Welcome to LookChem.com Sign In|Join Free

CAS

  • or

13081-18-0

Post Buying Request

13081-18-0 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

13081-18-0 Usage

Chemical Description

Ethyl trifluoropyruvate is a starting material for the synthesis of the novel diazo compound.

Chemical Properties

Clear pale yellow liquid

Uses

Different sources of media describe the Uses of 13081-18-0 differently. You can refer to the following data:
1. Ethyl Trifluoropyruvate is used as a reagent in the preparation of potential biologically active compounds such as in the highly enantioselective organocatalytic hydroxyalkylation of indoles .
2. Ethyl trifluoropyruvate acts as a building block in synthetic chemistry for the synthesis of fluorine containing compounds. It is also used as a reagent for the preparation of potential biologically active compounds like highly enantioselective organocatalytic hydroxyalkylation of indoles.
3. Ethyl 3,3,3-trifluoropyruvate may be used in the preparation of N-heteroaryl(trifluoromethyl)hydroxyalkanoic acid esters.

General Description

Ethyl 3,3,3-trifluoropyruvate is a trifluoromethylated compound. Enantioselective Friedel–Crafts alkylation of simple phenols and indoles with ethyl 3,3,3-trifluoropyruvate under different reaction conditions have been reported.

Check Digit Verification of cas no

The CAS Registry Mumber 13081-18-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,0,8 and 1 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 13081-18:
(7*1)+(6*3)+(5*0)+(4*8)+(3*1)+(2*1)+(1*8)=70
70 % 10 = 0
So 13081-18-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H3F3O3/c1-10-3(9)2(8)4(5,6)7/h1H3

13081-18-0 Well-known Company Product Price

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

  • (T1434)  Ethyl Trifluoropyruvate  >98.0%(GC)

  • 13081-18-0

  • 5g

  • 480.00CNY

  • Detail
  • TCI America

  • (T1434)  Ethyl Trifluoropyruvate  >98.0%(GC)

  • 13081-18-0

  • 25g

  • 1,390.00CNY

  • Detail
  • Alfa Aesar

  • (B20611)  Ethyl trifluoropyruvate, 97%   

  • 13081-18-0

  • 5g

  • 473.0CNY

  • Detail
  • Alfa Aesar

  • (B20611)  Ethyl trifluoropyruvate, 97%   

  • 13081-18-0

  • 25g

  • 2003.0CNY

  • Detail

13081-18-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl trifluoropyruvate

1.2 Other means of identification

Product number -
Other names Ethyl 3,3,3-trifluoropyruvate

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:13081-18-0 SDS

13081-18-0Synthetic route

2-fluoro-2-ethoxy-trifluoropropionic acid ethyl ester
10186-66-0

2-fluoro-2-ethoxy-trifluoropropionic acid ethyl ester

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Conditions
ConditionsYield
With SbF583%
With sulfuric acid; silica gel
With sulfuric acid; silica gel at 140℃;
2-fluoro-2-ethoxy-trifluoropropionic acid ethyl ester
10186-66-0

2-fluoro-2-ethoxy-trifluoropropionic acid ethyl ester

A

1-fluoroethane
353-36-6

1-fluoroethane

B

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Conditions
ConditionsYield
antimony pentafluoride In neat (no solvent)A n/a
B 83%
ethyl 3,3,3-trifluoro-2-hydroxypropanoate
94726-00-8

ethyl 3,3,3-trifluoro-2-hydroxypropanoate

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Conditions
ConditionsYield
With sodium hypochlorite pentahydrate In acetonitrile at 20℃; for 0.5h; Reagent/catalyst; Solvent;69%
ethyl 3,3,3-trifluoropyruvate ethylhemiketal
26728-43-8

ethyl 3,3,3-trifluoropyruvate ethylhemiketal

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Conditions
ConditionsYield
With sulfuric acid under 16.5017 - 49.505 Torr;67%
Bromotrifluoromethane
75-63-8

