183610-70-0

Basic information

• Product Name: 2-Amino-3-(trifluoromethyl)pyridine
• Synonyms: 3-(TRIFLUOROMETHYL)-2-PYRIDINAMINE;3-TRIFLUOROMETHYL-PYRIDIN-2-YLAMINE;2-AMINO-3-(TRIFLUOROMETHYL)PYRIDINE;3-(Trifluoromethyl)pyridin-2-amine;3-(TrifluoroMethyl)1-2-pyridinaMine;3-(TrifluoroMethyl)-2-pyridiMine;2-PyridinaMine, 3-(trifluoroMethyl)-;3-(Trifluoromethyl)pyridin-2-amine, 2-Amino-alpha,alpha,alpha-trifluoro-3-picoline
• CAS NO: 183610-70-0
• Molecular Formula: C₆H₅F₃N₂
• Molecular Weight: 162.11
• Product Categories: Amines and Anilines;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;Amines;Pyridines;Fluorine series
• Mol File: 183610-70-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 70-72°C
• Boiling Point: 203.2 °C at 760 mmHg
• Flash Point: 76.7 °C
• Appearance: /
• Density: 1.368 g/cm³
• Vapor Pressure: 0.28mmHg at 25°C
• Refractive Index: 1.478
• Storage Temp.: Room temperature.
• PKA: 4.18±0.36(Predicted)
• CAS DataBase Reference: 2-Amino-3-(trifluoromethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-(trifluoromethyl)pyridine(183610-70-0)
• EPA Substance Registry System: 2-Amino-3-(trifluoromethyl)pyridine(183610-70-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-36-43
• Safety Statements: 26-36/37/39
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 183610-70-0(Hazardous Substances Data)

Usage

Uses

2-?Amino-?3-?(trifluoromethyl)?pyridine is a reagent used in the preparation of novel propanamide derivatives functioning as fatty acid amide inhibitors.

InChI:InChI=1/C6H5F3N2/c7-6(8,9)4-2-1-3-11-5(4)10/h1-3H,(H2,10,11)

Synthetic route

2-fluoro-3-trifluoromethylpyridine (65753-52-8) → 2-amino-3-trifluoromethylpyridine (183610-70-0)

Conditions	Yield
With ammonia In water at 130℃; under 22502.3 Torr; for 10h; Temperature;	95%

(4-methoxy-benzyl)-(3-trifluoromethyl-pyridin-2-yl)-amine (911112-72-6) → 2-amino-3-trifluoromethylpyridine (183610-70-0)

Conditions	Yield
Stage #1: (4-methoxy-benzyl)-(3-trifluoromethyl-pyridin-2-yl)-amine With sulfuric acid at 5 - 23℃; for 0.5h; Stage #2: With sodium hydroxide In water at 0℃;	92%

2-chloro-3-trifluoromethyl-pyridine (65753-47-1) → 2-amino-3-trifluoromethylpyridine (183610-70-0)

Conditions	Yield
With ammonia In water at 175℃; for 24h;	71%
With ammonia In water at 175℃; for 72h;
Multi-step reaction with 2 steps 1: hydrogen fluoride / 48 h / 130 °C / 60006 Torr / Autoclave 2: ammonia / water / 10 h / 130 °C / 22502.3 Torr View Scheme

methanol (67-56-1) + 8-Trifluoromethyl-tetrazolo[1,5-a]pyridine (143812-76-4) → 2-amino-3-trifluoromethylpyridine (183610-70-0) + 2-methoxy-4-trifluoromethyl-1H-1,3-diazepine (177211-80-2)

Conditions	Yield
In 1,4-dioxane at 25℃; for 1.33333h; Irradiation;	A 5% B 47%

2-amino-3-trifluoromethylpyridine (183610-70-0) → 5-bromo-3-(trifluoromethyl)pyridin-2-amine (79456-34-1)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 0 - 20℃;	99%
With N-Bromosuccinimide In acetonitrile at 5 - 23℃; for 1h;	98%
With N-Bromosuccinimide In acetonitrile at 20℃;	93%

2-amino-3-trifluoromethylpyridine (183610-70-0) → 5-iodo-3-(trifluoromethyl)pyridin-2-amine

Conditions	Yield
With N-iodo-succinimide; acetic acid at 0 - 20℃; for 90h;	89%
Stage #1: 2-amino-3-trifluoromethylpyridine With N-iodo-succinimide; acetic acid at 0 - 20℃; Stage #2: With sodium hydrogencarbonate In water Cooling with ice;	76%
With N-iodo-succinimide	76%
With N-iodo-succinimide In acetic acid at 0 - 20℃;	76%
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃;	70%

2-amino-3-trifluoromethylpyridine (183610-70-0) → 5-chloro-3-(trifluoromethyl)pyridin-2-amine (79456-33-0)

