1584-03-8

Basic information

• Product Name: Perfluoro-2-methyl-2-pentene
• Synonyms: PERFLUORO-2-METHYL-2-PENTENE 98;2-Methylpent-2-ene, perfluoro-;2-Pentene, 1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)-;1,1,1,3,4,4,5,5,5-nonafluoro-2-(trifluoromethyl)pent-4-ene;PERFLUORO(2-METHYL-2-PENTENE) TECH 90%;Nonafluoro-2-(trifluoromethyl)pent-2-ene;Perfluoro(2-methylpent-2-ene)90%;2-(Trifluoromethyl)perfluoro-2-pentene
• CAS NO: 1584-03-8
• Molecular Formula: C₆F₁₂
• Molecular Weight: 300.05
• EINECS: 216-436-1
• Mol File: 1584-03-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 48-50 °C
• Boiling Point: 53-61 °C(lit.)
• Flash Point: 10 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.622 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.31 psi ( 20 °C)
• Refractive Index: ca. 1.3
• Storage Temp.: Flammables area
• Water Solubility: insoluble
• CAS DataBase Reference: Perfluoro-2-methyl-2-pentene(CAS DataBase Reference)
• NIST Chemistry Reference: Perfluoro-2-methyl-2-pentene(1584-03-8)
• EPA Substance Registry System: Perfluoro-2-methyl-2-pentene(1584-03-8)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11
• Safety Statements: 16-29-33
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 1584-03-8(Hazardous Substances Data)

Usage

Uses

Used in Textile and Leather Industry:
Perfluoro-2-methyl-2-pentene is used as a waterproof and oilproof finishing agent for the textile and leather industries. Its chemical properties provide a durable and effective barrier against water and oil, enhancing the performance and longevity of these materials.
Used in Polyurethane Foam Manufacturing:
In the polyurethane foam industry, Perfluoro-2-methyl-2-pentene is utilized as a blowing agent. This application takes advantage of its ability to create a stable and consistent foam structure, which is essential for the production of high-quality polyurethane foams used in various applications such as furniture, bedding, and insulation.

InChI:InChI=1/C6F12/c7-2(3(8,9)6(16,17)18)1(4(10,11)12)5(13,14)15

Upstream product

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Downstream Products

• 30320-29-7 1,1,1,2,3,5,5,6,6,7,7,7-dodecafluoro-2,4-bis(trifluoromethyl)hept-3-ene 
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• 78686-92-7 1-(perfluoro-2-methyl-1-ethyl-1-propenyl)-4-pyridone 
• 421-20-5 Methyl fluorosulfonate 
• 53352-88-8 pentafluoropropionyl(trifluoromethyl)ketene 
• 54376-60-2 2-(Trifluoromethyl)-3-methoxy-1,1,1,3,4,4,5,5,5-nonafluoropentane 
• 59736-11-7 3-methoxy-2-trifluoromethyloctafluoro-2-pentene 
• 59736-12-8 3-ethoxyperfluoro-2-methyl-2-pentene 
• 59736-13-9 3-ethoxy-1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethyl-pent-2-ene 
• 59736-16-2 (Z)-1,3-diethoxyperfluoro-2-methyl-1-pentene 
• 121578-35-6 2-hydro-3-methylperfluoro-2-methylpentane 
• 121560-64-3 3-hydro-2-methylperfluoro-2-methylpentane 
• 121560-65-4 2-methylperfluoro-2-methyl-3-pentyl radical 
• 106054-52-8 1,1,1,2,2,3,5,5,5-Nonafluoro-3-(2,2,3,3-tetrafluoro-propoxy)-4-trifluoromethyl-pentane 

Relevant articles and documents

REACTION OF 2-TRIFLUOROMETHYLPERFLUORO-2-PENTENYL FLUOROSULFATE WITH NUCLEOPHILIC REAGENTS

2-Trifluoromethylperfluoro-2-pentenyl fluorosulfate undergoes SN2' nucleophilic reactions.The reaction of this fluorosulfate with halide salts gives an equilibrium mixture of 1-halo-2-trifluoromethylperfluoro-2-pentene and 2-trifluoromethyl-3-haloperfluoro-1-pentene.

ADDITION OF tert-PERFLUOROALKYL BROMIDES AT A MULTIPLE BOND, INITIATED BY ELECTRON TRANSFER

The thermodynamics of the dissociation of the radical-anions of perfluoroalkyl halides was determined by quantum-chemical methods.The conditions for the addition of tertiary perfluoroalkyl bromides to alkenes, initiated by electron transfer, were obtained.

Functionalization of saturated fluorocarbons

A method is described for transforming perfluoroalkanes and perfluorocycloalkanes bearing tertiary fluorine into perfluoroenolates, which can be variously derivatized.

