1-(Trifluoromethyl)cyclohex-2-en-1-ol

Base Information

• Chemical Name: 1-(Trifluoromethyl)cyclohex-2-en-1-ol
• CAS No.: 118143-28-5
• Molecular Formula: C7H9 F3 O
• Molecular Weight: 166.143
• Hs Code.: 2906199090
• DSSTox Substance ID: DTXSID60446743
• Nikkaji Number: J376.465F
• Mol file: 118143-28-5.mol

Synonyms:1-(trifluoromethyl)cyclohex-2-en-1-ol;118143-28-5;3-HYDROXY-3-(TRIFLUOROMETHYL)CYCLOHEXENE;2-Cyclohexen-1-ol,1-(trifluoromethyl)-;DTXSID60446743;DFFKUOBCTWPVOA-UHFFFAOYSA-N;1-(trifluoromethyl)cyclohex-2-enol;AKOS006287779;1-(Trifluoromethyl)-2-cyclohexen-1-ol

Chemical Property of 1-(Trifluoromethyl)cyclohex-2-en-1-ol

Chemical Property:

• PSA: 20.23000
• LogP: 2.01990
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 166.06054939
• Heavy Atom Count: 11
• Complexity: 173

Purity/Quality:

98%min ^*data from raw suppliers

3-HYDROXY-3-(TRIFLUOROMETHYL)CYCLOHEXENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC=CC(C1)(C(F)(F)F)O

Technology Process of 1-(Trifluoromethyl)cyclohex-2-en-1-ol

There total 5 articles about 1-(Trifluoromethyl)cyclohex-2-en-1-ol 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: 98.0%

cyclohexenone (930-68-7) + (trifluoromethyl)trimethylsilane (81290-20-2) → 1-(trifluoromethyl)-2-cyclohexen-1-ol (118143-28-5)

Guidance literature:

With N-(EtOCH₂CH₂OCH₂)-N-methylmorpholinium bis(CF₃SO₂)amide; cesium fluoride; at 25 ℃; for 0.5h;

DOI:10.1039/b412480b

Reference yield: 92.0%

Trimethyl-(1-trifluoromethyl-cyclohex-2-enyloxy)-silane (247912-53-4) → 1-(trifluoromethyl)-2-cyclohexen-1-ol (118143-28-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ol990844r

Reference yield:

cyclohexenone (930-68-7) + (trifluoromethyl)trimethylsilane (81290-20-2) → 3-(trifluoromethyl)cyclohexanone (585-36-4) + 1-(trifluoromethyl)-2-cyclohexen-1-ol (118143-28-5)

Guidance literature:

With hydrogenchloride; tetrabutyl ammonium fluoride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, 0 deg C - rt;

DOI:10.1021/jo00003a017

upstream raw materials:

cyclohexenone

(trifluoromethyl)trimethylsilane

Trimethyl-(1-trifluoromethyl-cyclohex-2-enyloxy)-silane

Downstream raw materials:

3-trifluoromethyl-2-cyclohexene-1-one

Refernces

• 1、 Kim, Jinwi,Shreeve, Jean'ne M.. "The first Cu(I)-mediated nucleophilic trifluoromethylation reactions using (trifluoromethyl)trimethylsilane in ionic liquids". . p. 2728 - 2734. Retrieved 2007/10/03.
• 2、 Singh, Rajendra P.,Kirchmeier, Robert L.,Shreeve, Jean'ne M.. "CsF-catalyzed nucleophilic trifluoromethylation of trans-enones with trimethyl(trifluoromethyl)silane: A facile synthesis of trans-α-trifluoromethyl allylic alcohols". . p. 1047 - 1049. Retrieved 2008/02/09.