5042-30-8

Basic information

• Product Name: 2,2,2-TRIFLUOROETHYLHYDRAZINE
• Synonyms: 2,2,2-Trifluoroethylhydrazine solution 70 wt. % in H2O;2,2,2-TRIFLUOROETHYLHYDRAZINE;2,2,2-TRIFLUOROETHYLHYDRAZINE, 70 WT. % SOLUTION IN WATER;2,2,2-Trifluoroethylhydrazine (70% in water);2,2,2-Trifluoroethylhydrazine,aqueoussolution;2,2,2-Trifluoroethylhydrazine, 70 wt% aqueous solution;2,2,2-trifluoroethylhydrazine solution;Trifluoroethylhydrazine.
• CAS NO: 5042-30-8
• Molecular Formula: C₂H₅F₃N₂
• Molecular Weight: 114.07
• EINECS: 225-734-0
• Product Categories: Aliphatics;Hydrazines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 5042-30-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 97°C (estimate)
• Flash Point: 109 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.294 g/mL at 25 °C
• Vapor Pressure: 76.5mmHg at 25°C
• Refractive Index: n20/D 1.361
• Storage Temp.: Flammables area
• PKA: 5.38±0.10(Predicted)
• CAS DataBase Reference: 2,2,2-TRIFLUOROETHYLHYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRIFLUOROETHYLHYDRAZINE(5042-30-8)
• EPA Substance Registry System: 2,2,2-TRIFLUOROETHYLHYDRAZINE(5042-30-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22
• Safety Statements: 36-36/37
• RIDADR: UN 1993 3/PG 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 5042-30-8(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW TO GREEN LIQUID

Uses

2,2,2-trifluoroethylhydrazine was added to myoglobin to study its interaction with heme protein. It was also used to determine aldehydes and acetone simultaneously in water.

InChI:InChI=1/C2H7F3N2/c3-2(4,5)1-7-6/h1,7H2,6H3/q+2

Synthetic route

tert-butyl 2-(2,2,2-trifluoroethyl)hydrazinecarboxylate → 2,2,2,trifluoroethylhydrazine (5042-30-8)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃;

2,2,2,trifluoroethylhydrazine (5042-30-8) + acetoacetic acid methyl ester (105-45-3) → 3-methyl-1-(2,2,2-trifluoroethyl)-5-pyrazolone (76552-51-7)

Conditions	Yield
In ethanol at 20 - 60℃;	99%

4-chloro-N-dimethylaminomethylene-2-thiophene carboxamide (910553-57-0) + 2,2,2,trifluoroethylhydrazine (5042-30-8) → 5-(4-chloro-thiophen-2-yl)-1-(2,2,2-trifluoro-ethyl)-1H-[1,2,4]triazole

Conditions	Yield
With acetic acid In water at 90℃; for 0.75h;	99%

2,2,2,trifluoroethylhydrazine (5042-30-8) + acetylacetone (123-54-6) → 3,5-dimethyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole (141354-19-0)

Conditions	Yield
In ethanol Reflux;	99%
With hydrogenchloride In water at 60℃; for 1.5h;	36 g

2,2,2,trifluoroethylhydrazine (5042-30-8) + N-(4-bromobenzylidene)glycine methyl ester (139575-14-7, 120672-87-9) → 5-p-bromophenyl-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: N-(4-bromobenzylidene)glycine methyl ester With silver(I) acetate; caesium carbonate In acetonitrile at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In acetonitrile at 20℃; for 48h; Schlenk technique;	99%

2,2,2,trifluoroethylhydrazine (5042-30-8) + methyl N-(4-chlorobenzylidene)glycinate (76862-09-4) → 5-(4-chlorophenyl)-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazin-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: methyl N-(4-chlorobenzylidene)glycinate With silver(I) acetate; caesium carbonate In tetrahydrofuran at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In tetrahydrofuran at 20℃; for 36h; Schlenk technique;	97%

