5-Amino-2-chloropyridine supplier

Name
5-Amino-2-chloropyridine
EINECS 226-322-3
CAS No. 5350-93-6
Article Data64
CAS DataBase
Density 1.326 g/cm³
Solubility
Melting Point 80-84 °C
Formula C₅H₅ClN₂
Boiling Point 292.6 °C at 760 mmHg
Molecular Weight 128.561
Flash Point 130.7 °C
Transport Information
Appearance light yellow to brown crystalline powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Pyridine,5-amino-2-chloro- (6CI,8CI);2-Chloro-5-aminopyridine;6-Chloro-3-aminopyridine;6-Chloropyridin-3-ylamine;NSC 81;6-Chloro-pyridin-3-ylamine;3-Amino-6-chloropyridine;
PSA 38.91000
LogP 1.89840

Synthetic route

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

: 5350-93-6
6-Chloro-pyridin-3-ylamine

Conditions

Conditions	Yield
With titanium for 0.25h;	99%
With hydrogen In ethyl acetate at 50℃; under 7600.51 Torr; for 6h; Autoclave; chemoselective reaction;	99%
With borane-ammonia complex In methanol; water at 20℃; for 0.0833333h;	99%

: 69045-79-0
2-choro-5-iodopyridine

: 5350-93-6
6-Chloro-pyridin-3-ylamine

Conditions

Conditions	Yield
With copper(l) iodide; ammonia; potassium carbonate; L-proline In water; dimethyl sulfoxide at 25℃; for 12h; Inert atmosphere;	90%

: 13198-73-7
2-Chloro-5-nitropyridine-1-oxide

: 5350-93-6
6-Chloro-pyridin-3-ylamine

Conditions

Conditions	Yield
With molybdenum(V) chloride; zinc In tetrahydrofuran; water for 1.5h; Heating;	49%

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

: 353-43-5
boron dimethyl-trifluoro sulphide

A: 5350-93-6
6-Chloro-pyridin-3-ylamine

B: 98198-73-3
6-chloro-2-(methylthio)pyridin-3-amine

Conditions

Conditions	Yield
In dichloromethane at 60℃; for 3h; Temperature; Sealed tube;	A 30% B 35%

...Expand

: 6271-78-9
6-chloro-3-pyridinecarboxamide

: 5350-93-6
6-Chloro-pyridin-3-ylamine

Conditions

Conditions	Yield
With potassium hydroxide; bromine at 70℃; Versetzen der abgekuehlten Reaktionsmischung mit Essigsaeure und darauf mit Alkalilauge;
With sodium hydroxide; bromine In tetrahydrofuran at 5 - 70℃; Hoffmann rearrangement;

: 31301-51-6
2-chloro-5-fluoropyridine

A: 5350-93-6
6-Chloro-pyridin-3-ylamine

B: 21717-96-4
2-amino-5-fluoropyridine

Conditions

Conditions	Yield
With ammonium hydroxide at 180℃; for 52h; Yield given. Yields of byproduct given;
With ammonium hydroxide at 180℃; for 52h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 6271-78-9
6-chloro-3-pyridinecarboxamide

: 7726-95-6
bromine

KOH-solution: KOH-solution

: 5350-93-6
6-Chloro-pyridin-3-ylamine

...Expand

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

: 7664-93-9
sulfuric acid

copper-cathode: copper-cathode

A: 462-08-8
pyridin-3-ylamine

B: 5350-93-6
6-Chloro-pyridin-3-ylamine

Conditions

Conditions	Yield
at 75℃; elektrochemische Reduktion;

...Expand

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

: 64-17-5
ethanol

palladium: palladium

A: 462-08-8
pyridin-3-ylamine

B: 5350-93-6
6-Chloro-pyridin-3-ylamine

C: 6,6'-dichloro-[3,3']azoxypyridine

Conditions

Conditions	Yield
Hydrogenation;

...Expand

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

A: 462-08-8
pyridin-3-ylamine

B: 5350-93-6
6-Chloro-pyridin-3-ylamine

C: 1184916-49-1
C5H11ClN2

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran at 37℃; under 2250.23 - 3000.3 Torr; for 18h;	A 75 %Chromat. B 2.8 %Chromat. C 10.2 %Chromat.

