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PERFLUORO-TERT-BUTANOL, also known as Nonafluoro-tert-butyl Alcohol or 'artificial blood,' is a clear colorless liquid with unique chemical properties. It is a perfluorinated compound that has found various applications in different industries due to its specific characteristics.

2378-02-1

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2378-02-1 Usage

Uses

Used in Energy Storage Industry:
PERFLUORO-TERT-BUTANOL is used as a key component for the production of SO2-based electrolytes for rechargeable battery cells. Its application reason is to improve the stability, performance, and reduce the production cost of these battery cells, making them more efficient and economically viable for widespread use.
Used in Medical Industry:
PERFLUORO-TERT-BUTANOL, due to its 'artificial blood' nickname, has potential applications in the medical field. Its use as a blood substitute or in blood-related medical procedures could be a significant breakthrough, especially in situations where blood transfusions are not possible or when there is a shortage of blood supplies. The specific application reason in this industry would be to provide a safe and effective alternative to natural blood for various medical procedures and treatments.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 1124, 1992 DOI: 10.1021/jo00030a018

Check Digit Verification of cas no

The CAS Registry Mumber 2378-02-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,7 and 8 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2378-02:
(6*2)+(5*3)+(4*7)+(3*8)+(2*0)+(1*2)=81
81 % 10 = 1
So 2378-02-1 is a valid CAS Registry Number.
InChI:InChI=1/C4HF9O/c5-2(6,7)1(14,3(8,9)10)4(11,12)13/h14H

2378-02-1 Well-known Company Product Price

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  • TCI America

  • (N0692)  Nonafluoro-tert-butyl Alcohol  >98.0%(GC)

  • 2378-02-1

  • 1g

  • 590.00CNY

  • Detail
  • TCI America

  • (N0692)  Nonafluoro-tert-butyl Alcohol  >98.0%(GC)

  • 2378-02-1

  • 5g

  • 1,790.00CNY

  • Detail
  • TCI America

  • (N0692)  Nonafluoro-tert-butyl Alcohol  >98.0%(GC)

  • 2378-02-1

  • 25g

  • 2,990.00CNY

  • Detail
  • Alfa Aesar

  • (B22442)  Perfluoro-tert-butanol, 99%   

  • 2378-02-1

  • 1g

  • 799.0CNY

  • Detail
  • Alfa Aesar

  • (B22442)  Perfluoro-tert-butanol, 99%   

  • 2378-02-1

  • 5g

  • 2461.0CNY

  • Detail
  • Alfa Aesar

  • (B22442)  Perfluoro-tert-butanol, 99%   

  • 2378-02-1

  • 25g

  • 9823.0CNY

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2378-02-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

1.2 Other means of identification

Product number -
Other names nonafluoro-tert-butyl alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:2378-02-1 SDS

2378-02-1Synthetic route

bismuth
7440-69-9

bismuth

tris-(trifluoromethyl)methyl hypochlorite
27579-40-4

tris-(trifluoromethyl)methyl hypochlorite

A

Bi(3+)*3(CF3)3CO(1-) = Bi{(CF3)3CO}3
88392-03-4

Bi(3+)*3(CF3)3CO(1-) = Bi{(CF3)3CO}3

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
byproducts: (CF3)2CO, CF3Cl, Cl2; reaction mixt. maintained at 0°C for 40 h and at room temp. for 94 h and between 25 and 30°C for 6 h; addn. of additional (CF3)3COCl; volatiles removed at room temp. under vac.; elem. anal.;A 93%
B n/a
(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

Hexafluoroacetone
684-16-2

Hexafluoroacetone

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With potassium fluoride In acetonitrile Mechanism; a) 9 h, -40 deg C, b) 3 h, 18 deg C; other carbonyl compounds, variation of conditions: xfluorinated tertiary alcohols and alkoxides from nucleophilic trifluoromethylation of carbonyl compounds;91.3%
With potassium fluoride In acetonitrile 1) -40 deg C, 9 h, 2) 18 deg C, 3 h;91.3%
(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With tetramethylammonium fluoride In 1,2-dimethoxyethane at -30 - 20℃;87%
1,1,1-trichloro-3,3,3-trifluoro-2-(trifluoromethyl)propan-2-ol
7594-49-2

1,1,1-trichloro-3,3,3-trifluoro-2-(trifluoromethyl)propan-2-ol

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With antimony pentafluoride for 3h; Heating;85%
With antimony pentafluoride
Carbonyl fluoride
353-50-4

