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21249-93-4

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21249-93-4 Usage

General Description

(2,2,2-Trifluoroethyl)benzene is an organic compound with the chemical formula C8H7F3. It is a colorless liquid with a sweet aromatic odor, and it is commonly used as a solvent and intermediate in the production of pharmaceuticals and agrochemicals. The compound is formed by adding a trifluoroethyl group to a benzene ring, resulting in a molecule with three fluorine atoms and a benzene structure. It is highly flammable and should be handled with caution due to its potential health hazards. Additionally, it is not readily biodegradable and can persist in the environment, posing potential risks to ecosystems.

Check Digit Verification of cas no

The CAS Registry Mumber 21249-93-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,2,4 and 9 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 21249-93:
(7*2)+(6*1)+(5*2)+(4*4)+(3*9)+(2*9)+(1*3)=94
94 % 10 = 4
So 21249-93-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H7F3/c9-8(10,11)6-7-4-2-1-3-5-7/h1-5H,6H2

21249-93-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name (2,2,2-Trifluoroethyl)benzene

1.2 Other means of identification

Product number -
Other names 2,2,2-trifluoroethylbenzene

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:21249-93-4 SDS

21249-93-4Synthetic route

benzyl bromide
100-39-0

benzyl bromide

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide; N-(EtOCH2CH2OCH2)-N-methylmorpholinium bis(CF3SO2)amide at 80℃; for 8h;90%
With C13H27CuN2O(1+) In N,N-dimethyl-formamide at 25℃; for 112h;58 %Spectr.
1,1,1-trifluoro-2-iodoethane
353-83-3

1,1,1-trifluoro-2-iodoethane

phenylboronic acid
98-80-6

phenylboronic acid

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With [2,2]bipyridinyl; nickel(II) bromide dimethoxyethane; potassium phosphate In dimethyl sulfoxide at 80℃; for 12h; Reagent/catalyst; Solvent; Concentration; Inert atmosphere; Sealed tube;85%
metyhyl chlorodifluoroacetate
1514-87-0

metyhyl chlorodifluoroacetate

benzyl bromide
100-39-0

benzyl bromide

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 110 - 120℃; for 8h;84%
With potassium fluoride; copper(l) iodide In various solvent(s) at 80℃; for 8h;68%
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 100 - 120℃; for 7h;
2,2-difluoro-2-(fluorosulfonyl)acetate
680-15-9

2,2-difluoro-2-(fluorosulfonyl)acetate

iodomethylbenzene
620-05-3

iodomethylbenzene

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With copper(l) iodide In N,N-dimethyl-formamide at 70℃; for 2h;81%
With copper In N,N-dimethyl-formamide at 80℃; for 3h;80%
2',2'-difluorostyrene
405-42-5

2',2'-difluorostyrene

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether In N,N-dimethyl-formamide at 150℃; for 8h; hydrofluorination;75%
benzyl bromide
100-39-0

benzyl bromide

Potassium; difluoro-(1,1,2,2-tetrafluoro-2-fluorosulfonyl-ethoxy)-acetate

Potassium; difluoro-(1,1,2,2-tetrafluoro-2-fluorosulfonyl-ethoxy)-acetate

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With copper(l) iodide In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide at 40℃; for 3h;74%
1,1,1-trifluoro-2-chloroethane
75-88-7

1,1,1-trifluoro-2-chloroethane

chlorobenzene
108-90-7

chlorobenzene

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; nickel dibromide; zinc In N,N-dimethyl acetamide at 80℃; for 12h; Inert atmosphere; Schlenk technique;74%
With 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; nickel dibromide; zinc In N,N-dimethyl acetamide at 80℃; for 12h; Inert atmosphere; Schlenk technique;74%
bromobenzene
108-86-1

bromobenzene

1,1,1-trifluoro-2-chloroethane
75-88-7

1,1,1-trifluoro-2-chloroethane

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; nickel dibromide; zinc In N,N-dimethyl acetamide at 80℃; for 12h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;73%
With 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; nickel dibromide; zinc In N,N-dimethyl acetamide at 80℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;73 %Spectr.
2,2-difluoro-2-(fluorosulfonyl)acetate
680-15-9

2,2-difluoro-2-(fluorosulfonyl)acetate

benzyl bromide
100-39-0

benzyl bromide

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 3.5h;72.4%
With copper In N,N-dimethyl-formamide at 80℃; for 3h;70%
With copper(l) iodide In various solvent(s) at 55℃; for 8h;70%
ethyl 2,2-difluoro-2-(fluorosulfonyl)acetate
756-21-8

ethyl 2,2-difluoro-2-(fluorosulfonyl)acetate

benzyl alcohol
100-51-6

benzyl alcohol

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 70℃; for 9h;72%
benzyl fluorosulfonyldifluoroacetate

benzyl fluorosulfonyldifluoroacetate

A

benzyl fluoride
350-50-5

benzyl fluoride

B

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With copper(l) iodide In N,N-dimethyl-formamide at 60℃; for 7h;A n/a
B 71%
benzyl bromide
100-39-0

