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920-66-1

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920-66-1 Usage

Description

Hexafluoroisopropanol (HFIP) is a viscous and colorless liquid with scary odorless. It is an ideal solvent for dissolving polyamides and esters, and it can be used to analyze nylon. Typically, a small amount of sodium trifluoroacetate can be added to the eluent to reduce the aggregation of the sample. HFIP has a certain viscosity, but its boiling point is very low, so we need to analyst under the conditions of 40 ° C to reduce the back pressure of the column. Hexafluoroisopropanol is also a highly polar solvent that results in a non-linearity of the calibration curve obtained from the mixed column bed column. Therefore, Agilent has developed a special column-PL HFIPgel column for this solvent, which has a porous structure that is not affected by solvents.

Clinical application

Hexafluoroisopropanol(1,1,1,3,3,3-Hexafluoro-2-propanol) can be used to prepare a variety of high-end chemicals such as fluorosurfactants, fluorine-containing emulsifiers, fluorine-containing pharmaceuticals, and used as a solvent or cleaning agent for electronics industry. The drug can be used as a fluorinated solvent to increase the efficiency of the reaction of rhodium (I)-catalyzed [4 + 2] intramolecular addition reaction of ether bound alkynyl diene and the [5 + 2] cycloaddition of alkynyl vinyl cyclopropane. The drug is a liquid peptide chemical solvent, a highly soluble solvent for peptide and peptide intermediates. The drug can be used for the analysis of multiple polymers.

Hazards

1,1,1,3,3,3-Hexafluoro-2-propanol?derives from a propan-2-ol. It is a clear colorless oily liquid with an aromatic odor. (NTP, 1992) Combustible, may cause burns to skin, eyes and mucous membranes.

Preparation

1,1,1,3,3,3-Hexafluoro-2-propanol is prepared from hexafluoropropylene through hexafluoroacetone, which is then hydrogenated. (CF3)2CO + H2 → (CF3)2CHOH

Chemical Properties

Different sources of media describe the Chemical Properties of 920-66-1 differently. You can refer to the following data:
1. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) is a clear, colorless, oily, combustible liquid. Odor is described as aromatic.
2. Colorless liquid

Uses

Different sources of media describe the Uses of 920-66-1 differently. You can refer to the following data:
1. Hexafluoroisopropanol is used to produce high-end chemicals, such as fluorinated surfactants, fluorinated emulsifier and fluorinated medicine, etc. HFIP is used as a solvent or cleaner in electronic industry.
2. 1,1,1,3,3,3-Hexafluoro-2-propanol effects the native state of proteins, denaturing them as well as stabilizing the α-helical conformation of unfolded proteins and polypeptides.
3. It is used as a polar solvent and exhibits strong hydrogen bonding properties.It dissolves substances that are hydrogen-bond acceptors, such as amides, ethers and a wide range of polymers, including those that are not soluble in the most common organic solvents.
4. Usually used for preparing hexafluoroalcohol-functionalized methacrylate polymers for lithographic/nanopatterning materials.

Definition

ChEBI: An organofluorine compound formed by substitution of all the methyl protons in propan-2-ol by fluorine. It is a metabolite of inhalation anesthetic sevoflurane.

General Description

1,1,1,3,3,3-Hexafluoro-2-propanol is a solution-phase peptide chemistry solvent. This fluorinated polar solvent of high ionizing power facilitates Friedel–Crafts-type reactions, using covalent reagents in the absence of a Lewis acid catalyst. It also enhances the efficiency of rhodium(I)-catalyzed [4+2] intramolecular cycloaddition of ether-tethered alkynyl dienes and [5+2] cycloaddition of alkynyl vinylcyclopropanes. 1,1,1,3,3,3-Hexafluoro-2-propanol clusters catalyzes the epoxidation of cyclooctene and 1-octene with hydrogen peroxide.

Air & Water Reactions

Water soluble.

Reactivity Profile

1,1,1,3,3,3-Hexafluoro-2-propanol is incompatible with acids, acid chlorides and oxidizing agents.

Fire Hazard

1,1,1,3,3,3-Hexafluoro-2-propanol is probably combustible.

Potential Exposure

A specialty solvent for some poly mers; a lavatory reagent.

