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

• 1、 Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua. "Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer". . p. 9561 - 9568. Retrieved 2021/08/06.
• 2、 -. "Preparation method of methyl p-aminophenylacetate". Paragraph 0045; 0046; 0047; 0048; 0049; 0050. . Retrieved 2019/01/14.