7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN

Base Information

• Chemical Name: 7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN
• CAS No.: 575-03-1
• Molecular Formula: C10H5F3O3
• Molecular Weight: 230.143
• Hs Code.: 29322090
• European Community (EC) Number: 624-706-9
• NSC Number: 138174
• DSSTox Substance ID: DTXSID80206109
• Nikkaji Number: J655.930A
• Wikidata: Q72482042
• Pharos Ligand ID: 1CMQ2KAHRSDN
• Metabolomics Workbench ID: 74327
• ChEMBL ID: CHEMBL104679
• Mol file: 575-03-1.mol

Synonyms:4-(Trifluoromethyl)-7-hydroxycoumarin;4-(Trifluoromethyl)umbelliferone;7-Hydroxy-4-(trifluoromethyl)-2H-chromen-2-one;7-Hydroxy-4-(trifluoromethyl)coumarin;NSC 138174;

Chemical Property of 7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN

Chemical Property:

• Appearance/Colour: Off-white to light yellow or pink powder
• Vapor Pressure: 0.000308mmHg at 25°C
• Melting Point: 178-180 °C(lit.)
• Refractive Index: 1.546
• Boiling Point: 311.4 °C at 760 mmHg
• PKA: 7.23±0.20(Predicted)
• Flash Point: 142.2 °C
• PSA: 50.44000
• Density: 1.569 g/cm³
• LogP: 2.51740
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMF: soluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 230.01907850
• Heavy Atom Count: 16
• Complexity: 335

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): T
• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)OC(=O)C=C2C(F)(F)F
• Uses: Suitable as pH-indicator. Trifluoromethylumbelliferone is a slightly longer wavelength analog of 4-methylcoumarin (4-MU) with a pKa that more closely matches physiological pH values. 7-Hydroxy-4-(trifluoromethyl)coumarin is an halogenated metabolite of Coumarin (C755380), an naturally occurring organic compound that exists in many plants. Coumarin is the precursor molecule in the synthesis of various synthetic anti-coagulant such as warfarin (W498500)/.

Technology Process of 7-HYDROXY-4-(TRIFLUOROMETHYL)COUMARIN

There total 17 articles about 7-HYDROXY-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: 99.0%

ethyl 4,4,4-trifluoroacetoacetate (372-31-6) + recorcinol (108-46-3) → 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one (575-03-1)

Guidance literature:

With iodine; In toluene; at 80 ℃;

DOI:10.1080/00397910600773692

Reference yield: 80.0%

ethyl 4,4,4-trifluoroacetoacetate (372-31-6) + recorcinol (108-46-3) → C14H4F6O4 + 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one (575-03-1)

Guidance literature:

3 A molecular sieve; at 120 ℃; Product distribution / selectivity;

Reference yield:

7-ethoxy-4-trifluoromethyl-chromen-2-one (115453-82-2) → 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one (575-03-1)

Guidance literature:

With human cytochrome P₄₅₀₁B₁ cDNA microsomes; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1093/mutage/12.2.83

upstream raw materials:

ethyl 4,4,4-trifluoroacetoacetate

recorcinol

7-ethoxy-4-trifluoromethyl-chromen-2-one

7-benzyloxy-4-trifluoromethylcoumarin

Downstream raw materials:

7-Methoxy-4-(trifluoromethyl)coumarin

7-hydroxy-8-n-propyl-4-(trifluoromethyl)-2H-chromen-2-one

C₁₃H₁₂F₃O₅P

C₁₄H₁₄F₃O₅P

Refernces

• 1、 Emmadi, Narender Reddy,Atmakur, Krishnaiah,Chennapuram, Madhu,Nanubolu, Jagadeesh Babu. "Synthesis of amidoalkyl chromen-2-ones by one pot three component reaction under solvent free conditions". . p. 14501 - 14506. Retrieved 2014.
• 2、 Jiao, Jia,Wu, Hongshuai,Chen, Fanghui,Chen, Renjie,Sun, Baiwang,Wang, Mingliang. "Delivery of coumarin-containing all-: Trans retinoic acid derivatives via targeted nanoparticles encapsulating indocyanine green for chemo/photothermal/photodynamic therapy of breast cancer". . p. 8805 - 8814. Retrieved 2018.
• 3、 Qiao, Lili,Hao, Shuanghong. "Novel trifluoromethylcoumarinyl urea derivatives: Synthesis, characterization, fluorescence, and bioactivity". . . Retrieved 2018.
• 4、 Crespi, Charles L.,Penman, Bruce W.,Steimel, Dorothy T.,Smith, Theresa,Yang, Chung S.,Sutter, Thomas R.. "Development of a human lymphoblastoid cell line constitutively expressing human CYP1B1 cDNA: Substrate specificity with model substrates and promutagens". . p. 83 - 89. Retrieved 1997.
• 5、 Cisse, Lamine,Djande, Abdoulaye,Capo-Chichi, Martine,Delatre, Franois,Saba, Adama,Tine, Alphonse,Aaron, Jean-Jacques. "Revisiting the photophysical properties and excited singlet-state dipole moments of several coumarin derivatives". . p. 428 - 436. Retrieved 2011.
• 6、 Kecel-Gunduz, Serda,Budama-Kilinc, Yasemin,Gok, Bahar,Bicak, Bilge,Akman, Gizem,Arvas, Busra,Aydogan, Feray,Yolacan, Cigdem. "Computer-aided anticancer drug design: In vitro and in silico studies of new iminocoumarin derivative". . . Retrieved 2021.
• 7、 Chai, Xin,Duan, Mojie,Fu, Weitao,Gong, Zhou,Hou, Tingjun,Lei, Yixuan,Li, Dan,Liao, Jianing,Pang, Jinping,Shan, Luhu,Sheng, Rong,Tang, Chun,Tang, Qing,Wang, Xuwen,Xu, Xiaohong,Zhang, Minkui. "Discovery of a Novel Androgen Receptor Antagonist Manifesting Evidence to Disrupt the Dimerization of the Ligand-Binding Domain via Attenuating the Hydrogen-Bonding Network between the Two Monomers". . p. 17221 - 17238. Retrieved 2021/12/06.