Conditions | Yield |
---|---|
With N-chloro-N-fluoro-benzenesulfonamide; 1,3-dimethylimidazolium chloride In dichloromethane at 25℃; for 1.5h; Reagent/catalyst; Concentration; Solvent; Temperature; | 99% |
With bromine; chlorine In acetonitrile for 2h; Solvent; UV-irradiation; | 99.4% |
With N-ethylpyridinium chloride aluminum trichloride; chlorine In acetonitrile for 0.833333h; Solvent; Reagent/catalyst; Microwave irradiation; | 99.4% |
2,2-dimethyl-3-(5-chloropyrid-2-yl)-4-4H-1,3-benzoxazine
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With hydrogenchloride for 8h; Heating; | 95% |
N-(3-bromo-5-chloropyridin-2-yl)pyridin-1-ium-1-aminide
A
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In acetonitrile; benzene at 80℃; for 24h; | A 90% B 2% |
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; potassium carbonate In acetonitrile; benzene at 80℃; for 24h; Product distribution; Further Variations:; Reagents; | A 5% B 56% |
pent-4-ynenitrile
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With iron(III) chloride; chlorine; sodium hydroxide In chloroform; water at 40 - 45℃; for 5h; Solvent; Inert atmosphere; | 89.1% |
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With triethylammonium formate; platinum on activated charcoal In acetonitrile for 4h; Heating; | 87% |
Conditions | Yield |
---|---|
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; chemoselective reaction; | 84% |
5-chloro-2-nitropyridine
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With sulfuric acid; hydrogen In ethanol at 25℃; Electrochemical reaction; | 82% |
With boron dimethyl-trifluoro sulphide In dichloromethane at 60℃; for 0.5h; Sealed tube; | 72% |
With hydrogenchloride; sodium hydrogensulfide | |
With hydrogenchloride; tin(ll) chloride | |
With ammonium hydroxide; iron(II) sulfate |
pyridinium N-(5'-chloropyridin-2'-yl)aminide
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With zinc In acetic acid for 29h; Ambient temperature; | 79% |
A
5-chloro-2-pyridylamine
B
5-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine
Conditions | Yield |
---|---|
With polyphosphoric acid at 160 - 180℃; for 0.0833333h; Fischer Indole Synthesis; | A 72% B 6% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hypochlorite at 10 - 25℃; for 6h; Overall yield = 5.82 g; | A 71.6% B n/a |
A
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With polyphosphoric acid for 14h; Fischer Indole Synthesis; Inert atmosphere; Heating; | A 30% B 49% |
A
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With polyphosphoric acid at 160 - 180℃; for 0.0833333h; Fischer Indole Synthesis; | A 40% B 28% |
A
5-chloro-2-pyridylamine
B
3-chloro-6-methyl-6,7,8,9-tetrahydro-5H-pyrido-[3',4':4,5]pyrrolo[2,3-b]pyridine
Conditions | Yield |
---|---|
With polyphosphoric acid for 14h; Fischer Indole Synthesis; Inert atmosphere; Heating; | A 29% B 36% |
A
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With polyphosphoric acid at 160 - 180℃; for 0.0833333h; Fischer Indole Synthesis; | A 36% B 25% |
2-aminopyridine
A
5-chloro-2-pyridylamine
B
3,5-dichloropyridin-2-amine
Conditions | Yield |
---|---|
With chloroform; chlorine | |
With chlorine; acetic acid | |
With chloroform; chlorine; acetic acid |
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With copper(l) chloride |
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 68 percent / CHCl3 / 4 h / Heating 2: 95 percent / conc. HCl / 8 h / Heating View Scheme |
3-hydroxy-2-nitropyridine
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: acetic acid anhydride; nitric acid 2: phosphorus (V)-chloride / 130 °C 3: methanol; N2H4 4: silver acetate; water 5: FeSO4; aqueous NH3 View Scheme | |
Multi-step reaction with 5 steps 1: acetic acid; acetic acid anhydride; nitric acid 2: phosphorus (V)-chloride / 130 °C 3: methanol; N2H4 4: silver acetate; water 5: FeSO4; aqueous NH3 View Scheme |
(3-chloro-6-nitro-[2]pyridyl)-hydrazine
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: silver acetate; water 2: FeSO4; aqueous NH3 View Scheme |
3-hydroxy-2,6-dinitropyridine
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: phosphorus (V)-chloride / 130 °C 2: methanol; N2H4 3: silver acetate; water 4: FeSO4; aqueous NH3 View Scheme |
