4-Nitrophenylacetonitrile

Base Information

• Chemical Name: 4-Nitrophenylacetonitrile
• CAS No.: 555-21-5
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• Hs Code.: 29269095
• European Community (EC) Number: 209-085-0
• NSC Number: 5396
• UNII: 086Q9Q6WOT
• DSSTox Substance ID: DTXSID3060297
• Nikkaji Number: J10.626G
• Wikidata: Q27236377
• Mol file: 555-21-5.mol

Synonyms:p-nitrophenylacetonitrile

Chemical Property of 4-Nitrophenylacetonitrile

Chemical Property:

• Appearance/Colour: cream to yellow crystalline powder
• Vapor Pressure: 0.000113mmHg at 25°C
• Melting Point: 113-115 °C(lit.)
• Refractive Index: 1.577
• Boiling Point: 336.3 °C at 760 mmHg
• Flash Point: 157.2 °C
• PSA: 69.61000
• Density: 1.272 g/cm³
• LogP: 2.18408
• Storage Temp.: Store below +30°C.
• Solubility.: Solubility Insoluble in water, soluble in ethanol, ether
• Water Solubility.: INSOLUBLE
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrophenylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 14-22-36/37-36-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC#N)[N+](=O)[O-]
• Uses: p-Nitrophenylacetonitrile is used as a radical inhibitor in the polymerization of vinyl acetate. In the preparation of p-nitrophenylacetic acid. 4-Nitrophenylacetonitrile is used as a radical inhibitor in the polymerization of vinyl acetate. Toxic compound to tetrahymena pyriformis.

Technology Process of 4-Nitrophenylacetonitrile

There total 61 articles about 4-Nitrophenylacetonitrile 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%

tetra-n-butylammonium cyanide (10442-39-4) + 1-((methoxymethoxy)methyl)-4-nitrobenzene (139884-17-6) → 4-Nitrophenylacetonitrile (555-21-5,34512-13-5,174848-08-9)

Guidance literature:

With 1-(n-butyl)-3-methylimidazolium tetrachloroindate; at 135 - 140 ℃; for 0.0333333h; chemoselective reaction; Microwave irradiation; Neat (no solvent);

DOI:10.1016/j.tetlet.2010.04.056

Reference yield: 88.0%

phenylacetonitrile (140-29-4) → 4-Nitrophenylacetonitrile (555-21-5,34512-13-5,174848-08-9)

Guidance literature:

With sulfuric acid; nitric acid; at 10 - 20 ℃; for 1h;

DOI:10.1016/j.bioorg.2020.103977

Reference yield: 76.0%

4-iodophenylacetonitrile (51628-12-7) → 4-Nitrophenylacetonitrile (555-21-5,34512-13-5,174848-08-9)

Guidance literature:

With 1,10-Phenanthroline; iron(II) sulfate; potassium nitrate; In dimethyl sulfoxide; at 20 ℃; for 48h; UV-irradiation; Inert atmosphere;

DOI:10.1021/acscatal.1c02272

upstream raw materials:

phenylacetonitrile

methanol

p-nitro-phenyl-acetonitrile

2-(4-nitrophenyl)-3-phenylacrylonitrile

Downstream raw materials:

3-(3-nitro-phenyl)-2-(4-nitro-phenyl)-acrylonitrile

3-hydroxy-3-(3-nitro-phenyl)-2-(4-nitro-phenyl)-propionitrile

(Z)-α-(p-nitrophenyl)-β-(2-furyl)acrylonitrile

2-(4-nitro-phenyl)-3c-[2]thienyl-acrylonitrile

Refernces

10.1021/ja00846a035

The study investigates the impact of cationic micelles, specifically hexadecyltrimethylammonium bromide (CTABr), on the acidity of carbon acids and phenols, as well as the electronic and 'H nuclear magnetic resonance (NMR) spectral characteristics of nitro carbanions in micelles. The researchers found that CTABr micelles significantly enhance the acid dissociation of various carbon acids and phenols, with the effect being most pronounced for nitro carbanions. The study involved several chemicals, including 4-nitrophenylacetonitriles, 1-nitroindene, 4-nitrophenol, and 2,6-di-tert-butyl-4-nitrophenol, which were used to examine the changes in their acid dissociation constants (pKa values) in the presence of CTABr micelles. Additionally, the visible and 'H NMR spectra of these nitro carbanions were analyzed to understand the interactions between the carbanions and CTABr molecules. The results showed that CTABr micelles cause a red shift in the visible spectra of nitro carbanions and induce upfield shifts in the 'H NMR signals of the aromatic protons of the carbanions and the N+(CH3)3 protons of the surfactant, indicating tight interactions. The study concludes that the presence of CTABr micelles enhances the acidity of carbon acids and phenols by stabilizing the anionic form through tight association with the surfactant molecules, and the spectral changes observed are attributed to the unique interactions within the micelle environment rather than chemical reactions.