1,1,1,3',3',3'-hexafluoro-propanol
acryloyl chloride
1,1,1,3,3,3-hexafluoroisopropyl acrylate
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) at 20℃; for 20.0833h; |
1,1,1,3,3,3-hexafluoroisopropyl acrylate
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
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% |
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% |
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
N-(o-bromobenzyl)-6-pent-4-enylpiperidin-2-one
1,1,1,3,3,3-hexafluoroisopropyl (E)-6-[1-(2-bromobenzyl)-6-oxopiperidin-2-yl]hex-2-enoate
Conditions | Yield |
---|---|
Grubbs catalyst first generation In dichloromethane at 20℃; for 12h; | 92% |
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
benzaldehyde
1,1,1,3,3,3-hexafluoropropan-2-yl (R)-3-hydroxy-2-methylene-3-phenylpropanoate
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% |
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
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
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
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
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
3,3-diethyl-5,5-dimethylmorpholin-2-one
Conditions | Yield |
---|---|
With silver(I) acetate; palladium diacetate at 60℃; | 89% |
1,1,1,3,3,3-hexafluoroisopropyl acrylate
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
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% |
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
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
Conditions | Yield |
---|---|
With ethylaluminum dichloride In dichloromethane at -78℃; for 0.166667h; Inert atmosphere; diastereoselective reaction; | 85% |
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
β-naphthaldehyde
1,1,1,3,3,3-hexafluoropropan-2-yl (S)-3-hydroxy-2-methylene-3-(naphthalen-2-yl)-propanoate
Conditions | Yield |
---|---|
With α-isocupreine In N,N-dimethyl-formamide at -55℃; for 48h; Morita-Baylis-Hillman Alkylation; Inert atmosphere; enantioselective reaction; | 84% |
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
(S)-N-tert-butoxycarbonylvalinal
A
tert-butyl (3S,4S)-[5-((1,1,1,3,3,3-hexafluoropropan-2-yloxy)carbonyl)-4-hydroxy-2-methylhex-5-en-3-yl]carbamate
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% |
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% |
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% |
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
tert-butyl (cyclohept-1-en-1-yloxy)dimethylsilane
Conditions | Yield |
---|---|
With ethylaluminum dichloride In dichloromethane at -78℃; for 4h; | 82% |
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
bis(pinacol)diborane
1,1,1,3,3,3-hexafluoro-propan-2-yl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
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% |
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
1-triisopropylsiloxy-1-cyclohexene
Conditions | Yield |
---|---|
With ethylaluminum dichloride In dichloromethane at -78℃; for 4h; | 80% |
1,1,1,3,3,3-hexafluoroisopropyl acrylate
4-chloro-3-nitro-benzaldehyde
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
1,1,1,3,3,3-hexafluoroisopropyl acrylate
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
tert-butoxycarbonyl-L-leucinal
A
tert-butyl (3S,4S)-[2-((1,1,1,3,3,3-hexafluoropropan-2-yloxy)carbonyl)-3-hydroxy-6-methylhept-1-en-4-yl]carbamate
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% |
The 1,1,1,3,3,3-Hexafluoroisopropyl acrylate is an organic compound with the formula C6H4F6O2. The IUPAC name of this chemical is 1,1,1,3,3,3-hexafluoropropan-2-yl prop-2-enoate. With the CAS registry number 2160-89-6, it is also named as 2-Propenoic acid, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ester. The product's categories are 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. Besides, it is a clear colorless liquid, which should be stored in a cold, dry place.
Physical properties about 1,1,1,3,3,3-Hexafluoroisopropyl acrylate are: (1)ACD/LogP: 1.80; (2)ACD/LogD (pH 5.5): 1.79; (3)ACD/LogD (pH 7.4): 1.79; (4)ACD/BCF (pH 5.5): 13.62; (5)ACD/BCF (pH 7.4): 13.62; (6)ACD/KOC (pH 5.5): 225.61; (7)ACD/KOC (pH 7.4): 225.61; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 26.3 Å2; (11)Index of Refraction: 1.326; (12)Molar Refractivity: 32.21 cm3; (13)Molar Volume: 159.3 cm3; (14)Polarizability: 12.77×10-24cm3; (15)Surface Tension: 18.2 dyne/cm; (16)Density: 1.394 g/cm3; (17)Flash Point: 10 °C; (18)Enthalpy of Vaporization: 34.9 kJ/mol; (19)Boiling Point: 110.3 °C at 760 mmHg; (20)Vapour Pressure: 23.9 mmHg at 25°C.
Uses of 1,1,1,3,3,3-Hexafluoroisopropyl acrylate: it can be used to produce -(1-hydroxy-propyl)-acrylic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester at temperature of -55 °C. This reaction is a kind of Addition. It will need reagent (3R,8R,9S)-10,11-dihydro-3,9-epoxy-6'-hydroxycinchonane and solvent dimethylformamide with reaction time of 4 hours. The yield is about 40%.
When you are using this chemical, please be cautious about it as the following:
It is highly flammable, and harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. When you are using it, Keep away from sources of ignition - No smoking, and wear suitable suitable protective clothing and gloves. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer).
You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(F)C(OC(=O)\C=C)C(F)(F)F
(2)InChI: InChI=1/C6H4F6O2/c1-2-3(13)14-4(5(7,8)9)6(10,11)12/h2,4H,1H2
(3)InChIKey: MNSWITGNWZSAMC-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C6H4F6O2/c1-2-3(13)14-4(5(7,8)9)6(10,11)12/h2,4H,1H2
(5)Std. InChIKey: MNSWITGNWZSAMC-UHFFFAOYSA-N
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