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CAS No.: | 1072-98-6 |
---|---|
Name: | 2-Amino-5-chloropyridine |
Article Data: | 39 |
Molecular Structure: | |
Formula: | C5H5ClN2 |
Molecular Weight: | 128.561 |
Synonyms: | AI3-52448;2-Pyridinamine, 5-chloro-;5-Chloro-2-pyridylamine; |
EINECS: | 214-020-4 |
Density: | 1.326 g/cm3 |
Melting Point: | 134-138 °C |
Boiling Point: | 257.8 °C at 760 mmHg |
Flash Point: | 94.7 °C |
Solubility: | 1 g/L (20 °C) in water |
Appearance: | beige to beige-brown crystalline powder |
Hazard Symbols: | Xn,Xi |
Risk Codes: | 22-36/37/38 |
Safety: | 22-24/25-37/39-26-36 |
PSA: | 38.91000 |
LogP: | 1.89840 |
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 |
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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