50.44000
• Density: 1.494±0.06 g/cm3(Predicted)
• LogP: 2.08520
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Insoluble in water; soluble in chloroform, N,N-dimethylformamide, dimethyl sulfoxide
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 212.02850037
• Heavy Atom Count: 15
• Complexity: 316

Purity/Quality:

98.5% ^*data from raw suppliers

6,8-Difluoro-7-hydroxy-4-methylcoumarin(DIFMU) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C(C(=C(C=C12)F)O)F
• Uses: 6,8-Difluoro-7-hydroxy-4-methylcoumarin (DIFMU) was used for the diagnostic detection of natural killer cell-activity.

Technology Process of 6,8-Difluoro-7-hydroxy-4-methylcoumarin

There total 9 articles about 6,8-Difluoro-7-hydroxy-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: 84.0%

ethyl acetoacetate (141-97-9) + 2,4-difluorobenzene-1,3-diol (195136-71-1) → 6,8-difluoro-7-hydroxy-4-methyl-2H-chromen-2-one (215868-23-8)

Guidance literature:

In methanesulfonic acid; at 0 - 20 ℃; for 28.33h;

DOI:10.1002/anie.201102965

Reference yield:

6,8-difluoro-4-methyl-2-oxo-2H-chromen-7-yl octanoate → Octanoic acid (124-07-2) + 6,8-difluoro-7-hydroxy-4-methyl-2H-chromen-2-one (215868-23-8)

Guidance literature:

With PS-PIAT; Candida antarctica lipase B; In phosphate buffer; for 0.0166667h; pH=7.2; Enzyme kinetics;

DOI:10.1002/anie.200701125

Reference yield:

6,8-difluoro-4-methyl-2-oxo-2H-chromen-7-yl octanoate → 6,8-difluoro-7-hydroxy-4-methyl-2H-chromen-2-one (215868-23-8)

Guidance literature:

With lipase B from Candida antarctica; In phosphate buffer; dimethyl sulfoxide; at 25 ℃; pH=6.8;

DOI:10.1021/ja017809b

upstream raw materials:

ethyl acetoacetate

2,4-difluorobenzene-1,3-diol

1,2,3,4-tetrafluorobenzene

1,3-difluoro-2,4-dimethoxy-5-nitrobenzene

Downstream raw materials:

6,8-difluoro-7-ethoxy-4-methylcoumarin

6,8-difluoro-O-(4,5-dimethoxy-2-nitrobenzyl)-7-hydroxy-4-methylcoumarin

Refernces

• 1、 Velonia, Kelly,Rowan, Alan E.,Nolte, Roeland J. M.. "Lipase polystyrene giant amphiphiles". . p. 4224 - 4225. Retrieved 2002.
• 2、 -. "FLUORINATED 4' ALKYLUMBELLIFERYL α-D-GLUCOPYRANOSIDES, BIOLOGICAL STERILIZATION INDICATORS INCLUDING THE SAME AND METHODS OF USING THE SAME". Page/Page column 60; 62. . Retrieved 2020/07/05.
• 3、 Dubiella, Christian,Cui, Haissi,Groll, Michael. "Tunable Probes with Direct Fluorescence Signals for the Constitutive and Immunoproteasome". supporting information. p. 13330 - 13334. Retrieved 2016/10/30.