Shipping

UN1760 Corrosive liquids, n.o.s., Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Distil it from 3A molecular sieves, retaining the middle fraction. It has been prepared by reduction of hexafluoroacetone in tetrahydrofuran (THF), In this case hexafluoropropanol forms a stable 1:1 complex which distils at 99-100o/760mm (n 25 1.3283), The complex is decomposed by mixing with 20% oleum and distilling in a vacuum, and the distillate is redistilled to give pure hexafluoropropan-2-ol with b 59o/760mm. The 1H NMR shows a doublet at 4.52ppm (JH,H 2Hz). The benzoyl derivative, [10315-85-2] M 272.1, has m 53.9o after crystalllisation from pentane at -50o, and its IR has at 1760cm-1. [Middleton & Lindsey J Am Chem Soc 86 4948 1964, Urry et al. J Org Chem 32 347 1967.] It has very high peptide solubilising properties, alone or with CH2Cl2 [use as a solvent: Narita et al. Bull Chem Soc Jpn 61 281 1988, Biochemistry 29 2639 1990.] It is CORROSIVE, causes severe eye irritation.

Incompatibilities

HFIP is incompatible with acids, acid chlorides, and oxidizing agents.

Waste Disposal

May be incinerated. In accor dance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be dis posed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste contain ing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 920-66-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 0 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 920-66:
(5*9)+(4*2)+(3*0)+(2*6)+(1*6)=71
71 % 10 = 1
So 920-66-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H3F5N2O2/c12-5-6(13)8(15)10(9(16)7(5)14)20-11(19)4-1-17-3-18-2-4/h1-3H

920-66-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (H0424)  1,1,1,3,3,3-Hexafluoro-2-propanol  >99.0%(GC)

  • 920-66-1

  • 25g

  • 395.00CNY

  • Detail
  • TCI America

  • (H0424)  1,1,1,3,3,3-Hexafluoro-2-propanol  >99.0%(GC)

  • 920-66-1

  • 100g

  • 1,180.00CNY

  • Detail
  • TCI America

  • (H0424)  1,1,1,3,3,3-Hexafluoro-2-propanol  >99.0%(GC)

  • 920-66-1

  • 250g

  • 1,990.00CNY

  • Detail
  • TCI America

  • (H0424)  1,1,1,3,3,3-Hexafluoro-2-propanol  >99.0%(GC)

  • 920-66-1

  • 500g

  • 3,450.00CNY

  • Detail
  • Alfa Aesar

  • (A12747)  1,1,1,3,3,3-Hexafluoro-2-propanol, 99+%   

  • 920-66-1

  • 5g

  • 252.0CNY

  • Detail
  • Alfa Aesar

  • (A12747)  1,1,1,3,3,3-Hexafluoro-2-propanol, 99+%   

  • 920-66-1

  • 25g

  • 682.0CNY

  • Detail
  • Alfa Aesar

  • (A12747)  1,1,1,3,3,3-Hexafluoro-2-propanol, 99+%   

  • 920-66-1

  • 100g

  • 1658.0CNY

  • Detail
  • Sigma-Aldrich

  • (52517)  1,1,1,3,3,3-Hexafluoro-2-propanol  for GC derivatization, ≥99.8%

  • 920-66-1

  • 52517-10ML

  • 1,677.78CNY

  • Detail
  • Sigma-Aldrich

  • (52517)  1,1,1,3,3,3-Hexafluoro-2-propanol  for GC derivatization, ≥99.8%

  • 920-66-1

  • 52517-50ML

  • 6,622.20CNY

  • Detail
  • Fluka

  • (42060)  1,1,1,3,3,3-Hexafluoro-2-propanol  eluent additive for LC-MS

  • 920-66-1

  • 42060-10X1ML

  • 1,852.11CNY

  • Detail
  • Fluka

  • (42060)  1,1,1,3,3,3-Hexafluoro-2-propanol  eluent additive for LC-MS

  • 920-66-1

  • 42060-50ML

  • 2,337.66CNY

  • Detail

920-66-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1,1,3,3,3-hexafluoropropan-2-ol

1.2 Other means of identification

Product number -
Other names 1,1,1,3,3,3-Hexafluoro-2-propanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:920-66-1 SDS

920-66-1Synthetic route

Hexafluoroacetone
684-16-2

Hexafluoroacetone

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
With isopropyl alcohol at 240℃; for 6h; uncatalyzed Meerwein-Ponndorf-Verley reduction;96%
With K(1+)*(C54H46P3Ru)(1-)*C10H8*(C2H5)2O; hydrogen In toluene at 85℃; under 4650.4 Torr; for 2h;
With sodium tetrahydroborate In water
1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether
26103-07-1

