373-88-6

Basic information

• Product Name: 2,2,2-Trifluoroethylamine hydrochloride
• Synonyms: 2,2,2-Trifluoroethyla;2,2,2-trifluoroethan-1-aMine chloride;2,2,2-TrifluoroethylaMine Hydrochloride, 97+%;TAF;TRIFLUOROETHYLAMINE HYDROCHLORIDE;2,2,2-TRIFLUOROETHYLAMINE HYDROCHLORIDE;2,2,2-TRIFLUORO-ETHYL-AMMONIUM CHLORIDE;2-AMINO-1,1,1-TRIFLUOROETHANE HYDROCHLORIDE
• CAS NO: 373-88-6
• Molecular Formula: C₂H₄F₃N*ClH
• Molecular Weight: 135.52
• EINECS: 206-771-1
• Mol File: 373-88-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 220-222 °C (subl.)(lit.)
• Boiling Point: 36 °C at 760 mmHg
• Flash Point: 27.6oC
• Appearance: white to light yellow crystalline powder
• Density: 1,24g/cm
• Vapor Pressure: 501mmHg at 25°C
• Refractive Index: 1,3-1,302
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: It is Soluble in 0.7 to water, but soluble in ethanol and chloroform, slightly soluble in benzene, hardly soluble in ether.
• Sensitive: Hygroscopic
• BRN: 3652103
• CAS DataBase Reference: 2,2,2-Trifluoroethylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-Trifluoroethylamine hydrochloride(373-88-6)
• EPA Substance Registry System: 2,2,2-Trifluoroethylamine hydrochloride(373-88-6)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-24/25-36-26
• WGK Germany: 3
• RTECS: KS0250000
• F: 3-10-21
• TSCA: T
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 373-88-6(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO LIGHT YELLOW CRYSTALLINE POWDER

Uses

2,2,2-Trifluoroethylamine Hydrochloride is a reagent in the synthesis of arachidonylethanolamide analogs. These show affinity for CB1 and CB2 cannabinoid receptors.

Safety Profile

Moderately toxic by unspecifiedroute. When heated to decomposition it emits very toxicfumes of F??, NOx, and HCl.

InChI:InChI=1/C2H4F3N/c3-2(4,5)1-6/h1,6H2/p+1

Synthetic route

trifluoroethylamine (753-90-2) → 2,2,2-trifluroethylamine hydrochloride (373-88-6)

Conditions	Yield
With hydrogenchloride In ethanol; water at 25 - 50℃; for 1h; Temperature;	96.3%

benzylamine (100-46-9) + trifluoroacetic acid (76-05-1) → 2,2,2-trifluroethylamine hydrochloride (373-88-6)

Conditions	Yield
Stage #1: benzylamine; trifluoroacetic acid With tetrachloromethane; TEA; triphenylphosphine In chloroform at 80℃; for 0.666667h; Stage #2: With TEA; water at 80℃; for 12h; Stage #3: With hydrogenchloride In methanol for 12h; Heating;	94%

[1-Phenyl-meth-(E)-ylidene]-(2,2,2-trifluoro-ethyl)-amine → 2,2,2-trifluroethylamine hydrochloride (373-88-6)

Conditions	Yield
With hydrogenchloride In diethyl ether for 4h; Ambient temperature;	87%

N-(2,2,2-trifluoroethyl)benzamide (348-08-3) → 2,2,2-trifluroethylamine hydrochloride (373-88-6)

Conditions	Yield
With hydrogenchloride In methanol for 24h; Heating;

1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → 3a,6a-dihydro-5-(phenylmethyl)-3-(trifluoromethyl)pyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione (1428147-22-1)

Conditions	Yield
Stage #1: 2,2,2-trifluroethylamine hydrochloride With sodium nitrite In dodecane; water Inert atmosphere; Stage #2: 1-benzyl-1H-pyrrole-2,5-dione In diethyl ether at 20℃; Inert atmosphere;	100%