...Expand

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

A: 462-08-8
pyridin-3-ylamine

B: 5350-93-6
6-Chloro-pyridin-3-ylamine

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrazine hydrate In methanol at 80℃; for 0.0833333h; Overall yield = 87 %;

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 1050501-88-6
2-bromo-6-chloro-pyridin-3-amine

Conditions

Conditions	Yield
Stage #1: 6-Chloro-pyridin-3-ylamine With bromine; sodium acetate; acetic acid at 20℃; for 1h; Stage #2: With water; sodium carbonate; sodium chloride In ethyl acetate	99.8%
With bromine; sodium acetate; acetic acid at 20℃; for 1h;	99.8%
With bromine; sodium acetate; acetic acid at 20℃; for 1h;	99.8%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

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

: 171178-45-3
tert-butyl (6-chloropyridin-3-yl)carbamate

Conditions

Conditions	Yield
In tert-butyl alcohol at 50℃; Inert atmosphere;	99.3%
In 1,4-dioxane for 45h; Reflux; Inert atmosphere;	96%
In 1,4-dioxane for 18h; Heating;	94%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 49609-84-9
2-Chloronicotinoyl chloride

: 152038-51-2
2-Chloro-N-(2'-chloro-5'-pyridinyl)pyridine-3-carboxamide

Conditions

Conditions	Yield
In chloroform; ethyl acetate Ambient temperature;	99%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 110-13-4
2,5-hexanedione

: 478548-84-4
1-(2-chloropyridine)-5-yl-2,5-dimethyl-1H-pyrrole

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In water; toluene at 133℃; for 5h; Dean-Stark;	97%
With toluene-4-sulfonic acid In toluene for 2h; Heating;	91%
With toluene-4-sulfonic acid In toluene at 100℃; for 5h; Dean-Stark;	82%
With toluene-4-sulfonic acid In toluene at 100℃; for 5h; Dean-Stark;	77%
With toluene-4-sulfonic acid In toluene at 100℃; for 3h; Dean-Stark;

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 33025-60-4
1-(3-hydroxy-1H-indol-1-yl)ethanone

: 869958-43-0
C15H12ClN3O

Conditions

Conditions	Yield
toluene-4-sulfonic acid In toluene at 130℃; for 10h;	97%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 58551-83-0
2,4,6-trifluorobenzaldehyde

: 1145660-04-3
(E)-N-(6-chloropyridin-3-yl)-1-(2,4,6-trifluorophenyl)methanimine

Conditions

Conditions	Yield
In toluene at 110℃; for 96h; Dean-Stark;	97%
In toluene for 16h; Heating / reflux;

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 123-11-5
4-methoxy-benzaldehyde

: (6-chloropyridin-3-yl)-N-(4-methoxybenzyl)amine

Conditions

Conditions	Yield
With tin(II) chloride dihdyrate In methanol at 70℃; for 6h; chemoselective reaction;	97%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 98-80-6
phenylboronic acid

: 126370-67-0
6-phenylpyridin-3-amine

Conditions

Conditions	Yield
Stage #1: 6-Chloro-pyridin-3-ylamine; phenylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 25℃; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;	96%
With tetrabutylammomium bromide; potassium carbonate In water at 80℃; for 8h; Suzuki coupling;	92%
With tetrabutylammomium bromide; potassium carbonate In water at 80℃; for 10h; Suzuki coupling;	87%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

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

: 1044148-99-3
3-[di(tert-butoxycarbonyl)amino]-6-chloropyridine

Conditions

Conditions	Yield
In n-heptane at 20 - 115℃;	96%
With sodium hexamethyldisilazane In tetrahydrofuran