1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

sevoflurane
28523-86-6

sevoflurane

Conditions
ConditionsYield
With hydrogenchloride; potassium fluoride; water; Aliquat HTA-1 at 100℃; for 3h; Product distribution / selectivity;A 1.05 %Chromat.
B 93%
With potassium fluoride; potassium hydrogenfluoride; water; Aliquat 175 at 100℃; for 3h; Product distribution / selectivity;A 3.8 %Chromat.
B 89%
With potassium fluoride; potassium hydrogenfluoride; water; benzyl triethyl ammonium dichloride at 100℃; for 3h; Product distribution / selectivity;A 4 %Chromat.
B 88%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

Hexafluoroacetone
684-16-2

Hexafluoroacetone

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

1,1,3,3,3-pentafluoro-2-trimethylsiloxypropene
53841-59-1

1,1,3,3,3-pentafluoro-2-trimethylsiloxypropene

Conditions
ConditionsYield
With magnesium In N,N-dimethyl-formamide at -20 - 0℃; for 1h; Title compound not separated from byproducts.;A 3%
B 80%
heptafluoropropan-2-ol
24427-67-6

heptafluoropropan-2-ol

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
With ruthenium on active carbon; hydrogen fluoride; hydrogen at 0 - 25℃; under 7500.75 Torr; for 1h; chemoselective reaction;76%
N-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-benzamide
5022-41-3

N-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-benzamide

1,1,1,3,3,3-Hexafluoro-propan-2-olatebenzyl-methyl-methylene-ammonium;

1,1,1,3,3,3-Hexafluoro-propan-2-olatebenzyl-methyl-methylene-ammonium;

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

2-phenyl-4,4-bis(trifluoromethyl)-5-N-methylbenzylamino-2-oxazoline
93032-16-7

2-phenyl-4,4-bis(trifluoromethyl)-5-N-methylbenzylamino-2-oxazoline

Conditions
ConditionsYield
In pyridine for 25h; Product distribution; Irradiation;A 60%
B 35%
methyl(1,1,1,3,3,3-hexafluoro-2-propoxo){1,2-bis(diphenylphosphino)ethane}palladium
115981-43-6

methyl(1,1,1,3,3,3-hexafluoro-2-propoxo){1,2-bis(diphenylphosphino)ethane}palladium

A

methane
34557-54-5

methane

B

ethene
74-85-1

ethene

C

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
In further solvent(s) Thermolysis of starting complex (diphenylmethane, vac., 150°C).; GLC.;A 15%
B 2%
C 57%
piperidine
110-89-4

piperidine

Hexafluoroacetone
684-16-2

Hexafluoroacetone

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

3-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-5-(1H-1-trifluoromethyl-2,2,2-trifluoroethyl)-pyridine
108440-27-3

3-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-5-(1H-1-trifluoromethyl-2,2,2-trifluoroethyl)-pyridine

C

2,2’-(pyridine-3,5-diyl)bis(1,1,1,3,3,3-hexafluoropropan-2-ol)
108440-28-4

2,2’-(pyridine-3,5-diyl)bis(1,1,1,3,3,3-hexafluoropropan-2-ol)

Conditions
ConditionsYield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 90℃;A n/a
B 50.5%
C 21.3%
methyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel
115981-38-9

methyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel

A

methane
34557-54-5

methane

B

ethane
74-84-0

ethane

C

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
In further solvent(s) Thermolysis of soln. of metal complex in diphenylmethane (under vac., 150°C).; GLC.;A 46%
B 16%
C <1
ethyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel
115981-39-0

ethyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel

A

ethane
74-84-0

ethane

B

ethene
74-85-1

ethene

C

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
In further solvent(s) Thermolysis of starting compd. (diphenylmethane, vac., 150°C).; GLC.;A 32%
B 43%
C <1
benzaldehyde
100-52-7

benzaldehyde

Hexafluoroacetone
684-16-2

Hexafluoroacetone

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis{2,6-bis(diphenylmethyl)-4-methylphenyl}-imidazolin-2-ylidene In tetrahydrofuran at 40℃; Inert atmosphere;A 11%
B 31%
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

