661-95-0

Usage

Uses

Used in Fire Protection Industry:
1,2-Dibromohexafluoropropane is used as a fire-extinguishing agent for the manufacturing of fire-extinguishing microcapsules. These microcapsules consist of a fire-extinguishing agent and a polymeric shell, which are designed to enhance the efficiency and safety of fire suppression systems.
The application reason for using 1,2-Dibromohexafluoropropane in this context is its ability to effectively suppress fires while being encapsulated within a protective polymeric shell, ensuring that the fire-extinguishing agent is delivered in a controlled and safe manner.

InChI:InChI=1S/C3Br2F6/c4-1(6,2(5,7)8)3(9,10)11

Synthetic route

perfluoropropylene (116-15-4) → 1,2-dibromohexafluoropropane (661-95-0)

Conditions	Yield
With bromine at 100℃; Cooling with acetone-dry ice;	99.41%
With bromine at 20℃; for 19h;	95%
With bromine for 19h;	95%

perfluoropropylene (116-15-4) + Bromine(I) trifluoromethanesulfonate (70142-16-4) → 1,2-dibromohexafluoropropane (661-95-0) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + Trifluoro-methanesulfonic acid 2-bromo-1,1,2,3,3,3-hexafluoro-propyl ester (73323-45-2)

Conditions	Yield
at -111 - -5℃; for 24h;	A n/a B n/a C 80%

1,1,1,3,3,3-hexafluoropropane (690-39-1) → 1,2-dibromohexafluoropropane (661-95-0) + 1,1,1,3,3,3-hexafluoroisopropyl bromide (2252-79-1)

Conditions	Yield
With bromine at 600℃;

HFC-227ca (2252-84-8) → bromodifluoromethane (1511-62-2) + 1,2-dibromohexafluoropropane (661-95-0) + Bromotrifluoromethane (75-63-8) + dibromodifluoromethane (75-61-6) + 1-bromo-1,1,2,2-tetrafluoro-ethane (354-07-4) + bromopentafluoroethane (354-55-2)

Conditions	Yield
With bromine under 0.05 Torr; Rate constant; Product distribution; Irradiation; Infrared multiphoton dissociation with Br2 as a scavenger.;

perfluoropropylene (116-15-4) → 1,2-dibromohexafluoropropane (661-95-0) + 2-bromo-1,1,1,2,3,3,3-heptafluoropropane (422-77-5) + 2-bromohexafluoropropyl fluorosulfate (41255-95-2) + 2-hydrohexafluoropropyl fluorosulfate (684-35-5)

Conditions	Yield
With bromine; antimony pentafluoride; fluorosulphonic acid for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

heptafluorobutyric Acid (375-22-4) + bromine (7726-95-6) → 1,2-dibromohexafluoropropane (661-95-0) + perfluoropropyl bromide (422-85-5)

Conditions	Yield
at 260℃; Reaktion des Natrium-Salzes;

perfluoropropylene (116-15-4) + water (7732-18-5) + bromine (7726-95-6) → 1,2-dibromohexafluoropropane (661-95-0)

1,1,1,3,3,3-hexafluoropropane (690-39-1) + bromine (7726-95-6) → 1,2-dibromohexafluoropropane (661-95-0) + 1,1,1,3,3,3-hexafluoroisopropyl bromide (2252-79-1)

Conditions	Yield
at 600℃;

2-(2-bromo-1,1,2,3,3,3-hexafluoropropanoxy)-1,3-dichlorobenzene + 2,6-Dichlorophenol (87-65-0) + 1-thiopropane (107-03-9) → 1,2-dibromohexafluoropropane (661-95-0)

Conditions	Yield
With potassium carbonate

1,2-dibromohexafluoropropane (661-95-0) → 2,2-dibromo-1,1,1,3,3,3-hexafluoropropane (38568-21-7)

Conditions	Yield
With ACF In chloroform-d1 at 25℃; for 2h; Reagent/catalyst;	100%
aluminium trichloride In N,N-dimethyl-formamide at 150℃; for 120h;	72%
With aluminium trichloride at 150℃; for 216h;	67%

1,2-dibromohexafluoropropane (661-95-0) → 2-bromo-1,1,1,2,3,3,3-heptafluoropropane (422-77-5)