(4-fluorobenzylideneamino)acetic acid methyl ester (479499-37-1) + 2,2,2,trifluoroethylhydrazine (5042-30-8) → 5-p-fluorophenyl-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: (4-fluorobenzylideneamino)acetic acid methyl ester With caesium carbonate; silver carbonate In tetrahydrofuran at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In tetrahydrofuran at 20℃; for 2h; Schlenk technique;	96%

2,2,2,trifluoroethylhydrazine (5042-30-8) + methyl 2-(1-naphthalenemethyleneamino)acetate → 5-(1-naphthyl)-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: methyl 2-(1-naphthalenemethyleneamino)acetate With silver fluoride; caesium carbonate In tetrahydrofuran at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In tetrahydrofuran at 20℃; for 30h; Schlenk technique;	96%

2,2,2,trifluoroethylhydrazine (5042-30-8) + methyl 2-((naphthalen-2-yl)methyleneamino)-acetate (104249-92-5) → 5-(2-naphthyl)-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: methyl 2-((naphthalen-2-yl)methyleneamino)-acetate With silver(I) acetate; caesium carbonate In tetrahydrofuran at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In tetrahydrofuran at 20℃; for 24h; Schlenk technique;	95%

(3E)-1-benzoyl-3-(dimethylamino)methylidenepyrrolidin-2-one (958462-15-2) + 2,2,2,trifluoroethylhydrazine (5042-30-8) → N-{2-[5-hydroxy-1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]ethyl}benzamide (958462-23-2)

Conditions	Yield
With hydrogenchloride In propan-1-ol for 4h; Heating;	94%

2,2,2,trifluoroethylhydrazine (5042-30-8) + C12H13NO4 (868659-09-0) → 5-((4-methoxycarbonyl)phenyl)-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: C12H13NO4 With silver(I) acetate; caesium carbonate In tetrahydrofuran at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In tetrahydrofuran at 20℃; for 24h; Schlenk technique;	93%

4-(3-Bromo-thiophene-2-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester (452910-10-0) + 2,2,2,trifluoroethylhydrazine (5042-30-8) → 4-{(3-bromo-thiophen-2-yl)-[(2,2,2-trifluoro-ethyl)-hydrazono]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (452911-06-7)

Conditions	Yield
In butan-1-ol at 110℃;	92%

2,2,2,trifluoroethylhydrazine (5042-30-8) + C21H23NO → C21H19F3N2

Conditions	Yield
In isopropyl alcohol at 160℃; for 2.5h; Microwave irradiation;	92%

2,2,2,trifluoroethylhydrazine (5042-30-8) + phenacyldiphenylphosphine oxide (1733-58-0) → diphenylphosphorylmethyl N-(2,2,2-trifluoroethyl)phenylhydrazone

Conditions	Yield
In ethanol for 18h; Heating;	91%

2,2,2,trifluoroethylhydrazine (5042-30-8) + C21H23NO2 → C21H19F3N2O + C21H19F3N2O

Conditions	Yield
In isopropyl alcohol at 140℃; for 2h; Microwave irradiation; regioselective reaction;	A 90% B n/a

2,2,2,trifluoroethylhydrazine (5042-30-8) + 2-(3-ethylsulfonyl-5-formylpyridin-2-yl)-5-(trifluoromethylthio)benzo[d]oxazole → 5-ethylsulfonyl-6-{5-(trifluoromethylthio)benzo[d]oxazol-2-yl}nicotinaldehyde (2,2,2-trifluoroethyl)hydrazone

Conditions	Yield
With acetic acid In chloroform at 20℃; for 4h;	89%

2,2,2,trifluoroethylhydrazine (5042-30-8) + methyl 2-((anthracen-9-yl)methyleneamino)-acetate (1539282-63-7) → 5-(9-anthracen-9-yl)-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: methyl 2-((anthracen-9-yl)methyleneamino)-acetate With silver(I) acetate; caesium carbonate In acetonitrile at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In acetonitrile at 20℃; for 48h; Schlenk technique;	88%

2,2,2,trifluoroethylhydrazine (5042-30-8) + 2-[(4-bromophenyl)methoxymethylene]propanedinitrile → 5-amino-3-(4-bromophenyl)-1-(2,2,2-trifluoroethyl)pyrazole-4-carbonitrile