Carbonyl fluoride

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With potassium fluoride In acetonitrile for 18h; -40 deg C to r.t.;77.1%
nanofluoro-tert-butylamine
2809-92-9

nanofluoro-tert-butylamine

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With trifluoroacetic acid; sodium nitrite In water at 20℃; for 1h;70%
Vinylidene fluoride
75-38-7

Vinylidene fluoride

C4BrF9O
178984-96-8

C4BrF9O

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

Hexafluoroacetone
684-16-2

Hexafluoroacetone

C

2-(2-Bromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

2-(2-Bromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

D

2-(2,2-Dibromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

2-(2,2-Dibromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

Conditions
ConditionsYield
at -88 - 24℃; for 12h; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;A n/a
B n/a
C 31%
D n/a
at -88 - 24℃; for 12h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
C4BrF9O
178984-96-8

C4BrF9O

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

Hexafluoroacetone
684-16-2

Hexafluoroacetone

C

2-(2-Bromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

2-(2-Bromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

D

2-(2,2-Dibromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

2-(2,2-Dibromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

Conditions
ConditionsYield
at -88 - 24℃; for 12h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
CH3C6H3CH2OS(OC(CF3)3)2

CH3C6H3CH2OS(OC(CF3)3)2

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

A

CH3C6H3CH2OSCO(CF3)3(1+)*CF3SO3(1-)

CH3C6H3CH2OSCO(CF3)3(1+)*CF3SO3(1-)

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

bis(nonafluoro-tert-butoxy)(pentafluorophenylsulfanyl)trifluorophenylsulfur(IV)
71212-59-4

bis(nonafluoro-tert-butoxy)(pentafluorophenylsulfanyl)trifluorophenylsulfur(IV)

water
7732-18-5

water

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

bis(pentafluorophenyl) disulfide
1494-06-0

bis(pentafluorophenyl) disulfide

C

pentafluorophenyl pentafluorobenzenethiosulfonate
63113-87-1

pentafluorophenyl pentafluorobenzenethiosulfonate

Conditions
ConditionsYield
hydrolysis at 25°C;
bis(nonafluoro-tert-butoxy)(trifluoromethyl)trifluoromethylsulfanylsulfur(IV)
71192-83-1

bis(nonafluoro-tert-butoxy)(trifluoromethyl)trifluoromethylsulfanylsulfur(IV)

water
7732-18-5

water

A

Bis(trifluoromethyl)disulfid
372-64-5

Bis(trifluoromethyl)disulfid

B

Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester
358-15-6

Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester

C

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
hydrolysis at 25°C;
nanofluoro-tert-butylamine
2809-92-9

nanofluoro-tert-butylamine

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

1,1,1,3,3,3-hexafluoro-2-nitroso-2-trifluoromethyl-propane
354-93-8

1,1,1,3,3,3-hexafluoro-2-nitroso-2-trifluoromethyl-propane

Conditions
ConditionsYield
With sodium nitrite In sulfuric acid At 0°C then at -10°C;
With NaNO2 In sulfuric acid aq. H2SO4; At 0°C then at -10°C;
nonafluoro-tert-butyl trifluoromethanesulfinate
52225-54-4

nonafluoro-tert-butyl trifluoromethanesulfinate

A

Carbonyl fluoride
353-50-4

Carbonyl fluoride

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

C

silicon tetrafluoride
7783-61-1

silicon tetrafluoride

Conditions
ConditionsYield
byproducts: SO2; hydrolyzes in moist air at 25°C;
CrO2{(CF3)3CO}2
88391-99-5

CrO2{(CF3)3CO}2

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

chromic acid
7738-94-5

chromic acid

Conditions
ConditionsYield
With water detected by NMR;
C16H12F9NO4
1192744-27-6

C16H12F9NO4

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With NADPH:cytochrome P450 reductase; NADPH In water-d2; water; acetonitrile at 37℃; for 0.25h; pH=7.6; Kinetics; Concentration; Reagent/catalyst; aq. phosphate buffer; Inert atmosphere; Enzymatic reaction;
C3H7NO*C4HF9O

C3H7NO*C4HF9O

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

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

N,N-dimethyl-formamide

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C4HF9O*C4H9NO

C4HF9O*C4H9NO

A

N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C2H6OS*C4HF9O

C2H6OS*C4HF9O

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C4HF9O*C6H15O4P

C4HF9O*C6H15O4P

A

triethyl phosphate
78-40-0

triethyl phosphate

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C4HF9O*C6H18N3OP

C4HF9O*C6H18N3OP

A

N,N,N,N,N,N-hexamethylphosphoric triamide
680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
PhF-Al(OC(CF3)3)3
1086659-07-5