Bromotrifluoromethane

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Conditions
ConditionsYield
With zinc In pyridine at 20℃; for 2h; other esters; other perfluoroalkyl iodide;38%
With zinc In pyridine at 20℃; for 2h;38%
With zinc In pyridine at 20℃; 1) pyridine, 20 deg C;38%
ethanol
64-17-5

ethanol

α,α-dihydroxyperfluoropropionic acid
10321-14-9

α,α-dihydroxyperfluoropropionic acid

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Conditions
ConditionsYield
With hydrogenchloride Heating;
Hexafluoropropene oxide
428-59-1

Hexafluoropropene oxide

ethanol
64-17-5

ethanol

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

allylbenzene
300-57-2

allylbenzene

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

(E)-2-hydroxy-5-phenyl-2-trifluoromethyl-pent-4-enoic acid ethyl ester

(E)-2-hydroxy-5-phenyl-2-trifluoromethyl-pent-4-enoic acid ethyl ester

Conditions
ConditionsYield
silver hexafluoroantimonate; (S)-SEGPHOS-PdCl2 In dichloromethane at 20℃; for 0.5h; Ene reaction;100%
With silver hexafluoroantimonate; (R)-(2,2'-bis(diphenylphosphanyl)biphenyl)dichloroplatinum(II) In dichloromethane at -20℃; for 1h;83%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

methylenecyclohexane
1192-37-6

methylenecyclohexane

ethyl 2-(cyclohexenylmethyl)-3,3,3-trifluoro-2-hydroxypropanoate

ethyl 2-(cyclohexenylmethyl)-3,3,3-trifluoro-2-hydroxypropanoate

Conditions
ConditionsYield
silver hexafluoroantimonate; (S)-SEGPHOS-PdCl2 In dichloromethane at 20℃; for 0.25h; Ene reaction;100%
With silver hexafluoroantimonate; [(R)-BINAPHANE]PdCl2 In dichloromethane at 20℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;78%
With silver hexafluoroantimonate; chiral SEGPHOS-Pd(II) In dichloromethane at 20℃; for 0.25h; Friedel-Crafts reaction;
allylbenzene
300-57-2

allylbenzene

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

2-hydroxy-5-phenyl-2-trifluoromethyl-pent-4-enoic acid ethyl ester

2-hydroxy-5-phenyl-2-trifluoromethyl-pent-4-enoic acid ethyl ester

Conditions
ConditionsYield
With silver hexafluoroantimonate; chiral SEGPHOS-Pd(II) In dichloromethane at 20℃; for 0.5h; Friedel-Crafts reaction;100%
methanol
67-56-1

methanol

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

ethyl 3,3,3-trifluoropyruvate methylhemiketal

ethyl 3,3,3-trifluoropyruvate methylhemiketal

Conditions
ConditionsYield
at 20℃;100%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

3-(trifluoromethyl)quinoxalin-2-ol
58457-64-0

3-(trifluoromethyl)quinoxalin-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at 45℃;100%
In tetrahydrofuran at 40 - 50℃;
indole
120-72-9

indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

(2S)-3,3,3-trifluoro-2-hydroxy-2-(indol-3-yl)propionic acid ethyl ester

(2S)-3,3,3-trifluoro-2-hydroxy-2-(indol-3-yl)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: ethyl-3,3,3-trifluoropyruvate With copper(II) bis[bis((trifluoromethyl)sulfonyl)amide]; 1,5-bis[(4S,5S)-1-(4-nitrobenzoyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]benzene In toluene at -78℃; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere;
Stage #2: indole In toluene at -78℃; for 4h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
99%
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Catalytic behavior; Temperature; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;99.3%
Stage #1: indole With C78H78N12O6 In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere;
Stage #2: ethyl-3,3,3-trifluoropyruvate In tetrahydrofuran at -20℃; for 12h; Inert atmosphere; enantioselective reaction;
92%
With (3aS,11aS,14aR,16bR)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Schlenk technique; Inert atmosphere; enantioselective reaction;
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

