791-22-0

Basic information

• Product Name: 1,4-Bis(2',3'-epoxypropyl)perfluorobutane
• Synonyms: 2,2'-(2,2,3,3,4,4,5,5-Octafluorohexane-1,6-diyl)dioxirane 97%;2,2'-(2,2,3,3,4,4,5,5-Octafluorohexane-1,6-diyl)dioxirane97%;2,2'-(2,2,3,3,4,4,5,5-Octafluorohexane-1,6-diyl)bis(oxirane);1,4-BIS(EPOXYPROPYL)OCTAFLUOROBUTANE;1,4-BIS(2',3'-EPOXYPROPYL)OCTAFLUORO-N-BUTANE;1,4-BIS(2',3'-EPOXYPROPYL)PERFLUORO-1-BUTANE;1,4-BIS(2',3'-EPOXYPROPYL)-PERFLUORO-N-BUTANE;1,4-Bis(2',3'-epoxypropyl)perfluorobutane
• CAS NO: 791-22-0
• Molecular Formula: C10H10F8O2
• Molecular Weight: 314.17
• Mol File: 791-22-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 90/1.5mm
• Flash Point: 133°C(lit.)
• Appearance: /
• Density: 1.506
• Refractive Index: 1.379
• CAS DataBase Reference: 1,4-Bis(2',3'-epoxypropyl)perfluorobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Bis(2',3'-epoxypropyl)perfluorobutane(791-22-0)
• EPA Substance Registry System: 1,4-Bis(2',3'-epoxypropyl)perfluorobutane(791-22-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 791-22-0(Hazardous Substances Data)

Usage

General Description

1,4-Bis(2',3'-epoxypropyl)perfluorobutane, also known as bisphenol AF, is a chemical compound used in the production of epoxy resins and as a surface protectant in various industrial applications. It is highly resistant to heat, chemicals, and electrical insulation, making it a valuable component in the manufacturing of electronic and aerospace materials. However, bisphenol AF has been linked to potential health risks, including endocrine disruption and reproductive toxicity, leading to growing concerns about its widespread use and potential environmental impact. As a result, there are ongoing efforts to find alternative, safer materials to replace bisphenol AF in various industrial applications.

Upstream product

• 755-18-0 (2,9-Diiodo-4,4,5,5,6,6,7,7-octafluorodecane-1,10-diyl) diacetate 
• 273215-26-2 2,9-Diiodo-4,4,5,5,6,6,7,7-octafluorodecane-1,10-diol 

Relevant articles and documents

Fluorinated epoxides: 5. Highly selective synthesis of diepoxides from α,ω-diiodoperfluoroalkanes. Regioselectivity of nucleophilic epoxide-ring opening and new amphiphilic compounds and monomers

An improved procedure for the radical addition of α,ω-diiodoperfluoroalkanes I-(CF2CF2)n-I (n=2, 3) to allyl acetate that afford the corresponding bis-adducts AcOCH2CHICH2(CF2CF2) nCH2CHI-CH2OAc (2a-2b) has been developed. The primary bis-adducts 2a-2b suffered a subsequent rearrangement in the addition mixture to afford semi-rearranged adducts AcOCH2CHICH2-(CF2CF2) n-CH2CH-(OAc)CH2I (3a-3b) in an amount of ca. 15% rel. at reaction temperatures. Both adducts 2a-2b and rearranged adducts 3a-3b were converted to diepoxides CH2(-O-)CHCH2(CF2CF2) nCH2CH-(-O-)CH2 (4a-4b) with high chemoselectivity in two ways: the selectivity of the direct epoxidation of 2a-2b and/or 3a-3b with potassium hydroxide was extremely dependent on the solvent; the second method included hydrolysis of 2a-2b and/or 3a-3b to bis-iodohydrins 5a-5b and 6a-6b that were easily transformed to the diepoxides 4a-4b. Ring-opening reactions of bis-epoxides 4a-4b with hydroxy compounds in the presence of boron trifluoride etherate took place at the terminal carbon atom of both epoxide rings with complete regioselectivity. A convenient transformation of the diepoxides to the corresponding amphiphilic tetrols (14a-14b) via dioxolane intermediates was accomplished with overall yields of 57-65% . Base-catalyzed ring-opening by methacrylic acid was not completely regioselective (89% terminal attack on both oxirane rings) and afforded a mixture of regioisomeric bis-methacrylates (16a-16b and 17a-17b) bearing two hydroxyl groups. In contrast, epoxide ring-opening with morpholine was completely regioselective in both diepoxides 4a and 4b.