5-(4-chlorobenzyl)-1H-tetrazole

Base Information

• Chemical Name: 5-(4-chlorobenzyl)-1H-tetrazole
• CAS No.: 14064-61-0
• Molecular Formula: C8H7 Cl N4
• Molecular Weight: 194.623
• Hs Code.: 2933990090
• European Community (EC) Number: 664-228-8
• DSSTox Substance ID: DTXSID30352342
• Nikkaji Number: J2.204.707H
• Wikidata: Q82129421
• Mol file: 14064-61-0.mol

Synonyms:14064-61-0;5-(4-chlorobenzyl)-1H-tetrazole;5-(4-Chloro-Benzyl)-2H-Tetrazole;5-(4-chlorobenzyl)-2H-tetrazole;5-[(4-chlorophenyl)methyl]-2H-tetrazole;5-(4-Chlorobenzyl)-2H-1,2,3,4-tetraazole;5-[(4-chlorophenyl)methyl]-2H-1,2,3,4-tetrazole;2H-Tetrazole, 5-[(4-chlorophenyl)methyl]-;2H-Tetrazole,5-[(4-chlorophenyl)methyl]-;Maybridge1_004018;5-(4'-chlorobenzyl)tetrazole;5-[(4-chlorophenyl)methyl]-1H-1,2,3,4-tetrazole;SCHEMBL6505678;HMS552O14;DTXSID30352342;BBL039128;CCG-17757;MFCD00205200;STK313033;AKOS000263099;AKOS000310276;AB04761;HR-0372;CS-0240679;EU-0006997;FT-0619640;EN300-229642;SR-01000453019;SR-01000453019-1;YIE

Chemical Property of 5-(4-chlorobenzyl)-1H-tetrazole

Chemical Property:

• Vapor Pressure: 3.4E-06mmHg at 25°C
• Melting Point: 164 °C
• Boiling Point: 387°Cat760mmHg
• PKA: 4.69±0.10(Predicted)
• Flash Point: 219.9°C
• PSA: 54.46000
• Density: 1.402g/cm³
• LogP: 1.44390
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 194.0359239
• Heavy Atom Count: 13
• Complexity: 158

Purity/Quality:

98%min ^*data from raw suppliers

5-(4-chlorobenzyl)-2H-tetraazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC2=NNN=N2)Cl

Technology Process of 5-(4-chlorobenzyl)-1H-tetrazole

There total 4 articles about 5-(4-chlorobenzyl)-1H-tetrazole 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: 96.0%

p-chlorobenzyl cyanide (140-53-4) → 5-((4’-chlorophenyl)methyl)tetrazole (14064-61-0)

Guidance literature:

With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; for 24h; Reflux;

DOI:10.1016/j.bioorg.2018.04.021

Reference yield:

2-(4-chlorophenyl)acetamide (20101-92-2) → 5-((4’-chlorophenyl)methyl)tetrazole (14064-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic anhydride; triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2: sodium azide; triethylamine hydrochloride / toluene / 16 h / 110 °C / Inert atmosphere

With sodium azide; triethylamine hydrochloride; triethylamine; trifluoroacetic anhydride; In dichloromethane; toluene;

DOI:10.1021/acs.orglett.9b02633

Reference yield:

4-chlorophenylacetic Acid (1878-66-6) → 5-((4’-chlorophenyl)methyl)tetrazole (14064-61-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide; tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C

2.1: trifluoroacetic anhydride; triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

3.1: sodium azide; triethylamine hydrochloride / toluene / 16 h / 110 °C / Inert atmosphere

With sodium azide; oxalyl dichloride; triethylamine hydrochloride; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.orglett.9b02633

upstream raw materials:

p-chlorobenzyl cyanide

2-(4-chlorophenyl)acetamide

4-chlorophenylacetic Acid

Downstream raw materials:

5-(4-chlorobenzyl)-2-(4-nitrophenyl)tetrazole

5-(4-chlorobenzyl)-1-(4-nitrophenyl)tetrazole

2-(4-chlorobenzyl)-5-phenyl-1,3,4-oxadiazole

Refernces

• 1、 Khalafi-Nezhad, Ali,Mohammadi, Somayeh. "Highly efficient synthesis of 1- and 5-substituted 1H-tetrazoles using chitosan derived magnetic ionic liquid as a recyclable biopolymer-supported catalyst". . p. 4362 - 4371. Retrieved 2013.
• 2、 Nasrollahzadeh, Mahmoud,Bayat, Yadollah,Habibi, Davood,Moshaee, Saeed. "FeCl3-SiO2 as a reusable heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide". . p. 4435 - 4438. Retrieved 2009.
• 3、 Lakshmi Kantam,Shiva Kumar,Sridhar. "Nanocrystalline ZnO as an efficient heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles". . p. 1212 - 1214. Retrieved 2005.
• 4、 Wong, Jeff Y. F.,Lewandowska, Agnieszka,Trowse, Benjamin R.,Barker, Graeme. "Lithiation Substitution of Unprotected Benzyltetrazoles". supporting information. p. 7069 - 7072. Retrieved 2019/09/30.
• 5、 Bhagat, Saket B.,Telvekar, Vikas N.. "L -Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1 H -Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide". supporting information. p. 874 - 879. Retrieved 2018/02/16.