PhF-Al(OC(CF3)3)3

water
7732-18-5

water

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

C

C8HAlF18O3

C8HAlF18O3

Conditions
ConditionsYield
In fluorobenzene Schlenk technique;
C15H9AlF28O3Si

C15H9AlF28O3Si

tert-butyl alcohol
75-65-0

tert-butyl alcohol

A

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

B

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

C

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

D

C15H10AlF27O4Si

C15H10AlF27O4Si

Conditions
ConditionsYield
In dichloromethane; dichloromethane-d2 at -30 - 20℃; Inert atmosphere; Schlenk technique; Glovebox;
tert-butyldimethylsilanol
18173-64-3

tert-butyldimethylsilanol

C15H9AlF28O3Si

C15H9AlF28O3Si

A

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

C

tert-butyldimethylfluorosilane
2357-76-8

tert-butyldimethylfluorosilane

D

C18H16AlF27O4Si

C18H16AlF27O4Si

E

C15H10AlF27O4Si

C15H10AlF27O4Si

Conditions
ConditionsYield
In dichloromethane; dichloromethane-d2 at -78℃; Inert atmosphere; Schlenk technique; Glovebox;
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

nonafluoro-tert-butyl hypofluorite
2203-56-7

nonafluoro-tert-butyl hypofluorite

Conditions
ConditionsYield
With fluorine; cesium fluoride at -196 - 10℃; for 3 - 4h; Inert atmosphere;100%
With cesium fluoride; fluorine at -78℃; for 0.333333h;98%
Stage #1: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol With cesium fluoride at -196 - 20℃;
Stage #2: With fluorine at -78℃; for 0.333333h;
97%
With fluorine
With fluorine; cesium fluoride at -78 - 20℃; under 225.023 Torr;
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

sodium 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-olate

sodium 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-olate

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 0.5h;100%
With sodium hydride In diethyl ether at 20℃; for 2h; Inert atmosphere; Glovebox;84%
With sodium hydride In diethyl ether at 20℃; for 3h; Inert atmosphere; Glovebox; Cooling with ice;80%
With sodium hydride In diethyl ether
lithium aluminium tetrahydride
16853-85-3

lithium aluminium tetrahydride

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Li[AlPFTB4]
274933-96-9

Li[AlPFTB4]

Conditions
ConditionsYield
In pentane at 20℃;100%
In diethyl ether; toluene for 21h; Inert atmosphere; Reflux;
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

1,2,3,4-tetra-O-acetyl-β-D-glucopyranose
13100-46-4

1,2,3,4-tetra-O-acetyl-β-D-glucopyranose

C18H19F9O10

C18H19F9O10

Conditions
ConditionsYield
Stage #1: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol; 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose With triphenylphosphine In tetrahydrofuran at 20 - 75℃; for 0.0833333h; Inert atmosphere;
Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 75℃; for 3.3h; Inert atmosphere;
99.9%
Re(C3(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)
380907-37-9

Re(C3(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Re(CCHC(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)(1+)

Re(CCHC(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)(1+)

Conditions
ConditionsYield
In dichloromethane-d2 under N2, in NMR tube; 10 equiv. of HOC(CF3)3 syringed into soln. of Re complex in CD2Cl2 cooled to -78°C (dry ice-acetone bath); not isolated; detd. by (31)P NMR spectroscopy;99%
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

potassium perfluoro-tert-butoxide
29646-16-0

potassium perfluoro-tert-butoxide

Conditions
ConditionsYield
With potassium hydride In diethyl ether at -78 - 20℃; Inert atmosphere;99%
With potassium hydroxide In ethanol at 0 - 20℃; for 0.5h; Glovebox;93%
With potassium hydride In diethyl ether Inert atmosphere; Glovebox;
With potassium hydride In diethyl ether
bismuth
7440-69-9

bismuth

tris-(trifluoromethyl)methyl hypochlorite
27579-40-4

tris-(trifluoromethyl)methyl hypochlorite

A

Bi(3+)*3(CF3)3CO(1-) = Bi{(CF3)3CO}3
88392-03-4

Bi(3+)*3(CF3)3CO(1-) = Bi{(CF3)3CO}3

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
byproducts: (CF3)2CO, CF3Cl, Cl2; reaction mixt. maintained at 0°C for 40 h and at room temp. for 94 h and between 25 and 30°C for 6 h; addn. of additional (CF3)3COCl; volatiles removed at room temp. under vac.; elem. anal.;A 93%
B n/a
(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

