5-Amino-2-fluoropyridine supplier

Name
5-Amino-2-fluoropyridine
EINECS 675-011-2
CAS No. 1827-27-6
Article Data15
CAS DataBase
Density 1.257 g/cm³
Solubility
Melting Point 86-87 °C
Formula C₅H₅FN₂
Boiling Point 264 °C at 760 mmHg
Molecular Weight 112.107
Flash Point 113.5 °C
Transport Information
Appearance light yellow cryst
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Pyridine,5-amino-2-fluoro- (7CI,8CI);3-Amino-6-fluoropyridine;6-Fluoropyridin-3-amine;6-Fluoropyridin-3-ylamine;2-fluoropyridin-5-amine;
PSA 38.91000
LogP 1.38410

Synthetic route

: 456-24-6
2-Fluoro-5-nitropyridine

: 1827-27-6
2-fluoro-5-aminopyridine

Conditions

Conditions	Yield
With hydrogen; sodium sulfate; palladium on activated charcoal In toluene	94%
With 5%-palladium/activated carbon; hydrogen; sodium sulfate In toluene for 15h;	75%
With hydrogen; nickel In ethyl acetate	70%

: 369-50-6
6-fluoronicotinamide

: 1827-27-6
2-fluoro-5-aminopyridine

Conditions

Conditions	Yield
With sodium hydroxide; bromine In tetrahydrofuran at 5 - 70℃; Hoffmann rearrangement;

: 4548-45-2
2-chloro-5-nitropyridine

: 1827-27-6
2-fluoro-5-aminopyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / KF / dimethylsulfoxide / 18 h / 70 °C 2: 70 percent / H2 / Raney Ni / ethyl acetate View Scheme
Multi-step reaction with 2 steps 1: potassium fluoride / acetonitrile 2: palladium-carbon / ethanol View Scheme

: 4548-45-2
2-chloro-5-nitropyridine

potassium-salt of/the/ 4-acetylamino-benzenesulfinic acid: potassium-salt of/the/ 4-acetylamino-benzenesulfinic acid

: 1827-27-6
2-fluoro-5-aminopyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / CsF / various solvent(s) / 18 h / 130 °C 2: 94 percent / H2, Na2SO4 / 5percent Pd/C / toluene View Scheme

: 1827-27-6
2-fluoro-5-aminopyridine

: 87-13-8
diethyl 2-ethoxymethylenemalonate

: 1093114-31-8
2-(6-fluoro-3-pyridyl)-aminomethylene-malonic acid diethyl ester

Conditions

Conditions	Yield
at 120℃; for 3h;	100%

: 24424-99-5
di-tert-butyl dicarbonate

: 1827-27-6
2-fluoro-5-aminopyridine

: 171178-41-9
(6-fluoro-pyridin-3-yl)-carbamic acid, tert-butyl ester

Conditions

Conditions	Yield
In tert-butyl alcohol at 40℃; for 4h;	96%
In hexane; tert-butyl alcohol at -15 - 40℃; for 22h;	96%
In tert-butyl alcohol at -18 - 40℃; for 22h;	96%

: 4-(2-((tert-butoxycarbonyl)amino)cyclopropyl)benzoic acid

: 1827-27-6
2-fluoro-5-aminopyridine

: C20H22FN3O3

Conditions

Conditions	Yield
With triethylamine; 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 18h;	96%

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: 1827-27-6
2-fluoro-5-aminopyridine

: (η6-p-cymene)RuCl2(2-fluoro-5-aminopyridine)

Conditions

Conditions	Yield
In diethyl ether for 10h; Reflux; Inert atmosphere;	95%
In methanol at 60℃; Inert atmosphere;	90%

: 1827-27-6
2-fluoro-5-aminopyridine

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 1143578-58-8
2,2,2-trichloroethyl (6-fluoropyridin-3-yl)carbamate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 1h;	92%
With pyridine In acetonitrile at 0 - 20℃; for 1h;	83%

