2-Nitrophenylacetonitrile

Base Information

• Chemical Name: 2-Nitrophenylacetonitrile
• CAS No.: 610-66-2
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• Hs Code.: 29269090
• European Community (EC) Number: 210-231-0
• NSC Number: 99338
• UNII: 7859F455K6
• DSSTox Substance ID: DTXSID7025768
• Nikkaji Number: J31.170G
• Wikidata: Q27266640
• ChEMBL ID: CHEMBL1300441
• Mol file: 610-66-2.mol

Synonyms:Acetonitrile,(o-nitrophenyl)-(7CI,8CI);(2-Nitrophenyl)acetonitrile;(o-Nitrophenyl)acetonitrile;2-Nitrobenzeneacetonitrile;2-Nitrobenzyl cyanide;o-Nitrobenzacetonitrile;o-Nitrobenzyl cyanide;

Chemical Property of 2-Nitrophenylacetonitrile

Chemical Property:

• Appearance/Colour: light brown solid
• Vapor Pressure: 0.000864mmHg at 25°C
• Melting Point: 82-85 ºC
• Refractive Index: 1.577
• Boiling Point: 304.6 °C at 760 mmHg
• Flash Point: 138 °C
• PSA: 69.61000
• Density: 1.272 g/cm³
• LogP: 2.18408
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: <0.01 g/100 mL at 20℃
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 213

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Nitrobenzyl Cyanide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CC#N)[N+](=O)[O-]
• Uses: 2-Nitrophenylacetonitrile was used in synthesis of 2 or 2,4-substituted α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones. It was used in the synthesis of strychnine.

Technology Process of 2-Nitrophenylacetonitrile

There total 33 articles about 2-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: 76.0%

phenylacetonitrile (140-29-4) → 2-nitro-benzeneacetonitrile (610-66-2)

Guidance literature:

With nitric acid; acetic acid; at 0 - 40 ℃;

DOI:10.1016/j.ejmech.2016.07.011

Reference yield: 18.0%

chloroacetonitrile (107-14-2) + nitrobenzene (98-95-3,26969-40-4) → 2-nitro-benzeneacetonitrile (610-66-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -20 - -10 ℃; for 0.00833333h;

Reference yield: 18.0%

(phenylthio)acetonitrile (5219-61-4) + nitrobenzene (98-95-3,26969-40-4) → 2-nitro-benzeneacetonitrile (610-66-2) + 4-Nitrophenylacetonitrile (555-21-5,34512-13-5,174848-08-9)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; at 30 ℃; for 1.5h;

DOI:10.1021/jo01296a045

upstream raw materials:

2-hydroxyimino-3-(2-nitro-phenyl)-propionic acid

nitro-phenyl-acetic acid amide

acetic anhydride

phenylacetonitrile

Downstream raw materials:

indole

2-(2-nitrophenyl)acetic acid

2-aminophenylacetonitrile

2,3-Bis(2-nitrophenyl)propanenitrile

Refernces

• 1、 -. "Corresponding amine nitrile and method of manufacturing thereof". Paragraph 0153; 0154; 0155; 0162; 0163. . Retrieved 2018/05/07.
• 2、 Lee, So Jeong,Fowler, Joanna S.,Alexoff, David,Schueller, Michael,Kim, Dohyun,Nauth, Alexander,Weber, Carina,Kim, Sung Won,Hooker, Jacob M.,Ma, Ling,Qu, Wenchao. "An efficient and practical synthesis of [2-11C]indole via superfast nucleophilic [11C]cyanation and RANEY Nickel catalyzed reductive cyclization". . p. 11235 - 11243. Retrieved 2015/12/01.