(Z)-1,1,1,4,4,4-HEXAFLUORO-2-BUTENE

Base Information

• Chemical Name: (Z)-1,1,1,4,4,4-HEXAFLUORO-2-BUTENE
• CAS No.: 692-49-9
• Molecular Formula: C4H2F6
• Molecular Weight: 164.05
• Hs Code.: 2903399090
• DSSTox Substance ID: DTXSID90985276
• Wikidata: Q72481701
• Mol file: 692-49-9.mol

Synonyms:(Z)-1,1,1,4,4,4-HEXAFLUORO-2-BUTENE

Chemical Property of (Z)-1,1,1,4,4,4-HEXAFLUORO-2-BUTENE

Chemical Property:

• Vapor Pressure: 60.435kPa at 20.01℃
• Boiling Point: 9℃
• Flash Point: -21℃
• PSA: 0.00000
• Density: 1.356
• LogP: 2.66720
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 164.00606904
• Heavy Atom Count: 10
• Complexity: 110

Purity/Quality:

99% min ^*data from raw suppliers

(Z)-1,1,1,4,4,4-Hexafluoro-2-butene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(=CC(F)(F)F)C(F)(F)F
• Uses: Z-1,1,1,4,4,4-Hexafluoro-2-butene is a useful compound in regards to heat transfer applications due to the stability of the carbon fluorine bond.

Technology Process of (Z)-1,1,1,4,4,4-HEXAFLUORO-2-BUTENE

There total 16 articles about (Z)-1,1,1,4,4,4-HEXAFLUORO-2-BUTENE 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: 56.0%

4-fluorobenzaldehyde (459-57-4) + (E)-triethyl(1,1,1,4,4,4-hexafluorobuten-2-yl)silane → 1,1,1,4,4,4-hexafluoro-2(Z)-butene (692-49-9) + (Z)-1-triethylsiloxy-2,3-bis(trifluoromethyl)-1-(4-fluorophenyl)prop-2-ene

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,2-dimethoxyethane; at -50 - 20 ℃; Reagent/catalyst; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.jfluchem.2021.109922

Reference yield:

1,1,1-trifluoro-2,2-dichloroethane (306-83-2) → 1,1,1,4,4,4-hexafluoro-2(Z)-butene (692-49-9) + trans-1,1,1,4,4,4-hexafluoro-2-butene (66711-86-2) + Vinylidene fluoride (75-38-7) + 1,1,3,3,3-pentafluoro-2-methyl-1-propene (2253-00-1)

Guidance literature:

With diethylamine; copper; at 20 ℃; for 64h; under 915.2 - 1018.63 Torr; Product distribution / selectivity; Inert atmosphere;

Reference yield:

1,1,1-trifluoro-2,2-dichloroethane (306-83-2) + dibutylamine (111-92-2) → 1,1,1,4,4,4-hexafluoro-2(Z)-butene (692-49-9) + trans-1,1,1,4,4,4-hexafluoro-2-butene (66711-86-2) + Vinylidene fluoride (75-38-7) + 1,1,1-trifluoro-3-aza-2-hepten

Guidance literature:

copper(I) chloride; copper; at 20 - 80 ℃; under 966.916 - 1328.93 Torr; Product distribution / selectivity; Inert atmosphere;

upstream raw materials:

2,2,2-trifluorodiazoethane

rac-4,4,4-trifluoro-3-hydroxybutanoic acid

1,1,1,4,4,4-hexafluoro-2-butanol

2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene

Downstream raw materials:

trifluoroacetic acid

1,1,4,4-tetrafluorobutadiene

(HC((CMe)(2,6-iPr₂C₆H₃N))2)AlF₂

1,1,1-trifluoro-but-2-ene

Refernces

Molybdenum chloride catalysts for Z-selective olefin metathesis reactions

10.1038/nature21043

The study focuses on the development of molybdenum chloride catalysts for Z-selective olefin metathesis reactions, which is a significant advancement in the field of chemistry. The researchers utilized molybdenum monoaryloxide chloride complexes to catalyze the formation of higher-energy (Z) isomers of trifluoromethyl-substituted alkenes through cross-metathesis reactions with Z-1,1,1,4,4,4-hexafluoro-2-butene, a commercially available and inexpensive compound typically considered inert. The study also improved the efficiency and Z selectivity of transformations involving Z-1,2-dichloroethene and 1,2-dibromoethene. These molybdenum complexes enabled the synthesis of biologically active molecules and trifluoromethyl analogues of medicinally relevant compounds, which can enhance bioavailability, metabolic stability, lipophilicity, or binding selectivity. The study's purpose was to address the challenges in synthesizing trifluoromethyl-substituted olefins, a crucial moiety in agrochemicals and materials research, by providing a more direct and practical method for their preparation. The study employed density functional theory calculations to elucidate the origins of the observed activity and selectivity levels, contradicting previously proposed principles.