3-pyridinecarboxaldehyde (500-22-1) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → (pyridine-3-ylmethylene)(2,2,2-trifluoroethyl)amine (1424799-68-7)

Conditions	Yield
With sodium hydroxide In water; toluene at 20℃; Cooling with ice;	100%
With triethylamine In acetonitrile at 0 - 20℃; for 15h;	84%

2,2,2-trifluroethylamine hydrochloride (373-88-6) + 1H-pyrazole-4-carbaldehyde (35344-95-7) → (1H-pyrazol-4-ylmethylene)(2,2,2-trifluoroethyl)amine (1424799-64-3)

Conditions	Yield
With sodium hydroxide In water; toluene at 20℃; Cooling with ice;	100%

2,2,2-trifluroethylamine hydrochloride (373-88-6) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2,2,2-trifluoroethyl)acetamide (170655-44-4)

Conditions	Yield
Stage #1: 2,2,2-trifluroethylamine hydrochloride With tert-butyl methyl ether; sodium hydroxide In water at 20℃; for 0.5h; Stage #2: chloroacetyl chloride at 5 - 10℃; for 1h;	100%
With potassium carbonate In dichloromethane; water at 0 - 30℃; for 3.16667h;	87.2%
Stage #1: 2,2,2-trifluroethylamine hydrochloride With sodium hydroxide In tert-butyl methyl ether; water at 0℃; for 0.5h; Stage #2: chloroacetyl chloride In tert-butyl methyl ether; water at 0℃; for 1h;	63%
Stage #1: 2,2,2-trifluroethylamine hydrochloride With sodium hydroxide In tert-butyl methyl ether; water at 0 - 5℃; for 0.5h; Stage #2: chloroacetyl chloride In tert-butyl methyl ether; water at 5 - 10℃; for 1h;

1-ethenyl-4-methylbenzene (622-97-9) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → (+/-)-1-methyl-4-((trans)-2-(trifluoromethyl)cyclopropyl)benzene

Conditions	Yield
With dmap; meso-tetraphenylporphyrin iron(III) chloride; sulfuric acid; sodium acetate; sodium nitrite In water at 20℃; for 14.0167h; Inert atmosphere; diastereoselective reaction;	99%
With dmap; meso-tetraphenylporphyrin iron(III) chloride; sulfuric acid; sodium acetate; sodium nitrite In water for 14h; Inert atmosphere;

2,2,2-trifluroethylamine hydrochloride (373-88-6) + propynoic acid methyl ester (922-67-8) → 3-trifluoromethyl-1H-pyrazole-5-carboxylic acid methyl ester (6833-82-5)

Conditions	Yield
With sodium nitrite In dichloromethane; water at 0 - 20℃; for 24h;	99%
With sodium nitrite In dichloromethane; water at 20℃; for 72h;
With sodium nitrite In dichloromethane; water at 0 - 20℃;

1-phenylbut-3-yn-2-one (31739-46-5) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → 2-phenyl-1-[5-(trifluoromethyl)-1H-pyrazol-3-yl]ethanone

Conditions	Yield
With sodium nitrite In dichloromethane; water at 0 - 20℃; for 24h;	99%

ethynyl(diphenyl)phosphine oxide (6104-48-9) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → 3-(diphenylphosphoryl)-5-(trifluoromethyl)-1H-pyrazole

Conditions	Yield
With sodium nitrite In dichloromethane; water at 0 - 20℃; for 24h;	99%

2,2,2-trifluroethylamine hydrochloride (373-88-6) + methyl ethenyl sulphone (3680-02-2) → 3-(methylsulfonyl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole

Conditions	Yield
Stage #1: 2,2,2-trifluroethylamine hydrochloride; methyl ethenyl sulphone With sodium nitrite In dichloromethane; water at 20℃; for 14h; Stage #2: With silica gel In ethyl acetate; toluene	99%

ethyl vinyl sulfone (1889-59-4) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → 3-(ethylsulfonyl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole

