2160-89-6

Basic information

• Product Name: 1,1,1,3,3,3-Hexafluoroisopropyl acrylate
• Synonyms: 2,2,2-Trifluoro-1-(trifluoromethyl)ethyl acrylate;2-Propenoic acid, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ester;2-propenoicacid,2,2,2-trifluoro-1-(trifluoromethyl)ethylester;ACRYLIC ACID 1,1,1,3,3,3-HEXAFLUOROISOPROPYL ESTER;1,1,1,3,3,3-HEXAFLUOROISOPROPYL ACRYLATE;1H-1-(TRIFLUOROMETHYL)TRIFLUOROETHYL ACRYLATE;HFIP-A;HEXAFLUORO-2-PROPYL ACRYLATE
• CAS NO: 2160-89-6
• Molecular Formula: C₆H₄F₆O₂
• Molecular Weight: 222.09
• EINECS: 218-479-1
• Product Categories: monomer;Acrylic Monomers;C6 to C7Monomers;Carbonyl Compounds;Esters;Fluorinated AcrylicsSelf Assembly&Contact Printing;Fluorine-Containing Monomers for 157 nm UV Lithography Resist PolymersPhotonic and Optical Materials;Lithography Monomers;Low Refractive Index Monomers;Waveguide Materials
• Mol File: 2160-89-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 84 °C
• Flash Point: 50 °F
• Appearance: clear colorless liquid
• Density: 1.33 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.22 psi ( 20 °C)
• Refractive Index: n20/D 1.319(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Insoluble
• BRN: 2094742
• CAS DataBase Reference: 1,1,1,3,3,3-Hexafluoroisopropyl acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1,3,3,3-Hexafluoroisopropyl acrylate(2160-89-6)
• EPA Substance Registry System: 1,1,1,3,3,3-Hexafluoroisopropyl acrylate(2160-89-6)

Safety Data

• Hazard Codes: Xi,N,F
• Statements: 36/37/38-51/53-11
• Safety Statements: 26-28-61-37/39-16
• RIDADR: UN 3272 3/PG 2
• WGK Germany: 2
• TSCA: T
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 2160-89-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

1,1,1,3,3,3-Hexafluoroisopropyl acrylate is used in agrochemical, pharmaceutical and dyestuff field.

InChI:InChI=1/C6H4F6O2/c1-2-3(13)14-4(5(7,8)9)6(10,11)12/h2,4H,1H2

Synthetic route

1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + acryloyl chloride (814-68-6) → 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) at 20℃; for 20.0833h;

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + (E)-(pent-3-en-1-yn-1-yl)cyclohexane → 1,1,1,3,3,3-hexafluoropropan-2-yl (S,E)-3-cyclohexyl-2-(prop-1-en-1-yl) cyclobut-2-ene-1-carboxylate

Conditions	Yield
With C27H34Br2CoNOP; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; zinc In toluene at 23℃; for 15h; Inert atmosphere; Glovebox; Sealed tube; enantioselective reaction;	99%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + (E)-(pent-3-en-1-yn-1-yl)cyclohexane → 1,1,1,3,3,3-hexafluoropropan-2-yl (E)-3-cyclohexyl-2-(prop-1-en-1-yl) cyclobut-2-ene-1-carboxylate

Conditions	Yield
With C21H18Br2CoNOP; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; zinc In toluene at 23℃; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;	99%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + C12H16OS → C18H20F6O3S

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;	98%

iodobenzene (591-50-4) + 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) → (E)-3-Phenyl-acrylic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

Conditions	Yield
With PdAS-V; triethylamine In toluene at 100℃; for 5h; Heck reaction;	95%
With triethylamine; poly{bis[(N-iPr-acrylamide)5-co-((4-vinylphenyl)PPh2)]PdCl2} In toluene at 100℃; for 5h; Heck reaction;	95%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + N-(o-bromobenzyl)-6-pent-4-enylpiperidin-2-one (606123-24-4) → 1,1,1,3,3,3-hexafluoroisopropyl (E)-6-[1-(2-bromobenzyl)-6-oxopiperidin-2-yl]hex-2-enoate (606123-37-9)

Conditions	Yield
Grubbs catalyst first generation In dichloromethane at 20℃; for 12h;	92%

1,4-Oxathiane (15980-15-1) + 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) → C10H12F6O3S

