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73602-61-6

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73602-61-6 Usage

Application

The t-butyldimethylsilyl (TBDMS) group is the most widely used 2'-OH protection in synthesis of oligoribonucleotides. The TBDMS-group became much used particularly after it was combined with phosphoroamidite methodology and was also the choice when H-phosphonate based RNA-synthesis was introduced. Removal of TBDMS-protection is most commonly done with 1 M tetrabutylammonium fluoride (TBAF) in tetrahydrofuran (THF). These conditions has proven efficient.

Chemical Properties

clear yellow liquid

Uses

Different sources of media describe the Uses of 73602-61-6 differently. You can refer to the following data:
1. Triethylamine trihydrofluoride acts as a mild and selective fluorinating agent used in the synthesis of acid fluorides and alkyl fluorides. It is also used in the synthesis of vicinal difluorides from epoxides, 3-fluoroazetidine. It is utilized as a selective reagent for the cleavage of O-silyl groups in carbohydrates, nucleotides and cyanohydrins. It is actively involved in the electrochemical fluorodeiodination of alkyl iodides and fluorodesilylation in beta-lactams.
2. Mild and selective reagent that has been used in the fluorination of a wide variety of compounds. For a review, see Aldrichimica Acta.

General Description

Triethylamine trihydrofluoride (TREAT-HF) is a mild and selective reagent for the fluorination of a wide variety of compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 73602-61-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,6,0 and 2 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 73602-61:
(7*7)+(6*3)+(5*6)+(4*0)+(3*2)+(2*6)+(1*1)=116
116 % 10 = 6
So 73602-61-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H8FNO/c9-7-4-2-1-3-6(7)8(11)5-10/h1-4H,5,10H2

73602-61-6 Well-known Company Product Price

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

  • (T2022)  Triethylamine Trihydrofluoride  >95.0%(T)

  • 73602-61-6

  • 10g

  • 470.00CNY

  • Detail
  • Alfa Aesar

  • (L14417)  Triethylamine trihydrofluoride, ca 37% HF   

  • 73602-61-6

  • 5g

  • 158.0CNY

  • Detail
  • Alfa Aesar

  • (L14417)  Triethylamine trihydrofluoride, ca 37% HF   

  • 73602-61-6

  • 25g

  • 538.0CNY

  • Detail
  • Alfa Aesar

  • (L14417)  Triethylamine trihydrofluoride, ca 37% HF   

  • 73602-61-6

  • 100g

  • 1910.0CNY

  • Detail
  • Aldrich

  • (344648)  Triethylaminetrihydrofluoride  98%

  • 73602-61-6

  • 344648-5G

  • 244.53CNY

  • Detail
  • Aldrich

  • (344648)  Triethylaminetrihydrofluoride  98%

  • 73602-61-6

  • 344648-25G

  • 534.69CNY

  • Detail
  • Aldrich

  • (344648)  Triethylaminetrihydrofluoride  98%

  • 73602-61-6

  • 344648-100G

  • 1,705.86CNY

  • Detail
  • Aldrich

  • (344648)  Triethylaminetrihydrofluoride  98%

  • 73602-61-6

  • 344648-500G

  • 8,570.25CNY

  • Detail

73602-61-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Triethylamine trihydrofluoride

1.2 Other means of identification

Product number -
Other names N,N-diethylethanamine,trihydrofluoride

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:73602-61-6 SDS

73602-61-6Synthetic route

2,2,3,3-tetrafluoropropanol
76-37-9

2,2,3,3-tetrafluoropropanol

perfluoropropanoyl fluoride
422-61-7

perfluoropropanoyl fluoride

A

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

B

1H,1H,3H-perfluoropropyl perfluoropropionate

1H,1H,3H-perfluoropropyl perfluoropropionate

Conditions
ConditionsYield
With triethylamine at 5 - 20℃; for 5h;A 88%
B 91%
perfluoro(2-propoxypropionyl) fluoride
2062-98-8, 125037-08-3

perfluoro(2-propoxypropionyl) fluoride

2,2,3,3-tetrafluoropropanol
76-37-9

2,2,3,3-tetrafluoropropanol

A

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

B

1H,1H,3H-perfluoropropyl perfluoro-α-propoxypropionate

1H,1H,3H-perfluoropropyl perfluoro-α-propoxypropionate

Conditions
ConditionsYield
With triethylamine at 5 - 20℃;
2,2,3,3-tetrafluoropropanol
76-37-9