Hexafluoroacetone
684-16-2

Hexafluoroacetone

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With potassium fluoride In acetonitrile Mechanism; a) 9 h, -40 deg C, b) 3 h, 18 deg C; other carbonyl compounds, variation of conditions: xfluorinated tertiary alcohols and alkoxides from nucleophilic trifluoromethylation of carbonyl compounds;91.3%
With potassium fluoride In acetonitrile 1) -40 deg C, 9 h, 2) 18 deg C, 3 h;91.3%
(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With tetramethylammonium fluoride In 1,2-dimethoxyethane at -30 - 20℃;87%
1,1,1-trichloro-3,3,3-trifluoro-2-(trifluoromethyl)propan-2-ol
7594-49-2

1,1,1-trichloro-3,3,3-trifluoro-2-(trifluoromethyl)propan-2-ol

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With antimony pentafluoride for 3h; Heating;85%
With antimony pentafluoride
Carbonyl fluoride
353-50-4

Carbonyl fluoride

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With potassium fluoride In acetonitrile for 18h; -40 deg C to r.t.;77.1%
nanofluoro-tert-butylamine
2809-92-9

nanofluoro-tert-butylamine

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With trifluoroacetic acid; sodium nitrite In water at 20℃; for 1h;70%
Vinylidene fluoride
75-38-7

Vinylidene fluoride

C4BrF9O
178984-96-8

C4BrF9O

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

Hexafluoroacetone
684-16-2

Hexafluoroacetone

C

2-(2-Bromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

2-(2-Bromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

D

2-(2,2-Dibromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

2-(2,2-Dibromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

Conditions
ConditionsYield
at -88 - 24℃; for 12h; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;A n/a
B n/a
C 31%
D n/a
at -88 - 24℃; for 12h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
C4BrF9O
178984-96-8

C4BrF9O

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

Hexafluoroacetone
684-16-2

Hexafluoroacetone

C

2-(2-Bromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

2-(2-Bromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

D

2-(2,2-Dibromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

2-(2,2-Dibromo-1,1-difluoro-ethoxy)-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

Conditions
ConditionsYield
at -88 - 24℃; for 12h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
CH3C6H3CH2OS(OC(CF3)3)2

CH3C6H3CH2OS(OC(CF3)3)2

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

A

CH3C6H3CH2OSCO(CF3)3(1+)*CF3SO3(1-)

CH3C6H3CH2OSCO(CF3)3(1+)*CF3SO3(1-)

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

bis(nonafluoro-tert-butoxy)(pentafluorophenylsulfanyl)trifluorophenylsulfur(IV)
71212-59-4

bis(nonafluoro-tert-butoxy)(pentafluorophenylsulfanyl)trifluorophenylsulfur(IV)

water
7732-18-5

water

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

bis(pentafluorophenyl) disulfide
1494-06-0

bis(pentafluorophenyl) disulfide

C

pentafluorophenyl pentafluorobenzenethiosulfonate
63113-87-1

pentafluorophenyl pentafluorobenzenethiosulfonate

Conditions
ConditionsYield
hydrolysis at 25°C;
bis(nonafluoro-tert-butoxy)(trifluoromethyl)trifluoromethylsulfanylsulfur(IV)
71192-83-1

bis(nonafluoro-tert-butoxy)(trifluoromethyl)trifluoromethylsulfanylsulfur(IV)

water
7732-18-5

water

A

Bis(trifluoromethyl)disulfid
372-64-5

Bis(trifluoromethyl)disulfid

B

Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester
358-15-6

Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester

C

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
hydrolysis at 25°C;
nanofluoro-tert-butylamine
2809-92-9

nanofluoro-tert-butylamine

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

1,1,1,3,3,3-hexafluoro-2-nitroso-2-trifluoromethyl-propane
354-93-8

1,1,1,3,3,3-hexafluoro-2-nitroso-2-trifluoromethyl-propane

Conditions
ConditionsYield
With sodium nitrite In sulfuric acid At 0°C then at -10°C;
With NaNO2 In sulfuric acid aq. H2SO4; At 0°C then at -10°C;
nonafluoro-tert-butyl trifluoromethanesulfinate
52225-54-4

nonafluoro-tert-butyl trifluoromethanesulfinate

A

Carbonyl fluoride
353-50-4

Carbonyl fluoride

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

C

silicon tetrafluoride
7783-61-1

silicon tetrafluoride

Conditions
ConditionsYield
byproducts: SO2; hydrolyzes in moist air at 25°C;
CrO2{(CF3)3CO}2
88391-99-5