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;	91%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + benzaldehyde (100-52-7) → 1,1,1,3,3,3-hexafluoropropan-2-yl (R)-3-hydroxy-2-methylene-3-phenylpropanoate (253197-70-5)

Conditions	Yield
With 4-(3-ethyl-4-oxa-1-azatricyclo[4,4,0,0(3,8)]dec-5-yl)quinolin-6-ol In tetrahydrofuran; N,N-dimethyl-formamide at -55℃; for 24h; Morita-Baylis-Hillman Alkylation; enantioselective reaction;	90%
Stage #1: benzaldehyde With 4-[(5S)-3-ethyl-4-oxa-1-azatricyclo[4.4.0.03,8]decan-5-yl]quinolin-6-yl (2,2,2-trichloroacetyl)carbamate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Morita-Baylis-Hillman reaction; Molecular sieve; Stage #2: 1,1,1,3,3,3-hexafluoroisopropyl acrylate In N,N-dimethyl-formamide at -55℃; for 3h; Morita-Baylis-Hillman reaction; optical yield given as %ee; enantioselective reaction;	83%
With 4-(3-ethyl-4-oxa-1-azatricyclo[4,4,0,0(3,8)]dec-5-yl)quinolin-6-ol In N,N-dimethyl-formamide at -55℃; for 48h; Baylis-Hillman reaction;	75%
With (3R,8R,9S)-10,11-dihydro-3,9-epoxy-6'-hydroxy-cinchonane In N,N-dimethyl-formamide at -55℃; for 48h; Baylis-Hillman reaction;	75%

tetrahydrothiopyran-4-ol (29683-23-6) + 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) → C11H14F6O3S

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;	90%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + tert-Butyl-((8R,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yloxy)-dimethyl-silane (96157-01-6) → (4bS,6aS,6bR,7R,8aS,9aS,9bR)-6b-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6a-methyl-5,6,6a,6b,7,8,8a,9,9a,9b,10,11-dodecahydro-4bH-cyclobuta[3,4]cyclopenta[1,2-a]phenanthrene-7-carboxylic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester + (4bS,6aS,6bR,7S,8aS,9aS,9bR)-6b-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6a-methyl-5,6,6a,6b,7,8,8a,9,9a,9b,10,11-dodecahydro-4bH-cyclobuta[3,4]cyclopenta[1,2-a]phenanthrene-7-carboxylic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

Conditions	Yield
With ethylaluminum dichloride In dichloromethane at -60℃; for 0.166667h; Temperature; Inert atmosphere; Overall yield = 86 %; diastereoselective reaction;	A n/a B 89%
With ethylaluminum dichloride In dichloromethane at -78℃; for 4h; Title compound not separated from byproducts;

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + tert-Butyl-((8R,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yloxy)-dimethyl-silane (96157-01-6) → (4bS,6aS,6bR,7S,8aS,9aS,9bR)-6b-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6a-methyl-5,6,6a,6b,7,8,8a,9,9a,9b,10,11-dodecahydro-4bH-cyclobuta[3,4]cyclopenta[1,2-a]phenanthrene-7-carboxylic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

Conditions	Yield
With ethylaluminum dichloride In dichloromethane at -40℃; for 0.166667h; Temperature; Inert atmosphere; diastereoselective reaction;	89%
Multi-step reaction with 2 steps 1: ethylaluminum dichloride / dichloromethane / 0.17 h / -60 °C / Inert atmosphere 2: ethylaluminum dichloride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: ethylaluminum dichloride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere 2: ethylaluminum dichloride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere View Scheme

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + 3,3-diethyl-5,5-dimethylmorpholin-2-one (264279-67-6) → C16H21F6NO4

Conditions	Yield
With silver(I) acetate; palladium diacetate at 60℃;	89%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + 1-(((dimethyl(oxo)- λ6-sulfanylidene)methyl)sulfonyl)-4-methylbenzene → 1,1,1,3,3,3-hexafluoropropan-2-yl 2-(6-methyl-3-oxo-2,3-dihydro-1H-inden-1-yl)acetate

Conditions	Yield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1,1,1,3',3',3'-hexafluoro-propanol; sodium acetate at 100℃; for 24h; Glovebox;	88%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + (2R,3S)-3-triethylsiloxy-2-methyl-3-phenylpropanal → 1,1,1,3,3,3-hexafluoropropan-2-yl (3R,4S,5R)-3-hydroxy-5-triethylsiloxy-4-methyl-2-methylene-5-phenylpentanoate

