3,5-Dinitrostyrene

Base Information

• Chemical Name: 3,5-Dinitrostyrene
• CAS No.: 72918-18-4
• Molecular Formula: C8H6 N2 O4
• Molecular Weight: 194.147
• Hs Code.: 2904209090
• DSSTox Substance ID: DTXSID70479880
• Nikkaji Number: J522.088B
• Wikidata: Q82314204
• Mol file: 72918-18-4.mol

Synonyms:3,5-Dinitrostyrene;72918-18-4;1,3-DINITRO-5-VINYL-BENZENE;1,3-dinitro-5-vinylbenzene;SCHEMBL7595668;DTXSID70479880;CRKUWNMRJQROHR-UHFFFAOYSA-N;AKOS006331311;AKOS015966966

Chemical Property of 3,5-Dinitrostyrene

Chemical Property:

• Boiling Point: 303.9±35.0 °C(Predicted)
• PSA: 91.64000
• Density: 1.396±0.06 g/cm3(Predicted)
• LogP: 3.19240
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 194.03275668
• Heavy Atom Count: 14
• Complexity: 233

Purity/Quality:

99%min ^*data from raw suppliers

1,3-DINITRO-5-VINYL-BENZENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]

Technology Process of 3,5-Dinitrostyrene

There total 10 articles about 3,5-Dinitrostyrene 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: 89.0%

3,5-dinitroiodobenzene (6276-04-6) + vinyl magnesium bromide (1826-67-1) → 1,3-dinitro-5-vinylbenzene (72918-18-4)

Guidance literature:

vinyl magnesium bromide; With zinc(II) chloride; In tetrahydrofuran; at 0 - 20 ℃; for 1.16667h;

3,5-dinitroiodobenzene; With bis-triphenylphosphine-palladium(II) chloride; 2,6-di-tert-butyl-4-methyl-phenol; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1021/jo048051s

Reference yield: 31.0%

3,5-dinitrobromobenzene (18242-39-2) + 2,4,6-trivinylcyclotriboroxane*pyridine complex → 1,3-dinitro-5-vinylbenzene (72918-18-4)

Guidance literature:

3,5-dinitrobromobenzene; 2,4,6-trivinylcyclotriboroxane*pyridine complex; With potassium carbonate; In 1,4-dioxane; water; Sealed tube;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 95 ℃; for 18h; Sealed tube;

DOI:10.1016/j.ejmech.2016.12.006

Reference yield:

ethene (74-85-1) + para-iodoanisole (696-62-8) + 3,5-dinitroiodobenzene (6276-04-6) → 4-Methoxystyrene (637-69-4,24936-44-5) + 1,3-dinitro-5-vinylbenzene (72918-18-4)

Guidance literature:

With sodium acetate; palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 90 ℃; for 0.5h; under 7600.51 Torr; Inert atmosphere; Autoclave;

DOI:10.1002/aoc.1756

upstream raw materials:

3,5-dinitroiodobenzene

vinyl magnesium bromide

meta-dinitrobenzene

3,5-dinitrobromobenzene

Downstream raw materials:

1-(1,2-Dihydroxyethyl)-3,5-dinitrobenzene

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

(E)-3,5-dinitro-1-styrylbenzene

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

Refernces

• 1、 Nobre, Sabrina M.,Muniz, Mauro N.,Seferin, Marcus,Da Silva, Wagner M.,Monteiro, Adriano L.. "The synthesis of non-symmetrical stilbene analogs of trans-resveratrol using the same Pd catalyst in a sequential double-Heck arylation of ethylene". scheme or table. p. 289 - 293. Retrieved 2012/01/04.
• 2、 -. "Contrast media". . . Retrieved 2008/06/13.