3-chloro-2,6-dinitro-pyridine
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methanol; N2H4 2: silver acetate; water 3: FeSO4; aqueous NH3 View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride; chlorine In water; Petroleum ether |
Conditions | Yield |
---|---|
With ammonium acetate |
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water / 0.92 h / 140 °C / Microwave irradiation; Inert atmosphere; Sealed tube 2: ammonium acetate View Scheme |
5-chloro-2-pyridylamine
pivaloyl chloride
N-(5-Chloro-pyridin-2-yl)-2,2-dimethylpropanamide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 1.08333h; | 99% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran; toluene | 100% |
With potassium hexamethylsilazane In tetrahydrofuran; toluene | 100% |
With potassium hexamethylsilazane In tetrahydrofuran; toluene | 100% |
With potassium hexamethylsilazane In tetrahydrofuran; toluene | 99% |
With potassium hexamethylsilazane In tetrahydrofuran; toluene | 99% |
5-chloro-2-pyridylamine
2-(2-nitrophenyl)acetic acid
N-(5-chloropyridin-2-yl)-2-(2-nitrophenyl)acetamide
Conditions | Yield |
---|---|
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 100% |
5-chloro-2-pyridylamine
5-Chloroisatoic anhydride
2-amino-5-chloro-N-(5-chloro-pyridin-2-yl)-benzamide
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-pyridylamine With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 0.5h; Stage #2: 5-Chloroisatoic anhydride In tetrahydrofuran; toluene at -78 - 20℃; | 100% |
Stage #1: 5-chloro-2-pyridylamine With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; for 0.5h; Stage #2: 5-Chloroisatoic anhydride In tetrahydrofuran; toluene at -78 - 20℃; | 99% |
Stage #1: 5-chloro-2-pyridylamine With dmap; potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; Inert atmosphere; Stage #2: 5-Chloroisatoic anhydride In tetrahydrofuran; toluene at -78 - 20℃; for 10h; Inert atmosphere; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20 - 70℃; for 16.5h; | 100% |
5-chloro-2-pyridylamine
2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)phenyl]-4H-pyrido[3,4-d][1,3]oxazin-4-one
3-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-4-carboxamide
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-pyridylamine; allylmagnesium bromide In tetrahydrofuran; diethyl ether at 0℃; for 0.0833333h; Stage #2: 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)phenyl]-4H-pyrido[3,4-d][1,3]oxazin-4-one In tetrahydrofuran; diethyl ether at 0 - 20℃; | 99% |
5-chloro-2-pyridylamine
2,3-pyrazinedicarboxylic anhydride
3-((5-chloropyridin-2-yl)carbamoyl)pyrazine-2-carboxylic acid
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; | 99% |
In tetrahydrofuran at 20℃; for 1h; | 99% |
In dichloromethane at 5 - 20℃; for 3.5h; Product distribution / selectivity; | |
Stage #1: 5-chloro-2-pyridylamine; 2,3-pyrazinedicarboxylic anhydride In toluene at 20 - 52℃; for 2.5h; Stage #2: With hydrogenchloride In water at 10 - 15℃; for 1h; |
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
In chloroform at 20℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h; | 99% |
5-chloro-2-pyridylamine
phenyl chloroformate
phenyl 5-chloropyridin-2-ylcarbamate
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 2h; Cooling with ice; | 98% |
With pyridine at 20℃; |
5-chloro-2-pyridylamine
N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide
N-{2,2-dichloro-1-[(5-chloro-2-pyridinyl)amino]-2-phenylethyl}-4-chlorobenzenesulfonamide
Conditions | Yield |
---|---|
In 1,4-dioxane at 20℃; for 4h; | 98% |
Conditions | Yield |
---|---|
With praseodymium(III) chloride In ethanol at 60℃; for 1h; Temperature; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 98% |
5-chloro-2-pyridylamine
2-methoxy-pyridine-5-boronic acid
Conditions | Yield |
---|---|
With potassium acetate; PdCl2[P(tBu)2(p-Me2NC6H4)]2 In water; butan-1-ol at 100℃; Suzuki-Miyaura cross-coupling; | 97% |
5-chloro-2-pyridylamine
2-nitro-3-methoxybenzoyl chloride
N-(5-chloro-2-pyridinyl)-2-nitro-3-methoxyphenylcarboxamide
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; | 97% |
5-chloro-2-pyridylamine
2-bromo-1-[3-nitro-4-(trifluoromethyl)phenyl]ethanone
6-chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
In acetonitrile at 100℃; for 18h; | 97% |