: 1147550-11-5
ammonium thiocyanate

: 1827-27-6
2-fluoro-5-aminopyridine

: 1-(6-fluoropyridin-3-yl)thiourea

Conditions

Conditions	Yield
Stage #1: ammonium thiocyanate With benzoyl chloride In acetone for 0.25h; Reflux; Stage #2: 2-fluoro-5-aminopyridine In acetone at 40℃; for 1.5h; Stage #3: With sodium hydroxide at 60℃; for 2.5h;	91%

: 1827-27-6
2-fluoro-5-aminopyridine

: 5006-22-4
Cyclobutanecarbonyl chloride

: 1421785-53-6
N-(6-fluoropyridin-3-yl)cyclobutanecarboxamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	86%

: 38267-96-8
6-bromo-4-chloroquinozoline

: 1827-27-6
2-fluoro-5-aminopyridine

: 6-bromo-N-(6-fluoropyridin-3-yl)quinazolin-4-amine

Conditions

Conditions	Yield
In isopropyl alcohol at 90℃; for 4h;	85.2%

: 1827-27-6
2-fluoro-5-aminopyridine

: 940958-93-0
2-fluoro-5-hydrazinylpyridine

Conditions

Conditions	Yield
With hydrogenchloride; tin(ll) chloride; sodium nitrite	85%
Stage #1: 2-fluoro-5-aminopyridine With hydrogenchloride; sodium nitrite In water at -20 - 10℃; for 0.5h; Stage #2: With tin(ll) chloride In water at -20 - 10℃; for 1h; Stage #3: With potassium hydroxide In water	68%
Stage #1: 2-fluoro-5-aminopyridine With hydrogenchloride; sodium nitrite In water at 0℃; for 1.5h; Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In water at 0℃; for 1h;	40%
Stage #1: 2-fluoro-5-aminopyridine With hydrogenchloride; tin(ll) chloride; sodium nitrite In water at 0 - 5℃; for 4h; Stage #2: With potassium hydroxide In water pH=14;	39%
Stage #1: 2-fluoro-5-aminopyridine With hydrogenchloride; sodium nitrite In water at -20 - 20℃; for 0.5h; Stage #2: With tin(II) chloride dihdyrate In water at -20℃; for 1h;

: 57294-38-9
N-(tert-butoxycarbonyl)-4-aminobutanoic acid

: 1827-27-6
2-fluoro-5-aminopyridine

: 1323277-18-4
tert-butyl 4-(6-fluoropyridin-3-ylamino)-4-oxobutylcarbamate

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;	83%

: 329-15-7
4-trifluoromethyl-phenyl acetyl chloride

: 1827-27-6
2-fluoro-5-aminopyridine

: C13H8F4N2O

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 8h; Cooling with ice;	83%

: C15H11ClN2O

: 1827-27-6
2-fluoro-5-aminopyridine

: 1-benzyl-3,4-dihydro-3-(6-fluoropyridin-3-yl)-4-iminoquinazolin-2(1H)-one

Conditions

Conditions	Yield
Stage #1: 2-fluoro-5-aminopyridine With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: C15H11ClN2O In tetrahydrofuran at -78 - 20℃; for 2h;	82%

: 1355324-97-8
2-chloro-N-(2-(cyclohexylamino)-2-oxo-1-(o-tolyl)ethyl)-N-(3-fluorophenyl)acetamide

: 1827-27-6
2-fluoro-5-aminopyridine

: 1355326-85-0
N-cyclohexyl-2-(N-(3-fluorophenyl)-2-((6-fluoropyridin-3-yl)amino)acetamido)-2-(o-tolyl)acetamide

