Trifluoromethylstyrene

Base Information

• Chemical Name: Trifluoromethylstyrene
• CAS No.: 705-89-5
• Molecular Formula: C₉H₇F₃
• Molecular Weight: 172.15
• DSSTox Substance ID: DTXSID20707367
• Mol file: 705-89-5.mol

Synonyms:trifluoromethylstyrene;705-89-5;DTXSID20707367;HKADMMFLLPJEAG-UHFFFAOYSA-N

Chemical Property of Trifluoromethylstyrene

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 172.04998471
• Heavy Atom Count: 12
• Complexity: 152

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Trifluoromethylstyrene

There total 87 articles about Trifluoromethylstyrene 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%

E-styryl iodide (42599-24-6) + (trifluoromethyl)trimethylsilane (81290-20-2) → (E)-3,3,3-trifluoro-1-phenylpropene (705-89-5,74031-42-8,74031-46-2)

Guidance literature:

With potassium fluoride; copper(l) iodide; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; at 80 ℃; for 16h;

DOI:10.1002/adsc.201100528

Reference yield: 92.0%

bromobenzene (108-86-1,52753-63-6) + trifluoromethyacrylic acid (381-98-6) → (E)-3,3,3-trifluoro-1-phenylpropene (705-89-5,74031-42-8,74031-46-2)

Guidance literature:

With palladium diacetate; potassium carbonate; copper(II) oxide; In 1-methyl-pyrrolidin-2-one; at 130 ℃; for 15h; Reagent/catalyst; Temperature; Time; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00551

Reference yield: 89.0%

Togni's reagent II (887144-94-7) + potassium (E)-trifluoro(styryl)borate (201852-49-5) → (E)-3,3,3-trifluoro-1-phenylpropene (705-89-5,74031-42-8,74031-46-2)

Guidance literature:

With iron(II) chloride; In acetonitrile; at 20 ℃; for 24h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201108267

upstream raw materials:

iodotrifluoromethane

bromostyrene

pentafluoroethyl phenyl ketone

3,3,3-trichloro-1-phenyl-propene

Downstream raw materials:

1,1-Difluoro-3-phenyl-1-propene

N,N-dibenzyl-1,1,1-trifluoro-3-phenylpropan-2-amine

(3,3,3-trifluoropropyl)benzene

Refernces

• 1、 Zhang, Min,Lin, Jin-Hong,Xiao, Ji-Chang. "A Readily Available Trifluoromethylation Reagent and Its Difunctionalization of Alkenes". supporting information. p. 6079 - 6083. Retrieved 2021/08/16.
• 2、 Liang, Yumeng,Taya, Akihito,Zhao, Zhengyu,Saito, Norimichi,Shibata, Norio. "Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD/Olah's reagent under solvent-free conditions". . p. 3052 - 3058. Retrieved 2021/01/15.