5-chloro-2-pyridylamine
N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide
N-(6-chloro-2-phenylimidazo[1,2-a]pyridine-3-yl)-4-chlorobenzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-pyridylamine; N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide In 1,4-dioxane at 20℃; for 4h; Stage #2: With sodium hydroxide at 20℃; for 5h; | 97% |
5-chloro-2-pyridylamine
acetoacetic acid methyl ester
7-chloro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
Conditions | Yield |
---|---|
With bismuth(III) chloride at 100℃; for 3h; Green chemistry; | 97% |
5-chloro-2-pyridylamine
alpha-(3-methylphenoxy)acetophenone
Conditions | Yield |
---|---|
With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h; | 97% |
5-chloro-2-pyridylamine
allyl oxalyl chloride
Conditions | Yield |
---|---|
In acetonitrile at 30 - 50℃; | 96.5% |
5-chloro-2-pyridylamine
5-methoxy-2-nitro-benzoic acid
5-methoxy-2-nitro-N-(5-chloro-pyridine-2-yl)benzamide
Conditions | Yield |
---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 1h; Solvent; Temperature; | 96.2% |
With pyridine; trichlorophosphate In acetonitrile at 0 - 30℃; for 1h; Inert atmosphere; | 94% |
With pyridine; trichlorophosphate In acetonitrile at 19 - 28℃; for 1h; | 88.2% |
5-chloro-2-pyridylamine
4-chlorobenzaldehyde
phosphonic acid diethyl ester
diethyl
Conditions | Yield |
---|---|
at 80 - 100℃; | 96% |
5-chloro-2-pyridylamine
p-toluenesulfonyl chloride
N-[5-Chloro-1H-pyridin-(2Z)-ylidene]-4-methyl-benzenesulfonamide
Conditions | Yield |
---|---|
With pyridine at 80 - 90℃; | 96% |
5-chloro-2-pyridylamine
methyl 2-(4-bromophenyl)-2-diazoacetate
methyl 2-(4-bromophenyl)-2-((5-chloropyridin-2-yl)amino)acetate
Conditions | Yield |
---|---|
at 102℃; for 12h; Inert atmosphere; | 96% |
5-chloro-2-pyridylamine
tert-butylisonitrile
2-chloro-3-carbaldehydepyridine
Conditions | Yield |
---|---|
With iodine In ethanol at 70℃; for 0.5h; Solvent; Temperature; | 96% |
5-chloro-2-pyridylamine
6-chloro-2-phenylimidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In acetonitrile at 120℃; for 24h; | 96% |
5-chloro-2-pyridylamine
Conditions | Yield |
---|---|
With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h; | 96% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 2h; Cooling; | 96% |
5-chloro-2-pyridylamine
1-(hydroxymethyl)-1,2,4-triazole
Conditions | Yield |
---|---|
In ethanol for 3h; Heating; | 95.87% |
The IUPAC name of 2-Amino-5-Chloropyridine is 5-chloropyridin-2-amine. With the CAS registry number 1072-98-6, it is also named as 2-Pyridinamine, 5-chloro-. The product's categories are Nitrogen Cyclic Compounds; Amines; Bromides; Pyridines; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines Derivates; Chloropyridines; Halopyridines; Heterocyclic Building Blocks. It is beige to beige-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: 1.69; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.62; (4)ACD/LogD (pH 7.4): 1.68; (5)ACD/BCF (pH 5.5): 9.76; (6)ACD/BCF (pH 7.4): 11.2; (7)ACD/KOC (pH 5.5): 170.92; (8)ACD/KOC (pH 7.4): 196.14; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (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: 49.54 kJ/mol; (18)Vapour Pressure: 0.0142 mmHg at 25°C; (19)Tautomer Count: 2; (20)Exact Mass: 128.014126; (21)MonoIsotopic Mass: 128.014126; (22)Topological Polar Surface Area: 38.9; (23)Heavy Atom Count: 8; (24)Complexity: 76.8.
Preparation of 2-Amino-5-Chloropyridine: It can be obtained by 2,2-dimethyl-3-(5-chloropyrid-2-yl)-4-4H-1,3-benzoxazine. This reaction needs reagent conc. HCl by heating. The reaction time is 8 hours. The yield is 95%.
Uses of 2-Amino-5-Chloropyridine: It is used to produce herbicide and drug Zopiclone. It also can be used in organic synthesis. For example: it can react with hexane-2,5-dione to get N-(5-chloro-2-pyridyl)-2,5-dimethylpyrrole. This reaction must react at temperature of 100 °C for 3 hours. The yield is 32%.
When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust and avoid contact with skin and eyes. 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(ncc1Cl)N
2. InChI:InChI=1/C5H5ClN2/c6-4-1-2-5(7)8-3-4/h1-3H,(H2,7,8)
3. InChIKey:MAXBVGJEFDMHNV-UHFFFAOYAS
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