Conditions

Conditions	Yield
In ethanol for 16h; Reflux;	81%

: 1827-27-6
2-fluoro-5-aminopyridine

: 75176-19-1
N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester

: 1109790-64-8
(2S,4S)-benzyl 2-(6-fluoropyridin-3-ylcarbamoyl)-4-methoxypyrrolidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-fluoro-5-aminopyridine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; Stage #2: N-<(phenylmethoxy)carbonyl>-4(S)-methoxy-(S)-proline methyl ester In tetrahydrofuran at 20℃; for 14h;	80%

: (1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-D-alanine

: 1827-27-6
2-fluoro-5-aminopyridine

: (R)-2-((1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-N-(6-fluoropyridin-3-yl)propanamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h;	80%

: 1827-27-6
2-fluoro-5-aminopyridine

: 68347-91-1
6-phenylimidazo<2,1-b>thiazole-3-acetic acid

: 1388831-91-1
N-(6-fluoropyridin-3-yl)-2-(6-phenylimidazo[2,1-b]thiazol-3-yl)acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	77%

: 459-57-4
4-fluorobenzaldehyde

: 1827-27-6
2-fluoro-5-aminopyridine

: N-(4-fluorobenzyl)-2-fluoro-5-aminopyridine

Conditions

Conditions	Yield
Stage #1: 4-fluorobenzaldehyde; 2-fluoro-5-aminopyridine With acetic acid at 20℃; for 1h; Stage #2: With sodium cyanoborohydride at 10 - 15℃; for 0.5h;	75.6%

: 1827-27-6
2-fluoro-5-aminopyridine

: 68347-92-2
6-(4'-chlorophenyl)imidazo<2,1-b>thiazole-3-acetic acid

: 1388831-93-3
2-(6-(4-chlorophenyl)imidazo[2,1-b]thiazol-3-yl)-N-(6-fluoropyridin-3-yl)acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	74%

: 1827-27-6
2-fluoro-5-aminopyridine

: 864866-13-7
5-azido-2-fluoropyridine

Conditions

Conditions	Yield
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 0 - 20℃; for 5h;	72.1%
Stage #1: 2-fluoro-5-aminopyridine With hydrogenchloride; sodium nitrite In water at -15 - -10℃; for 0.166667h; Stage #2: With sodium azide In water at 0℃; for 0.166667h;	62%

: 4023-34-1
cyclopropanecarboxylic acid chloride

: 1827-27-6
2-fluoro-5-aminopyridine

: 112959-64-5
N-(2-fluoro-5-pyridyl)cyclopropane carboxamide

Conditions

Conditions	Yield
With pyridine In dichloromethane	72%

: 3140-73-6
2-chloro-4,6-dimethoxy-1 ,3,5-triazine

: 1827-27-6
2-fluoro-5-aminopyridine

: N-(6-fluoropyridin-3-yl)-4,6-dimethoxy-1,3,5-triazin-2-amine

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 70℃; for 4h;	72%

: 3303-84-2
3-(tert-butyloxycarbonylamino)propionic acid

: 1827-27-6
2-fluoro-5-aminopyridine

: 1037411-75-8
tert-Butyl 3-(6-fluoropyridin-3-ylamino)-3-oxopropylcarbamate

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h;	70.6%

: 1001353-78-1
(S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)-2-methylpyrrolidine-2-carboxylic acid

: 1827-27-6
2-fluoro-5-aminopyridine

: BMS-754807

Conditions

Conditions	Yield
Stage #1: (S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)-2-methylpyrrolidine-2-carboxylic acid With thionyl chloride In N,N-dimethyl-formamide at 5 - 20℃; for 1h; Stage #2: 2-fluoro-5-aminopyridine In N,N-dimethyl-d6-formamide for 24h;	70%
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 45℃; for 18h;	18%

: 333-20-0
potassium thioacyanate

: 1827-27-6
2-fluoro-5-aminopyridine

: 865663-86-1
5-fluorothiazolo[5,4-b]pyridin-2-amine

Conditions

Conditions	Yield
With bromine; acetic acid at 0 - 20℃; for 16.5h;	69.2%
With bromine; acetic acid at 0℃; for 0.5h;	69.2%
With bromine; acetic acid at 20℃; for 4h;	61.8%

