679-13-0

Basic information

• Product Name: TETRAFLUOROSUCCINYL DIFLUORIDE
• Synonyms: TETRAFLUOROSUCCINYL DIFLUORIDE;TETRAFLUOROSUCCINYL FLUORIDE;TETRAFLUOROBUTANE-1,4-DIOYL DIFLUORIDE;Perfluorosuccinoylfluoride;Tetrafluorobutane-1,4-dioyl difluoride 97%;Tetrafluorobutane-1,4-dioyldifluoride97%
• CAS NO: 679-13-0
• Molecular Formula: C₄F₆O₂
• Molecular Weight: 194.03
• Mol File: 679-13-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 30 °C
• Flash Point: 26.1 °C
• Appearance: /
• Density: 1.595 g/cm³
• Vapor Pressure: 48.1mmHg at 25°C
• Refractive Index: 1.283
• CAS DataBase Reference: TETRAFLUOROSUCCINYL DIFLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAFLUOROSUCCINYL DIFLUORIDE(679-13-0)
• EPA Substance Registry System: TETRAFLUOROSUCCINYL DIFLUORIDE(679-13-0)

Safety Data

• Hazard Codes: C,T
• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• HazardClass: TOXIC, CORROSIVE
• Hazardous Substances Data: 679-13-0(Hazardous Substances Data)

Usage

General Description

Tetrafluorosuccinyl difluoride is a chemical compound with the formula C4F6O2. It is a colorless liquid that is reactive and highly toxic. It is commonly used as a fluorinating agent in organic synthesis, specifically for the introduction of fluorine atoms into organic compounds. It is also used as a reagent in the production of pharmaceuticals, agrochemicals, and materials science. Due to its highly reactive nature, it must be handled with extreme caution and proper safety measures to avoid harmful exposure.

InChI:InChI=1/C4F6O2/c5-1(11)3(7,8)4(9,10)2(6)12

Synthetic route

tetrafluorosuccinic acid (377-38-8) → perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
With N-(2-chloro-1,1,2-trifluoroethyl)diethylamine; aluminum (III) chloride; boron trifluoride diethyl etherate In diethyl ether at 20 - 25℃; for 1h; Reagent/catalyst; Temperature;	87.6%
With N-(2-chloro-1,1,2-trifluoroethyl)diethylamine; boron trifluoride diethyl etherate In diethyl ether at 20 - 70℃; under 1 - 3 Torr; for 1h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	87.6%

1,2,5,6-diepoxyperfluorohexane (140173-03-1) → perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
at 210 - 220℃; for 6h;	85%

C16F30O6 → perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
With potassium fluoride at 100℃; for 5h; Large scale;	85%
With potassium fluoride at 100℃; for 5h;	85%

4-butanolide (96-48-0) → perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
Electrochemical reaction;	83%

tetrafluorosuccinic acid disodium salt → perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
With sulfur tetrafluoride at 150℃; for 5h;	81%

Perfluoro-1,5-hexadiene (356-35-4) → perfluorosuccinic difluoride (679-13-0) + 1,2,5,6-diepoxyperfluorohexane (140173-03-1) + 2,2,3,3-Tetrafluoro-3-(2,3,3-trifluoro-oxiranyl)-propionyl fluoride (140173-04-2)

Conditions	Yield
With air for 32h; Irradiation;	A n/a B 65% C n/a
With air for 32h; Irradiation;	A n/a B n/a C 27%

1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane (375-50-8) → hexafluoro-dihydro-furan-2-one (702-35-2) + perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
With sulfur trioxide	A 7% B n/a

tetrafluorosuccinyl chloride (356-15-0) → perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
With sodium fluoride

1,4-bis(fluorosulfonyloxy)octafluorobutane (78522-71-1) → perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
With potassium fluoride In diethylene glycol dimethyl ether
With cesium fluoride at 50℃;

Perfluoro-1,5-hexadiene (356-35-4) → 1,2-epoxyperfluoro-5-hexene (15453-10-8) + perfluorosuccinic difluoride (679-13-0) + 1,2,5,6-diepoxyperfluorohexane (140173-03-1) + 2,2,3,3-Tetrafluoro-3-(2,3,3-trifluoro-oxiranyl)-propionyl fluoride (140173-04-2) + COF2

Conditions	Yield
With air at 25℃; Product distribution; Irradiation; var. time;

2,2,3,3,3-pentafluoro-propionic acid 1,1,2,2,3,3,4,4-octafluoro-4-(2,2,3,3,3-pentafluoro-propionyloxy)-butyl ester → perfluoropropanoyl fluoride (422-61-7) + perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
With sodium fluoride at 100℃; for 0.25h;	A n/a B 52 % Spectr.

succinoyl dichloride (543-20-4) → perfluorosuccinic difluoride (679-13-0)

Conditions	Yield
With fluorine at 180℃; for 4h;

perfluorosuccinic difluoride (679-13-0) → Tetrafluorobutanedioyl fluoride iodide + Tetrafluorobutanedioyl diiodide