Dimethyl-phenyl-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-silane
151623-41-5

Dimethyl-phenyl-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-silane

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

(2,2,2-trifluoroethoxy)dimethylphenylsilane
109629-96-1

(2,2,2-trifluoroethoxy)dimethylphenylsilane

Conditions
ConditionsYield
With potassium 2,2,2-trifluoroethoxide at 30℃; Rate constant; μ = 0.05 M with potassium trifluoroacetate;
Hexafluoroacetone
684-16-2

Hexafluoroacetone

A

hexafluoroacetone hydrate
677-71-4

hexafluoroacetone hydrate

B

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

C

1,1,1,3,3,5,5,5-octafluoro-4-hydroxy-4-trifluoromethyl-pentan-2-one
52772-37-9

1,1,1,3,3,5,5,5-octafluoro-4-hydroxy-4-trifluoromethyl-pentan-2-one

D

1,1,1,3,5,5,5-Heptafluoro-4-hydroxy-4-trifluoromethyl-pentan-2-one
115397-49-4

1,1,1,3,5,5,5-Heptafluoro-4-hydroxy-4-trifluoromethyl-pentan-2-one

Conditions
ConditionsYield
With tin(ll) chloride In N,N-dimethyl-formamide at 95℃; for 29h; sealed ampul;A 3 % Chromat.
B 25 % Chromat.
C 62 % Chromat.
D 4 % Chromat.
With tin(ll) chloride In N,N-dimethyl-formamide at 95℃; for 29h; sealed ampul;A 3 % Chromat.
B 25 % Chromat.
C 62 % Chromat.
D 4 % Chromat.
With tin(ll) chloride In N,N-dimethyl-formamide at 95℃; for 29h; sealed ampul;A 3 % Chromat.
B 25 % Chromat.
C 25 % Chromat.
D 4 % Chromat.
Dibenzo[a,j]acridine; compound with 1,1,1,3,3,3-hexafluoro-propan-2-ol

Dibenzo[a,j]acridine; compound with 1,1,1,3,3,3-hexafluoro-propan-2-ol

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

dibenz[a,j]acridine
224-42-0

dibenz[a,j]acridine

Conditions
ConditionsYield
In tetrachloromethane at 19.9℃; Thermodynamic data; Equilibrium constant;
In n-heptane at 19.9℃; Thermodynamic data; Equilibrium constant;
Dimethyl-phenyl-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-silane
151623-41-5

Dimethyl-phenyl-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-silane

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

dimethylphenylsilanol
5272-18-4

dimethylphenylsilanol

Conditions
ConditionsYield
With Na2CO3 buffer; sodium hydrogencarbonate In acetonitrile at 30℃; Rate constant; μ = 0.06 M (NaCl);
1,1,1,3,3,3-hexafluoropropan-2-yl 2-phenylethanoate

1,1,1,3,3,3-hexafluoropropan-2-yl 2-phenylethanoate

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

phenylacetic acid anion
7631-42-7

phenylacetic acid anion

Conditions
ConditionsYield
With potassium chloride; hydroxide In 1,4-dioxane; water at 25℃; Rate constant; also for the pig liver esterase catalysed hydrolysis;
(4-Nitro-phenyl)-acetic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

(4-Nitro-phenyl)-acetic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

4-nitrobenzeneacetic acid
104-03-0

4-nitrobenzeneacetic acid

Conditions
ConditionsYield
In hexane; chloroform Rate constant; Ambient temperature; antibody IgG 27H9 as catalyst; 15percent Bicine buffer (pH = 9.0);
1,1,1,3,3,3-hexafluoroisopropyl acrylate
2160-89-6

1,1,1,3,3,3-hexafluoroisopropyl acrylate

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

acrylic acid
79-10-7

acrylic acid

Conditions
ConditionsYield
With (3R,8R,9S)-10,11-dihydro-3,9-epoxy-6'-hydroxy-cinchonane In d7-N,N-dimethylformamide at -40℃;
1,1,1,3,3,3-hexafluoroisopropyl nitrite

1,1,1,3,3,3-hexafluoroisopropyl nitrite

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
With nitric acid Kinetics; Equilibrium constant; Further Variations:; Temperatures; Pressures;
1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether
26103-07-1