: 4-bromo-6-acetamido-1H-indole-2-carboxylic acid ethyl ester

: 1827-27-6
2-fluoro-5-aminopyridine

: 4-((6-fluoropyridin-3-yl)amino)-6-acetylamino-1H-indole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos In 1,4-dioxane at 90℃; for 1h; Microwave irradiation; Inert atmosphere;	68.9%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos In 1,4-dioxane at 100℃; Inert atmosphere; Microwave irradiation;	68.9%

: 1827-27-6
2-fluoro-5-aminopyridine

: 60169-72-4
1-benzyl-pyrrolidine-2-carboxylic acid

: 1-benzyl-N-(6-fluoropyridin-3-yl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 2-fluoro-5-aminopyridine With trimethylaluminum In toluene at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-benzyl-pyrrolidine-2-carboxylic acid In toluene at 80℃; for 18h; Inert atmosphere;	68.1%

: 1001353-08-7
(S)-methyl 1-(4-(5-cyano-1H-pyrazol-3-ylamino)pyrrolo[1,2-f][1,2,4]triazin-2-yl)-2-methylpyrrolidine-2-carboxylate

: 1827-27-6
2-fluoro-5-aminopyridine

: (S)-1-(4-(5-cyano-1H-pyrazol-3-ylamino)pyrrolo[1,2-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 21h;	68%

: 773-64-8
2-mesitylenesulphonyl chloride

: 1827-27-6
2-fluoro-5-aminopyridine

: N-(6-fluoro-pyridin-3-yl)-2,4,6-trimethyl-benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	68%

5-Amino-2-fluoropyridine Specification

The 5-Amino-2-fluoropyridine is an organic compound with the formula C₅H₅FN₂. The IUPAC name of this chemical is 6-fluoropyridin-3-amine. With the CAS registry number 1827-27-6, it is also named as 2-Fluoro-5-aminopyridine. The product's categories are Fluorin-contained Pyridine Series; Pyridine; Pharmacetical; Pyridine Series; Pyridines; Boronic Acid.

Physical properties about 5-Amino-2-fluoropyridine are: (1)ACD/LogP: 0.26; (2)#H bond acceptors: 2; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 1; (5)Polar Surface Area: 16.13 Å²; (6)Index of Refraction: 1.554; (7)Molar Refractivity: 28.57 cm³; (8)Molar Volume: 89.1 cm³; (9)Polarizability: 11.32×10^-24cm³; (10)Surface Tension: 47.7 dyne/cm; (11)Density: 1.257 g/cm³; (12)Flash Point: 113.5 °C; (13)Enthalpy of Vaporization: 50.19 kJ/mol; (14)Boiling Point: 264 °C at 760 mmHg; (15)Vapour Pressure: 0.00994 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-fluoro-5-nitro-pyridine. This reaction will need reagent H₂, Na₂SO₄, catalyst 5percent Pd/C and solvent toluene. The yield is about 94%.

Uses of 5-Amino-2-fluoropyridine: it can be used to produce (6-fluoro-pyridin-3-yl)-carbamic acid tert-butyl ester by heating. It will need solvent 1,2-dichloro-ethane with reaction time of 16 hours. The yield is about 88%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ncc1N)F
(2)InChI: InChI=1/C5H5FN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2
(3)InChIKey: YTHMOBMZVVFNBE-UHFFFAOYAO
(4)Std. InChI: InChI=1S/C5H5FN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2
(5)Std. InChIKey: YTHMOBMZVVFNBE-UHFFFAOYSA-N

Product Name

5-Amino-2-fluoropyridine

Synthetic route

5-Amino-2-fluoropyridine Specification

Related Products

Hot Products