2-Chloro-3-methyl-5-nitropyridine

Base Information

• Chemical Name: 2-Chloro-3-methyl-5-nitropyridine
• CAS No.: 22280-56-4
• Molecular Formula: C6H5ClN2O2
• Molecular Weight: 172.571
• Hs Code.: 29333999
• European Community (EC) Number: 244-889-5
• NSC Number: 63887
• UNII: 45ZN7UCB3M
• DSSTox Substance ID: DTXSID70176827
• Nikkaji Number: J285.471F
• Wikidata: Q72454417
• Mol file: 22280-56-4.mol

Synonyms:2-Chloro-3-methyl-5-nitropyridine;22280-56-4;2-Chloro-5-nitro-3-picoline;2-chloro-5-nitro-3-methylpyridine;Pyridine, 2-chloro-3-methyl-5-nitro-;MFCD00173686;2-Chloro-3-methyl-5-Nitro pyridine;45ZN7UCB3M;EINECS 244-889-5;NSC-63887;NSC63887;2-chloro-3-methyl-5-nitro-pyridine;UNII-45ZN7UCB3M;SCHEMBL801244;OSIOIGXJUZTWRI-UHFFFAOYSA-;DTXSID70176827;2-Chloro-3-methyl-5nitropyridine;BCP22226;CS-D0963;BBL101878;NSC 63887;STL555675;2-chloro-3-methyl -5-nitro-pyridine;AKOS005064142;PB25986;PS-4180;SB20915;AC-10878;SY004411;2-Chloro-3-methyl-5-nitropyridine, 97%;A4785;AM20050960;C2020;FT-0611730;EN300-63950;W-206744;Z991524294

Chemical Property of 2-Chloro-3-methyl-5-nitropyridine

Chemical Property:

• Appearance/Colour: Light beige to cream colored crystalline powder
• Vapor Pressure: 0.00504mmHg at 25°C
• Melting Point: 78-80 °C
• Refractive Index: 1.575
• Boiling Point: 284.7 °C at 760 mmHg
• PKA: -3.61±0.10(Predicted)
• Flash Point: 126 °C
• PSA: 58.71000
• Density: 1.406 g/cm³
• LogP: 2.47480
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: soluble in Methanol
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 172.0039551
• Heavy Atom Count: 11
• Complexity: 159

Purity/Quality:

98% ^*data from raw suppliers

2-C- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-41-37/38-22
• Safety Statements: 37/39-26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CN=C1Cl)[N+](=O)[O-]

Technology Process of 2-Chloro-3-methyl-5-nitropyridine

There total 5 articles about 2-Chloro-3-methyl-5-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: 92.0%

2-hydroxy-3-methyl-5-nitropyridine (21901-34-8) → 2-chloro-3-methyl-5-nitropyridine (22280-56-4)

Guidance literature:

With trichlorophosphate; at 120 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm900716v

Reference yield:

2-amino-3-methyl-5-nitropyridine (18344-51-9) → 2-hydroxy-3-methyl-5-nitropyridine (21901-34-8) + 2-chloro-3-methyl-5-nitropyridine (22280-56-4)

Guidance literature:

With hydrogenchloride; calcium chloride; sodium nitrite; Erhitzen des Reaktionsprodukts mit Wasser;

DOI:10.1021/jo01154a021

Reference yield:

3-methylpyridin-2-ylamine (1603-40-3) → 2-chloro-3-methyl-5-nitropyridine (22280-56-4)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂SO₄; HNO₃

2: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser

3: phosphoryl chloride

With hydrogenchloride; sulfuric acid; nitric acid; calcium chloride; sodium nitrite; trichlorophosphate;

DOI:10.1021/jo01154a021

upstream raw materials:

2-amino-3-methyl-5-nitropyridine

2-hydroxy-3-methyl-5-nitropyridine

3-methylpyridin-2-ylamine

Downstream raw materials:

5-methylpyridin-3-amine

methyl-1 (methyl-3 nitro-5 pyridyl-2)-thio-2 imidazole

2-hydroxy-3-methyl-5-nitropyridine

6-chloro-5-methylpyridin-3-amine

Refernces

• 1、 -. "THE NITROPYRIDINYL ETHYLENEIMINE COMPOUND, THE PHARMACEUTICAL COMPOSITION CONTAINING IT, THE PREPARATION METHOD AND USE THEREOF". Page/Page column 10. . Retrieved 2011/10/10.
• 2、 Hartz, Richard A.,Ahuja, Vijay T.,Zhuo, Xiaoliang,Mattson, Ronald J.,Denhart, Derek J.,Deskus, Jeffrey A.,Vrudhula, Vivekananda M.,Pan, Senliang,Ditta, Jonathan L.,Shu, Yue-Zhong,Grace, James E.,Lentz, Kimberley A.,Lelas, Snjezana,Li, Yu-Wen,Molski, Thaddeus F.,Krishnananthan, Subramaniam,Wong, Henry,Qian-Cutrone, Jingfang,Schartman, Richard,Denton, Rex,Lodge, Nicholas J.,Zaczek, Robert,Macor, John E.,Bronson, Joanne J.. "A strategy to minimize reactive metabolite formation: Discovery of (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-[6-(difluoromethoxy)-2, 5-dimethylpyridin-3-ylamino]-5-oxo-4,5-dihydropyrazine-2-carbonitrile as a potent, orally bioavailable corticotropin-releasing factor-1 receptor antagonist". experimental part. p. 7653 - 7668. Retrieved 2010/09/03.