benzyl bromide

methyl 3-oxa-ω-fluorosulfonylperfluoropentanoate
88986-32-7

methyl 3-oxa-ω-fluorosulfonylperfluoropentanoate

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With copper(l) iodide In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide at 80℃; for 4h;70%
With copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 8h;62%
benzyl 2-bromo-2,2-difluoroacetate
155820-63-6

benzyl 2-bromo-2,2-difluoroacetate

A

benzyl fluoride
350-50-5

benzyl fluoride

B

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 8h;A 2 % Spectr.
B 68%
toluene-4-sulfonic acid 2,2,2-trifluoro-1-phenyl-ethyl ester
13652-13-6

toluene-4-sulfonic acid 2,2,2-trifluoro-1-phenyl-ethyl ester

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate63%
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature;
benzyl chlorodifluoroacetate

benzyl chlorodifluoroacetate

A

benzyl fluoride
350-50-5

benzyl fluoride

B

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 100℃; for 10h;A 4%
B 59%
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 100℃; for 10h; Product distribution; copper(I) iodide-initiated trifluoromethyl-dehydroxylation of benzyl, prop-2-ynyl and allyl chlorodifluoro-, bromofifluoro and fluorosulfonyldifluoroacetates, effect of KF on product yields;A 4%
B 59%
1-chloro-2,2,2-trifluoroethylbenzene
384-65-6

1-chloro-2,2,2-trifluoroethylbenzene

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethylene glycol dimethyl ether at 110 - 115℃; for 12h;57%
2,2-difluoro-2-(fluorosulfonyl)acetate
680-15-9

2,2-difluoro-2-(fluorosulfonyl)acetate

benzyl chloride
100-44-7

benzyl chloride

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 4h;53%
metyhyl chlorodifluoroacetate
1514-87-0

metyhyl chlorodifluoroacetate

benzyl chloride
100-44-7

benzyl chloride

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 110 - 120℃; for 8h;46%
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 100 - 120℃; for 7h;
ethyl 2-chloro-2,2-difluoroacetate
383-62-0

ethyl 2-chloro-2,2-difluoroacetate

benzyl alcohol
100-51-6

benzyl alcohol

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 100℃; for 10h;43%
benzyl chloride
100-44-7

benzyl chloride

methyl 3-oxa-ω-fluorosulfonylperfluoropentanoate
88986-32-7

methyl 3-oxa-ω-fluorosulfonylperfluoropentanoate

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 8h;42%
Ethyl bromodifluoroacetate
667-27-6

Ethyl bromodifluoroacetate

benzyl alcohol
100-51-6

benzyl alcohol

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 90℃; for 8h;39%
1,1,1-trifluoro-2-chloroethane
75-88-7

1,1,1-trifluoro-2-chloroethane

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
Stage #1: 1,1,1-trifluoro-2-chloroethane With (1S,2S)-N1,N1,N2,N2-tetramethylcyclohexane-1,2-diamine; cobalt(II) chloride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
Stage #2: phenylmagnesium bromide In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;
32%
1,1,1-trifluoro-2-iodoethane
353-83-3

1,1,1-trifluoro-2-iodoethane

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
Stage #1: 1,1,1-trifluoro-2-iodoethane With (1S,2S)-N1,N1,N2,N2-tetramethylcyclohexane-1,2-diamine; cobalt(II) chloride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
Stage #2: phenylmagnesium bromide In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;
25%
Stage #1: 1,1,1-trifluoro-2-iodoethane With trans-N,N,N′,N′-tetramethylcyclohexane-1,2-diamine; cobalt(II) chloride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
Stage #2: phenylmagnesium bromide In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;
25%
phenylacetic acid
103-82-2

phenylacetic acid

A

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

B

phenylacetyl fluoride
370-84-3

phenylacetyl fluoride

Conditions
ConditionsYield
With sulfur tetrafluoride
iodobenzene
591-50-4

iodobenzene

1,1,1-trifluoro-2-iodoethane
353-83-3

1,1,1-trifluoro-2-iodoethane

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With copper In N,N-dimethyl-formamide at 190℃;
1,1,1-trifluoroacetophenone
434-45-7

1,1,1-trifluoroacetophenone

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With hydrazine hydrate In diethylene glycol
Multi-step reaction with 3 steps
1: 89 percent / NaBH4 / methanol / Ambient temperature
2: 83 percent / SOCl2, pyridine / benzene / 2 h / Heating
3: zinc / ethanol / 10 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 89 percent / NaBH4 / methanol / Ambient temperature
2: 83 percent / SOCl2, pyridine / benzene / 2 h / Heating
3: 1.) zinc; 2.) bromine / 1.) ethanol, reflux, 10 h; 2.) n-hexane, r.t., 5 h
View Scheme
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

benzyl bromide
100-39-0

benzyl bromide

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
(i) Cu, HMPT, (ii) /BRN= 385801/; Multistep reaction;
perfluoropropylene
116-15-4

perfluoropropylene

sec-Butylbenzene
135-98-8, 36383-15-0

sec-Butylbenzene

A

ethylbenzene
100-41-4

ethylbenzene

B

perfluoro-(1,2-dimethylcyclobutane)
2994-71-0

perfluoro-(1,2-dimethylcyclobutane)