(S)-3,3,3-trifluoro-2-hydroxy-2-(5-chloroindol-3-yl)propionic acid ethyl ester

(S)-3,3,3-trifluoro-2-hydroxy-2-(5-chloroindol-3-yl)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: ethyl-3,3,3-trifluoropyruvate With copper(II) bis[bis((trifluoromethyl)sulfonyl)amide]; 1,5-bis[(4S,5S)-1-(4-nitrobenzoyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]benzene In toluene at -78℃; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere;
Stage #2: 5-chloro-1H-indole In toluene at -78℃; for 17h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
99%
Stage #1: 5-chloro-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;99.3%
With cinchonidine In diethyl ether at -8℃;
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

(S)-3,3,3-trifluoro-2-hydroxy-2-(5-bromoindol-3-yl)propionic acid ethyl ester

(S)-3,3,3-trifluoro-2-hydroxy-2-(5-bromoindol-3-yl)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 5-bromo-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;99.1%
Stage #1: ethyl-3,3,3-trifluoropyruvate With copper(II) bis[bis((trifluoromethyl)sulfonyl)amide]; 1,5-bis[(4S,5S)-1-(4-nitrobenzoyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]benzene In toluene at -78℃; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere;
Stage #2: 5-bromo-1H-indole In toluene at -78℃; for 17h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
96%
With cinchonidine In diethyl ether at -8℃;
With cinchonidine In diethyl ether at -8℃; for 3h; enantioselective reaction;
carbamic acid-(1-trichloromethyl-1-methyl-ethyl ester)
89416-45-5

carbamic acid-(1-trichloromethyl-1-methyl-ethyl ester)

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Ethyl 2-(2,2,2-Trichloro-tert-butoxycarbonylamino)-2-hydroxy-3,3,3-trifluoropropionate
126535-85-1

Ethyl 2-(2,2,2-Trichloro-tert-butoxycarbonylamino)-2-hydroxy-3,3,3-trifluoropropionate

Conditions
ConditionsYield
In dichloromethane99%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

benzamide
55-21-0

benzamide

Ethyl 2-benzoylamino-2-hydroxy-3,3,3-trifluoropropionate
126535-81-7

Ethyl 2-benzoylamino-2-hydroxy-3,3,3-trifluoropropionate

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;99%
indole
120-72-9

indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

(+/-)-3,3,3-trifluoro-2-hydroxy-2-(indol-3-yl)propionic acid ethyl ester

(+/-)-3,3,3-trifluoro-2-hydroxy-2-(indol-3-yl)propionic acid ethyl ester

Conditions
ConditionsYield
With (SIr,RC)-[(η5-C5Me5)Ir{(R)-propane-1,2-diylbis(diphenylphosphane)}(H2O)][SbF6]2 In dichloromethane for 0.333333h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Optical yield = 65 %ee;99%
With gallium(III) triflate In dichloromethane at 20℃; for 2h; Friedel-Crafts hydroxyalkylation;98%
With K-10 montmorillonite In toluene at 60℃; for 0.0666667h; Friedel-Crafts hydroxyalkylation;98%
1-methylindole
603-76-9

1-methylindole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(1-methyl-indol-3-yl)-propionic acid ethyl ester

3,3,3-trifluoro-2-hydroxy-2-(1-methyl-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
With gallium(III) triflate In dichloromethane at 20℃; for 2h; Friedel-Crafts hydroxyalkylation;99%
With (SIr,RC)-[(η5-C5Me5)Ir{(R)-propane-1,2-diylbis(diphenylphosphane)}(H2O)][SbF6]2 In dichloromethane for 0.333333h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Optical yield = 47 %ee;99%
With K-10 montmorillonite In toluene at 60℃; for 0.0666667h; Friedel-Crafts hydroxyalkylation;95%
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(2-methyl-1H-indol-3-yl)-propionic acid ethyl ester

