4-{4-[4-(Trifluoromethoxy)phenoxy]piperidino}benzenol

Base Information

• Chemical Name: 4-{4-[4-(Trifluoromethoxy)phenoxy]piperidino}benzenol
• CAS No.: 681482-81-5
• Molecular Formula: C18H18F3NO3
• Molecular Weight: 353.341
• DSSTox Substance ID: DTXSID10470098
• Nikkaji Number: J2.566.039K
• Wikidata: Q82298081
• Mol file: 681482-81-5.mol

Synonyms:681482-81-5;4-{4-[4-(trifluoromethoxy)phenoxy]piperidino}benzenol;4-(4-(4-(Trifluoromethoxy)phenoxy)piperidin-1-yl)phenol;4-[4-(4-Trifluoromethoxyphenoxy)piperidin-1-yl]phenol;4-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]phenol;SS-3227;4-(4-[4-(Trifluoromethoxy)phenoxy]piperidino)benzenol;Phenol, 4-[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]-;SCHEMBL57855;DTXSID10470098;AKOS005110868;CS-0326656;A1-09453;4-(4-[4-(Trifluoromethoxy)phenoxy]piperidino)phenol;4-[4-(4-trifluoromethoxyphenoxy)-piperidin-1-yl]phenol;1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine;1-(4-Hydroxyphenyl)-4-[4-(Trifluoromethoxy)phenoxy]piperidine

Chemical Property of 4-{4-[4-(Trifluoromethoxy)phenoxy]piperidino}benzenol

Chemical Property:

• Melting Point: 113-114°C
• Boiling Point: 461.2±45.0 °C(Predicted)
• PKA: 12.25±0.30(Predicted)
• PSA: 41.93000
• Density: 1.308±0.06 g/cm3(Predicted)
• LogP: 4.40360
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 353.12387792
• Heavy Atom Count: 25
• Complexity: 397

Purity/Quality:

97%, ^*data from raw suppliers

4-[4-(4-Trifluoromethoxyphenoxy)piperidin-1-yl]phenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1OC2=CC=C(C=C2)OC(F)(F)F)C3=CC=C(C=C3)O
• Uses: 4-[4-(4-Trifluoromethoxyphenoxy)piperidin-1-yl]phenol is an intermediate in the synthesis of Delamanid (D230660), a novel anti-tuberculosis medication that inhibits mycolic acid synthesis and shows potent in-vitro and in-vivo activity against drug-resistant strains of Mycobacterium tuberculosis.

Technology Process of 4-{4-[4-(Trifluoromethoxy)phenoxy]piperidino}benzenol

There total 6 articles about 4-{4-[4-(Trifluoromethoxy)phenoxy]piperidino}benzenol 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: 99.67%

1-(4-benzyloxy-phenyl)-4-(4-trifluoromethoxy-phenoxy)-piperidine (1083099-55-1) → 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine (681482-81-5)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In ethanol; at 60 - 61 ℃; for 3h; under 3040.2 Torr; Product distribution / selectivity;

Reference yield: 96.74%

4-(4-(4-trifluoromethoxy-phenoxy)piperidin-1-yl)phenol para-toluenesulfonic acid salt (866109-93-5) → 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine (681482-81-5)

Guidance literature:

With water; potassium carbonate; at 20 - 30 ℃; for 1 - 2h; Product distribution / selectivity;

Reference yield: 94.0%

1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenoxy)piperidine (681482-80-4) → 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine (681482-81-5)

Guidance literature:

With ethanol; pyridinium p-toluenesulfonate; at 70 ℃; for 24h;

DOI:10.1021/jm060957y

upstream raw materials:

1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenoxy)piperidine

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene

1,4-Cyclohexanedione

4-(4-(trifluoromethoxy)phenoxy)piperidine

Downstream raw materials:

4-(4-(4-trifluoromethoxy-phenoxy)piperidin-1-yl)phenol para-toluenesulfonic acid salt

lithium 4-(4-(4-trifluoromethoxy-phenoxy)piperidin-1-yl)phenolate

(R)-1-(4-((2-methyloxiran-2-yl)-methoxy)phenyl)-4-(4-(trifluoro-methoxy)phenoxy)piperidine

Refernces

• 1、 -. "Method for preparing Delmanid high-purity intermediate by one-pot method". Paragraph 0046-0065. . Retrieved 2019/01/06.
• 2、 Sasaki, Hirofumi,Haraguchi, Yoshikazu,Itotani, Motohiro,Kuroda, Hideaki,Hashizume, Hiroyuki,Tomishige, Tatsuo,Kawasaki, Masanori,Matsumoto, Makoto,Komatsu, Makoto,Tsubouchi, Hidetsugu. "Synthesis and antituberculosis activity of a novel series of optically active 6-nitro-2,3-dihydroimidazo[2,1-b]oxazoles". . p. 7854 - 7860. Retrieved 2007/10/03.