C

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

D

1,1,1-trifluoro-2-methylbutane
75121-29-8

1,1,1-trifluoro-2-methylbutane

Conditions
ConditionsYield
at 250℃; for 72h; Further byproducts given;A 1.5 % Turnov.
B 1 % Turnov.
C 5 % Turnov.
D 8 % Turnov.
1-chloro-2,2,2-trifluoroethylbenzene
384-65-6

1-chloro-2,2,2-trifluoroethylbenzene

A

2',2'-difluorostyrene
405-42-5

2',2'-difluorostyrene

B

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

Conditions
ConditionsYield
With zinc In ethanol for 10h; Heating; Title compound not separated from byproducts;
(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

benzene
71-43-2

benzene

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Conditions
ConditionsYield
With triethylsilane; fluorotris(pentafluorophenyl)phosphonium tetrakis(pentafluorophenyl)borate at 20℃; for 4h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Glovebox;93%
2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

2-bromo-1,3,5-trimethyl-4-phenethylbenzene

2-bromo-1,3,5-trimethyl-4-phenethylbenzene

Conditions
ConditionsYield
With triethylsilane; fluorotris(pentafluorophenyl)phosphonium tetrakis(pentafluorophenyl)borate In dichloromethane at 20℃; for 2h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Glovebox;62%
pentamethylbenzene,
700-12-9

pentamethylbenzene,

(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

1,2,3,4,5-pentamethyl-6-phenethylbenzene
32853-51-3

1,2,3,4,5-pentamethyl-6-phenethylbenzene

Conditions
ConditionsYield
With triethylsilane; fluorotris(pentafluorophenyl)phosphonium tetrakis(pentafluorophenyl)borate at 80℃; for 10h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Glovebox;60%
(2,2,2-trifluoroethyl)benzene
21249-93-4

(2,2,2-trifluoroethyl)benzene

4-(2,2,2-trifluoroethyl)benzene-1-sulfonyl chloride
883146-03-0

4-(2,2,2-trifluoroethyl)benzene-1-sulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid In dichloromethane at 20℃; for 4h;53%

21249-93-4Relevant articles and documents

Active trifluoromethylating agents from well-defined copper(I)-CF 3 complexes

Dubinina, Galyna G.,Furutachi, Hideki,Vicic, David A.

, p. 8600 - 8601 (2008)

The first examples of isolable and structurally characterized Cu(I)-CF3 complexes are reported. N-Heterocyclic carbene (NHC)-supported copper tert-butoxide complexes reacted with Me3Si-CF3 to afford new (NHC)Cu-CF3 complexes whose structures were dependent on whether or not the C4-C5 positions of the five-membered NHC rings were saturated. In situ generated (SIiPr)Cu-CF3 cleanly transferred its trifluoromethyl group to a number of organic halides under mild conditions. Copyright

Using Chlorotrifluoroethane for Trifluoroethylation of (Hetero)aryl Bromides and Chlorides via Nickel Catalysis

Li, Xuefei,Gao, Xing,He, Chun-Yang,Zhang, Xingang

supporting information, p. 1400 - 1405 (2021/02/20)

A nickel-catalyzed reductive cross-coupling between industrial chemical CF3CH2Cl and (hetero)aryl bromides and chlorides has been reported. The reaction is synthetically simple without the preparation of arylmetals and exhibits high functional group tolerance. The utility of this protocol has been demonstrated by the late-stage modification of pharmaceuticals, providing a facile route for medicinal chemistry.

Preparation method of trifluoroethyl compounds

-

Paragraph 0052; 0053; 0054; 0055; 0056; 0057; 0058, (2020/01/25)

The invention discloses a preparation method of trifluoroethyl compounds. The trifluoroethyl compounds are synthesized by directly using cheap and abundant industrial raw materials 2-chloro-1,1,1-trifluoroethane and halogenated substances as raw materials by stirring in a polar solvent under the action of a catalytic system using cheap and an easily available alkali metal nickel salt catalyst anda pyridine ligand for reacting under mild reaction conditions of 50-90 DEG C for 12-24 hours, and the efficient introduction of the trifluoroethyl groups to aromatic ring groups or heterocyclic aryl groups can be realized to prepare the trifluoroethyl compounds. The method has the advantages of mild reaction conditions, simple operation, low cost of raw materials and catalysts, good compatibilityof substrate functional groups, easy expansion of reaction scale, simple separation of products and suitability for industrial production.

Metal-Free Construction of the C(sp3)-CF3 Bond: Trifluoromethylation of Hydrazones with Togni's Reagent under Mild Conditions

Zeng, Huiying,Luo, Zhen,Han, Xinlong,Li, Chao-Jun

, p. 5948 - 5951 (2019/08/29)

A metal-free trifluoromethylation of hydrazones with Togni's reagent under mild conditions was developed. Various functional groups including ester, methoxy, dimethoxy, nitro, halogen, and heterocyclic compounds were tolerated. This simple and green strategy provides a practical tool to construct C(sp3)-CF3 bonds.

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