2-Amino-4-chloro-3-nitropyridine

Base Information

• Chemical Name: 2-Amino-4-chloro-3-nitropyridine
• CAS No.: 6980-08-1
• Molecular Formula: C5H4ClN3O2
• Molecular Weight: 173.559
• Hs Code.: 2933399090
• European Community (EC) Number: 807-518-3
• DSSTox Substance ID: DTXSID60990059
• Nikkaji Number: J3.124.216I
• Wikidata: Q72434613
• Mol file: 6980-08-1.mol

Synonyms:2-Amino-4-chloro-3-nitropyridine;6980-08-1;4-chloro-3-nitropyridin-2-amine;2-Amino-3-nitro-4-chloropyridine;4-Chloro-3-nitro-pyridin-2-ylamine;2-PYRIDINAMINE, 4-CHLORO-3-NITRO-;MFCD04116097;4-Chloro-3-nitropyridin-2-ylamine;1855-64-7;4-Chloro-3-nitro-2-pyridinamine;4-chloro-3-nitro-pyridin-2-amine;SCHEMBL783847;DTXSID60990059;DIRINUVNYFAWQF-UHFFFAOYSA-N;3-Nitro-4-chloropyridine-2-amine;4-chloro-2-amino-3-nitropyridine;4-Chloro-3-nitro-2-aminopyridine;BCP10172;BBL101706;GEO-02458;STL555502;AKOS005256521;4-Chloro-3-nitropyridin-2(1H)-imine;CS-W008722;PB30811;AC-25097;AS-11333;SY029042;AM20061451;FT-0648853;EN300-137052;J-515029;W-200058

Chemical Property of 2-Amino-4-chloro-3-nitropyridine

Chemical Property:

• Vapor Pressure: 0.000183mmHg at 25°C
• Melting Point: 174-176°C
• Refractive Index: 1.657
• Boiling Point: 329 °C at 760 mmHg
• PKA: 1.31±0.47(Predicted)
• Flash Point: 152.8 °C
• PSA: 84.73000
• Density: 1.596 g/cm³
• LogP: 2.32980
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in dimethyl formamide, dimethyl sulfoxide, hot ethanol,
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 172.9992041
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-4-chloro-3-nitropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(C(=C1Cl)[N+](=O)[O-])N
• Description: It is usually used as the intermediate or raw material in organic synthesis and pharmaceutical industry. Specifically, this chemical can act as the intermediate in the synthesis of 5-amino-azaoxindole derivatives.1 Moreover, this substance may be involved in the preparation of pharmaceutically active compounds that can be used in the treatment of proliferative disorders, as well as other diseases or conditions in which aurora kinase and/or FLT3 activity is implicated.2 In addition, this chemical has been demonstrated to function as the intermediate in the synthesis of 1-deaza-6-methylthiopurine ribonucleoside, which is proved to exhibit cytotoxicty.3 Besides, 2-amino-4-chloro-3-nitropyridine can be utilized to fabricate central nervous system (CNS) active compounds.4
• Uses: 2-Amino-4-chloro-3-nitropyridine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Technology Process of 2-Amino-4-chloro-3-nitropyridine

There total 3 articles about 2-Amino-4-chloro-3-nitropyridine 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: 54.0%

4-chloro-3-nitropyridine (13091-23-1) → 4-amino-3-nitropyridine (1681-37-4) + 4-chloro-3-nitro-2-pyridinamine (6980-08-1) + 2,6-diamino-4-chloro-3-nitropyridine (40497-64-1) + 2-amino-4-chloro-5-nitropyridine (24484-96-6)

Guidance literature:

With potassium permanganate; ammonia; at -33 ℃; for 5h;

Reference yield: 41.0%

2-Amino-4-chloropyridine (19798-80-2) → 4-chloro-3-nitro-2-pyridinamine (6980-08-1) + 2-amino-4-chloro-5-nitropyridine (24484-96-6)

Guidance literature:

2-Amino-4-chloropyridine; With sulfuric acid; nitric acid; at 0 - 5 ℃;

With sulfuric acid; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2012.07.140

Reference yield:

N-nitro-2-amino-4-chloropyridine (24484-97-7) → 4-chloro-3-nitro-2-pyridinamine (6980-08-1) + 2-amino-4-chloro-5-nitropyridine (24484-96-6)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; Product distribution; other substituted 2- and 4-amino-pyridines; other temp.;

upstream raw materials:

4-chloro-3-nitropyridine

N-nitro-2-amino-4-chloropyridine

2-Amino-4-chloropyridine

Downstream raw materials:

4-methoxy-3-nitro-pyridin-2-ylamine

4-(3-aminophenoxy)-3-nitropyridin-2-amine

4-(3-N-(tert-butoxycarbonyl)aminophenoxy)-3-nitropyridin-2-amine

4-N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-4-N-methyl-3-nitropyridine-2,4-diamine

Refernces

• 1、 Tzvetkov, Nikolay T.,Neumann, Beate,Stammler, Hans-Georg,Antonov, Liudmil. "A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form". supporting information. p. 6455 - 6466. Retrieved 2016/09/23.
• 2、 Tzvetkov, Nikolay T.,Müller, Christa E.. "Facile synthesis of 5-amino- and 7-amino-6-azaoxindole derivatives". . p. 5597 - 5601. Retrieved 2012/11/07.