2-Nitrobenzonitrile

Base Information

• Chemical Name: 2-Nitrobenzonitrile
• CAS No.: 612-24-8
• Molecular Formula: C7H4 N2 O2
• Molecular Weight: 148.121
• Hs Code.: 2926909090
• European Community (EC) Number: 210-301-0
• NSC Number: 1994
• UNII: DRC6U29FCI
• DSSTox Substance ID: DTXSID80210100
• Nikkaji Number: J2.994G
• Wikidata: Q27276562
• Mol file: 612-24-8.mol

Synonyms:2-Nitrobenzonitrile;612-24-8;o-Nitrobenzonitrile;Benzonitrile, 2-nitro-;o-Cyanonitrobenzene;BENZONITRILE, o-NITRO-;2-Cyanonitrobenzene;MFCD00007044;Nitrobenzonitrile;2-nitro-benzonitrile;CCRIS 2326;2-cyano-1-nitrobenzene;NSC 1994;EINECS 210-301-0;UNII-DRC6U29FCI;DRC6U29FCI;AI3-16688;NSC-1994;1219795-50-2;2-nitrobenzenecarbonitrile;NSC1994;2-nitrobenzenenitrile;2-Nitrobenzoic acid nitrile;SCHEMBL56638;NITROBENZONITRILE, 2-;DTXSID80210100;CK1052;AKOS005141851;AC-7382;AM82820;CS-W016340;PS-5303;2-Nitrobenzonitrile, >=99.0% (GC);LS-38763;SY005983;FT-0613183;N0171;EN300-51194;A833110;A928568;Q27276562;Z57899730;F0001-1611

Chemical Property of 2-Nitrobenzonitrile

Chemical Property:

• Appearance/Colour: YELLOW CRYSTALLINE POWDER
• Vapor Pressure: 0.000902mmHg at 25°C
• Melting Point: 107-109 °C(lit.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 165 °C (16 mmHg)
• Flash Point: 137.6 °C
• PSA: 69.61000
• Density: 1.31 g/cm³
• LogP: 1.98968
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 148.027277375
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

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

2-Nitrobenzonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 20/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C#N)[N+](=O)[O-]
• Uses: ET catalysis of Au25 in intramolecular cascade reaction of 2-nitrobenzonitrile, from which 2-amniobenzamide (a precursor of significant pharmaceuticals20,21) is produced with high yield. fluorodenitration of 2-nitrobenzonitrile with Rb18F in DMSO gave an 85% yield of the 18F-labelled benzonitrile after only 20 minutes at 150°C.

Technology Process of 2-Nitrobenzonitrile

There total 103 articles about 2-Nitrobenzonitrile 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: 99.0%

2-nitro-benzaldehyde (552-89-6) → o-nitrobenzonitrile (612-24-8)

Guidance literature:

2-nitro-benzaldehyde; With hydroxylamine hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 0.0833333h;

With potassium hydrogen difluoride; 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate; In water; at 20 ℃; for 3h;

DOI:10.1002/chem.201805175

Reference yield: 96.0%

o-nitroiodobenzene (609-73-4) + potassium ferrocyanide → o-nitrobenzonitrile (612-24-8)

Guidance literature:

With C₃₀H₂₄N₃OPPd; triethylamine; In N,N-dimethyl-formamide; at 100 ℃; for 24h;

DOI:10.1016/j.ica.2015.02.002

Reference yield: 95.0%

2-(2-nitrophenyl)-1,3,4-oxadiazole (89898-92-0) → o-nitrobenzonitrile (612-24-8)

Guidance literature:

With sodium t-butanolate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.3184/174751914X14007780679741

upstream raw materials:

tetrachloromethane

2-nitro-benzaldehyde-((E)-O-benzoyl oxime )

ortho-nitrobenzoic acid

(Z)-2-nitrobenzaldehyde oxime

Downstream raw materials:

2-((2-nitrophenyl)amino)benzonitrile

2-methoxybenzamide

2-nitrobenzamidine

anthranilic acid amide

Refernces

• 1、 Pal, Shantanu,Sahoo, Subrata. "Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products". . p. 18067 - 18080. Retrieved 2021/12/06.
• 2、 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.