3-Bromo-4-methyl-5-nitropyridine

Base Information

• Chemical Name: 3-Bromo-4-methyl-5-nitropyridine
• CAS No.: 69872-15-7
• Molecular Formula: C6H5BrN2O2
• Molecular Weight: 217.022
• European Community (EC) Number: 802-214-7
• DSSTox Substance ID: DTXSID00500853
• Wikidata: Q72447517
• Mol file: 69872-15-7.mol

Synonyms:3-BROMO-4-METHYL-5-NITROPYRIDINE;69872-15-7;3-Bromo-4-methyl-5-nitro-pyridine;3-Bromo-4-methy-5nitro-pyridine;MFCD11847767;Pyridine, 3-bromo-4-methyl-5-nitro-;SCHEMBL951700;DTXSID00500853;WFCIQRPATFRBOY-UHFFFAOYSA-N;3-bromo-5-nitro-4-methylpyridine;CL0154;AKOS007930528;AB64738;CS-W003806;AC-23257;AS-18513;SY024652;AM20061453;FT-0660704;EN300-129508;A836676;AU-004/43508239

Chemical Property of 3-Bromo-4-methyl-5-nitropyridine

Chemical Property:

• Vapor Pressure: 0.013mmHg at 25°C
• Melting Point: 57-58 °C
• Refractive Index: 1.6
• Boiling Point: 268.644 °C at 760 mmHg
• PKA: -0.51±0.28(Predicted)
• Flash Point: 116.272 °C
• PSA: 58.71000
• Density: 1.709 g/cm³
• LogP: 2.58390
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 215.95344
• Heavy Atom Count: 11
• Complexity: 159

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Bromo-4-methyl-5-nitropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=NC=C1[N+](=O)[O-])Br
• Uses: 3-Bromo-4-methyl-5-nitropyridine is an intermediate used in the synthesis of 4-bromo-6-azaindole and other azaindole derivatives.

Technology Process of 3-Bromo-4-methyl-5-nitropyridine

There total 6 articles about 3-Bromo-4-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: 85.0%

3-bromo-4-chloro-5-nitropyridine (31872-63-6) + diethyl malonate (105-53-3) → 3-bromo-4-methyl-5-nitropyridine (69872-15-7)

Guidance literature:

diethyl malonate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

3-bromo-4-chloro-5-nitropyridine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

With hydrogenchloride; In water; N,N-dimethyl-formamide; for 16h; Reflux;

DOI:10.1021/jm401625b

Reference yield:

4-hydroxy-3-nitropyridine (5435-54-1) → 3-bromo-4-methyl-5-nitropyridine (69872-15-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bromine / water / 2 h / 50 °C

2.1: diethylamine; trichlorophosphate / 5 h / Reflux

3.1: sodium hydride / N,N-dimethyl-formamide / 0 °C

3.2: 1 h / 0 °C

4.1: hydrogenchloride; water / 16 h / Reflux

With hydrogenchloride; water; bromine; sodium hydride; diethylamine; trichlorophosphate; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.11.070

Reference yield:

diethyl 2-(3-bromo-5-nitro-4-pyridyl)propanedioate (69872-14-6) → 3-bromo-4-methyl-5-nitropyridine (69872-15-7)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 15h;

upstream raw materials:

3-bromo-4-chloro-5-nitropyridine

diethyl 2-(3-bromo-5-nitro-4-pyridyl)propanedioate

diethyl malonate

3-bromo-5-nitropyridin-4-ol

Downstream raw materials:

4-bromo-2-phenyl-1H-pyrrolo[2,3-c]pyridine

4-bromo-2-phenyl-1H-pyrrolo[2,3-c]pyridin-1-ol

5-bromo-4-methylpyridin-3-amine

tert-butyl 4-bromo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Refernces

• 1、 -. "BICYCLIC DERIVATIVES". . . Retrieved 2020/07/14.
• 2、 Chekler, Eugene L. Piatnitski,Unwalla, Rayomond,Khan, Taukeer A.,Tangirala, Raghuram S.,Johnson, Mark,St. Andre, Michael,Anderson, James T.,Kenney, Thomas,Chiparri, Sue,McNally, Chris,Kilbourne, Edward,Thompson, Catherine,Nagpal, Sunil,Weber, Gregory,Schelling, Scott,Owens, Jane,Morris, Carl A.,Powell, Dennis,Verhoest, Patrick R.,Gilbert, Adam M.. "1-(2-hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile derivatives as potent and tissue selective androgen receptor modulators". supporting information. p. 2462 - 2471. Retrieved 2014/04/17.