1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether

dichlorosevo
28523-85-5

dichlorosevo

formaldehyde di[2,2,2-trifluoro-1-(trifluoromethyl)ethyl] acetal

formaldehyde di[2,2,2-trifluoro-1-(trifluoromethyl)ethyl] acetal

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
With sulfuric acid; water for 18h; Conversion of starting material; Heating / reflux;
Hexafluoroacetone
684-16-2

Hexafluoroacetone

A

1,1,1-trifluoro-2-propanone
421-50-1

1,1,1-trifluoro-2-propanone

B

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

C

hydrogen fluoride
7664-39-3

hydrogen fluoride

Conditions
ConditionsYield
With hydrogen; catalyst
1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether
26103-07-1

1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
With water at 90℃; for 1.5h; Product distribution / selectivity;21.2 %Chromat.
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

Hexafluoroacetone
684-16-2

Hexafluoroacetone

A

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

B

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

C

pentafluoroprop-1-en-2-ol
53841-56-8

pentafluoroprop-1-en-2-ol

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; Hexafluoroacetone With magnesium In N,N-dimethyl-formamide at -20 - 0℃; for 1h;
Stage #2: With sulfuric acid at -30 - 0℃; for 4h; Further stages. Title compound not separated from byproducts.;
A n/a
B n/a
C 7.1 g
C4H4F6O2

C4H4F6O2

sevoflurane
28523-86-6

sevoflurane

A

formaldehyde fluoromethyl [2,2,2-trifluoro-1-(trifluoromethyl)ethyl] acetal
194039-91-3

formaldehyde fluoromethyl [2,2,2-trifluoro-1-(trifluoromethyl)ethyl] acetal

B

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

methyl 3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propionate
7594-51-6

methyl 3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propionate

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
With pyridine hydrochloride In N,N-dimethyl-formamide at 120℃; Product distribution / selectivity;
C3H2F6O*C3H7NO

C3H2F6O*C3H7NO

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C3H2F6O*C4H9NO
22868-56-0

C3H2F6O*C4H9NO

A

N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

B

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C2H6OS*C3H2F6O
22868-53-7

C2H6OS*C3H2F6O

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C3H2F6O*C6H15O4P

C3H2F6O*C6H15O4P

A

triethyl phosphate
78-40-0

triethyl phosphate

B

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C3H2F6O*C5H13N3

C3H2F6O*C5H13N3

A

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

N,N,N',N'-tetramethylguanidine
80-70-6

N,N,N',N'-tetramethylguanidine

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

cubyl trifluoromethanesulphonate
125762-86-9

cubyl trifluoromethanesulphonate

cubyl hexafluoroisopropyl ether

cubyl hexafluoroisopropyl ether

Conditions
ConditionsYield
for 0.0833333h; Ambient temperature;100%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

2,2,2-trifluoro-1-(trifluoromethyl)ethyl sulfamate

2,2,2-trifluoro-1-(trifluoromethyl)ethyl sulfamate

Conditions
ConditionsYield
With formic acid; isocyanate de chlorosulfonyle In 1-methyl-pyrrolidin-2-one; acetonitrile at 0 - 23℃; Inert atmosphere;100%
With sulphamoyl chloride In N,N-dimethyl acetamide
With formic acid; isocyanate de chlorosulfonyle In dimethyl amine; acetonitrile at 0 - 20℃; for 16.1667h;
With formic acid; isocyanate de chlorosulfonyle In N,N-dimethyl acetamide; acetonitrile at 20℃; Cooling with ice;
C14H11NO2
947697-83-8

C14H11NO2

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

C17H13F6NO3

C17H13F6NO3

Conditions
ConditionsYield
silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 25℃;100%
CH2Cl2:MeOH

CH2Cl2:MeOH

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

A

2,3,5-Tri-O-p-Methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S)-2,4-benzylidenedioxy-3-(sulfooxy)butyl]-episulfoniumylidene]-D-arabinitol

2,3,5-Tri-O-p-Methoxybenzyl-1,4-dideoxy-1,4-[[(2S,3S)-2,4-benzylidenedioxy-3-(sulfooxy)butyl]-episulfoniumylidene]-D-arabinitol

B

(2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol
160882-26-8

(2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol

Conditions
ConditionsYield
With potassium carbonateA 100%
B n/a
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Sodium Tris(1,1,1,3,3,3-hexafluoroisopropoxy)borohydride