Conditions	Yield
With sulfolane; potassium fluoride at 120 - 175℃; under 2250.23 - 10126 Torr; for 6h;	95.8%
With sulfolane; potassium fluoride at 125 - 175℃; under 2250.23 - 10126 Torr; for 5h;	83%
With potassium fluoride In N,N-dimethyl-formamide at 90 - 140℃; for 3h;
With sulfolane; potassium fluoride at 125℃; for 27h; Autoclave; Inert atmosphere;

1,2-dibromohexafluoropropane (661-95-0) + 1,7-Octadiene (3710-30-3) → (cis/trans)-1-Bromomethyl-2-(3-bromo-2-trifluoromethyl-2,3,3-trifluoropropyl)cyclohexane (143766-78-3, 143766-79-4)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; iron In ethanol at 60℃; for 13h;	88%

1,2-dibromohexafluoropropane (661-95-0) + potassium phenolate (100-67-4) → 1-phenoxy-2-hydroperfluoropropane (357-98-2) + (2-Bromo-1,1,2,3,3,3-hexafluoro-propoxy)-benzene (95519-57-6)

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Ambient temperature;	A 2% B 80%

1,2-dibromohexafluoropropane (661-95-0) + aniline (62-53-3) → 4-[1-[bromo(difluoro)methyl]-1,2,2,2-tetrafluoro-ethyl]aniline

Conditions	Yield
With sodium thiosulfate; sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate In tert-butyl methyl ether; water at 20 - 40℃;	65%
With sodium dithionite; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In tert-butyl methyl ether; water for 3h;	33%

1,2-dibromohexafluoropropane (661-95-0) → 1-bromo-1,1,2,3,3,3-hexafluoro-propane (2252-78-0) + perfluoropropylene (116-15-4) + 1,1,1,2,3,3-hexafluoropropane (431-63-0) + 2-bromo-1,1,1,2,3,3-hexafluoro-propane (2252-80-4)

Conditions	Yield
With tri-n-butyl-tin hydride for 1.5h; Product distribution; Heating;	A 53% B 3% C 14% D 21%

1,2-dibromohexafluoropropane (661-95-0) + o-toluidine (95-53-4) → 4-[1-(bromo-difluoro-methyl)-1,2,2,2-tetrafluoro-ethyl]-2-methyl-phenylamine (686745-74-4)

Conditions	Yield
With sodium thiosulfate; sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate In tert-butyl methyl ether; water at 20 - 40℃; for 18h;	53%

piperidine (110-89-4) + 1,2-dibromohexafluoropropane (661-95-0) → 1-(1,1,2,3,3,3-hexafluoro-propyl)-piperidine (2643-19-8) + 1-pentafluoropropenyl-piperidine (2588-69-4) + 1-(2,3,3,3-tetrafluoro-propionyl)-piperidine (27096-52-2) + 1-(2-Bromo-1,1,2,3,3,3-hexafluoro-propyl)-piperidine (113985-85-6)

Conditions	Yield
With sodium hydride; triethylamine In N,N-dimethyl-formamide at -5℃; for 6h;	A 1 % Spectr. B 20% C n/a D 33%

1,2-dibromohexafluoropropane (661-95-0) + diethylamine (109-89-7) → hexafluoropropene-diethylamine adduct (309-88-6) + diethyl-(pentafluoro-propenyl)-amine (363-75-7) + (2-Bromo-1,1,2,3,3,3-hexafluoro-propyl)-diethyl-amine (113939-51-8)

Conditions	Yield
With sodium hydride; triethylamine In N,N-dimethyl-formamide at -5℃; for 6h;	A 1 % Spectr. B 21% C 32%
With n-butyllithium; triethylamine In N,N-dimethyl-formamide at -5℃; for 6h; Product distribution; various temperatures, time, and reagents;	A 1 % Spectr. B 20 % Spectr. C 65 % Spectr.