Novel Fluorine-Bridged Polyfluorinated Iodine Structures. Presence of Fluorine as the Central Atom in a Five-Center Six-Electron Bond

The reaction of tris(dialkylamino)sulfonium perfluoro-2-methyl-2-pentyl carbanion with perfluoro iodides (RfI) leads to novel structures of the form f-I-F-I-Rf>-.The crystal structure for RfI = pentafluorophenyl iodide reveals discrete ion pairs.The crystal structure for RfI = 1,4-diiodooctafluorobutane shows an extended polymeric structure with (CF2)4 groups bridged by - units.The I-F bond distances are 0.3 - 0.4 Angstroem longer than normal fluorine-iodine distances but are > 1.0 Angstroem shorter than the sum of the van der Waals radii.The Rf-I-F bond angles are quasi-linear wheras the I-F-I bond angles deviate from linearity by 10 degree - 20 degree.High-level ab initio calculations of c-I-F>- and c-I-CF3>- are presented.The free ions are calculated to have linear structures at I and at the central fluorine.The Rf-I bond distances are calculated to be slightly longer than those in a free Rf-I compound, and the I-Fc bond distances are significantly elongated as compared to free I-F.The vibrational analysis shows a very low bending frequency of 28 cm-1 at the central fluorine in -.Analysis of the wave functions shows that the bonding in these structures is best described by a five-center, six-electron (5c 6e) hypervalent ? bond and not as an ion-dipole complex.The 5c 6e bond is stabilized by more electronegative elements at the central and terminal positions and less electronegative elements at the other two positions.The negative charge is found at the central and terminal positions.The alkyl fluorides stabilize the excess negative charge at the terminal position by negative anionic hyperconjugation.

OLIGOMERIZATION OF PERFLUOROPROPYLENE CATALYZED BY ?-BIS(ARENE)CHROMIUM(0) COMPLEXES

Oligomerization of perfluoropropylene catalyzed by four ?-bis(arene)chromium(0) complexes (arene = benzene, diphenyl, 1,3,5-trimethylbenzene and hexamethylbenzene) were compared.Besides dimers (I, II) and trimers (III, IV) reported previously , two defluorotrimers VA and VB were found to be present in the oligomer mixtures.The formation of VA and VB was shown to be derived from trimer IV by hydrogenation followed by elimination of two moles of hydrogen fluoride.

On reactions of carbon disulphide induced by 'naked' fluoride part 2: Reactions with 2-H-heptafluoropropane, hexafluoropropene, and bis (2,2,2-trifluoroethyl) amine

The reaction of CS2 and tetramethylammonium fluoride (TMAF) with 2-H-heptafluoropropane (R227) leads to 2,4-bis(hexafluoroisopropylidene)-1,3-dithietane as well as to the tetramethylammonium salt of heptafluorodithioisobutyric acid. The latter anion resulted also from the reaction of CS2 and CsF with hexafluoropropene (HFP), whereas CS2, TMAF and HFP reacted to compounds derived from HFP dimerization. N,N-bis (2,2,2-trifluoroethyl) dithiocarbamic acid anion was obtained from bis (trifluoroethyl) amine reacted with CS2 and TMAF.

Reactions Involving Fluoride Ion. Part 40. Amines as Initiators of Fluoride Ion Catalysed Reactions

Tetrakis(dimethylamino)ethene (TDAE) and trimethylamine react with anhydrous unsaturated fluorocarbons to produce, 'in situ', powerful fluoride-ion sources.These are used to iniate carbon-carbon bond forming reactions eg. oligomerisation and polyfluoroalkylation, and many of these reactions occur efficiently in the absence of a solvent.

Synthesis of (2E)-2-(tetrafluoroethylidene)-3,3-bis(trifluoromethyl)-2,3-dihydrothiazolo[3,2- a]benzimidazole

The reaction of benzimidazoline-2-thione with perfluoro-2-methylpent-2-ene in the presence of triethylamine afforded (2E)-2-(tetrafluoroethylidene)-3,3-bis(trifluoromethyl)-2,3-dihydrothiazolo[3,2- a]benzimidazole whose structure was confirmed by X-ray diffraction analysis. The reaction pathways are discussed.

REACTIONS OF TERTIARY PERFLUOROALKYL HALIDES WITH HALIDE ANIONS

The reactivities of the F-tert.-alkyl halides (CF3CF2CF2(CF3)2CX (1a-c: X = I, Br Cl)) towards the corresponding lithium halides LiY (2a-c: Y = I, Br, Cl), in acetonitrile, reflect the electron acceptor properties of compounds 1 and the donator strength of the anions Y(1-).The tertiary carbanion F-2-methylpentanide acts as the key intermediate in the formation of the main products (F-2-methyl-2-pentene, F-2-methyl-1-pentene and F-2-hydro-2-methylpentane), and also of the halide substitution products obtained from 1a.No support for the participation of any perfluoroalkyl radical could be found.

Synthesis method of heptafluoroisobutyronitrile

The invention provides a synthesis method of heptafluoroisobutyronitrile. The synthesis method comprises the following steps of: A) carrying out ozone cracking on a hexafluoropropylene dimer in the presence of a fluorocarbon solvent and alcohol to prepare heptafluoroisobutyrate; and B) carrying out a reaction between the obtained heptafluoroisobutyrate with ammonia, and dehydrating to obtain heptafluoroisobutyronitrile. DHFP dimer ozone cracking reaction conditions are mild, the raw material conversion rate and the product yield are high, and the whole production process is safe, simple, convenient and reliable in technological operation and easy for industrial production.