2,2,3,3-tetrafluoropropanol

2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoyl fluoride
375-84-8

2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoyl fluoride

A

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

B

1H,1H,3H-perfluoropropyl perfluoroenanthate

1H,1H,3H-perfluoropropyl perfluoroenanthate

Conditions
ConditionsYield
With triethylamine at 5 - 20℃;
trifluoroacetyl fluoride
354-34-7

trifluoroacetyl fluoride

2,2,3,3,4,4,5,5-octafluoropentan-1-ol
355-80-6

2,2,3,3,4,4,5,5-octafluoropentan-1-ol

A

1,1,5-trihydroperfluoroamyl trifluoroacetate
79614-48-5

1,1,5-trihydroperfluoroamyl trifluoroacetate

B

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

Conditions
ConditionsYield
With triethylamine at 5 - 20℃;
diethylamino-sulfur trifluoride
38078-09-0

diethylamino-sulfur trifluoride

C6H15N*2FH*H(1+)*BF4(1-)

C6H15N*2FH*H(1+)*BF4(1-)

A

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

B

ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate

ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate

Conditions
ConditionsYield
In [D3]acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Molecular sieve;
triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

triethylamine
121-44-8

triethylamine

triethylammonium dihydrofluoride

triethylammonium dihydrofluoride

Conditions
ConditionsYield
100%
In tetrahydrofuran
biphenyl-2-ylcarbamic Acid 1-(2-{5-[(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]pentylcarbamoyl}ethyl)piperidin-4-yl Ester
743460-39-1

biphenyl-2-ylcarbamic Acid 1-(2-{5-[(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]pentylcarbamoyl}ethyl)piperidin-4-yl Ester

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

biphenyl-2-ylcarbamic Acid 1-(2-{5-[(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]pentylcarbamoyl}ethyl)piperidin-4-yl Ester
743460-40-4

biphenyl-2-ylcarbamic Acid 1-(2-{5-[(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]pentylcarbamoyl}ethyl)piperidin-4-yl Ester

Conditions
ConditionsYield
In dichloromethane for 10h;100%
pyridin-1-ium [3-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrazol-1-yl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl]sulfatee

pyridin-1-ium [3-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrazol-1-yl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl]sulfatee

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

triethylammonium [3-[4-(hydroxymethyl)pyrazol-1-yl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl]sulfate

triethylammonium [3-[4-(hydroxymethyl)pyrazol-1-yl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl]sulfate

Conditions
ConditionsYield
In acetonitrile at 40℃; for 2.5h; Inert atmosphere;100%
biphenyl-2-ylcarbamic Acid 1-{2-[3-(3-{[(R)-2-(tert-butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}benzyl)ureido]ethyl}-piperidin-4-yl Ester
743461-30-5

biphenyl-2-ylcarbamic Acid 1-{2-[3-(3-{[(R)-2-(tert-butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}benzyl)ureido]ethyl}-piperidin-4-yl Ester

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

biphenyl-2-ylcarbamic acid 1-{2-[3-(3-{[(R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}benzyl)ureido]ethyl}piperidin-4-yl ester ditrifluoroacetate

biphenyl-2-ylcarbamic acid 1-{2-[3-(3-{[(R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}benzyl)ureido]ethyl}piperidin-4-yl ester ditrifluoroacetate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 15h;99%
[Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(OtAm)]

[Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(OtAm)]

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C27H36AuFN2

C27H36AuFN2

Conditions
ConditionsYield
In benzene99%
[Rh(OH)(cod)]2

[Rh(OH)(cod)]2

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

[(1,5-cyclooctadiene)3Rh3(μ3-OH)2](1+)FHF(1-)

[(1,5-cyclooctadiene)3Rh3(μ3-OH)2](1+)FHF(1-)

Conditions
ConditionsYield
In tetrahydrofuran byproducts: H2O; (glovebox); addn. of a soln. of fluorine compd. in THF to a mixt. of rhodium complex in THF, stirring at room temp. for 45 min; sepn. of ppt., washing with THF, ether, drying in vac.; elem. anal.;98%
[Ir(hydroxide)(1,5-cyclooctadiene)(1,3-diisopropylimidazol-2-ylidene)]

[Ir(hydroxide)(1,5-cyclooctadiene)(1,3-diisopropylimidazol-2-ylidene)]

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

Conditions
ConditionsYield
In benzene at 20℃; for 4.5h; Inert atmosphere; Schlenk technique;97%
1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C16H18BFINO6

C16H18BFINO6

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.116667h; Sealed tube; regioselective reaction;96%
1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione
2232-12-4

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

2-methyl-phenylethynylboronic acid MIDA ester
1237789-57-9

2-methyl-phenylethynylboronic acid MIDA ester

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C14H14BFINO4

C14H14BFINO4

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.333333h; Sealed tube; regioselective reaction;96%
1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione
2232-12-4

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

C11H16BNO4

C11H16BNO4

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C11H16BFINO4

C11H16BFINO4

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.333333h; Sealed tube; regioselective reaction;96%
cannabidiol (t-butyldimethylsilyloxy)acetate
1110599-03-5

cannabidiol (t-butyldimethylsilyloxy)acetate

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

cannabidiol glycolate
1110598-88-3

cannabidiol glycolate

Conditions
ConditionsYield
In dichloromethane at -15 - 5℃; for 65h;95%
(4S,5R)-ethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-meth-yl-1,3,2-dioxathiolane-4-carboxylate 2,2-dioxide
879551-01-6

