3-Nitrophthalonitrile

Base Information

• Chemical Name: 3-Nitrophthalonitrile
• CAS No.: 51762-67-5
• Molecular Formula: C8H3N3O2
• Molecular Weight: 173.131
• Hs Code.: 29269090
• European Community (EC) Number: 450-650-8
• DSSTox Substance ID: DTXSID5073531
• Nikkaji Number: J383.042J
• Wikidata: Q72495937
• Mol file: 51762-67-5.mol

Synonyms:3-Nitrophthalonitrile;51762-67-5;3-nitrobenzene-1,2-dicarbonitrile;2,3-Dicyanonitrobenzene;1,2-Benzenedicarbonitrile, 3-nitro-;3-Nitro-1,2-benzenedicarbonitrile;1,2-Dicyano-3-nitrobenzene;3-Nitrophthalodinitrile;MFCD00191558;3-Nitro-1,2-dicyanobenzene;nitrophthalonitrile;3-nitro-phthalonitrile;3-Nitrophthalonitrile?;Cambridge id 5127932;3-Nitro-o-benzene dinitrile;3-Nitrophthalonitrile, 99%;3-NITRO PHTHALONITRILE;SCHEMBL220318;2-cyano-3-nitrophenyl cyanide;DTXSID5073531;SCHEMBL17347340;AMY17942;AKOS000813810;AKOS034830330;CS-W017559;PS-5048;AC-23691;LS-29705;SY012041;FT-0601391;N0566;EC 450-650-8;EN300-240230;O11040;3-Nitrophthalonitrile 3-Nitro-1,2-dicyanobenzene;A828760;J-512976;F0017-1930

Chemical Property of 3-Nitrophthalonitrile

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 3.63E-06mmHg at 25°C
• Melting Point: 162-165 °C
• Refractive Index: 1.602
• Boiling Point: 386.1 °C at 760 mmHg
• Flash Point: 187.3 °C
• PSA: 93.40000
• Density: 1.41 g/cm³
• LogP: 1.86136
• Storage Temp.: room temp
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 173.022526347
• Heavy Atom Count: 13
• Complexity: 302

Purity/Quality:

≥99% ^*data from raw suppliers

3-Nitrophthalonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36-45-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)[N+](=O)[O-])C#N)C#N
• Uses: 3-Nitrophthalonitrile can be used in solar cells. Dyes and metabolites.

Technology Process of 3-Nitrophthalonitrile

There total 5 articles about 3-Nitrophthalonitrile 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: 83.0%

3-nitrophthalamide (96385-50-1) → 3-nitrobenzene-1,2-dicarbonitrile (51762-67-5)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield:

phthalonitrile (91-15-6) → 4-Nitrophthalonitrile (31643-49-9) + 3-nitrobenzene-1,2-dicarbonitrile (51762-67-5)

Guidance literature:

With methanesulfonic acid; Nitrogen dioxide; ozone; iron(III) chloride; In acetonitrile; at -10 - 20 ℃; for 28h;

DOI:10.1039/b301847d

Reference yield:

3-nitrophthalic acid (603-11-2) → 3-nitrobenzene-1,2-dicarbonitrile (51762-67-5)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂

2: aq. NH₃

3: POCl₃

With ammonium hydroxide; thionyl chloride; trichlorophosphate;

DOI:10.1016/j.cplett.2006.03.073

upstream raw materials:

phosgene

3-nitrophthalamide

phthalonitrile

3-nitrophthalic acid

Downstream raw materials:

2,3-dicyano-N,N-dimethylaniline

3-methoxybenzene-1,2-dicarbonitrile

1,2-dicyano-3-phenoxybenzene

3-(phenylthio)-phthalonitrile

Refernces

• 1、 Peng, Xinhua,Fukui, Naoyuki,Mizuta, Masayuki,Suzuki, Hitomi. "Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios". . p. 2326 - 2335. Retrieved 2007/10/03.
• 2、 -. "Carboxylic acids and derivates thereof". . . Retrieved 2008/06/13.