661-95-0

Basic information

• Product Name: 1,2-DIBROMOHEXAFLUOROPROPANE
• Synonyms: (+/-)-1,2-DIBROMOHEXAFLUOROPROPANE;1,2-DIBROMOHEXAFLUOROPROPANE;1,2-dibromo-1,1,2,3,3,3-hexafluoro-propan;1,2-Dibromo-1,1,2,3,3,3-hexafluoropropane;Propane, 1,2-dibromo-1,1,2,3,3,3-hexafluoro-;1,2-Dibromohexafluoropropane,95%;1,2-Dibromohexafluoropropane 98%;1,2-Dibromohexafluoropropane98%
• CAS NO: 661-95-0
• Molecular Formula: C₃Br₂F₆
• Molecular Weight: 309.83
• EINECS: 211-550-8
• Mol File: 661-95-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: -95 °C
• Boiling Point: 73 °C
• Flash Point: 71-72°C
• Appearance: /
• Density: 2.169
• Refractive Index: 1.3605
• CAS DataBase Reference: 1,2-DIBROMOHEXAFLUOROPROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIBROMOHEXAFLUOROPROPANE(661-95-0)
• EPA Substance Registry System: 1,2-DIBROMOHEXAFLUOROPROPANE(661-95-0)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RTECS: TX8800000
• TSCA: Yes
• Hazardous Substances Data: 661-95-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

1,2-Dibromohexafluoropropane is used in method of manufacturing fire-extinguishing microcapsules comprising fire-extinguishing agent and polymeric shell.

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

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

Downstream Products

• 1246013-21-7 C₁₀H₇F₅S 
• 1262665-43-9 4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)aniline 
• 849370-61-2 1-(2-bromo-1,1,2,3,3,3-hexafluoropropyloxy)-4-methyl-3-nitrobenzene 
• 849370-58-7 1-(2-bromo-1,1,2,3,3,3-hexafluoropropyloxy)-4-chlorobenzene 
• 686745-74-4 4-[1-(bromo-difluoro-methyl)-1,2,2,2-tetrafluoro-ethyl]-2-methyl-phenylamine 
• 7726-95-6 bromine 
• 116-15-4 perfluoropropylene 
• 2252-78-0 1-bromo-1,1,2,3,3,3-hexafluoro-propane 
• 431-63-0 1,1,1,2,3,3-hexafluoropropane 
• 2252-80-4 2-bromo-1,1,1,2,3,3-hexafluoro-propane 
• 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 articles and documents

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).

Polyhaloalkylaryls

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

Preparation of polyhaloalkanes

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