2-Bromo-4-nitroaniline

Base Information

• Chemical Name: 2-Bromo-4-nitroaniline
• CAS No.: 13296-94-1
• Molecular Formula: C6H5BrN2O2
• Molecular Weight: 217.022
• Hs Code.: 29214200
• European Community (EC) Number: 236-318-3
• NSC Number: 28330
• DSSTox Substance ID: DTXSID3065405
• Nikkaji Number: J38.255H
• Wikidata: Q72448438
• Mol file: 13296-94-1.mol

Synonyms:2-Bromo-4-nitroaniline;13296-94-1;Benzenamine, 2-bromo-4-nitro-;ANILINE, 2-BROMO-4-NITRO-;2-bromo-4-nitrobenzenamine;(2-bromo-4-nitrophenyl)amine;2-BROMO-4-NITRO-ANILINE;EINECS 236-318-3;MFCD00025152;NSC 28330;BRN 2803493;3-12-00-01675 (Beilstein Handbook Reference);2-Bromo-4-nitrophenylamine;4-Amino-3-bromonitrobenzene;NSC28330;2-bromo4-nitroaniline;WLN: ZR BE DNW;SCHEMBL1181388;2-Bromo-4-nitroaniline, 98%;DTXSID3065405;BCP05869;AB3184;NSC-28330;STK397828;AKOS000275959;AKOS025293427;AB01462;AC-3720;CS-W005164;PS-4135;NCGC00334447-01;LS-19619;SY004549;AM20020401;B4873;BB 0254402;FT-0612052;EN300-08034;AB01326673-02;J-508317;Z104492192

Chemical Property of 2-Bromo-4-nitroaniline

Chemical Property:

• Appearance/Colour: dark orange solid.
• Vapor Pressure: 4.01E-05mmHg at 25°C
• Melting Point: 104 °C
• Refractive Index: 1.669
• Boiling Point: 351.8 °C at 760 mmHg
• PKA: -1.18±0.10(Predicted)
• Flash Point: 166.6 °C
• PSA: 71.84000
• Density: 1.812 g/cm³
• LogP: 3.04390
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 215.95344
• Heavy Atom Count: 11
• Complexity: 159

Purity/Quality:

98% ^*data from raw suppliers

2-Bromo-4-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 23/24/25-33
• Safety Statements: 28-37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])Br)N
• Uses: 2-Bromo-4-nitroaniline is used as a reagent in the synthesis of novel tetrahydrothienopyridopyrimidine derivatives which exhibit antibacterial and antifungal activity against a variety of microorganisms in vitro. Also used as a reagent in synthesis of dialkylimidazole inhibitors of Trypanosoma cruzi sterol 14α-demethylase as anti-Chagas disease agents.

Technology Process of 2-Bromo-4-nitroaniline

There total 23 articles about 2-Bromo-4-nitroaniline 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: 99.0%

4-nitro-aniline (100-01-6,104810-17-5) → 2-bromo-4-nitroaniline (13296-94-1)

Guidance literature:

With 1-butyl-3-methylimidazolium tribromide; at 25 ℃; for 0.666667h;

DOI:10.1055/s-2004-831239

Reference yield: 84.0%

4-nitro-aniline (100-01-6,104810-17-5) → 2,6-dibromo-4-nitroaniline (827-94-1) + 2-bromo-4-nitroaniline (13296-94-1)

Guidance literature:

With dihydrogen peroxide; potassium bromide; In water; acetonitrile;

DOI:10.1016/j.poly.2012.09.036

Reference yield: 66.0%

m-nitrobromobenzene (585-79-5) → 2-bromo-4-nitroaniline (13296-94-1)

Guidance literature:

With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;

DOI:10.1021/jo970582b

upstream raw materials:

3,4-dibromonitrobenzene

N-acetyl-2-bromoaniline

p-nitrobenzanilide

N-(2-bromo-4-nitro-phenyl)-acetamide

Downstream raw materials:

Nonanoic acid (2-bromo-4-nitro-phenyl)-amide

5-nitroindole

2-amino-5-nitro-4'-methoxystilbene

N-(2-bromo-4-nitrophenyl)-2-nitrobenzenesulfonamide

Refernces

• 1、 Salmasi, Reihaneh,Gholizadeh, Mostafa,Salimi, Alireza,Garrison, Jered C.. "The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions". . p. 2019 - 2028. Retrieved 2016.
• 2、 Khalifa, Aisha,Conway, Lorna,Geoghegan, Kimberly,Evans, Paul. "Ammonium formate-based one-pot reductive Heck reactions for the construction of cyclic sulfonamides". . p. 4559 - 4562. Retrieved 2017.
• 3、 Lungerich, Dominik,Reger, David,H?lzel, Helen,Riedel, René,Martin, Max M. J. C.,Hampel, Frank,Jux, Norbert. "A Strategy towards the Multigram Synthesis of Uncommon Hexaarylbenzenes". . p. 5602 - 5605. Retrieved 2016.
• 4、 Joema, S. E.,Juliet Brintha, C. S.,Suma, V. K.. "Crystal growth, spectroscopic and theoretical investigation of nonlinear optical 2?bromo-4-nitroaniline single crystals for NLO and optoelectronic applications". . . Retrieved 2022/01/14.
• 5、 Li, Ming-Fang,Wang, Jian,Ke, Yong-Xin,Pan, Song-Cheng,Yin, Hong,Du, Wenting,Li, Jing-Hua. "A metal-free aerobic oxidative bromination of anilines and aryl ketones with 2-methylpyridinium nitrate as a reusable ionic liquid". . p. 267 - 270. Retrieved 2020/01/08.