Conditions	Yield
Stage #1: ethyl vinyl sulfone; 2,2,2-trifluroethylamine hydrochloride With sodium nitrite In dichloromethane; water at 20℃; for 14h; Stage #2: With silica gel In ethyl acetate; toluene	99%

1-(vinylsulfonyl)-3-methylbenzene (5535-53-5) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → 3-((3-methylphenyl)sulfonyl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole

Conditions	Yield
Stage #1: 1-(vinylsulfonyl)-3-methylbenzene; 2,2,2-trifluroethylamine hydrochloride With sodium nitrite In dichloromethane; water at 20℃; for 14h; Stage #2: With silica gel In ethyl acetate; toluene	99%

methyl 2-(2-bromophenyl)-3-hydroxybut-2-enoate (1243144-97-9) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → (Z)-methyl 2-(2-bromophenyl)-3-((2,2,2-trifluoroethyl)amino)but-2-enoate

Conditions	Yield
With lithium methanolate; acetic acid In methanol; ethanol at 85℃; for 18h; Inert atmosphere;	98.4%

L-N-Boc-Ala (15761-38-3) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → tert-butyl (S)-1-(2,2,2-trifluoroethylcarbamoyl)ethylcarbamate (934178-98-0)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 16h;	98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane

Boc-(R)-Ala (3744-87-4, 7764-95-6, 15761-38-3) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → N2-(tert-butoxycarbonyl)-N-(2,2,2-trifluoroethyl)-D-alaninamide (934179-15-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 16h;	98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 16h;
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;

Boc-D-Val-OH (22838-58-0) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → (R)-tert-butyl 3-methyl-1-oxo-1-(2,2,2-trifluoroethylamino)butan-2-ylcarbamate (1429906-02-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	12.81 g

ethyl 2-(3-nitropyridin-2-yl)acrylate (1461708-12-2) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → ethyl 3-(3-nitropyridin-2-yl)-5-(trifluoromethyl)-4,5-dihydro-3Hpyrazole-3-carboxylate

Conditions	Yield
With sodium nitrite In dichloromethane; water at 0 - 20℃; for 24h;	98%

carbon monoxide (201230-82-2) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) + trimethyl orthoformate (149-73-5) + 3-amino-4-iodobenzonitrile → C11H6F3N3O

Conditions	Yield
With palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine In toluene at 110℃; under 7500.75 Torr; for 20h; Autoclave;	98%

tolyl vinyl sulfone (5535-52-4) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → 3-((4-methylphenyl)sulfonyl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole

Conditions	Yield
Stage #1: tolyl vinyl sulfone; 2,2,2-trifluroethylamine hydrochloride With sodium nitrite In dichloromethane; water at 20℃; for 14h; Stage #2: With silica gel In ethyl acetate; toluene	98%

2,2,2-trifluroethylamine hydrochloride (373-88-6) + p-tert-butyl benzoyl chloride (1710-98-1) → 4-tert-butyl-N-(2,2,2-trifluoroethyl)benzamide (1228117-67-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	97%

2,2,2-trifluroethylamine hydrochloride (373-88-6) + dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → dimethyl 5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3,4-dicarboxylate

Conditions	Yield
With sodium nitrite In dichloromethane; water at 0 - 20℃; for 24h;	97%

2,2,2-trifluroethylamine hydrochloride (373-88-6) + acrylonitrile (107-13-1) → 5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carbonitrile (69918-43-0)

Conditions	Yield
With sodium nitrite In dichloromethane; water at 0 - 20℃; for 24h;	97%

carbon monoxide (201230-82-2) + 4-fluoro-2-iodoaniline (61272-76-2) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) + trimethyl orthoformate (149-73-5) → C10H6F4N2O

Conditions	Yield
With palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine In toluene at 110℃; under 7500.75 Torr; for 20h; Autoclave;	97%

4-bromonitrosobenzene (3623-23-2) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) + dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → dimethyl 2-(4-bromophenyl)-3-(trifluoromethyl)isoxazolidine-4,5-dicarboxylate