Conditions	Yield
With N-chloro-succinimide In N,N-dimethyl-formamide at 60℃; for 1h;	88%
With N-chloro-succinimide In N,N-dimethyl-formamide at 60℃; for 1h;	88%
With N-chloro-succinimide In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;

cyclohexanone (108-94-1) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 4-(trifluoromethyl)benzo[4,5]imidazo[1,2-a]pyridine

Conditions	Yield
With iodine; oxygen In 1,1,2,2-tetrachloroethane at 160℃; for 24h; Green chemistry;	88%

2-amino-3-trifluoromethylpyridine (183610-70-0) → C6H5F3N2O

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In acetone at 0 - 20℃; for 12.5h;	81%

2-amino-3-trifluoromethylpyridine (183610-70-0) → 5-nitro-3-(trifluoromethyl)pyridin-2-amine (1121056-94-7)

Conditions	Yield
With sulfuric acid; nitric acid In water at 0 - 50℃; for 3.25h;	75%

2-chloro-5-(1-chloroethyl)pyridine + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 1-[1-(6-chloro-3-pyridyl)ethyl]-3-(trifluoromethyl)pyridin-2-imine

Conditions	Yield
With sodium iodide In acetonitrile at 82℃; for 72h;	75%

1-Bromo-2-butanone (816-40-0) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 2-ethyl-8-(trifluoromethyl)imidazo[1,2-a]pyridine (1167570-72-0)

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In ethanol Heating / reflux;	74%

methyl 3-bromo-2-oxopropanoate (7425-63-0) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 8-trifluoromethyl-imidazo[1,2-a]pyridine-2-carboxylic acid methyl ester (1206972-73-7)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 3h;	72%

2-amino-3-trifluoromethylpyridine (183610-70-0) → 3-(trifluoromethyl)pyridine-2-(1H)-one (22245-83-6)

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 70℃; for 1h;	69%

methyl 3-hydroxy-2-methylidene-3-phenylpropionate (18020-59-2) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 3-(benzyl)-9-(trifluoromethyl)-2H-pyrido[1,2-a]pyrimidin-2-one

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol Reflux;	67%

cyclohexanone (108-94-1) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 4-(trifluoromethyl)-6,7,8,9-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine

Conditions	Yield
With sulfur In neat (no solvent) at 110℃; for 16h; Inert atmosphere; regioselective reaction;	65%

1-(3-(methoxymethoxy)phenyl)prop-2-yn-1-yl acetate + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 3-(3-(methoxymethoxy)phenyl)-2-methyl-8-(trifluoromethyl)imidazo[1,2-a]pyridine

Conditions	Yield
With copper acetylacetonate; N-ethyl-N,N-diisopropylamine; 2,6-bis(4,5-dihydrooxazol-2-yl)pyridine In methanol at 20℃; for 6h; Inert atmosphere; regioselective reaction;	61%

2-(4-((2-(trifluoromethyl)pyridin-4-yl)amino)phenyl)propanoic acid (1210909-06-0) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → N-(3-(trifluoromethyl)pyridin-2-yl)-2-(4-((2-(trifluoromethyl)pyridin-4-yl)amino)phenyl)propanamide

Conditions	Yield
Stage #1: 2-(4-((2-(trifluoromethyl)pyridin-4-yl)amino)phenyl)propanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h; Stage #2: 2-amino-3-trifluoromethylpyridine In acetonitrile at 20℃;	59%

ibuprofen (15687-27-1) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 2-(4-isobutylphenyl)-N-(3-(trifluoromethyl)pyridin-2-yl)propanamide

Conditions	Yield
Stage #1: ibuprofen With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h; Stage #2: 2-amino-3-trifluoromethylpyridine In acetonitrile at 20℃; for 36h;	59%

tert-butyl 4-(10-bromo-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate + 2-amino-3-trifluoromethylpyridine (183610-70-0) → tert-butyl 4-(2-oxo-10-{[3-(trifluoromethyl)pyridin-2-yl]amino}-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate

Conditions	Yield
With potassium phosphate; t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate In tert-butyl alcohol at 110℃; Inert atmosphere;	58%

3-methoxyphenylglyoxal (32025-65-3) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 2-chloro-3-(3-methoxyphenyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridine (1167571-66-5)

Conditions	Yield
Stage #1: 3-methoxyphenylglyoxal; 2-amino-3-trifluoromethylpyridine In dichloromethane for 1h; Heating / reflux; Stage #2: With thionyl chloride In tetrachloromethane for 0.5h; Heating / reflux; Stage #3: With potassium carbonate In water	56%

methyl 2-hydroxymethylacrylate (15484-46-5) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 3-methyl-9-(trifluoromethyl)-2H-pyrido[1,2-a]pyrimidin-2-one