CrO2{(CF3)3CO}2

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

chromic acid
7738-94-5

chromic acid

Conditions
ConditionsYield
With water detected by NMR;
C16H12F9NO4
1192744-27-6

C16H12F9NO4

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
With NADPH:cytochrome P450 reductase; NADPH In water-d2; water; acetonitrile at 37℃; for 0.25h; pH=7.6; Kinetics; Concentration; Reagent/catalyst; aq. phosphate buffer; Inert atmosphere; Enzymatic reaction;
C3H7NO*C4HF9O

C3H7NO*C4HF9O

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

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

N,N-dimethyl-formamide

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C4HF9O*C4H9NO

C4HF9O*C4H9NO

A

N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C2H6OS*C4HF9O

C2H6OS*C4HF9O

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C4HF9O*C6H15O4P

C4HF9O*C6H15O4P

A

triethyl phosphate
78-40-0

triethyl phosphate

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
C4HF9O*C6H18N3OP

C4HF9O*C6H18N3OP

A

N,N,N,N,N,N-hexamethylphosphoric triamide
680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Conditions
ConditionsYield
In octanol at 24.84℃; Equilibrium constant;
PhF-Al(OC(CF3)3)3
1086659-07-5

PhF-Al(OC(CF3)3)3

water
7732-18-5

water

A

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

C

C8HAlF18O3

C8HAlF18O3

Conditions
ConditionsYield
In fluorobenzene Schlenk technique;
C15H9AlF28O3Si

C15H9AlF28O3Si

tert-butyl alcohol
75-65-0

tert-butyl alcohol

A

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

B

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

C

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

D

C15H10AlF27O4Si

C15H10AlF27O4Si

Conditions
ConditionsYield
In dichloromethane; dichloromethane-d2 at -30 - 20℃; Inert atmosphere; Schlenk technique; Glovebox;
tert-butyldimethylsilanol
18173-64-3

tert-butyldimethylsilanol

C15H9AlF28O3Si

C15H9AlF28O3Si

A

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

B

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

C

tert-butyldimethylfluorosilane
2357-76-8

tert-butyldimethylfluorosilane

D

C18H16AlF27O4Si

C18H16AlF27O4Si

E

C15H10AlF27O4Si

C15H10AlF27O4Si

Conditions
ConditionsYield
In dichloromethane; dichloromethane-d2 at -78℃; Inert atmosphere; Schlenk technique; Glovebox;
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

nonafluoro-tert-butyl hypofluorite
2203-56-7

nonafluoro-tert-butyl hypofluorite

Conditions
ConditionsYield
With fluorine; cesium fluoride at -196 - 10℃; for 3 - 4h; Inert atmosphere;100%
With cesium fluoride; fluorine at -78℃; for 0.333333h;98%
Stage #1: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol With cesium fluoride at -196 - 20℃;
Stage #2: With fluorine at -78℃; for 0.333333h;
97%
With fluorine
With fluorine; cesium fluoride at -78 - 20℃; under 225.023 Torr;
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

sodium 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-olate

sodium 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-olate

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 0.5h;100%
With sodium hydride In diethyl ether at 20℃; for 2h; Inert atmosphere; Glovebox;84%
With sodium hydride In diethyl ether at 20℃; for 3h; Inert atmosphere; Glovebox; Cooling with ice;80%
With sodium hydride In diethyl ether
lithium aluminium tetrahydride
16853-85-3

lithium aluminium tetrahydride

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Li[AlPFTB4]
274933-96-9

Li[AlPFTB4]

Conditions
ConditionsYield
In pentane at 20℃;100%
In diethyl ether; toluene for 21h; Inert atmosphere; Reflux;
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

1,2,3,4-tetra-O-acetyl-β-D-glucopyranose
13100-46-4

1,2,3,4-tetra-O-acetyl-β-D-glucopyranose

C18H19F9O10

C18H19F9O10

Conditions
ConditionsYield
Stage #1: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol; 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose With triphenylphosphine In tetrahydrofuran at 20 - 75℃; for 0.0833333h; Inert atmosphere;
Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 75℃; for 3.3h; Inert atmosphere;
99.9%
Re(C3(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)
380907-37-9

Re(C3(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Re(CCHC(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)(1+)

Re(CCHC(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)(1+)