1,2-dibromohexafluoropropane (661-95-0) + 2-(difluoromethoxy)aniline (22236-04-0) → 4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)aniline (1262665-43-9)

Conditions	Yield
With sodium dithionite; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In tert-butyl methyl ether; water at 18 - 30℃; for 48h;	26%

pyrrolidine (123-75-1) + 1,2-dibromohexafluoropropane (661-95-0) → 1-(1,1,2,3,3,3-hexafluoro-propyl)-pyrrolidine (711-16-0) + 1-(2-Bromo-1,1,2,3,3,3-hexafluoro-propyl)-pyrrolidine (113985-86-7) + 1-((E)-Pentafluoro-propenyl)-pyrrolidine (113985-88-9) + 2,3,3,3-Tetrafluoro-1-pyrrolidin-1-yl-propan-1-one (113985-87-8)

Conditions	Yield
With sodium hydride; triethylamine In N,N-dimethyl-formamide at -5℃; for 6h;	A 1 % Spectr. B 21% C 15 % Spectr. D n/a

2-Fluoroaniline (348-54-9) + 1,2-dibromohexafluoropropane (661-95-0) → 2-fluoro-4-(1-bromo-1,1,2,3,3,3-hexafluoro-2-propyl)aniline

Conditions	Yield
With sodium thiosulfate; sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate In tert-butyl methyl ether; water at 20 - 40℃; for 12h;	14%

1,2-dibromohexafluoropropane (661-95-0) + perfluoropropylene (116-15-4) → 1,4-dibromo-nonafluoro-2-trifluoromethyl-pentane (812-38-4)

Conditions	Yield
at 255℃; under 213297 Torr;

1,2-dibromohexafluoropropane (661-95-0) + perfluoropropylene (116-15-4) → 1,6-dibromo-dodecafluoro-2,4-bis-trifluoromethyl-heptane (865-72-5)

Conditions	Yield
at 250℃;

1,2-dibromohexafluoropropane (661-95-0) → perfluoropropylene (116-15-4)

Conditions	Yield
With acetic acid; zinc at 25℃;
With ethanol; zinc

1,2-dibromohexafluoropropane (661-95-0) + ethene (74-85-1) → 1,4-dibromo-1,1,2-trifluoro-2-(trifluoromethyl)butane (3871-35-0)

Conditions	Yield
With dibenzoyl peroxide

pyrrolidine (123-75-1) + 1,2-dibromohexafluoropropane (661-95-0) → 1-(1,1,2,3,3,3-hexafluoro-propyl)-pyrrolidine (711-16-0) + 1-(2-Bromo-1,1,2,3,3,3-hexafluoro-propyl)-pyrrolidine (113985-86-7) + 1-((E)-Pentafluoro-propenyl)-pyrrolidine (113985-88-9)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 40℃; for 20h;	A 15 % Spectr. B 13 % Spectr. C 1 % Spectr.

1,2-dibromohexafluoropropane (661-95-0) + perfluoroisobutylene (382-21-8) → 2-bromo-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane (754-43-8) + Perfluoro-4,4-dimethylpent-2-ene (72487-69-5)

Conditions	Yield
With cesium fluoride In diethylene glycol dimethyl ether for 2.5h; Product distribution; various vicinal dihalopolyfluoroalkanes;

1,2-dibromohexafluoropropane (661-95-0) → 2-hydroperfluoropropyl azide (2991-70-0) + 2-bromoperfluoropropyl azide

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide at 80℃; for 27h; Yield given. Yields of byproduct given;

1,2-dibromohexafluoropropane (661-95-0) + diethylamine (109-89-7) → hexafluoropropene-diethylamine adduct (309-88-6) + diethyl-(pentafluoro-propenyl)-amine (363-75-7) + N,N'-diethyl-1,2,2,2-tetrafluoropropionamide (392-63-2) + (2-Bromo-1,1,2,3,3,3-hexafluoro-propyl)-diethyl-amine (113939-51-8)

Conditions	Yield
With n-butyllithium; triethylamine In N,N-dimethyl-formamide at -5℃; for 2h;	A 1 % Spectr. B 20 % Spectr. C n/a D 65 % Spectr.

1,2-dibromohexafluoropropane (661-95-0) + allyl-trimethyl-silane (762-72-1) → 5-Bromo-4,5,5-trifluoro-4-trifluoromethyl-pent-1-ene (89965-96-8)

Conditions	Yield
With ethanolamine; triiron dodecarbonyl at 60℃; for 20h; sealed tube;	40 % Chromat.

