1-Bromo-3,5-dinitrobenzene

Base Information

• Chemical Name: 1-Bromo-3,5-dinitrobenzene
• CAS No.: 18242-39-2
• Molecular Formula: C6H3BrN2O4
• Molecular Weight: 247.005
• Hs Code.: 2904909090
• European Community (EC) Number: 804-805-5
• DSSTox Substance ID: DTXSID50864816
• Nikkaji Number: J514.460D
• Wikidata: Q72455106
• Mol file: 18242-39-2.mol

Synonyms:1-Bromo-3,5-dinitrobenzene;18242-39-2;1-bromo-3,5-dinitro-benzene;Benzene, 1-bromo-3,5-dinitro-;BROMODINITROBENZENE;5-BROMO-1,3-DINITROBENZENE;1-Bromo-3,5-dinitro benzene;63460-06-0;MFCD00156596;Benzene, 1-?bromo-?3,?5-?dinitro-;3,5-Dinitrobromobenzene;3-bromo 1,5-dinitrobenzene;1,3-Dinitro-5-bromobenzene;SCHEMBL1026447;DTXSID50864816;CS-M0502;AKOS015835359;AKOS015967332;AC-22965;SY030219;AM20030207;B5627;FT-0659179;EN300-67115;A20750

Chemical Property of 1-Bromo-3,5-dinitrobenzene

Chemical Property:

• Vapor Pressure: 0.00117mmHg at 25°C
• Melting Point: 75-76℃
• Refractive Index: 1.647
• Boiling Point: 309.335 °C at 760 mmHg
• Flash Point: 140.881 °C
• PSA: 91.64000
• Density: 1.91 g/cm³
• LogP: 3.31190
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 245.92762
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

99%, ^*data from raw suppliers

1-Bromo-3,5-dinitrobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C=C1[N+](=O)[O-])Br)[N+](=O)[O-]
• Uses: It is an important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field.

Technology Process of 1-Bromo-3,5-dinitrobenzene

There total 16 articles about 1-Bromo-3,5-dinitrobenzene 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: 96.0%

meta-dinitrobenzene (99-65-0) → 3,5-dinitrobromobenzene (18242-39-2)

Guidance literature:

With N-Bromosuccinimide; sulfuric acid; at 60 ℃; for 48h;

Reference yield: 79.0%

m-nitrobromobenzene (585-79-5) → 3,5-dinitrobromobenzene (18242-39-2)

Guidance literature:

With 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione; In sulfuric acid; water; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2009.02.010

Reference yield: 29.0%

2,4-dinitrobenzoic acid (610-30-0) → 3,5-dinitrobromobenzene (18242-39-2)

Guidance literature:

With copper(I) oxide; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bismuth (III) nitrate pentahydrate; oxygen; sodium bromide; In dimethyl sulfoxide; at 170 ℃; for 10h; regioselective reaction; Schlenk technique; Green chemistry;

DOI:10.1021/acs.orglett.9b00460

upstream raw materials:

meta-dinitrobenzene

4'-amino-3'-bromo-5'-nitro-acetophenone

2-bromo-4,6-dinitroaniline

2-bromo-4,6-dinitrobenzoic acid

Downstream raw materials:

1,3-dinitro-5-vinylbenzene

(E)-3,5-dinitro-4'-methoxystilbene

E-1-(phenyl)-2-(4'-methoxyphenyl)ethene

1-bromo-3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-5-nitrobenzene

Refernces

• 1、 Ghorbani-Vaghei, Ramin,Shahbazi, Hajar,Veisi, Hojat. "Mild bromination of unreactive aromatic compounds". . p. 2325 - 2327. Retrieved 2012.
• 2、 Huthmacher,Effenberger. "". . p. 693. Retrieved 1978.
• 3、 de Almeida, Leonardo S.,Esteves, Pierre M.,de Mattos, Marcio C.S.. "Superelectrophilic bromination of deactivated aromatic rings with tribromoisocyanuric acid-an experimental and DFT study". . p. 3001 - 3004. Retrieved 2009.
• 4、 Fawwaz, Muammar,Mishiro, Kenji,Nishii, Ryuichi,Makino, Akira,Kiyono, Yasushi,Shiba, Kazuhiro,Kinuya, Seigo,Ogawa, Kazuma. "A radiobrominated tyrosine kinase inhibitor for egfr with l858r/t790m mutations in lung carcinoma". . . Retrieved 2021/03/29.
• 5、 -. "Indole compound as well as preparation method, pharmaceutical composition and application thereof". Paragraph 0551-0556. . Retrieved 2019/12/02.