Conditions	Yield
Stage #1: 2,2,2-trifluroethylamine hydrochloride With sodium nitrite In water; 1,2-dichloro-ethane at 0℃; for 2h; Stage #2: 4-bromonitrosobenzene; dimethyl cis-but-2-ene-1,4-dioate In water; 1,2-dichloro-ethane at -78 - 70℃; for 16h;	96%

2,2,2-trifluroethylamine hydrochloride (373-88-6) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 3-(trifluoromethyl)-1H-pyrazole-4,5-di-carboxylate

Conditions	Yield
With sodium nitrite In dichloromethane; water at 0 - 20℃; for 24h;	96%

N-phenyl-maleimide (941-69-5) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → 5-phenyl-3-(trifluoromethyl)-3a,6a-dihydropyrrolo[3,4-c]pyrazole-4,6(3H,5H)-dione

Conditions	Yield
With sodium nitrite In dichloromethane; water at 0 - 20℃; for 24h;	96%

carbon monoxide (201230-82-2) + p-chloro-o-iodoaniline (63069-48-7) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) + trimethyl orthoformate (149-73-5) → C10H6ClF3N2O

Conditions	Yield
With palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine In toluene at 110℃; under 7500.75 Torr; for 20h; Autoclave;	96%

carbon monoxide (201230-82-2) + 2-iodophenylamine (615-43-0) + 2,2,2-trifluroethylamine hydrochloride (373-88-6) + trimethyl orthoformate (149-73-5) → 3-(2,2,2-trifluoroethyl)quinazolin-4(3H)-one

Conditions	Yield
With palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine In toluene at 110℃; under 7500.75 Torr; for 20h; Autoclave;	96%

C17H15NO + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → 2-phenyl-3-(o-tolyl)-7-(trifluoromethyl)-2,5,6-triazaspiro[3.4]oct-6-en-1-one

Conditions	Yield
Stage #1: 2,2,2-trifluroethylamine hydrochloride With sodium nitrite In water; acetonitrile at 0℃; for 1h; Schlenk technique; Stage #2: C17H15NO In water; acetonitrile at 60℃; Schlenk technique; Sealed tube; stereoselective reaction;	96%

C11H14S + 2,2,2-trifluroethylamine hydrochloride (373-88-6) → (4-ethylphenyl)(1,1,1-trifluoropent-4-en-2-yl)sulfane

Conditions	Yield
With meso-tetraphenylporphyrin iron(III) chloride; sodium nitrite In dichloromethane; water at 20℃; for 15h; Inert atmosphere;	96%

Upstream product

• 348-08-3 N-(2,2,2-trifluoroethyl)benzamide 
• 100-46-9 benzylamine 
• 76-05-1 trifluoroacetic acid 
• 75-46-7 trifluoromethan 
• 753-90-2 trifluoroethylamine 
• 79-22-1 methyl chloroformate 

Downstream Products

• 407-37-4 N-(2,2,2-trifluoroethyl)trifluoroacetamide 
• 214210-12-5 (N-2,2,2-trifluoroethyl)-3-bromobenzenesulfonic acid amide 
• 26930-21-2 N-(2,2,2-trifluoroethyl)-4-chlorobenzamide 
• 932730-52-4 CDDO-TFEA 
• 182438-98-8 9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoro-ethyl)-amide 
• 1401102-68-8 3-fluoro-3-{4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl}cyclobutanecarboxylic acid-(2,2,2-trifluoro-ethyl)amide 
• 1401102-67-7 3-fluoro-3-{4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl}cyclobutanecarboxylic acid-(2,2,2-trifluoro-ethyl)amide 
• 1401102-78-0 1-{4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl}azetidine-3-carboxylic acid-(2,2,2-trifluoro-ethyl)amide 
• 1459258-20-8 3-iodo-1-(4-methoxybenzyl)-N-(2,2,2-trifluoroethyl)-1H-pyrazolo[4,3-c]pyridin-4-amine 
• 900779-70-6 (+)-1-bromo-4-(1S,2S)-(2-(trifluoromethyl)cyclopropyl)benzene 

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