3,3,3-trifluoro-2-hydroxy-2-(2-methyl-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
With (SIr,RC)-[(η5-C5Me5)Ir{(R)-propane-1,2-diylbis(diphenylphosphane)}(H2O)][SbF6]2 In dichloromethane for 0.416667h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Optical yield = 76 %ee;99%
With K-10 montmorillonite In toluene at 60℃; for 0.0833333h; Friedel-Crafts hydroxyalkylation;97%
With aluminum (III) chloride In dichloromethane at 20℃; Friedel-Crafts Acylation;93%
In 1,1,1,3,3-pentafluorobutane at 20℃; for 0.5h; Inert atmosphere;91%
With N2,N2'-bis(pyridin-2-ylmethyl)-1,1'-binaphthyl-2,2'-diamine In dichloromethane at 0℃; for 24h; Friedel-Crafts Alkylation; enantioselective reaction;87%
5-methoxylindole
1006-94-6

5-methoxylindole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(5-methoxy-1H-indol-3-yl)-propionic acid ethyl ester

3,3,3-trifluoro-2-hydroxy-2-(5-methoxy-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
With (SIr,RC)-[(η5-C5Me5)Ir{(R)-propane-1,2-diylbis(diphenylphosphane)}(H2O)][SbF6]2 In dichloromethane for 0.333333h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Optical yield = 71 %ee;99%
With K-10 montmorillonite In toluene at 60℃; for 0.0833333h; Friedel-Crafts hydroxyalkylation;97%
In 1,1,1,3,3-pentafluorobutane at 20℃; for 0.5h; Inert atmosphere;96%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3-phenylaminocyclohex-2-enone
24706-50-1

3-phenylaminocyclohex-2-enone

3-hydroxy-1-phenyl-3-trifluoromethyl-3,5,6,7-tetrahydro-1H-indole-2,4-dione

3-hydroxy-1-phenyl-3-trifluoromethyl-3,5,6,7-tetrahydro-1H-indole-2,4-dione

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h; aldol condensation-cyclization;99%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

5,5-dimethyl-3-benzylamino-2-cyclohexen-1-one
889-31-6

5,5-dimethyl-3-benzylamino-2-cyclohexen-1-one

1-benzyl-3-hydroxy-6,6-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-1H-indole-2,4-dione

1-benzyl-3-hydroxy-6,6-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-1H-indole-2,4-dione

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h; aldol condensation-cyclization;99%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3-(benzylamino)cyclopent-2-en-1-one
149221-40-9

3-(benzylamino)cyclopent-2-en-1-one

2-(2-benzylamino-5-oxo-cyclopent-1-enyl)-3,3,3-trifluoro-2-hydroxy-propionic acid ethyl ester

2-(2-benzylamino-5-oxo-cyclopent-1-enyl)-3,3,3-trifluoro-2-hydroxy-propionic acid ethyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h; aldol condensation;99%
indole
120-72-9

indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

(2R)-3,3,3-trifluoro-2-hydroxy-2-(indol-3-yl)propionic acid ethyl ester

(2R)-3,3,3-trifluoro-2-hydroxy-2-(indol-3-yl)propionic acid ethyl ester

Conditions
ConditionsYield
With C32H40N4O4; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;99%
Stage #1: indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
98%
Stage #1: ethyl-3,3,3-trifluoropyruvate With copper (I) trifluoromethane sulfonate toluene complex; C24H26N2O2 In diethyl ether at -98 - 20℃; for 0.333333h; Inert atmosphere;
Stage #2: indole In diethyl ether at -98℃; for 1.5h; Friedel Crafts acylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
98%
Stage #1: ethyl-3,3,3-trifluoropyruvate With 2,6-bis(1-[toluene-4-sulfonyl]-[4S,5S]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)benzene; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at -78℃; for 0.5h; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere;
Stage #2: indole In dichloromethane at -78℃; for 3h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
95%
With Cu(2+)*2C32H40N4O4; Cu(2+)*C32H40N4O4 at 0℃; for 1h; Friedel-Crafts Alkylation; Schlenk technique; Inert atmosphere; enantioselective reaction;
5-fluoro-1H-indole
399-52-0

5-fluoro-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(5-fluoro-1H-indol-3-yl)-propionic acid ethyl ester