1,2-dibromohexafluoropropane (661-95-0) + ethenyltrimethylsilane (754-05-2) → (1,4-Dibromo-3,4,4-trifluoro-3-trifluoromethyl-butyl)-trimethyl-silane (89608-36-6)

Conditions	Yield
With ethanolamine; triiron dodecarbonyl at 60℃; for 20h;	38 % Chromat.

Upstream product

• 116-15-4 perfluoropropylene 
• 690-39-1 1,1,1,3,3,3-hexafluoropropane 
• 2252-84-8 HFC-227ca 
• 375-22-4 heptafluorobutyric Acid 
• 7726-95-6 bromine 
• 7732-18-5 water 
• 87-65-0 2,6-Dichlorophenol 
• 107-03-9 1-thiopropane 
• 70142-16-4 Bromine(I) trifluoromethanesulfonate 

Downstream Products

• 2252-78-0 1-bromo-1,1,2,3,3,3-hexafluoro-propane 
• 116-15-4 perfluoropropylene 
• 431-63-0 1,1,1,2,3,3-hexafluoropropane 
• 2252-80-4 2-bromo-1,1,1,2,3,3-hexafluoro-propane 
• 686745-74-4 4-[1-(bromo-difluoro-methyl)-1,2,2,2-tetrafluoro-ethyl]-2-methyl-phenylamine 
• 849370-61-2 1-(2-bromo-1,1,2,3,3,3-hexafluoropropyloxy)-4-methyl-3-nitrobenzene 
• 1246013-21-7 C₁₀H₇F₅S 
• 1262665-43-9 4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)aniline 
• 849370-58-7 1-(2-bromo-1,1,2,3,3,3-hexafluoropropyloxy)-4-chlorobenzene 
• 7726-95-6 bromine 
• 143766-78-3 (cis/trans)-1-Bromomethyl-2-(3-bromo-2-trifluoromethyl-2,3,3-trifluoropropyl)cyclohexane 
• 38568-21-7 2,2-dibromo-1,1,1,3,3,3-hexafluoropropane 
• 357-98-2 1-phenoxy-2-hydroperfluoropropane 
• 95519-57-6 (2-Bromo-1,1,2,3,3,3-hexafluoro-propoxy)-benzene 

Relevant academic research and scientific papers

PROCESSES FOR PRODUCING BRANCHED FLUOROALKYL OLEFINS

Processes for producing branched fluoroalkyl olefins are disclosed. In addition, novel halo-fluoroalkane intermediates are disclosed that may be used in the branched fluoroalkyl olefin production processes. Non-limiting examples of branched fluoroalkyl olefins include branched fluorobutenes, such as 1,3,4,4,4-pentafluoro-3-trifluoromethyl) but-1-ene (HFO-1438ezy). In some aspects, there is disclosed a method for deydrobrominating 4-bromo-1,1,1,2,4-pentafluoro-2-(trifluoromethyl)butane to produce 1,3,4,4,4-pentafluoro-3-(trifluoromethyl)but-1-ene (HFO-1438ezy).

A 1,2- two bromine six fluorine method for the preparation of

The invention relates to a method for preparing 1,2-dibromohexafluoropropane. The method comprises the following steps: (1) adding a catalyst into a mixture of bromine and a polar solvent, wherein the catalyst is transition metal element cationoid perfluorosulfonic acid ion exchange resin; (2) introducing hexafluoropropylene into the solution till the color of the liquid phase is colorless from red to obtain a crude 1,2-dibromohexafluoropropane product; (3) washing and distilling the crude 1,2-dibromohexafluoropropane product obtained in the step (2) to obtain 1,2-dibromohexafluoropropane. The method is stable in reaction, easy in heat conduction control, safe and efficient, and high in yield.

Polyhaloalkylaryls

The present invention relates to polyhaloalkylaryls, to a process for preparing them and to the use of the polyhaloalkylaryls for preparing active ingredients.