Conditions	Yield
With lithium iodide at 120℃; for 3.5h;	A 1% B 96%
With lithium iodide at 120℃; for 5h;	A 55% B 7%

perfluorosuccinic difluoride (679-13-0) → Tetrafluorobutanedioyl bromide fluoride + Tetrafluorobutanedioyl dibromide

Conditions	Yield
With lithium bromide at 250℃; for 5h;	A 1% B 88%
With lithium bromide at 250℃; for 5h;	A 56% B 19%

perfluorosuccinic difluoride (679-13-0) + 2-Isopropylimino-2-phenylethane (109106-15-2) → 1,8-Bis(isopropylamino)-1,8-diphenyl-4,4,5,5-tetrafluoroocta-1,7-dien-3,6-dione hydrofluoride

Conditions	Yield
In diethyl ether at 0℃; for 12h; Acylation;	88%

perfluorosuccinic difluoride (679-13-0) → tetrafluorosuccinyl chloride (356-15-0) + Tetrafluorobutanedioyl chloride fluoride

Conditions	Yield
With lithium chloride at 330℃; for 5h;	A 80% B 8%
With lithium chloride at 330℃; for 5h;	A 25% B 71%

perfluorosuccinic difluoride (679-13-0) + 2-isopropyliminopropane (3332-08-9) → 1'-Isopropylamino-1-ethylidene-3,3,4,4-tetrafluorocyclopentan-2,5-dione

Conditions	Yield
In cyclohexane at 0℃; for 12h; Acylation; Stork reaction; Cyclization;	80%

perfluoropropylene (116-15-4) + perfluorosuccinic difluoride (679-13-0) → 2H,7H-dodecafluoro-2,7-bis-trifluoromethyl-octane-3,6-dione (57070-04-9)

Conditions	Yield
With potassium fluoride In diethylene glycol dimethyl ether at 70 - 80℃; under 22.8015 Torr; for 5 - 20h; Product distribution / selectivity; Cooling with acetone-dry ice;	78%
With potassium fluoride In benzonitrile

perfluorosuccinic difluoride (679-13-0) + 2-Isopropylimino-2-phenylethane (109106-15-2) → 1'-Isopropylamino-1'-phenyl-1-methylene-3,3,4,4-tetrafluorocyclopentan-2,5-dione

Conditions	Yield
In chloroform at 30℃; for 12h; Acylation; Stork reaction; Cyclization;	75%

perfluorosuccinic difluoride (679-13-0) + 2-Isopropylimino-2-phenylethane (109106-15-2) → 1'-Isopropylamino-1'-phenyl-1-methylene-3,3,4,4-tetrafluorocyclopentan-2,5-dione + 1,8-Bis(isopropylamino)-1,8-diphenyl-4,4,5,5-tetrafluoroocta-1,7-dien-3,6-dione

Conditions	Yield
In diethyl ether at 0℃; for 12h; Acylation; Stork reaction; Cyclization;	A n/a B 67%

Hexafluoropropene oxide (428-59-1) + perfluorosuccinic difluoride (679-13-0) → perfluoro-2-methyl-3-oxaheptanedioyl fluoride (19190-57-9)

Conditions	Yield
With cesium fluoride at -10℃; Autoclave;	62%
With cesium fluoride Autoclave;	62%
With potassium fluoride In diethylene glycol dimethyl ether

perfluorosuccinic difluoride (679-13-0) + benzene (71-43-2) → 2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-dione (2525-85-1)

Conditions	Yield
With aluminium trichloride Heating;	60%

perfluorosuccinic difluoride (679-13-0) → 2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6)

Conditions	Yield
Stage #1: perfluorosuccinic difluoride With sodium tetrahydroborate In isopropyl alcohol at 5 - 80℃; for 3h; Stage #2: With sulfuric acid In isopropyl alcohol at 35℃; for 1h;	53%

perfluorosuccinic difluoride (679-13-0) → Tetrafluorobutanedioyl dibromide + Tetrafluorobutanedioyl bromide iodide + Tetrafluorobutanedioyl diiodide

Conditions	Yield
With lithium bromide; lithium iodide at 120℃; for 20h; Yields of byproduct given;	A n/a B 49% C n/a

perfluorosuccinic difluoride (679-13-0) → tetrafluorosuccinyl chloride (356-15-0) + Tetrafluorobutanedioyl bromide chloride + Tetrafluorobutanedioyl dibromide

Conditions	Yield
With lithium chloride; lithium bromide at 250℃; for 24h; Yields of byproduct given;	A n/a B 46% C n/a

perfluorosuccinic difluoride (679-13-0) → tetrafluorosuccinyl chloride (356-15-0) + Tetrafluorobutanedioyl chloride fluoride + Tetrafluorobutanedioyl chloride iodide + Tetrafluorobutanedioyl diiodide