Conditions	Yield
Stage #1: 2,2,2,trifluoroethylhydrazine With triethylamine In ethanol at 20℃; for 0.166667h; Stage #2: 2-[(4-bromophenyl)methoxymethylene]propanedinitrile In ethanol at 95℃; for 16h;	87%

2,2,2,trifluoroethylhydrazine (5042-30-8) + 2-amino-3-benzyloxycarbonyl-4-oxo-2-pentenoic acid ethyl ester (198135-04-5) → C17H17F3N2O4 (1400916-92-8)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 15h; regioselective reaction;	86%

ethyl 4-(2-iodoethoxy)-3-oxobutanoate (221446-38-4) + 2,2,2,trifluoroethylhydrazine (5042-30-8) → C8H9F3N2O2

Conditions	Yield
With sodium acetate In acetic acid at 110℃; for 12h;	86%

2,2,2,trifluoroethylhydrazine (5042-30-8) + glycine methyl ester (4-iodobenzaldehyde)imine (1337988-81-4) → 5-p-iodophenyl-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: glycine methyl ester (4-iodobenzaldehyde)imine With silver(I) acetate; caesium carbonate In tetrahydrofuran at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In tetrahydrofuran at 20℃; for 48h; Schlenk technique;	86%

2,2,2,trifluoroethylhydrazine (5042-30-8) + C14H17NO → 2,2,2-trifluoroethyl-4-(4-isopropylphenyl)-3,5-dimethyl-1H-pyrazole

Conditions	Yield
With hydrogenchloride; tricarbonyl(cycloheptatriene)molybdenum(0) In tetrahydrofuran; water at 70℃; for 16h; Sealed tube;	86%

tert-butyl 13-cyclohexyl-6-((2E,Z)-3-(dimethylamino)-2-(ethoxycarbonyl)-2-propenoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylate (1127234-89-2) + 2,2,2,trifluoroethylhydrazine (5042-30-8) → 13-cyclohexyl-6-[4-(ethoxycarbonyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl]-3-methoxy-7H-indolo[2,1-a] [2]benzazepine-10-carboxylic acid 1,1-dimethylethyl ester (1127236-92-3)

Conditions	Yield
With triethylamine In ethanol at 160℃; for 2h; Microwave irradiation;	84%

tert-butyl 13-cyclohexyl-6-((2E,Z)-3-(dimethylamino)-2-(ethoxycarbonyl)-2-propenoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylate (1127234-89-2) + 2,2,2,trifluoroethylhydrazine (5042-30-8) → 13-cyclohexyl-6-[4-(ethoxycarbonyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl]-3-methoxy-1H-indolo[2,1-a][2]benzazepine-10-carboxylic acid 1,1-dimethylethyl ester

Conditions	Yield
With triethylamine In ethanol at 160℃; for 2h; Microwave irradiation;	84%

2,2,2,trifluoroethylhydrazine (5042-30-8) + ethyl 7-iodo-3-oxoheptanoate (153851-18-4) → C9H11F3N2O

Conditions	Yield
With sodium acetate In acetic acid at 110℃; for 12h;	84%

2,2,2,trifluoroethylhydrazine (5042-30-8) + (E/Z)-2-(3-chloropyridine-2-carbonyl)-3-dimethylaminoacrylic acid ethyl ester (1072314-47-6) → 5-(3-chloropyridin-2-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazole-4-carboxylic acid ethyl ester (1423030-57-2)

Conditions	Yield
In ethanol for 2h; Reflux;	83%
In ethanol for 2h; Reflux;	83%

2,2,2,trifluoroethylhydrazine (5042-30-8) + ethyl 2-(4-nitrobenzyl)-3-oxohexanoate (137860-00-5) → 4-(4-Nitro-benzyl)-5-propyl-2-(2,2,2-trifluoro-ethyl)-2H-pyrazol-3-ol (137860-07-2)

