3-(5-Chloro-2-hydroxybenzyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one

Base Information

• Chemical Name: 3-(5-Chloro-2-hydroxybenzyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one
• CAS No.: 202821-81-6
• Molecular Formula: C16H10ClF3N2O3
• Molecular Weight: 370.715
• Hs Code.: 2934999090
• European Community (EC) Number: 806-268-2
• UNII: LW7MXS978N
• DSSTox Substance ID: DTXSID70174141
• Nikkaji Number: J2.015.928F
• Wikidata: Q27165366
• ChEMBL ID: CHEMBL45349
• Mol file: 202821-81-6.mol

Synonyms:3-((5-chloro-2-hydroxyphenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one;BMS 191011;BMS-191011;BMS191011

Chemical Property of 3-(5-Chloro-2-hydroxybenzyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 443.965oC at 760 mmHg
• PKA: 9.27±0.43(Predicted)
• Flash Point: 222.302oC
• PSA: 68.26000
• Density: 1.516g/cm3
• LogP: 3.92940
• Storage Temp.: Store at RT
• Solubility.: DMSO: soluble20mg/mL, clear (warmed)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 370.0332044
• Heavy Atom Count: 25
• Complexity: 535

Purity/Quality:

97% ^*data from raw suppliers

BMS 191011 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=NN(C(=O)O2)CC3=C(C=CC(=C3)Cl)O)C(F)(F)F
• Description: BMS 191011 is an activator of large-conductance calcium-activated potassium (KCa1.1/BK) channels that increases maximum potassium current to 126% of control in X. laevis oocytes expressing human KCa1.1 channels when used at a concentration of 1 μM. In vivo, BMS 191011 (10-100 μg/kg, i.v.) increases the diameter of retinal arterioles without affecting blood pressure or heart rate in rats, an effect that is reversed by the KCa1.1 channel blocker iberiotoxin .
• Uses: BMS 191011, is a potent opener of the large-conductance, Ca2+-activated potassium (maxi-K) channel. It has also shown neuroprotective properties in two distinct animal models of stroke- MCAO in the SHR rat and a normotensive model of focal stroke.

Technology Process of 3-(5-Chloro-2-hydroxybenzyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one

There total 9 articles about 3-(5-Chloro-2-hydroxybenzyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one 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: 90.0%

3-[(5-Chloro-2-methoxyphenyl)methyl]-5-[4-(trifluoromethyl)-phenyl]-1,3,4-oxadiazol-2(3H)-one (202822-68-2) → 3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)-phenyl]-1,3,4-oxadiazol-2(3H)-one (202821-81-6)

Guidance literature:

With methyl bromide; In dichloromethane; at 0 - 20 ℃; for 18h; Inert atmosphere;

Reference yield: 83.0%

4-chloro-2-hydroxymethylphenol (5330-38-1) + 5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-(3H)-one (202823-22-1) → 3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)-phenyl]-1,3,4-oxadiazol-2(3H)-one (202821-81-6)

Guidance literature:

4-chloro-2-hydroxymethylphenol; 5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-(3H)-one; With potassium carbonate; methyl iodide;

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

With boron tribromide; In dichloromethane;

DOI:10.1021/acs.joc.5b00664

Reference yield: 68.0%

→ 3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)-phenyl]-1,3,4-oxadiazol-2(3H)-one (202821-81-6)

Guidance literature:

upstream raw materials:

3-[(5-Chloro-2-methoxyphenyl)methyl]-5-[4-(trifluoromethyl)-phenyl]-1,3,4-oxadiazol-2(3H)-one

4-(trifluoromethyl)benzoic acid hydrazide

4-trifluoromethylbenzoic acid

5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-(3H)-one

Downstream raw materials:

4-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl chloroformate

3-[[5-chloro-2-[[(chloromethyl)carbonyl]oxy]-phenyl]methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one

carbonic acid bis-benzyloxy-phosphoryloxymethyl ester 4-chloro-2-[2-oxo-5-(4-trifluoromethyl-phenyl)-[1,3,4]oxadiazol-3-ylmethyl]-phenyl ester

phosphoric acid dibenzyl ester 4-chloro-2-[2-oxo-5-(4-trifluoromethyl-phenyl)-[1,3,4]oxadiazol-3-ylmethyl]-phenoxymethyl ester