Conditions	Yield
With 4-(3-ethyl-4-oxa-1-azatricyclo[4,4,0,0(3,8)]dec-5-yl)quinolin-6-ol In tetrahydrofuran; N,N-dimethyl-formamide at -55℃; for 72h; Morita-Baylis-Hillman Alkylation;	87%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + 4-nitrobenzaldehdye (555-16-8) → 1,1,1,3,3,3-hexafluoropropan-2-yl (R)-3-hydroxy-2-methylene-3-(4-nitrophenyl)-propanoate

Conditions	Yield
With C33H27F6FeN2PS; sodium hydroxide In tetrahydrofuran at 25℃; for 48h; Catalytic behavior; Reagent/catalyst; Morita-Baylis-Hillman Alkylation; enantioselective reaction;	85%
Stage #1: 4-nitrobenzaldehdye With 4-[(5S)-3-ethyl-4-oxa-1-azatricyclo[4.4.0.03,8]decan-5-yl]quinolin-6-yl (2,2,2-trichloroacetyl)carbamate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Morita-Baylis-Hillman reaction; Molecular sieve; Stage #2: 1,1,1,3,3,3-hexafluoroisopropyl acrylate In N,N-dimethyl-formamide at -55℃; for 2h; Morita-Baylis-Hillman reaction; optical yield given as %ee; enantioselective reaction;	63%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + tert-Butyl-((8R,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yloxy)-dimethyl-silane (96157-01-6) → (4bS,6aS,6bR,7R,8aS,9aS,9bR)-6b-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-6a-methyl-5,6,6a,6b,7,8,8a,9,9a,9b,10,11-dodecahydro-4bH-cyclobuta[3,4]cyclopenta[1,2-a]phenanthrene-7-carboxylic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

Conditions	Yield
With ethylaluminum dichloride In dichloromethane at -78℃; for 0.166667h; Inert atmosphere; diastereoselective reaction;	85%

3-hydroxypropyl benzoate (6946-99-2) + 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) → 2-(5-oxotetrahydrofuran-2-yl)ethyl benzoate

Conditions	Yield
With quinuclidin-3-yl benzenesulfonate; 3,3,3',3'-tetrakis(trifluoromethyl)-1,1'(3H,3'H)-spirobi<2,1-benzoxasilole>; C36H16F16IrN4(1+)*F6P(1-) In acetonitrile at 20℃; for 14h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;	85%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + β-naphthaldehyde (66-99-9) → 1,1,1,3,3,3-hexafluoropropan-2-yl (S)-3-hydroxy-2-methylene-3-(naphthalen-2-yl)-propanoate (1476067-48-7)

Conditions	Yield
With α-isocupreine In N,N-dimethyl-formamide at -55℃; for 48h; Morita-Baylis-Hillman Alkylation; Inert atmosphere; enantioselective reaction;	84%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + 3-nitro-benzaldehyde (99-61-6) → C13H9F6NO5

Conditions	Yield
With C33H27F6FeN2PS; sodium hydroxide In tetrahydrofuran at 25℃; for 48h; Morita-Baylis-Hillman Alkylation; enantioselective reaction;	84%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + (S)-N-tert-butoxycarbonylvalinal (79069-51-5) → tert-butyl (3S,4S)-[5-((1,1,1,3,3,3-hexafluoropropan-2-yloxy)carbonyl)-4-hydroxy-2-methylhex-5-en-3-yl]carbamate (916823-42-2) + (2R,6S)-2,6-bis((S)-1-((tert-butoxycarbonyl)amino)-2-methylpropyl)-5-methylidene-1,3-dioxan-4-one

Conditions	Yield
With 4-(3-ethyl-4-oxa-1-azatricyclo[4,4,0,0(3,8)]dec-5-yl)quinolin-6-ol In N,N-dimethyl-formamide at -55℃; for 46h;	A 83% B 3%

thiophene (110-01-0) + 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) → C10H12F6O2S

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;	83%

sulfure de pentamethylene (1613-51-0) + 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) → C11H14F6O2S

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;	83%

Tetrahydrothiopyran-4-one (1072-72-6) + 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) → C11H12F6O3S