Conditions
ConditionsYield
In dichloromethane-d2 under N2, in NMR tube; 10 equiv. of HOC(CF3)3 syringed into soln. of Re complex in CD2Cl2 cooled to -78°C (dry ice-acetone bath); not isolated; detd. by (31)P NMR spectroscopy;99%
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

potassium perfluoro-tert-butoxide
29646-16-0

potassium perfluoro-tert-butoxide

Conditions
ConditionsYield
With potassium hydride In diethyl ether at -78 - 20℃; Inert atmosphere;99%
With potassium hydroxide In ethanol at 0 - 20℃; for 0.5h; Glovebox;93%
With potassium hydride In diethyl ether Inert atmosphere; Glovebox;
With potassium hydride In diethyl ether
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Nb(N-2,6-Me2C6H3)(CH2SiMe3)3

Nb(N-2,6-Me2C6H3)(CH2SiMe3)3

Nb(N-2,6-Me2C6H3)(CH2SiMe3)2[OC(CF3)3]

Nb(N-2,6-Me2C6H3)(CH2SiMe3)2[OC(CF3)3]

Conditions
ConditionsYield
In hexane at -30 - 20℃;99%
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
2378-02-1

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol

Nb(N-2,6-iPr2C6H3)(CH2SiMe3)3

Nb(N-2,6-iPr2C6H3)(CH2SiMe3)3

Nb(N-2,6-iPr2C6H3)(CH2SiMe3)2[OC(CF3)3]

Nb(N-2,6-iPr2C6H3)(CH2SiMe3)2[OC(CF3)3]

Conditions
ConditionsYield
In hexane at -30 - 20℃;99%

2378-02-1Relevant articles and documents

Monitoring of biological one-electron reduction by 19F NMR using hypoxia selective activation of an 19F-labeled indolequinone derivative

Tanabe, Kazuhito,Harada, Hiroshi,Narazaki, Michiko,Tanaka, Kazuo,Inafuku, Kenichi,Komatsu, Hirokazu,Ito, Takeo,Yamada, Hisatsugu,Chujo, Yoshiki,Matsuda, Tetsuya,Hiraoka, Masahiro,Nishimoto, Sei-Ichi

, p. 15982 - 15983 (2009)

(Chemical Equation Presented) Biological reduction of fluorine-labeled indolequinone derivative (IQ-F) was characterized by 19F NMR for quantitative molecular understanding. The chemical shift change in 19F NMR allowed monitoring of the enzymatic reductio

Immobilized Platinum Hydride Species as Catalysts for Olefin Isomerizations and Enyne Cycloisomerizations

Bauer, Matthias,Cronin, Steve P.,Dyballa, Michael,Estes, Deven P.,Li, Zheng,Maier, Sarah,Nowakowski, Michal,Vu Dinh, Manh-Anh

, p. 1751 - 1757 (2021/06/28)

Platinum hydride species catalyze a number of interesting organic reactions. However, their reactions typically involve the use of high loadings of noble metal and are difficult to recycle, making them somewhat unsustainable. We have synthesized surface-immobilized Pt-H species via oxidative addition of surface OH groups to Pt(PtBu3)2 (1), a rarely used immobilization technique in surface organometallic chemistry. The hydride species thus made were characterized by infrared, magic-angle spinning nuclear magnetic resonance, and X-ray absorption spectroscopies and catalyzed both olefin isomerization and cycloisomerization of a 1,6 enyne (5) with a high selectivity and low Pt loading.

A janus-headed lewis superacid: Simple access to, and first application of Me3Si-F-Al(ORF)3

Rohde, Michael,Muller, Lutz O.,Himmel, Daniel,Scherer, Harald,Krossing, Ingo

supporting information, p. 1218 - 1222 (2014/04/03)

Upon reaction of gaseous Me3SiF with the in situ prepared Lewis acid Al(ORF)3, the stable ion-like silylium compound Me3Si-F-Al(ORF)3 1 forms. The Janusheaded 1 is a readily available smart Lewis acid that differentiates between hard and soft nucleophiles, but also polymerizes isobutene effectively. Thus, in reactions of 1 with soft nucleophiles (Nu), such as phosphanes, the silylium side interacts in an orbital-controlled manner, with formation of [Me3Si-Nu]+ and the weakly coordinating [F-Al(ORF)3]-or [(FRO)3Al-F-Al(ORF)3]- anions. If exchanged for hard nucleophiles, such as primary alcohols, the aluminum side reacts in a charge-controlled manner, with release of FSiMe3 gas and formation of the adduct R(H)O-Al(ORF)3. Compound 1 very effectively initiates polymerization of 8 to 21 mL of liquid C4H8 in 50 mL of CH2Cl2 already at temperatures between -57 and -30 8C with initiator loads as low as 10 mg in a few seconds with 100 % yield but broad polydispersities.

