Benzene, 1-nitro-4-(1-propenyl)-

Base Information

• Chemical Name: Benzene, 1-nitro-4-(1-propenyl)-
• CAS No.: 25798-60-1
• Molecular Formula: C9H9NO2
• Molecular Weight: 163.176
• Hs Code.: 2904209090
• DSSTox Substance ID: DTXSID10392928
• Mol file: 25798-60-1.mol

Synonyms:Benzene, 1-nitro-4-(1-propenyl)-;DTXSID10392928

Chemical Property of Benzene, 1-nitro-4-(1-propenyl)-

Chemical Property:

• PSA: 45.82000
• LogP: 3.15110
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 163.063328530
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Benzene, 1-nitro-4-(1-propenyl)-

There total 9 articles about Benzene, 1-nitro-4-(1-propenyl)- 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: 91.0%

p-nitrobenzene iodide (636-98-6) + 1-propenylmagnesium bromide (13154-14-8,13154-15-9,14092-04-7,1730-25-2) → (1-nitro-4-(prop-1-en-1-yl)benzene) (25798-60-1)

Guidance literature:

1-propenylmagnesium bromide; With gallium(III) trichloride; In tetrahydrofuran; hexane; dimethyl sulfoxide; at 25 ℃;

p-nitrobenzene iodide; With tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; hexane; dimethyl sulfoxide; Heating;

DOI:10.1055/s-2002-32608

Reference yield: 67.0%

p-nitrobenzene iodide (636-98-6) + Allyl acetate (591-87-7) → (1-nitro-4-(prop-1-en-1-yl)benzene) (25798-60-1)

Guidance literature:

With N,N-dimethylbutylamine; tetrabutyl-ammonium chloride; palladium on activated charcoal; In water; N,N-dimethyl-formamide; at 180 ℃; for 3h;

DOI:10.1021/ol051947e

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + C14H18N2O5 → (1-nitro-4-(prop-1-en-1-yl)benzene) (25798-60-1) + C20H32N2O5Si + 2-(((tert-butyldimethylsilyl)oxy)imino)-3-(4-nitrophenyl)propyl pivalate

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2h; Overall yield = 58 mg; Inert atmosphere;

DOI:10.1002/ejoc.202100469

upstream raw materials:

(p-nitrobenzyl)triphenylphosphonium bromide

acetaldehyde

4-nitrobenzyltriphenylarsonium bromide

p-nitrobenzene iodide

Downstream raw materials:

3-(4-nitrophenyl)-2-propenal

2-bromo-1-(4-nitrophenyl)propan-1-one

5-methyl-4-(4-nitrophenyl)-2-phenylthiazole

(E)-3-(4-nitrophenyl)prop-2-en-1-yl bromide

Refernces

• 1、 Mariampillai, Brian,Herse, Christelle,Laufens, Mark. "Intermolecular heck-type coupling of aryl iodides and allylic acetates". . p. 4745 - 4747. Retrieved 2007/10/03.
• 2、 Broos, Rene,Anteunis, Marc J. O.. "THE REACTION OF BENZYLTRIPHENYLARSONIUM YLIDES WITH ALDEHYDES. A NOTE ABOUT THE MECHANISM OF THE WITTIG REACTION.". . p. 271 - 280. Retrieved 2007/10/02.