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 343616-21-7
1-chlorosulfonyl-piperidine-2S-carboxylic acid 4-phenyl-butyl ester

: (S)-1-(6-Chloro-pyridin-3-ylsulfamoyl)-piperidine-2-carboxylic acid 4-phenyl-butyl ester

Conditions

Conditions	Yield
With 3,5-Lutidine In dichloromethane at 25℃;	96%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 59719-78-7
4-tert-butyl-3-nitrobenzoic acid

: 4-tert-butyl-N-(6-chloropyridin-3-yl)-3-nitrobenzamide

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;	96%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 15568-85-1
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

: 1354290-11-1
5-((6-chloropyridine-3-yl)-aminomethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions

Conditions	Yield
In isopropyl alcohol for 2h; Reflux;	95.8%
In isopropyl alcohol for 2h; Reflux;	95.8%
In isopropyl alcohol for 2h; Reflux;	91%
In isopropyl alcohol for 2h; Reflux;	91%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 163105-89-3
2-methoxy-pyridine-5-boronic acid

: 835876-08-9
6'-methoxy-[2,3']bipyridinyl-5-ylamine

Conditions

Conditions	Yield
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;	95%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 145934-89-0
2-chloro-5-hydrazinylpyridine

Conditions

Conditions	Yield
Stage #1: 6-Chloro-pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In water at 0℃; for 1h;	95%
Multi-step reaction with 6 steps 1: conc. aq. HCl / toluene; ethanol / 1 h / 25 °C 2: H2 / 5percent Pt/C / toluene; ethanol / 2 h / 2585.81 Torr 3: conc. aq. HCl / 0.33 h / 100 °C 4: 35 percent / aq. sodium nitrite / 1 h / 0 °C 5: 71 percent / acetic anhydride / 0.5 h / 100 °C 6: conc. aq. HCl / 25 °C View Scheme

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 463-71-8
thiophosgene

: 2-chloro-5-pyridinyl isothiocyanate

Conditions

Conditions	Yield
In dichloromethane; water at 20℃; for 18h;	95%
In chloroform
In chloroform

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 100-52-7
benzaldehyde

: N-benzyl-(6-chloropyridin-3-yl)amine

Conditions

Conditions	Yield
With tin(II) chloride dihdyrate In methanol at 70℃; for 6h; chemoselective reaction;	95%
With copper(I) iodide; phenylsilane In ethanol at 80℃; for 4h;	95%
With 2-amino-4(3H)-quinazolinone; phenylsilane; acetic acid In neat (no solvent) at 20℃; for 5h; Green chemistry;	83%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 64-18-6
formic acid

: 206006-29-3
N-(6-chloro-pyridin-3-yl)-formamide

Conditions

Conditions	Yield
for 2h; Reflux;	95%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

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

: tert-butyl (2-(4-((6-chloropyridin-3-yl)carbamoyl)phenyl)cyclopropyl)carbamate

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;	95%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 2-chloropyridine-5-yldiazonium tetrafluoroborate

Conditions

Conditions	Yield
With tetrafluoroboric acid; isopentyl nitrite In ethanol at -5 - 0℃; for 0.5h;	94%
With tetrafluoroboric acid; isopentyl nitrite In ethanol; water at -5℃; for 0.5h;	83%
With nitrous acid isobutyl ester; boron trifluoride diethyl etherate In 1,2-dimethoxyethane; dichloromethane at -10 - 20℃; for 0.75h;
With tetrafluoroboric acid; tert.-butylnitrite In ethanol; water at -5℃; for 0.333333h;

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 2-chloro-5-(N-methylacetamido)pyridine

: 75-36-5
acetyl chloride

: 29958-18-7
5-acetamido-2-chloropyridine

Conditions

Conditions	Yield
With triethylamine In dichloromethane	93%

...Expand

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 5720-07-0
4-methoxyphenylboronic acid