3,3,3-trifluoro-2-hydroxy-2-(5-fluoro-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: ethyl-3,3,3-trifluoropyruvate With copper(II) bis[bis((trifluoromethyl)sulfonyl)amide]; 1,5-bis[(4S,5S)-1-(4-nitrobenzoyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]benzene In toluene at -78℃; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere;
Stage #2: 5-fluoro-1H-indole In toluene at -78℃; for 4h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
99%
Stage #1: 5-fluoro-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;98.6%
Stage #1: 5-fluoro-1H-indole With C78H78N12O6 In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere;
Stage #2: ethyl-3,3,3-trifluoropyruvate In tetrahydrofuran at -20℃; for 12h; Inert atmosphere; enantioselective reaction;
87%
5-iodo-1H-indole
16066-91-4

5-iodo-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

(S)-3,3,3-trifluoro-2-hydroxy-2-(5-iodoindol-3-yl)propionic acid ethyl ester

(S)-3,3,3-trifluoro-2-hydroxy-2-(5-iodoindol-3-yl)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: ethyl-3,3,3-trifluoropyruvate With copper(II) bis[bis((trifluoromethyl)sulfonyl)amide]; 1,5-bis[(4S,5S)-1-(4-nitrobenzoyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]benzene In toluene at -78℃; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere;
Stage #2: 5-iodo-1H-indole In toluene at -78℃; for 17h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
99%
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;98.6%
With cinchonidine In diethyl ether at -8℃;
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

(R)-3,3,3-trifluoro-2-hydroxy-2-(5-chloroindol-3-yl)propionic acid ethyl ester

(R)-3,3,3-trifluoro-2-hydroxy-2-(5-chloroindol-3-yl)propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 5-chloro-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
Stage #1: ethyl-3,3,3-trifluoropyruvate With 2,6-bis(1-[toluene-4-sulfonyl]-[4S,5S]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)benzene; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at -78℃; for 0.5h; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere;
Stage #2: 5-chloro-1H-indole In dichloromethane at -78℃; for 19h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
95%
With cinchonine In diethyl ether at -8℃;
6-methylindole
3420-02-8

6-methylindole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(6-methyl-1H-indol-3-yl)-propionic acid ethyl ester
1265815-30-2

3,3,3-trifluoro-2-hydroxy-2-(6-methyl-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
In 1,1,1,3,3-pentafluorobutane at 20℃; for 0.5h; Inert atmosphere;99%
With triethylamine In dichloromethane at 0℃; Friedel Crafts alkylation;
With copper(II) bis(trifluoromethanesulfonate) In chloroform at 25℃; for 16h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique;
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester
1262999-81-4

3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 7-methyl-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;97.6%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester
1179934-54-3

3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
In 1,1,1,3,3-pentafluorobutane at 20℃; for 0.5h; Inert atmosphere;99%
With triethylamine In dichloromethane at 0℃; Friedel Crafts alkylation;
With copper(II) bis(trifluoromethanesulfonate) In chloroform at 25℃; for 16h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique;
5-fluoro-1H-indole
399-52-0

5-fluoro-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(5-fluoro-1H-indol-3-yl)-propionic acid ethyl ester

3,3,3-trifluoro-2-hydroxy-2-(5-fluoro-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 5-fluoro-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
7-ethyl-1H-indole
22867-74-9

7-ethyl-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(7-ethyl-1H-indol-3-yl)-propionic acid ethyl ester
1262999-77-8

3,3,3-trifluoro-2-hydroxy-2-(7-ethyl-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 7-ethyl-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

ethyl 2-hydroxy-4-p-tolyl-2-(trifluoromethyl)but-3-ynoate

ethyl 2-hydroxy-4-p-tolyl-2-(trifluoromethyl)but-3-ynoate

Conditions
ConditionsYield
With [Rh{(S,S)-4-NO2-Phebox-Bn}(OAc)2]*H2O In diethyl ether at 25℃; for 24h; Inert atmosphere; enantioselective reaction;99%
1-ethynyl-3-methyl-benzene
766-82-5