Sodium Tris(1,1,1,3,3,3-hexafluoroisopropoxy)borohydride

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
4-butoxy-2,2-bis-trifluoromethyl-oxetane
17129-00-9

4-butoxy-2,2-bis-trifluoromethyl-oxetane

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

C12H14F12O3
1226778-14-8

C12H14F12O3

Conditions
ConditionsYield
at 25 - 35℃;100%
Mo(N(2,6-diisopropylphenyl))(CHtBu)(CH2tBu)2

Mo(N(2,6-diisopropylphenyl))(CHtBu)(CH2tBu)2

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

Mo(N-2,6-i-Pr2C6H3)(CH2-t-Bu)3[OCH(CF3)2]

Mo(N-2,6-i-Pr2C6H3)(CH2-t-Bu)3[OCH(CF3)2]

Conditions
ConditionsYield
In neat (no solvent) under N2 atm. (CF3)2CHOH was added to Mo complex and stirred for 10 min; excess alcohol was removed in vacuo;99%
2-allyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl acetate
861104-99-6

2-allyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl acetate

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

C14H11F6NO2
1567381-18-3

C14H11F6NO2

Conditions
ConditionsYield
With acetylacetone at 58℃; for 38h; Time; Temperature;99%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

2-allyl-2,3-dihydro-3-hydroxy-isoindol-1-one
128425-74-1, 41764-19-6

2-allyl-2,3-dihydro-3-hydroxy-isoindol-1-one

C13H12F3NO2
1567381-17-2

C13H12F3NO2

Conditions
ConditionsYield
With acetylacetone at 58℃; for 38h;99%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

2-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-7-phenyloxepane

2-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-7-phenyloxepane

Conditions
ConditionsYield
With 1,1'-(phenyl-λ3-iodanediyl)bis(2-methoxypyridin-1-ium)trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; Molecular sieve; Inert atmosphere;99%
titanium(IV) isopropylate
546-68-9

titanium(IV) isopropylate

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

C12H16F12O4Ti

C12H16F12O4Ti

Conditions
ConditionsYield
at 70℃; for 2h; Inert atmosphere;99%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

2-chloro-N-(phenylmethoxy)propanamide
1303507-91-6

2-chloro-N-(phenylmethoxy)propanamide

anthranil
271-58-9

anthranil

1,1,1,3,3,3-hexafluoropropan-2-yl 2-((1-((benzyloxy)amino)-1-oxopropan-2-yl)amino)benzoate

1,1,1,3,3,3-hexafluoropropan-2-yl 2-((1-((benzyloxy)amino)-1-oxopropan-2-yl)amino)benzoate

Conditions
ConditionsYield
With sodium carbonate at 50℃; for 4h; Inert atmosphere; Schlenk technique;99%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

1-((1,1,1,3,3,3-hexafluoropropan-2-yloxy)-methyl)-4-nitrobenzene
1278547-62-8

1-((1,1,1,3,3,3-hexafluoropropan-2-yloxy)-methyl)-4-nitrobenzene

Conditions
ConditionsYield
With sodium In N,N-dimethyl-formamide for 2h; Reflux;98.8%
Methyl fluorosulfonate
421-20-5

Methyl fluorosulfonate

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

1,1,1,3,3,3-hexafluoro-2-methoxypropane
13171-18-1

1,1,1,3,3,3-hexafluoro-2-methoxypropane

Conditions
ConditionsYield
at 25℃; Temperature;98.8%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

methyl chloroformate
79-22-1

methyl chloroformate

carbonic acid methyl ester 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

carbonic acid methyl ester 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexafluoro-2-methoxypropane; triethylamine at 30℃; for 2h;98.6%
With water at 40℃; Kinetics; solvolysis;
chlorosulfonic acid
7790-94-5

chlorosulfonic acid

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

1,1,1,3,3,3-hexafluoropropyloxysulfonic acid
1616761-45-5

1,1,1,3,3,3-hexafluoropropyloxysulfonic acid

Conditions
ConditionsYield
at -15 - 140℃;98%
indole
120-72-9

indole

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

1,1,1,3,3,3-hexafluoro-2-(1H-indol-3-yl)propan-2-ol
23814-16-6

1,1,1,3,3,3-hexafluoro-2-(1H-indol-3-yl)propan-2-ol

Conditions
ConditionsYield
With copper diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine at 90℃; for 24h; Schlenk technique; regioselective reaction;98%
With bis(1-methyl-1-phenylethyl)peroxide; copper(I) bromide In tert-butyl alcohol at 140℃; for 12h; Sealed tube;54%
[Yb{N(SiMe3)2}3]
429658-02-6