Conditions	Yield
With lithium chloride; lithium iodide at 80℃; for 90h; Further byproducts given. Yields of byproduct given;	A n/a B n/a C 41% D n/a

perfluorosuccinic difluoride (679-13-0) + 2-isopropyliminopropane (3332-08-9) → 1'-Isopropylamino-1-ethylidene-3,3,4,4-tetrafluorocyclopentan-2,5-dione + 2,9-Bis(isopropylamino)-5,5,6,6-tetrafluorodeca-2,8-dien-4,7-dione

Conditions	Yield
In diethyl ether at 0℃; for 12h; Acylation; Stork reaction; Cyclization;	A n/a B 40%

perfluoropropylene (116-15-4) + perfluorosuccinic difluoride (679-13-0) → Perfluor-5-methyl-4-keto-hexansaeurefluorid (57070-00-5)

Conditions	Yield
With potassium fluoride In benzonitrile

perfluorosuccinic difluoride (679-13-0) → Octafluor-1,4-bis(fluoroxy)butan (16370-06-2)

Conditions	Yield
With fluorine; cesium fluoride

perfluorosuccinic difluoride (679-13-0) → 1,2-dibromo-1,1,2,2-tetrafluoroethane (124-73-2) + tetrafluorosuccinyl chloride (356-15-0) + 3-bromo-2,2,3,3-tetrafluoropropanoyl chloride (64053-15-2)

Conditions	Yield
With lithium chloride; lithium bromide at 350℃; for 5h; Yield given. Yields of byproduct given;

perfluorosuccinic difluoride (679-13-0) → 1,2-diiodotetrafluoroethane (354-65-4) + tetrafluorosuccinyl chloride (356-15-0) + 2,2,3,3-Tetrafluoro-3-iodo-propionyl fluoride (91095-98-6) + Perfluoro-3-iodopropanoyl chloride

Conditions	Yield
With lithium chloride; lithium iodide at 230℃; for 5.5h; Yield given. Further byproducts given. Yields of byproduct given;

perfluorosuccinic difluoride (679-13-0) → 2,2,3,3-tetrafluorosuccinamide (377-37-7)

Conditions	Yield
With ammonia

Upstream product

• 356-35-4 Perfluoro-1,5-hexadiene 
• 78522-71-1 1,4-bis(fluorosulfonyloxy)octafluorobutane 
• 543-20-4 succinoyl dichloride 
• 377-38-8 tetrafluorosuccinic acid 
• 375-50-8 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane 
• 96-48-0 4-butanolide 
• 140173-03-1 1,2,5,6-diepoxyperfluorohexane 
• 356-15-0 tetrafluorosuccinyl chloride 

Downstream Products

• 124-73-2 1,2-dibromo-1,1,2,2-tetrafluoroethane 
• 356-15-0 tetrafluorosuccinyl chloride 
• 64053-15-2 3-bromo-2,2,3,3-tetrafluoropropanoyl chloride 
• 354-65-4 1,2-diiodotetrafluoroethane 
• 91095-98-6 2,2,3,3-Tetrafluoro-3-iodo-propionyl fluoride 
• 425-61-6 2,2,3,3-tetrafluorobutane-1,4-diol 
• 63425-24-1 Methyl tetrafluoro-3-fluoroformylpropanate 
• 377-37-7 2,2,3,3-tetrafluorosuccinamide 
• 19190-57-9 perfluoro-2-methyl-3-oxaheptanedioyl fluoride 
• 2525-85-1 2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-dione 

Relevant articles and documents

Preparation method of fluorine-containing binary acyl fluoride

The invention discloses a preparation method of fluorine-containing binary acyl fluoride. Fluorine-containing dicarboxylic acid as a raw material is subjected to fluorination with a fluorination reagent under the action of a solvent and a catalyst to obtain the fluorine-containing binary acyl fluoride. During actual production, the fluorine-containing dicarboxylic acid is directly fluorinated intocorresponding fluorine-containing diacyl fluoride under the action of the organic solvent and the Lewis acid catalyst, and the organic solvent and the specific catalyst are matched with other conditions, so that from the fluorine-containing dicarboxylic acid can be effectively promoted.

PROCESS FOR PRODUCING FLUORINATED COMPOUND

To provide a process for producing a desired perfluorinated product at a high yield in a fluorination reaction of a partially fluorinated ester. A perfluorinated compound (4) is obtained by fluorinating in a liquid phase a compound (3) (wherein the fluorine content is at least 30 mass %) obtained by reacting a compound (1) and a compound (2), wherein the compound (1) is HOCH2—RA—CH2OH, the compound (2) is X1C(═O)—C(RB)(RC)(RD), RA is a bivalent saturated hydrocarbon group or the like which has no hetero atom such as an etheric oxygen atom, X1 is a halogen atom, and —C(RB)(RC)(RD) is a branched group.

METHODS OF MAKING HALOGENATED FLUORINATED ETHER-CONTAINING COMPOUNDS

Described herein are three methods for making halogenated fluorinated ether-containing compounds using a fluorinated olefin or hexafluoropropylene oxide.