Phthalonitrile

Base Information

• Chemical Name: Phthalonitrile
• CAS No.: 91-15-6
• Molecular Formula: C8H4N2
• Molecular Weight: 128.133
• Hs Code.: 29269095
• European Community (EC) Number: 202-044-8
• ICSC Number: 0670
• NSC Number: 17562
• UN Number: 3276
• UNII: 978627YAJU
• DSSTox Substance ID: DTXSID8029604
• Nikkaji Number: J3.921G
• Wikipedia: Phthalonitrile
• Wikidata: Q408783
• ChEMBL ID: CHEMBL3185350
• Mol file: 91-15-6.mol

Synonyms:1,2-benzenedicarbonitrile;1,2-dicyanobenzene;o-phthalodinitrile

Chemical Property of Phthalonitrile

Chemical Property:

• Appearance/Colour: off-white to tan powder
• Vapor Pressure: 0.000865mmHg at 25°C
• Melting Point: 137-139 °C(lit.)
• Refractive Index: 1.565
• Boiling Point: 304.6 °C at 760 mmHg
• Flash Point: 153.3 °C
• PSA: 47.58000
• Density: 1.24 g/cm³
• LogP: 1.42996
• Storage Temp.: Store below +30°C.
• Solubility.: benzene: 50 mg/mL, clear
• Water Solubility.: 0.56 g/L (25 ºC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.037448136
• Heavy Atom Count: 10
• Complexity: 178

Purity/Quality:

99%MIN, ^*data from raw suppliers

1,2-Dicyanobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-23/24/25
• Safety Statements: 36/37/39-45-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC=C(C(=C1)C#N)C#N
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may cause effects on the central nervous system.
• uses: Phthalonitrile is used as a starting material for producing phthalocyanine pigments (→ Phthalocyanines), fluorescent brightners, and photographic sensitizers.
• Uses: Phthalonitrile is used as an intermediate for chemical synthesis in the production of building blocks for colorants and coatings, life science and agricultural chemicals.?And also used as a precursor to phthalocyanine and other pigments, fluorescent brighteners, and photographic sensitizers.

Technology Process of Phthalonitrile

There total 102 articles about Phthalonitrile 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%

2-iodobenzonitrile (4387-36-4) + potassium ferrocyanide → phthalonitrile (91-15-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 12h;

DOI:10.1016/j.tetlet.2015.12.019

Reference yield: 89.0%

o-phthalic dicarboxaldehyde (643-79-8) → phthalonitrile (91-15-6)

Guidance literature:

With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride; In 1,2-dichloro-ethane; at 20 - 50 ℃; for 16h;

DOI:10.1016/j.tetlet.2019.04.043

Reference yield: 89.0%

potassiumhexacyanoferrate(II) trihydrate + 1-Bromo-2-iodobenzene (583-55-1) → phthalonitrile (91-15-6)

Guidance literature:

With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; In N,N-dimethyl acetamide; at 120 ℃; for 3h;

DOI:10.1055/s-0034-1379899

upstream raw materials:

phthalic anhydride

phthalimide

phthalamide

o-cyanobenzamide

Downstream raw materials:

isoindoline-1,3-dione-(4-chloro-phenylimine)-imine

1--1,3-diiminoisoindoline

6-[2-(4,6-diamino-1,3,5-triazin-2-yl)phenyl]-1,3,5-triazine-2,4-diamine

subphthalocyanine

Refernces

• 1、 Turchi, Stefania,Giomi, Donatella,Capaccioli, Caterina,Nesi, Rodolfo. "Hetero Diels-Alder reactions of 4,5-dicyanopyridazine with alkenes". . p. 11711 - 11720. Retrieved 1997.
• 2、 Heydari, Somayyeh,Habibi, Davood,Reza Faraji, Ali,keypour, Hassan,Mahmoudabadi, Masoumeh. "An overview on the progress and development on the palladium catalyzed direct cyanation". . . Retrieved 2020/10/02.
• 3、 Wang, Shengyu,Wang, Jianqiang,Pan, Junyi,Liu, Cheng,Gong, Xubin,Guo, Cheng. "Pd@CeO2-catalyzed cyanation of aryl iodides with K4Fe(CN)6·3H2O under visible light irradiation". . . Retrieved 2021/01/12.