[Yb{N(SiMe3)2}3]

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

[cis-(H2O)2(1,1,1,3,3,3-hexafluoro-iso-propoxide)2Yb(μ-1,1,1,3,3,3-hexafluoro-iso-propoxide)]2

[cis-(H2O)2(1,1,1,3,3,3-hexafluoro-iso-propoxide)2Yb(μ-1,1,1,3,3,3-hexafluoro-iso-propoxide)]2

Conditions
ConditionsYield
In toluene Inert atmosphere; Glovebox;98%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

cis-2-(2-bromophenyl)cyclobutan-1-ol

cis-2-(2-bromophenyl)cyclobutan-1-ol

2-(2-bromophenyl)-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)tetrahydrofuran

2-(2-bromophenyl)-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)tetrahydrofuran

Conditions
ConditionsYield
With 1,1'-(phenyl-λ3-iodanediyl)bis(2-methoxypyridin-1-ium)trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; Molecular sieve; Inert atmosphere;98%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

A

2-Phenylcyclopentanone
1198-34-1

2-Phenylcyclopentanone

B

2-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-6-phenyltetrahydro-2H-pyran

2-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-6-phenyltetrahydro-2H-pyran

Conditions
ConditionsYield
With 1,1'-(phenyl-λ3-iodanediyl)bis(2-methoxypyridin-1-ium)trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; Molecular sieve; Inert atmosphere;A n/a
B 98%
N-Ac-Leu
1188-21-2

N-Ac-Leu

1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

C11H15F6NO3

C11H15F6NO3

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 4.5h;98%

920-66-1Downstream Products

920-66-1Relevant articles and documents

1,1,1,3,3,3-Hexafluoroisopropanol as a Remarkable Medium for Atroposelective Sulfoxide-Directed Fujiwara-Moritani Reaction with Acrylates and Styrenes

Dherbassy, Quentin,Schwertz, Geoffrey,Chess, Matthieu,Hazra, Chinmoy Kumar,Wencel-Delord, Joanna,Colobert, Franoise

, p. 1735 - 1743 (2016)

Axially chiral biaryls are ubiquitous structural motifs of biologically active molecules and privileged ligands for asymmetric catalysis. Their properties are due to their configurationally stable axis, and therefore, the control of their absolute configuration is essential. Efficient access to atropo-enantioenriched biaryl moieties through asymmetric direct C-H activation, by using enantiopure sulfoxide as both the directing group (DG) and chiral auxiliary, is reported. The stereoselective oxidative Heck reactions are performed in high yields and with excellent atropo-stereoselectivities. The pivotal role of 1,1,1,3,3,3-hexafluoropropanol (HFIP) solvent, which enables a drastic increase in yield and stereoselectivity of this transformation, is evidenced and investigated. Finally, the synthetic usefulness of the herein disclosed transformation is showcased because the traceless character of the sulfoxide DG allows straightforward conversions of the newly accessed, atropopure sulfoxide-biaryls into several differently substituted axially chiral scaffolds.

Preparation method of hexafluoroisopropyl methyl ether

-

Paragraph 0072; 0073, (2019/06/30)

The invention discloses a preparation method of 1,1,1,3,3,3-hexafluoroisopropyl methyl ether. The preparation method includes reacting trifluoroacetate with formate to obtain 1,1,1,3,3,3-hexafluoroisopropanol, and applying a methylation reagent to the 1,1,1,3,3,3-hexafluoroisopropanol to obtain the 1,1,1,3,3,3-hexafluoroisopropyl methyl ether. The preparation method has the advantages that raw materials are cheap and easy to obtain, the preparation process is mild and the method is simple to operate.

Nickel N-heterocyclic carbene catalyzed C-C bond formation: A new route to aryl ketones

Gu, Li-Jun,Jin, Cheng,Zhang, Hong-Tao

supporting information, p. 8741 - 8744 (2015/06/08)

A novel nickel N-heterocyclic carbene catalyzed cross-coupling reaction of aryl aldehydes with boronic esters for the synthesis of aryl ketones was developed. This reaction provides a mild, practical method toward aryl ketones, which are versatile intermediates and building blocks in organic synthesis.

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