(4S,5R)-ethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-meth-yl-1,3,2-dioxathiolane-4-carboxylate 2,2-dioxide

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C11H18O8S*C6H15N*FH

C11H18O8S*C6H15N*FH

Conditions
ConditionsYield
In tetrahydrofuran at 60℃; for 1.5h; Solvent; Temperature; Concentration;95%
1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione
2232-12-4

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C13H14BFINO4

C13H14BFINO4

Conditions
ConditionsYield
In dichloromethane at 20℃; Sealed tube; regioselective reaction;95%
hydroxy(1,5-cyclooctadiene)rhodium(I) dimer

hydroxy(1,5-cyclooctadiene)rhodium(I) dimer

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

triphenylphosphine
603-35-0

triphenylphosphine

fluorotris(triphenylphosphine)rhodium(I)
36564-80-4

fluorotris(triphenylphosphine)rhodium(I)

Conditions
ConditionsYield
In diethyl ether under N2; Et3N*3HF added to stiring mixt. of Rh complex and PPh3 (molar ratio 1:1.4:18.5) in ether; stirred for 2 h; filtered; ppt. washed with ether; dried under vac.; elem. anal.;94%
In diethyl ether under N2; Et3N*3HF added to stiring mixt. of Rh complex and PPh3 (molar ratio 1:1.3:17) in ether; stirred at room temp. for 3 h; ppt. sepd.; washed with ether; dried under vac.;90%
In diethyl ether under N2; Et3N*3HF added to stiring mixt. of Rh complex and PPh3 (molar ratio 1:1.6:21.7) in ether; stirred for 2 h; filtered; ppt. washed with THF, benzene and ether; dried under vac. overnight;65%
1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione
2232-12-4

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

C11H14BNO4

C11H14BNO4

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C11H14BFINO4

C11H14BFINO4

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.25h; Sealed tube; regioselective reaction;94%
Ir(1,5-cyclooctadiene)(OH)(1,3-(2,6-diisopropylphenyl)imidazol-2-ylidene)

Ir(1,5-cyclooctadiene)(OH)(1,3-(2,6-diisopropylphenyl)imidazol-2-ylidene)

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

Conditions
ConditionsYield
In benzene at 20℃; for 4.5h; Inert atmosphere; Schlenk technique;93%
1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione
2232-12-4

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

C14H16BNO4

C14H16BNO4

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C14H16BFINO4

C14H16BFINO4

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.0333333h; Sealed tube; regioselective reaction;93%
1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione
2232-12-4

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

C14H16BNO5

C14H16BNO5

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

C14H16BFINO5

C14H16BFINO5

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.0333333h; Sealed tube; regioselective reaction;93%
triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

5'-O-tert-butyldiphenylsilyl-2'-O-[N,N dimethylaminooxyethyl]-5-methyluridine
212061-27-3

5'-O-tert-butyldiphenylsilyl-2'-O-[N,N dimethylaminooxyethyl]-5-methyluridine

2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methyluridine
212061-28-4

2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methyluridine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 24h;92.5%
[(1,5-cyclooctadiene)Rh((i-Pr3P)(F)]
726173-84-8

[(1,5-cyclooctadiene)Rh((i-Pr3P)(F)]

triethylamine tris(hydrogen fluoride)
73602-61-6

triethylamine tris(hydrogen fluoride)

[Rh(FHF)(1,5-cyclooctadiene)(P(i)Pr3)]
753014-15-2

[Rh(FHF)(1,5-cyclooctadiene)(P(i)Pr3)]

Conditions
ConditionsYield
In tetrahydrofuran byproducts: (C2H5)3N; (N2); a soln. of Rh complex treated with NEt3*3HF at room temp., stirredfor 50 min; evapd. (vac.), extd. (Et2O), the ext. filtered, evapd. (vac.), washed with n-pentane, dried (vac.); elem. anal.;92%

73602-61-6Relevant articles and documents

Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion

Lu, Deng-Fu,Zhu, Cheng-Liang,Sears, Jeffrey D.,Xu, Hao

supporting information, p. 11360 - 11367 (2016/10/12)

We herein report a new catalytic method for intermolecular olefin aminofluorination using earth-abundant iron catalysts and nucleophilic fluoride ion. This method tolerates a broad range of unfunctionalized olefins, especially nonstyrenyl olefins that are incompatible with existing olefin aminofluorination methods. This new iron-catalyzed process directly converts readily available olefins to internal vicinal fluoro carbamates with high regioselectivity (N vs F), many of which are difficult to prepare using known methods. Preliminary mechanistic studies demonstrate that it is possible to exert asymmetric induction using chiral iron catalysts and that both an iron-nitrenoid and carbocation species may be reactive intermediates.

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