The Al(ORF)3/H2O/phosphane [RF = C(CF3)3] System - Protonation of phosphanes and absolute bronsted acidity

Kraft, Anne,Possart, Josephine,Scherer, Harald,Beck, Jennifer,Himmel, Daniel,Krossing, Ingo

, p. 3054 - 3062 (2013/07/27)

The synthesis of the classical, neutral donor-acceptor adducts Ph 2MeP-/Ph3P-/Ph3As-Al(ORF) 3 and H2O-Al(ORF)3 [1, 2, 3, 4, ORF = OC(CF3)3] is reported. The intermediate H2O-Al(ORF)3 (4) was generated by substitution of PhF in PhF-Al(ORF)3 with H2O and was analyzed in a long-term NMR study over 22 days. This Bronsted acidic system was used in orienting experiments to protonate phosphanes such as PMePh2, PPh3, PCy3, P(tBu)3, and PCy2[2,4,6-(iPr)3C6H2]. Depending on the use of one or two equivalents of PhF-Al(ORF)3, the new weakly coordinating anions [(RFO)3Al(μ-OH) Al(ORF)3]- or [HOAl(ORF) 3]- were obtained. However, in dependence of the steric bulk of the phosphanes, stable and unreactive R3P-Al(OR F)3 adducts were also observed in the NMR experiments. The absolute acidity of the key H2O-Al(ORF)3 adduct was evaluated by the relaxed COSMO cluster-continuum (rCCC, COSMO = conductor-like screening model) model in fluorobenzene solution. For a 0.001 M solution of H2O-Al(ORF)3, the medium acidity resulted as -986 kJ mol-1 or a pHabs value of 173. Long-term hydrolysis of H2O-Al(ORF)3 (4), probably to give HORF and HOAl(ORF)2 followed by trimerization, gave [HOAl(ORF)2]3 (10), which was identified by X-ray diffraction. Small donor ligands such as Ph 2MeP, Ph3P, Ph3As, or even H2O form classical donor-acceptor adducts with the Lewis superacid Al(OR F)3 [RF = C(CF3)3]. FLP-like (FLP = frustrated Lewis pair) combinations of this Lewis acid, phosphanes, and water then lead to [HPR3]+ and two new weakly coordinating anions [HOAl(ORF)3]- and [(FRO)3Al(μ-OH)Al(ORF)3] -. The absolute acidity of H2O-Al(ORF) 3 is evaluated.

Hydrogen bonding between solutes in solvents octan-1-ol and water

Abraham, Michael H.,Gola, Joelle M. R.,Cometto-Muniz, J. Enrique,Acree, William E.

experimental part, p. 7651 - 7658 (2011/02/25)

The 1:1 equilibrium constants, K, for the association of hydrogen bond bases and hydrogen bond acids have been determined by using octan-1-ol solvent at 298 K for 30 acid-base combinations. The values of K are much smaller than those found for aprotic, rather nonpolar solvents. It is shown that the log K values can satisfactorily be correlated against αH 2?βH2, where αH 2 and βH2 are the 1:1 hydrogen bond acidities and basicities of solutes. The slope of the plot, 2.938, is much smaller than those for log K values in the nonpolar organic solvents previously studied. An analysis of literature data on 1:1 hydrogen bonding in water yields a negative slope for a plot of log K against αH 2?βH2, thus showing how the use of very strong hydrogen bond acids and bases does not lead to larger values of log K for 1:1 hydrogen bonding in water. It is suggested that for simple 1:1 association between monofunctional solutes in water, log K cannot be larger than about -0.1 log units. Descriptors have been obtained for the complex between 2,2,2-trifluoroethanol and propanone, and used to analyze solvent effects on the two reactants, the complex, and the complexation constant.

Convenient syntheses of 1,1,1,3,3,3-hexafluoro-2-organyl-propan-2-ols and the corresponding trimethylsilyl ethers

Babadzhanova,Kirij,Yagupolskii,Tyrra,Naumann

, p. 1813 - 1819 (2007/10/03)

A new convenient synthetic procedure to obtain various 1,1,1,3,3,3- hexafluoro-2-organyl-propan-2-ols and the corresponding trimethylsilyl ethers has been worked out starting from anhydrides or activated esters of carboxylic acids and trimethyl(trifluoromethyl)silane in the presence of tetramethylammonium fluoride. Conditions for the selective formation of 1,1,1,3,3,3-hexafluoro-2-organyl-propan-2-ols as well as the trimethylsilyl derivatives have been found.