Perfluoroalkylanilins

Production of perfluoroalkyl aniline derivatives (I) comprises reacting an aniline (II) with a dihalo perfluoroalkane (III) and reacting the intermediate product (IV) with an ionic fluoride. Production of perfluoroalkyl aniline derivatives of formula (I) comprises reacting an aniline of formula (II) with a dihaloperfluoroalkane of formula (III) and reacting the intermediate product of formula (IV) with an ionic fluoride. R1, R2 = H, 1-12C alkyl, COR, COOR' or 6-15C aralkyl, or NR1R2 is a 4-16C ring or NCO; R = 1-12C alkyl, 5-14C aryl or 6-15C aralkyl; R' = R or 2-12C alkenyl; R3-R6 = F or 1-12C perfluoroalkyl, or two can form a 4-20C perfluorocycloalkyl group; n = 1 or 2; R7 = R, OH, Cl, Br, F, NO2, CN, optionally protected formyl, 1-12C haloalkyl, A-B-D-E, A-E, A-SO2-E, A-B-SO2R9, A-SO3W or A-COW, or two R7 for a 5-12C cyclic group; A = 1-8C alkylene or is absent; B = O, S or NR8 or is absent; D = CO; E = R9, OR9, NHR10 or N(R10)2; R8 = H, 1-8C alkyl, 5-14C aryl or 6-15C aralkyl; R9 = 1-8C alkyl, 1-8C haloalkyl, 5-14C aryl or 6-15C aralkyl; R10 = 1-8C alkyl, 6-15C aralkyl or 6-14C aryl, or N(R10)2 is a 4-12C cyclic amino group; W = OH, NH2 or OM; M = alkali(ne earth) metal, NH4 or organic ammonium; m = 0-5; and Hal1, Hal2 = Cl, Br or I. An Independent claim is also included for compounds (IV).

Preparation of polyhaloalkanes

The present invention relates to a process for preparing polyhaloalkanes and to their use for preparing intermediates for agrochemicals and pharmaceuticals.

Infrared Multiphoton Dissociation of Heptafluoropropane

The dissociation yield and branching ratio in CO2-laser-induced multiphoton dissociation (MPD) of CF3CF2CHF2 were studied as a function of irradiation frequency (979.7, 1037.4, and 1081.1 cm-1) and laser fluence (focal fluence 2).Br2 was successfully employed to reveal the dissociation mechanisms by scavenging a number of primary and secondary dissociation fragments produced in the MPD.At low laser fluences the distributions of scavenged products were the same regardless of irradiation frequencies.The primary dissociation of CF3CF2CHF2 was found to proceed mainly via the higher activation energy channels (i.e., C-C ruptures: CF3CF2CHF2 -> C2F5 + CHF2, and CF3CF2CHF2 -> CF3 + C2HF4) rather than via HF elimination (CF3CF2CHF2 -> C3F6 + HF) in our experimental conditions.The observed branching ratio between the two C-C rupture channels (ca. 2:1) agreed with the results obtained by RRKM calculation.A remarkable difference in product distribution with respect to the irradiation frequency was observed at higher laser fluences.This indicates that the secondary photolysis of primarily produced radicals within the laser pulse occured significantly at higher fluences (i.e., C2F5 -> CF3 + CF2, CHF2 -> CF2 + H, CF3 -> CF2 + F, and C2HF4 -> CF2 + CHF2), depending strongly upon the irradiation frequencies.

Insecticidal urea substituted 2,3-dihydro- benzofuran and benzothiophene derivatives, compositions, and method of use thereof

Insecticidal compounds of the formula STR1 in which A and B are both halogen or hydrogen, or one of A and B is hydrogen, and the other of A and B is halogen; Z and W are independently O or S; the substituted benzofuranyl or benzothienyl group is attached at position 5 or 6; R is halogen; m is 0 to 3; R' is F or CF3 ; methods for their preparation and formulation, insecticidal compositions, and their use to control insects are disclosed.

Synthesis of Haloalkyl Esters of Trifluoromethanesulfonic Acid by the Regio- and Stereospecific Addition of Chlorine(I) and Bromine(I) Trifluoromethanesulfonate to Alkenes

The synthesis of a variety of haloalkyl esters of trifluoromethanesulfonic acid was achieved by the addition of CF3SO2OCl and CF3SO2OBr to alkenes.Addition to simple alkenes such as CH2CH2, CF2CH2, CF2CF2, CF2CFCl, CF2CCl2, CHClCHCl, and CHFCHF occur readily at low temperature to give the esters in high yield.With unsymmetrical alkenes, only one structural isomer is observed in every case.With the hypochlorite, cis- and trans-CHFCHF form a single different diastereomer.With the hypobromite, the same result is observed, and trans-CHClCHCl also gives only one diastereomer.A regio- and stereospecific cis-addition mechanism is proposed.