1-ethynyl-3-methyl-benzene

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

ethyl 2-hydroxy-4-m-tolyl-2-(trifluoromethyl)but-3-ynoate

ethyl 2-hydroxy-4-m-tolyl-2-(trifluoromethyl)but-3-ynoate

Conditions
ConditionsYield
With [Rh{(S,S)-4-NO2-Phebox-Bn}(OAc)2]*H2O In diethyl ether at 25℃; for 24h; Inert atmosphere; enantioselective reaction;99%
ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

phenylacetylene
536-74-3

phenylacetylene

(S)-ethyl 2-hydroxy-4-phenyl-2-(trifluoromethyl)but-3-ynoate
1315273-00-7

(S)-ethyl 2-hydroxy-4-phenyl-2-(trifluoromethyl)but-3-ynoate

Conditions
ConditionsYield
With C54H48N5O7Rh In diethyl ether at 25℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Large scale; enantioselective reaction;99%
With [Rh{(S,S)-4-NO2-Phebox-Bn}(OAc)2]*H2O In diethyl ether at 25℃; for 24h; Inert atmosphere; enantioselective reaction;95%
1-[2-(4-methoxyphenyl)ethynyl]-4-nitrobenzene
39082-40-1

1-[2-(4-methoxyphenyl)ethynyl]-4-nitrobenzene

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

ethyl 4-(4-methoxyphenyl)-3-(4-nitrophenyl)-2-(trifluoromethyl)-2H-oxete-2-carboxylate

ethyl 4-(4-methoxyphenyl)-3-(4-nitrophenyl)-2-(trifluoromethyl)-2H-oxete-2-carboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; (S)-BINAP-PdCl2 In dichloromethane at 0℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%

13081-18-0Relevant articles and documents

REACTIONS OF BROMORTRIFLUOROMETHANE WITH ACID DERIVATIVES IN THE PRESENCE OF ZINC.

Francese, C.,Tordeux, M.,Wakselman, C.

, p. 1029 - 1030 (1988)

Reaction of zinc with bromotrifluoromethane in pyridine gives poorly reactive trifluoromethyl zinc derivatives in the presence of ethyl benzoate whereas the Barbier condensation occurs with activated esters, like ethyl trifluoroacetate or ethyl oxalate, and cyclic anhydrides.

Synthesis of fluorinated 1,2,3-butatrienes from α-halovinyl organometallic reagents

Morken,Bachand, Patrick C.,Swenson, Dale C.,Burton, Donald J.

, p. 5430 - 5439 (2007/10/02)

The thermal stability and dimerization reaction of fluorinated α-halovinyl zinc and copper reagents, RR'C=CYM (Y = F, Cl, Br; M = ZnX, Cu), have been explored in detail. Dimerization of these vinyl carbenoids to betatrienes occurred when R was an aromatic (C6H5 or C6F5) and R' was a perfluoroalkyl group (CF3, C2F5, C3F7). The role of the α-halogen was determined; the α-F vinyl copper reagent (R = C6H5, R' = CF3) decomposed by oxidative dimerization to 1,3-dienes while the α-Br and -Cl copper reagents dimerized to butatrienes. The fluorinated butatrienes prepared in this study, (E)- and (Z)-R1R2C==C=C=CR1R2 (R1 = CF3, R2 = C6H5; R1 = C2F5, R2 = C6H5; R1 = n-C3F7, R2 = C6H5; R1 = CF3, R2 = C6F5) are available on a multigram scale and readily obtained with high isomeric purity. The geometry of one member of each isomeric pair of butatrienes was characterized by X-ray crystallography. The mechanism of the dimerization reaction has been determined to be a nucleophilic displacement/β-elimination process. Diels-Alder (1,2-addition), bromination (1,2-addition), and isomerizatioa reactions are described.

Process for the preparation of perfluoroalkyl ketones

-

, (2008/06/13)

A process for the preparation of a perfluoroalkyl ketone. A perfluoroalkyl halide, zinc and an ester are brought into contact with one another. Preferably a polar aprotic solvent and/or a pyridine is also present.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 13081-18-0