: 52057-98-4
6-(4-methoxyphenyl)-pyridin-3-ylamine

Conditions

Conditions	Yield
With potassium phosphate monohydrate; Ethyl 4-bromobenzoate; C52H49PRu; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 5h; Suzuki-Miyaura Coupling; Inert atmosphere;	93%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 145013-05-4
tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate

: 1448633-34-8
N,N’-di(tert-butoxycarbonyl)-N’’-(6-chloropyridin-3-yl)guanidine

Conditions

Conditions	Yield
With triethylamine; mercury dichloride In dichloromethane at 5 - 20℃; for 16h;	92%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxyIic acid

: C20H14ClF3N2O2

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 12h;	92%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 540-72-7
sodium thiocyanide

: 31784-71-1
5-chlorothiazolo[5,4-b]pyridin-2-amine

Conditions

Conditions	Yield
With bromine In acetic acid at 0℃; for 0.666667h;	91%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: C11H8ClN3O4S

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃;	91%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 866358-17-0
5-chlorosulfonyl-2-methyl-benzoic acid methyl ester

: 946492-89-3
5-(6-chloro-pyridin-3-ylsulfamoyl)-2-methyl-benzoic acid methyl ester

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 60℃; for 30h;	89%

: 5350-93-6
6-Chloro-pyridin-3-ylamine

: 780-69-8
triethoxyphenylsilane

: 126370-67-0
6-phenylpyridin-3-amine

Conditions

Conditions	Yield
With Pd((CH3)2C6H3NC(CH3)CHC(CH3)NC6H3(CH3)2)(CH3)(P(CH2CH3)3); tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 12h; Hiyama coupling; Inert atmosphere;	89%

5-Amino-2-chloropyridine Standards and Recommendations

Purity: 98%

5-Amino-2-chloropyridine Specification

The IUPAC name of 5-Amino-2-chloropyridine is 6-chloropyridin-3-amine. With the CAS registry number 5350-93-6, it is also named as 3-Pyridinamine, 6-chloro-. The product's categories are Pyridine; Amines; Blocks; Pyridines; Pyridine Derivative; Pyridine Series; Chloropyridines; Halopyridines; Boronic Acid; Heterocyclic Building Blocks. It is light yellow to brown crystalline powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.88; (4)ACD/LogD (pH 7.4): 0.88; (5)ACD/BCF (pH 5.5): 2.73; (6)ACD/BCF (pH 7.4): 2.73; (7)ACD/KOC (pH 5.5): 71.41; (8)ACD/KOC (pH 7.4): 71.44; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.607; (13)Molar Refractivity: 33.47 cm³; (14)Molar Volume: 96.8 cm³; (15)Polarizability: 13.27×10^-24 cm³; (16)Surface Tension: 54.3 dyne/cm; (17)Enthalpy of Vaporization: 53.21 kJ/mol; (18)Vapour Pressure: 0.00182 mmHg at 25°C; (19)Exact Mass: 128.014126; (20)MonoIsotopic Mass: 128.014126; (21)Topological Polar Surface Area: 38.9; (22)Heavy Atom Count: 8; (23)Complexity: 76.8.

Preparation of 5-Amino-2-chloropyridine: It can be obtained by 2-chloro-5-nitro-pyridine. This reaction needs reagents SnCl₂(H₂O)₂ and HCl. The yield is 92%.

Uses of 5-Amino-2-chloropyridine: It is used in organic synthesis. For example: it can react with 2-chloro-nicotinoyl chloride to get 2-Chloro-N-(2'-chloro-5'-pyridinyl)pyridine-3-carboxamide. This reaction needs solvents CHCl₃ and ethyl acetate at ambient temperature. The yield is 99%.

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

People can use the following data to convert to the molecule structure.
1. SMILES:c1cc(ncc1N)Cl
2. InChI:InChI=1/C5H5ClN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2
3. InChIKey:QAJYCQZQLVENRZ-UHFFFAOYAI

Product Name

5-Amino-2-chloropyridine

Synthetic route

5-Amino-2-chloropyridine Standards and Recommendations

5-Amino-2-chloropyridine Specification

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