Terephthalonitrile

Base Information

• Chemical Name: Terephthalonitrile
• CAS No.: 623-26-7
• Molecular Formula: C8H4N2
• Molecular Weight: 128.133
• Hs Code.: 29269095
• European Community (EC) Number: 210-783-2
• NSC Number: 144977,78439
• UNII: E6ITH5CIS3
• DSSTox Substance ID: DTXSID1060768
• Nikkaji Number: J2.091E
• Wikipedia: 1,4-Dicyanobenzene
• Wikidata: Q72468565
• ChEMBL ID: CHEMBL3248224
• Mol file: 623-26-7.mol

Synonyms:1,4-dicyanobenzene

Chemical Property of Terephthalonitrile

Chemical Property:

• Appearance/Colour: biege powder
• Vapor Pressure: 0.00217mmHg at 25°C
• Melting Point: 221-225 °C(lit.)
• Refractive Index: 1.565
• Boiling Point: 289.6 °C at 760 mmHg
• Flash Point: 142.8 °C
• PSA: 47.58000
• Density: 1.164 g/cm³
• LogP: 1.42996
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• Water Solubility.: 0.08 g/L (23 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.037448136
• Heavy Atom Count: 10
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

1,4-Dicyanobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC(=CC=C1C#N)C#N
• Uses: 1,4-dicyanobenzene as a new internal standard in utilizing solid-state infrared intensity methods for the determination of thiocyanate bonding. Used as photosensitizer in [2+2] cycloadditions, nitrile building block.

Technology Process of Terephthalonitrile

There total 281 articles about Terephthalonitrile 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: 56.0%

trimethylsilyl cyanide (7677-24-9) + 1,4-bromoiodobenzene (589-87-7) → terephthalonitrile (623-26-7) + 4-bromobenzenecarbonitrile (623-00-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; for 24h; Heating;

DOI:10.1021/jo00374a041

Reference yield: 54.0%

(4-bromo-phenyl)-phenylsulfanyl-diazene (52599-10-7) → terephthalonitrile (623-26-7) + 1,4-bis(phenylthio)benzene (3459-94-7) + phenyl(4-bromophenyl)sulfide (65662-88-6) + 4-(phenylthio)benzonitrile (51238-46-1)

Guidance literature:

With tetra-n-butylammonium cyanide; In dimethyl sulfoxide; at 25 ℃; for 1h; Irradiation;

DOI:10.1016/S0040-4020(01)86905-2

Reference yield: 53.0%

(4-bromo-phenyl)-phenylsulfanyl-diazene (52599-10-7) + tetra-n-butylammonium cyanide (10442-39-4) → terephthalonitrile (623-26-7) + 1,4-bis(phenylthio)benzene (3459-94-7) + phenyl(4-bromophenyl)sulfide (65662-88-6) + 4-(phenylthio)benzonitrile (51238-46-1)

Guidance literature:

With tetra-n-butylammonium cyanide; In dimethyl sulfoxide; at 25 ℃; for 1h; Irradiation;

DOI:10.1016/S0040-4020(01)86905-2

upstream raw materials:

benzenesulfonamide

terephthalic acid

para-dichlorobenzene

hydrogen cyanide

Downstream raw materials:

1,4-Diacetylbenzene

5-(4-cyanophenyl)tetrazole

4-cyanobenzamide

terephthalamide

Refernces

• 1、 Nakamura. "". . p. 1019,1020, 1022, 1023. Retrieved 1967.
• 2、 Amatore, Christian,Combellas, Catherine,Robveille, Sabine,Saveant, Jean-Michel,Thiebault, Andre. "Electrochemically Catalyzed Aromatic Nucleophilic Substitution. Reactivity of Cyanide Ions toward Aryl Radicals in Liquid Ammonia". . p. 4754 - 4760. Retrieved 1986.
• 3、 Chen, Haiqun,Huynh, Han Vinh,Liu, Ziwei,Lu, Yuchen,Meng, Qi,Teng, Qiaoqiao,Yuan, Dan,Zhao, Yaru. "Synthesis, Characterization, and Catalytic Study of Caffeine-Derived N-heterocyclic Carbene Palladium Complexes". . p. 161 - 168. Retrieved 2022/02/07.
• 4、 Sakurai, Shun,Tobisu, Mamoru. "Palladium-catalyzed decarbonylative cyanation of acyl fluorides and chlorides". supporting information. . Retrieved 2021/01/25.