4'-Hydroxycelecoxib

Base Information

• Chemical Name: 4'-Hydroxycelecoxib
• CAS No.: 170571-00-3
• Molecular Formula: C17H14F3N3O3S
• Molecular Weight: 397.378
• UNII: 1DIW8DT7Q3
• DSSTox Substance ID: DTXSID60432707
• Nikkaji Number: J1.322.028J
• Wikidata: Q27252289
• Metabolomics Workbench ID: 42554
• ChEMBL ID: CHEMBL745
• Mol file: 170571-00-3.mol

Synonyms:4'-Hydroxycelecoxib;Hydroxy Celecoxib;170571-00-3;hydroxycelecoxib;Celecoxib metabolite M3;HYDROXYMETHYL CELECOXIB;UNII-1DIW8DT7Q3;1DIW8DT7Q3;4-[5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide;PRIMARY ALCOHOL METABOLITE OF CELECOXIB;CHEMBL745;4-(5-(4-Hydroxymethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide;4-[5-[4-(Hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide;Benzenesulfonamide, 4-(5-(4-(hydroxymethyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)-;4-[5-(4-Hydroxymethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide;Hydroxymethylcelecoxib;4/'-Hydroxycelecoxib;D0T4VL;SCHEMBL6013984;DTXSID60432707;BCP33839;BDBM50057538;AKOS037645576;AS-6155;FT-0669774;J-010631;Q27252289;4-[5-(4-Hydroxymethyl-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-benzenesulfonamide;4-[5-(4-Hydroxymethylphenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide;4-[5-[4-(Hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]-benzenesulfonamide;4-{5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl}benzene-1-sulfonamide;Hydroxycelecoxib;4-(5-(4-(Hydroxymethyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide;Hydroxymethylcelecoxib (4-[5-[4-(Hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide);Hydroxymethylcelecoxib (4-[5-[4-(Hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide) 1.0 mg/ml in Methanol

Chemical Property of 4'-Hydroxycelecoxib

Chemical Property:

• Melting Point: 157-158℃ (benzene )
• Boiling Point: 584.6±60.0 °C(Predicted)
• PKA: 9.67±0.10(Predicted)
• PSA: 106.59000
• Density: 1.50±0.1 g/cm3(Predicted)
• LogP: 4.47890
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 397.07079698
• Heavy Atom Count: 27
• Complexity: 595

Purity/Quality:

98%min ^*data from raw suppliers

HydroxyCelecoxib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CO)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
• Uses: A metabolite of Celecoxib (C251000).

Technology Process of 4'-Hydroxycelecoxib

There total 9 articles about 4'-Hydroxycelecoxib 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: 81.0%

4-(5-(4-formylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide → Methylhydroxy-Celecoxib (170571-00-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.75h;

DOI:10.1039/d1cc04599g

Reference yield: 54.0%

4-[5-(4-bromomethylphenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide (170570-75-9) → Methylhydroxy-Celecoxib (170571-00-3)

Guidance literature:

With water; In acetone; for 110h; Reflux;

DOI:10.1016/j.bmc.2008.10.001

Reference yield:

4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide (169590-42-5,194044-54-7) → Methylhydroxy-Celecoxib (170571-00-3)

Guidance literature:

4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide; With N-Bromosuccinimide; Irradiation;

With sodium tetrahydroborate;

DOI:10.1080/00498250050078039

upstream raw materials:

4-[5-(4-bromomethylphenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide

4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-hydrazinobenzene-1-sulfonamide hydrochloride

Downstream raw materials:

4-{1-[4-(aminosulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl}benzyl nitrate

Refernces

• 1、 Kang, Ju Young,An, Won,Kim, Suho,Kwon, Na Yeon,Jeong, Taejoo,Ghosh, Prithwish,Kim, Hyung Sik,Mishra, Neeraj Kumar,Kim, In Su. "Synthesis of spirosuccinimidesviaannulative cyclization betweenN-aryl indazolols and maleimides under rhodium(iii) catalysis". . p. 10947 - 10950. Retrieved 2021/10/22.
• 2、 Abdellatif, Khaled R.A.,Chowdhury, Morshed Alam,Dong, Ying,Velazquez, Carlos,Das, Dipankar,Suresh, Mavanur R.,Knaus, Edward E.. "Diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of 5-(4-hydroxymethylphenyl)-1-(4-aminosulfonylphenyl)-3-trifluoromethyl-1H-pyrazole and its methanesulfonyl analog: Synthesis, biological evaluation and nitric oxide release studies". experimental part. p. 9694 - 9698. Retrieved 2009/04/07.