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;	83%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + tert-butyl (cyclohept-1-en-1-yloxy)dimethylsilane (68081-19-6) → (1RS,7SR,9RS)-1-(tert-butyldimethylsiloxy)-9-(1,1,1,3,3,3-hexafluoroisopropoxycarbonyl)bicyclo[5.2.0]nonane

Conditions	Yield
With ethylaluminum dichloride In dichloromethane at -78℃; for 4h;	82%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + β-naphthaldehyde (66-99-9) → 1,1,1,3,3,3-hexafluoropropan-2-yl (R)-3-hydroxy-2-methylene-3-(naphthalen-2-yl)propanoate

Conditions	Yield
With (3R,8R,9S)-10,11-dihydro-3,9-epoxy-6'-hydroxy-cinchonane In N,N-dimethyl-formamide at -55℃; for 58h; Baylis-Hillman reaction;	82%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + bis(pinacol)diborane (73183-34-3) → 1,1,1,3,3,3-hexafluoro-propan-2-yl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1454308-52-1)

Conditions	Yield
Stage #1: bis(pinacol)diborane With copper(II) carbonate; triphenylphosphine In water at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,1,1,3,3,3-hexafluoroisopropyl acrylate In water at 27℃; for 24h; Inert atmosphere;	82%
Stage #1: bis(pinacol)diborane With copper carbonate hydroxide; triphenylphosphine In water at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,1,1,3,3,3-hexafluoroisopropyl acrylate In water at 27℃; for 24h; Inert atmosphere;	82%
Stage #1: bis(pinacol)diborane With copper(II) carbonate; triphenylphosphine In water at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,1,1,3,3,3-hexafluoroisopropyl acrylate In water at 27℃; for 24h; Inert atmosphere;	82%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + hexan-1-ol (111-27-3) → γ-nonalactone (104-61-0)

Conditions	Yield
With quinuclidin-3-yl benzenesulfonate; 3,3,3',3'-tetrakis(trifluoromethyl)-1,1'(3H,3'H)-spirobi<2,1-benzoxasilole>; C36H16F16IrN4(1+)*F6P(1-) In acetonitrile at 20℃; for 14h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;	82%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + 1-triisopropylsiloxy-1-cyclohexene (80522-46-9) → (1RS,6SR,8RS)-1-(triisopropylsiloxy)-8-(1,1,1,3,3,3-hexafluoroisopropoxycarbonyl)bicyclo[4.2.0]octane

Conditions	Yield
With ethylaluminum dichloride In dichloromethane at -78℃; for 4h;	80%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → C13H8ClF6NO5

Conditions	Yield
With C33H27F6FeN2PS; sodium hydroxide In tetrahydrofuran at 25℃; for 48h; Morita-Baylis-Hillman Alkylation; enantioselective reaction;	80%

4-(phenylthio-methyl)-piperidine-1-carboxylic acid tert-butyl ester (875282-59-0) + 1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) → C23H29F6NO4S

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;	78%

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + tert-butoxycarbonyl-L-leucinal (58521-45-2) → tert-butyl (3S,4S)-[2-((1,1,1,3,3,3-hexafluoropropan-2-yloxy)carbonyl)-3-hydroxy-6-methylhept-1-en-4-yl]carbamate (916823-40-0) + 2,6-bis((S)-1-((tert-butoxycarbonyl)amino)-3-methylbutyl)-5-methylidene-1,3-dioxan-4-one

Conditions	Yield
With 4-(3-ethyl-4-oxa-1-azatricyclo[4,4,0,0(3,8)]dec-5-yl)quinolin-6-ol In N,N-dimethyl-formamide at -55℃; for 46h;	A 77% B 4%

Upstream product

• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 814-68-6 acryloyl chloride 

Downstream Products

• 253197-70-5 1,1,1,3,3,3-hexafluoropropan-2-yl (R)-3-hydroxy-2-methylene-3-phenylpropanoate 
• 606141-51-9 methyl (S)-2-methanesulfonylamino-2-phenylacetate 
• 875628-14-1 1,1,1,3,3,3-hexafluoropropan-2-yl (R)-3-hydroxy-2-methylene-5-phenylpentanoate 

Relevant articles and documents

DIELS-ALDER REACTION WITH FURANICS TO OBTAIN AROMATICS

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