Perfluoroalkyl hypobromites: Synthesis and reactivity with some fluoroalkenes

Anderson, John D.O.,DesMarteau, Darryl D.

, p. 147 - 152 (2007/10/03)

The first perfluoroalkyl hypobromites have been prepared by the reaction of bromine(I) fluorosulfate with perfluorinated tertiary alkoxides of general formula RfC(CF3)2ONa where Rf=CF3 or CF3CF2. These hypobromites are of lower thermal stability but they behave similarly to analogous hypochlorites and decompose rapidly above -20 °C to give CF3C(O) CF3 and either CF3Br or CF3CF2Br. New polyfluoroethers generated from the reaction of perfluoroalkyl hypobromites with fluoroalkenes have been characterized by 19F and 1H NMR spectroscopy, IR spectroscopy and MS.

Fluorinated Tertiary Alcohols and Alkoxides from Nucleophilic Trifluoromethylation of Carbonyl Compounds

Kotun, Stefan P.,Anderson, John D. O.,DesMarteau, Darryl D.

, p. 1124 - 1131 (2007/10/02)

(CH3)3SiCF3 reacts with fluoro ketones in the presence of excess KF in CH3CN to produce alkoxides derived from formal addition of CF3(1-) to the carbonyl carbon.These alkoxides may be isolated as such or acidified to the corresponding alcohols.Ketones to which this technique was applied include (CF3)2C=O, CF3C(O)CF2Cl, CF3C(O)CF2H, and 2C=O.The last compound reacts with replacement of one of its perfluoroisopropyl groups by CF3.With 2 equiv of TMS-CF3, the acid fluorides RC(O)F (R = CF3CF2, n-C3F7, n-C7F15) yield products of the form RC(CF3)2OX (X = K, H) due to both substitution and addition of CF3 at the carbonyl.Similarly, F2C=O with 3 equiv of TMS-CF3 provides a novel and high-yield synthesis of the perfluoro-tert-butoxide group.Phosgene does not appear to react directly with the TMS-CF3/KF system, but is converted first to CF2C=O.The intermediate ketone CF3CF2C(O)CF3 is observed in reactions of equimolecular amounts of CF3CF2C(O)F and TMS-CF3.

TRICHLOROMETHYLATION OF FLUOROKETONES

Zeifman, Yu. V.

, p. 370 - 373 (2007/10/02)

The nuclophilic trichloromethylation of fluoroketones was carried out by the reductive addition of CCl4 in the presence of aluminum or by the reaction of trichloroacetic acid in HMPTA.The trichloromethylcarbinols obtained were used in the synthesis of perfluorinated tertiary alcohols and trifluoromethylated 1,1-dichlorooxiranes. Keywords: fluoroketones, trichloromethylation, fluorine-containing trichloromethylcarbinols and 1,1-dichlorooxiranes, synthesis.

Oxidative displacement and addition reactions of F-tert -butyl hypochlorite with metal chlorides and oxidative additions to several elements

Canich, Joann M.,Gard, Gary L.,Shreeve, JeaN'Ne M.

, p. 441 - 444 (2008/10/08)

Transition-metal and post-transition-metal chlorides underwent oxidative displacement and oxidative addition reactions with F-tert-butyl hypochlorite to form new F-tert-butoxides. Thus, when (CF3)3COCl was reacted with VOCl3, TiCl4, and CrO2Cl2, the stable compounds VO[(CF3)3CO]3, Ti[(CF3)3CO]4, and CrO2[(CF3)3CO]2 were formed. With Vaska's compound, oxidative addition occurred at iridium but the phenyl groups of P(C6H5)3 were also involved. UCl4, Cu2Cl2, SnCl4, and SiCl4 did not react under the experimental conditions used. F-tert-Butyl hypochlorite has also been shown to add oxidatively to such elements as sulfur, lead, tellurium, bismuth, and iodine to form S[(CF3)3CO]4, Pb[(CF3)3CO]2, Te[(CF3)3CO]4, Bi[(CF3)3CO]3, and I[(CF3)3CO]3, respectively. With (C2H5)2NH, (CF3)3COH formed a 1:1 adduct.

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