Conditions	Yield
In ethanol for 3h; Heating;	82%

2,2,2,trifluoroethylhydrazine (5042-30-8) + ethyl 4-[1-(dimethylamino)-3-ethoxy-3-oxoprop-1-en-2-yl]-2-[(dimethylamino)methylideneamino]thiazole-5-carboxylate (1160217-28-6) → ethyl 2-amino-4-oxo-5-(2,2,2-trifluoroethylamino)-4,5-dihydrothiazolo[5,4-c]pyridine-7-carboxylate (1192309-23-1)

Conditions	Yield
With hydrogenchloride In ethanol; water for 2h; Reflux;	82%

2,2,2,trifluoroethylhydrazine (5042-30-8) + [(4-methyl-benzylidene)-amino]-acetic acid methyl ester → 5-(p-methylphenyl)-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: [(4-methyl-benzylidene)-amino]-acetic acid methyl ester With silver fluoride; sodium hydroxide In diethyl ether at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In diethyl ether at 20℃; for 12h; Schlenk technique;	82%

2,2,2,trifluoroethylhydrazine (5042-30-8) + glycine methyl ester (4-trifluoromethylbenzaldehyde)imine (286392-28-7) → 5-(p-(trifluoromethyl)phenyl)-6-trifluoromethyl-1,2,5,6-tetrahydro-1,2,4-triazine-3-carboxylic acid methyl ester

Conditions	Yield
Stage #1: glycine methyl ester (4-trifluoromethylbenzaldehyde)imine With silver(I) acetate; caesium carbonate In tetrahydrofuran at 20℃; for 0.05h; Schlenk technique; Stage #2: 2,2,2,trifluoroethylhydrazine In tetrahydrofuran at 20℃; for 1h; Schlenk technique;	82%

ethyl 3-{(1R,2R)-2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-2-[4-(methylthio)phenyl]-3-oxopropanoate (919109-90-3) + 2,2,2,trifluoroethylhydrazine (5042-30-8) → 3-{(1R,2R)-2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-4-[4-(methylthio)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-ol

Conditions	Yield
With magnesium sulfate In water; 1,1,2,2-tetrachloroethane at 120℃; for 72h; Inert atmosphere;	81%
With magnesium sulfate In 1,1,2,2-tetrachloroethane at 120℃; for 72h;

Downstream Products

• 70343-33-8 7-((Z)-4-methyl-benzylidene)-3-p-tolyl-2-(2,2,2-trifluoro-ethyl)-2,3,3a,4,6,7-hexahydro-thiopyrano[4,3-c]pyrazole 5,5-dioxide 
• 83319-91-9 7-((Z)-4-methyl-benzylidene)-3-p-tolyl-1-(2,2,2-trifluoro-ethyl)-1,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole 5,5-dioxide 
• 78097-12-8 4-[6-(2-Chloro-4-methoxy-phenoxy)-hexyl]-3,5-diethyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazole 
• 152713-75-2 ethyl 4-<(2'-cyanobiphenyl-4-yl)methyl>-3-n-propyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole-5-carboxylate 
• 138733-49-0 5-Butyl-4-(2'-cyano-biphenyl-4-ylmethyl)-2-(2,2,2-trifluoro-ethyl)-2H-pyrazole-3-carboxylic acid ethyl ester 
• 137860-74-3 4-<(2'-cyanobiphenyl-4-yl)methyl>-5-methoxymethyl-3-n-propyl-1-(2,2,2-trifluoroethyl)pyrazole 
• 137860-50-5 4'-[5-Hydroxy-3-isobutyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-4-ylmethyl]-biphenyl-2-carbonitrile 
• 137860-42-5 4'-[3-Butyl-5-methoxymethyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-4-ylmethyl]-biphenyl-2-carbonitrile 
• 137860-07-2 4-(4-Nitro-benzyl)-5-propyl-2-(2,2,2-trifluoro-ethyl)-2H-pyrazol-3-ol 
• 137860-28-7 4'-[5-Hydroxy-3-propyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-4-ylmethyl]-biphenyl-2-carbonitrile 
• 161463-13-4 4'-[3-Butyl-5-hydroxy-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-4-ylmethyl]-biphenyl-2-carbonitrile 
• 270585-04-1 5-isopropyl-3-methoxymethyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazole 

Relevant articles and documents

Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators

The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.