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol Reflux;	52%

chloroacetone (78-95-5) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 2-methyl-8-(trifluoromethyl)imidazo[1,2-a]pyridine (1167570-71-9)

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In ethanol Heating / reflux;	51%

1-phenylprop-2-ynyl acetate (16169-88-3, 84681-19-6, 116119-86-9, 116182-55-9) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 2-methyl-3-phenyl-8-(trifluoromethyl)imidazo[1,2-a]pyridine

Conditions	Yield
With copper acetylacetonate; N-ethyl-N,N-diisopropylamine; 2,6-bis(4,5-dihydrooxazol-2-yl)pyridine In methanol at 20℃; for 18h; Inert atmosphere; regioselective reaction;	50%

N-((3-bromo-5-methylphenyl)sulfonyl)-2-(naphthalen-2-yloxy)acetamide + 2-amino-3-trifluoromethylpyridine (183610-70-0) → N-((3-methyl-5-((3-(trifluoromethyl)pyridin-2-yl)amino)-phenyl)sulfonyl)-2-(naphthalen-2-yloxy)acetamide

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; Inert atmosphere;	50%

fluorobiprofen (5104-49-4) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 2-(2-fluoro-(1,1'-biphenyl)-4-yl)-N-(3-(trifluoromethyl)pyridin-2-yl)propanamide

Conditions	Yield
Stage #1: fluorobiprofen With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h; Stage #2: 2-amino-3-trifluoromethylpyridine In acetonitrile at 20℃; for 72h;	45%

phenylacetaldehyde (122-78-1) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 3-phenyl-8-(trifluoromethyl)imidazo[1,2-a]pyridine

Conditions	Yield
With sulfur In cyclohexane; dimethyl sulfoxide at 120℃; for 1h; Sealed tube;	41%

2-(6-chloro-carbazol-2-yl)-propionic acid (53716-49-7) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → 2-(6-chloro-9H-carbazol-2-yl)-N-(3-(trifluoromethyl)pyridin-2-yl)propanamide

Conditions	Yield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h; Stage #2: 2-amino-3-trifluoromethylpyridine In acetonitrile at 20℃; for 36h;	41%

2-chloropyrazin (14508-49-7) + 2-amino-3-trifluoromethylpyridine (183610-70-0) → C10H7F3N4

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 40h; Inert atmosphere;	29%

Upstream product

• 67-56-1 methanol 
• 143812-76-4 8-Trifluoromethyl-tetrazolo[1,5-a]pyridine 
• 65753-52-8 2-fluoro-3-trifluoromethylpyridine 
• 911112-72-6 (4-methoxy-benzyl)-(3-trifluoromethyl-pyridin-2-yl)-amine 
• 65753-47-1 2-chloro-3-trifluoromethyl-pyridine 

Downstream Products

• 1284244-27-4 4-{[6-bromo-3-chloro-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-(4,4-difluorocyclohexyl)-2-piperazinone 
• 1284244-29-6 4-{[3-chloro-6-cyclopropyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-(4-oxocyclohexyl)-2-piperazinone 
• 1284244-33-2 4-{[6-bromo-3-chloro-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-(4-oxocyclohexyl)-2-piperazinone 
• 1284243-02-2 4-{[3-chloro-6-(1H-pyrazol-4-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-phenyl-2-piperazinone 
• 1284245-44-8 4-{[3-chloro-6-propyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-cyclohexyl-2-piperazinone 
• 1284245-45-9 4-{[3-chloro-6-(2-methylpropyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-cyclohexyl-2-piperazinone 
• 1284245-47-1 4-{[6-butyl-3-chloro-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-cyclohexyl-2-piperazinone 
• 1284246-63-4 1-cyclohexyl-4-{[6-(3-furanyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-2-piperazinone 
• 1284246-66-7 4-{[3-chloro-6-(1-methylethyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-cyclohexyl-2-piperazinone 
• 1284246-69-0 4-{[3-chloro-6-(1-methylethyl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-(3-fluorophenyl)-2-piperazinone 
• 1284243-19-1 4-{[3-chloro-6-(1H-pyrazol-4-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-(3-fluorophenyl)-2-piperazinone 
• 1284243-24-8 4-{[3-chloro-6-(1H-pyrazol-4-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-(phenylmethyl)-2-piperazinone 
• 1284243-30-6 4-{[3-chloro-6-(1H-pyrazol-4-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-[2-(trifluoromethyl)phenyl]-2-piperazinone 
• 1284243-39-5 4-{[3-chloro-6-(1H-pyrazol-4-yl)-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbonyl}-1-(2-fluorophenyl)-2-piperazinone 

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