4-(2H-tetrazol-5-yl)benzonitrile

Base Information

• Chemical Name: 4-(2H-tetrazol-5-yl)benzonitrile
• CAS No.: 14389-10-7
• Molecular Formula: C8H5N5
• Molecular Weight: 171.161
• Hs Code.: 2933990090
• NSC Number: 338082
• DSSTox Substance ID: DTXSID10318926
• Nikkaji Number: J466.645C
• Wikidata: Q82075081
• Mol file: 14389-10-7.mol

Synonyms:14389-10-7;4-(2H-tetrazol-5-yl)benzonitrile;4-(2H-TETRAZOL-5-YL)-BENZONITRILE;NSC 338082;Benzonitrile, 4-(2H-tetrazol-5-yl)-;NSC338082;Benzonitrile,4-(2H-tetrazol-5-yl)-;SCHEMBL4402319;SCHEMBL9985391;DTXSID10318926;5-(4-Cyanophenyl)-1H-tetrazole;4-(1h-tetrazol-5-yl)benzonitrile;4-(1H-Tetrazole-5-yl)benzonitrile;AKOS006280355;AB23777;NSC-338082;FT-0725798;4-(1H-1,2,3,4-tetrazol-5-yl)benzonitrile;4-(2H-1,2,3,4-tetrazol-5-yl)benzonitrile;A808128;Z1198168683

Chemical Property of 4-(2H-tetrazol-5-yl)benzonitrile

Chemical Property:

• Vapor Pressure: 3.49E-07mmHg at 25°C
• Melting Point: 258-260 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Refractive Index: 1.651
• Boiling Point: 417.6 °C at 760 mmHg
• PKA: 3.52±0.10(Predicted)
• Flash Point: 137.6 °C
• PSA: 78.25000
• Density: 1.44 g/cm³
• LogP: 0.73838
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 171.05449518
• Heavy Atom Count: 13
• Complexity: 212

Purity/Quality:

98%min ^*data from raw suppliers

4-(2H-Tetrazol-5-yl)-benzonitrile 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)C2=NNN=N2

Technology Process of 4-(2H-tetrazol-5-yl)benzonitrile

There total 18 articles about 4-(2H-tetrazol-5-yl)benzonitrile 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: 100.0%

terephthalonitrile (623-26-7) → 5-(4-cyanophenyl)tetrazole (14389-10-7)

Guidance literature:

With sodium azide; copper(II) sulfate; In dimethyl sulfoxide; at 140 ℃; for 0.5h;

DOI:10.1590/S0103-50532013005000005

Reference yield: 97.0%

4-Cyanobenzyl alcohol (874-89-5) → 5-(4-cyanophenyl)tetrazole (14389-10-7)

Guidance literature:

With sodium azide; hydroxylamine hydrochloride; In water; at 20 ℃; for 3h;

DOI:10.1016/j.mcat.2020.111311

Reference yield: 97.0%

4-cyanobenzaldehyde oxime (52707-54-7,52707-59-2,64847-77-4) → 5-(4-cyanophenyl)tetrazole (14389-10-7)

Guidance literature:

With sodium azide; hydroxylamine hydrochloride; In water; at 70 ℃; for 5.33333h; Green chemistry;

DOI:10.1002/aoc.5273

upstream raw materials:

terephthalonitrile

4-cyanobenzaldehyde oxime

4-cyanobenzaldehyde

4-bromobenzenecarbonitrile

Downstream raw materials:

2-(4-pentenyl)-5-(p-cyanophenyl)tetrazole

2-(1'-iodopropyn-3'-yl)-5-(p-cyanophenyl)tetrazole

rac-(cyclopentadienyl)Fe(carbonyl)(P(OCH₃)3)(N₄CC₆H₄CN)

[(C₅H₅)(CO)(P(OCH₃)3)Fe(N₄CC₆H₄CN)Fe(CO)(P(OCH₃)3)(C₅H₅)]⁽¹⁺⁾*O₃SCF₃^(1-)=[(N₄CC₆H₄CN)(Fe(CO)(P(OCH₃)3)(C₅H₅))2]O₃SCF₃

Refernces

• 1、 Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash. "First report of the direct supporting of palladium–arginine complex on boehmite nanoparticles and application in the synthesis of 5-substituted tetrazoles". . . Retrieved 2017.
• 2、 Ghorbani-Choghamarani, Arash,Moradi, Parisa,Tahmasbi, Bahman. "Ni-S-methylisothiourea complexes supported on boehmite nanoparticles and their application in the synthesis of 5-substituted tetrazoles". . p. 56638 - 56646. Retrieved 2016.
• 3、 Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash,Moradi, Parisa. "Palladium fabricated on boehmite as an organic-inorganic hybrid nanocatalyst for C-C cross coupling and homoselective cycloaddition reactions". . p. 3717 - 3727. Retrieved 2020.
• 4、 Azadi, Gouhar,Ghorbani-Choghamarani, Arash,Shiri, Lotfi. "Copper(II) immobilized on Fe3O4@SiO2@l-Histidine: a reusable nanocatalyst and its application in the synthesis of 5-substituted 1H-tetrazoles". . p. 131 - 136. Retrieved 2017.
• 5、 Chermahini, Alireza Najafi,Teimouri, Abbas,Moaddeli, Ali. "Simple and efficient synthesis of 5-substituted 1-H-tetrazoles using metal-modified clay catalysts". . p. 168 - 173. Retrieved 2011.
• 6、 Fatahi, Hosna,Jafarzadeh, Mohammad,Pourmanouchehri, Zahra. "Synthesis of α-Aminonitriles and 5-Substituted 1H-Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES-supported Trifluoroacetic Acid". . p. 2090 - 2098. Retrieved 2019.
• 7、 Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Ghobadi, Massoud,Massahi, Shokofeh. "Pd-SBT@MCM-41: As an efficient, stable and recyclable organometallic catalyst for C-C coupling reactions and synthesis of 5-substituted tetrazoles". . . Retrieved 2017.
• 8、 Zarghani, Monireh,Akhlaghinia, Batool. "Magnetically separable Fe3O4@chitin as an eco-friendly nanocatalyst with high efficiency for green synthesis of 5-substituted-1H-tetrazoles under solvent-free conditions". . p. 31850 - 31860. Retrieved 2016.
• 9、 Ishihara, Kotaro,Kawashima, Mayumi,Shioiri, Takayuki,Matsugi, Masato. "Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Using Diphenyl Phosphorazidate". . p. 2225 - 2228. Retrieved 2016.
• 10、 Nasani, Rajendar,Saha, Manideepa,Mobin, Shaikh M.,Mukhopadhyay, Suman. "Microwave synthesis of mono- and bis-tetrazolato complexes via 1,3-dipolar cycloaddition of organonitriles with nickel(II)-bound azides: Isolation of 5-substituted tetrazoles from parent complex". . p. 24 - 36. Retrieved 2013.