2-Amino-5-chloropyridine

Base Information

• Chemical Name: 2-Amino-5-chloropyridine
• CAS No.: 1072-98-6
• Molecular Formula: C5H5ClN2
• Molecular Weight: 128.561
• Hs Code.: 29333999
• European Community (EC) Number: 214-020-4
• NSC Number: 26283
• UNII: J8TAP6NFD4
• DSSTox Substance ID: DTXSID0073247
• Nikkaji Number: J31.385H
• Wikidata: Q72434846
• Mol file: 1072-98-6.mol

Synonyms:2-amino-5-chloropyridine;5-chloro-2-pyridinamine

Chemical Property of 2-Amino-5-chloropyridine

Chemical Property:

• Appearance/Colour: beige to beige-brown crystalline powder
• Vapor Pressure: 0.0142mmHg at 25°C
• Melting Point: 134-138 °C
• Refractive Index: 1.5110 (estimate)
• Boiling Point: 257.8 °C at 760 mmHg
• PKA: 4.67±0.13(Predicted)
• Flash Point: 94.7 °C
• PSA: 38.91000
• Density: 1.326 g/cm³
• LogP: 1.89840
• Storage Temp.: Store below +30°C.
• Solubility.: 1.0g/l
• Water Solubility.: 1 g/L (20 ºC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.0141259
• Heavy Atom Count: 8
• Complexity: 76.8

Purity/Quality:

99% ^*data from raw suppliers

5-Chloro-2-pyridinamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC(=NC=C1Cl)N
• Uses: 5-Chloro-2-pyridinamine is a useful synthetic intermediate. It can be used to synthesize zopiclone (Z700500) which is a cyclopyrrolone member of a family of non-benzodiazepine GABAA receptor agonists.

Technology Process of 2-Amino-5-chloropyridine

There total 35 articles about 2-Amino-5-chloropyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.4%

2-aminopyridine (504-29-0) → 5-chloro-2-pyridylamine (1072-98-6)

Guidance literature:

With N-chloro-N-fluoro-benzenesulfonamide; 1,3-dimethylimidazolium chloride; In dichloromethane; at 25 ℃; for 1.5h; Reagent/catalyst; Concentration; Solvent; Temperature;

Reference yield: 95.0%

2,2-dimethyl-3-(5-chloropyrid-2-yl)-4-4H-1,3-benzoxazine (74405-03-1) → 5-chloro-2-pyridylamine (1072-98-6)

Guidance literature:

With hydrogenchloride; for 8h; Heating;

Reference yield: 90.0%

N-(3-bromo-5-chloropyridin-2-yl)pyridin-1-ium-1-aminide (171774-38-2) → 5-chloro-2-pyridylamine (1072-98-6) + 3-chloro-dipyrido[1,2-b;3',2'-d]pyrazole

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In acetonitrile; benzene; at 80 ℃; for 24h;

DOI:10.1021/jo801549u

upstream raw materials:

2-aminopyridine

5-chloro-2-nitropyridine

2,2-dimethyl-3-(5-chloropyrid-2-yl)-4-4H-1,3-benzoxazine

pyridinium N-(5'-chloropyridin-2'-yl)aminide

Downstream raw materials:

2-amino-5-chloro-3-nitropyridine

1-(5-Chloro-pyridin-2-yl)-3-[(1R,2R)-2-(6-fluoro-2-methoxy-3-propionyl-phenyl)-cyclopropyl]-urea

2-chloro-trans-cinnamic acid-(5-chloro-[2]pyridylamide)

2,5 dichloropyridine

Refernces

• 1、 Gan, Zongjie,Hu, Bin,Song, Qiao,Xu, Yungen. "Convenient chlorination of some special aromatic compounds using N-chlorosuccinimide". . p. 1074 - 1078. Retrieved 2012.
• 2、 Nu?ez, Araceli,García de Viedma, Aránzazu,Martínez-Barrasa, Valentín,Burgos, Carolina,Alvarez-Builla, Julio. "N-azinylpyridinium N-aminides: An approach to pyrazolopyridines via an intramolecular radical pathway". . p. 1093 - 1096. Retrieved 2002.
• 3、 -. "One-step high-efficient high-selective synthesis of 2 - amino -5 - chloro pyridine method (by machine translation)". Paragraph 0023; 0024; 0025; 0026; 0027; 0028. . Retrieved 2019/01/23.