622-79-7

Usage

Uses

Used in Chemical Synthesis:
BENZYL AZIDE is used as a reagent for the synthesis of stable 1,2,3-triazole derivatives. It plays a crucial role in introducing a PhCH2N group into a molecule, which is essential for the formation of these derivatives.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BENZYL AZIDE is used as a key intermediate in the synthesis of various biologically active compounds. Its ability to form stable 1,2,3-triazole derivatives makes it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Material Science:
BENZYL AZIDE is also employed in the field of material science, where it is used to synthesize novel materials with unique properties. The introduction of the PhCH2N group into a molecule can lead to the development of new materials with enhanced characteristics, such as improved stability or reactivity.

Synthesis Reference(s)

Tetrahedron Letters, 16, p. 471, 1975 DOI: 10.1016/S0040-4039(00)71896-XJournal of the American Chemical Society, 91, p. 4323, 1969 DOI: 10.1021/ja01043a071

Safety Profile

A heat-sensitive explosive.Explosive reaction with bis(trifluoromethyl)nitroxide.Upon decomposition it emits toxic fumes of NOx. Seealso AZIDES.

Synthesis

Sodium azide (3.58 g, 55.0 mmol) was added to DMSO (120 mL) and stirred vigorously until fully dissolved. Benzyl bromide 168 (6.54 mL, 55 mmol) was added. The reaction mixture was stirred at RT overnight. The colourless liquid was worked up with water (100 mL), and extracted with diethyl ether (3 x 100 mL). The extractions were washed with water (2 x 80 mL) and brine (80 mL). The ether layer was dried over MgSO4 and after filtration, it was evaporated to dryness, giving benzyl azide 73 as a colourless oil (6.9 g, 51.8 mmol, 94%): IR (neat) νm a x / cm– 1 3455, 3028, 2970, 2946, 2093, 1605, 1586, 1496, 1454, 1349, 1252; 1H NMR (400 MHz, CDCl 3 ) δ 7.44 – 7.28 (m, 5H), 4.33 (s, 2H); 1 3C NMR (100 MHz, CDCl 3 ) δ 135.55, 129.05, 128.52, 128.44, 55.00.

InChI:InChI=1/C7H8N3/c8-10-9-6-7-4-2-1-3-5-7/h1-5,8H,6H2/q+1

Upstream product

• 100-44-7 benzyl chloride 
• 620-05-3 iodomethylbenzene 
• 108-88-3 toluene 
• 4648-54-8 trimethylsilylazide 
• 100-39-0 benzyl bromide 
• 97325-73-0 1-Benzyl-4-methyl-5-phenyl-4,5-dihydro-1H-tetrazole 
• 86816-07-1 4-benzyloxytetrachloropyridine 
• 7664-93-9 sulfuric acid 
• 1924-84-1 1-nitroso-1-phenylmethyl-hydrazine 
• 3012-37-1 benzyl thiocyanate 
• 14642-79-6 benzyloxy-trimethylsilane 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 17122-97-3 (diazidomethyl)benzene 

Downstream Products

• 124940-34-7 1-(phenylmethyl)-1H-1,2,3-triazole-4-carboxaldehyde 
• 74649-49-3 N-benzyl-N'-methyl-triazene 
• 122239-52-5 1,3'-dibenzyl-5,5'-bis-(1-hydroxy-cyclohexyl)-1H,3'H-[4,4']bi[1,2,3]triazolyl 
• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 780-25-6 N-benzylidene benzylamine 
• 642-04-6 2,3,5,6-tetraphenylpyrazine 
• 17683-10-2 benzylphenyltriazene 
• 100-46-9 benzylamine 
• 32515-07-4 1-benzyl-4-phenyl-1H-1,2,3-triazol-5-amine 
• 108842-69-9 1-benzyl-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid 
• 83027-66-1 (1-benzyl-1H-[1,2,3]triazol-4-yl)-cyclohexylmethanol 
• 28798-81-4 (1-benzyl-[1,2,3]triazol-4-yl)methanol 
• 25784-56-9 4-amino-3-benzyl-1,2,3-triazole-5-carboxylic acid 
• 108717-96-0 1-benzyl-4-phenyl-1H-[1,2,3]triazole 

Relevant academic research and scientific papers

Mutagenicity of alkyl azides

Alkyl azides showed mutagenicity for S. typhimurium TA100 strain with S9 mix. However, no significant activity was observed for TA98 either with or without S9 mix or for TA100 without S9 mix. On the other hand, 3-azido-1,2- propanediol showed the enantios

Measurement and correlation of the solubility of (1-benzyl-1H-1,2,3-triazole-4-yl)methanol in water and alcohols at temperatures from 292.15 K to 310.15 K

The solubilities of (1-benzyl-1H-1,2,3-triazole-4-yl)methanol (BTZM) in water, methanol, ethanol, n-propanol, isopropanol, and n-butanol were measured at temperatures ranging from 292.15 K to 310.15 K by a dynamic method under normal atmospheric pressure. The results showed that it increased with the increasing temperature and the order of solvents was: Order: Methanol > ethanol > n-propanol > n-butanol > isopropanol > water except three points. The solubility data were correlated with the Van't Hoff equation, modified Apelblat equation, and λh equation. The average relative deviations (ARD) were 1.87%, 1.53%, and 1.71%, and the root-mean-square-deviations (RMSD) were 2.37 × 10-2, 1.51 × 10-2, and 2.12 × 10-2, respectively. It was found that the modified Apelblat equation gave the best correlation results. Furthermore, the dissolution enthalpy of BTZM was calculated by the modified Apelblat equation.

Combinatorial synthesis of new fluorescent scaffolds using click chemistry

Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.

Click generated o-Cresolphthalein linked 1,2,3-triazole derivative for selective Pb(II) ion recognition

Present report describes the “turn-on” absorbance response of a molecular assembly o-Cresolphthalein appended 1,4-disubstituted 1,2,3-triazole (o-CPT) on complexation with Pb(II) ions. Copper (I) catalyzed alkyne-azide cycloaddition reaction, a highly versatile and stereoselective approach to stitch diverse structural units has been employed to generate the designed receptor that has been successfully characterized through IR, NMR (1H, 13C) and mass spectroscopic techniques. UV-Visible absorption spectral behavior of o-CPT was examined with a series of metal ions (Mn (II), Ce (III), Hg (II), Ni (II), Pb (II), Zn (II), Fe (II), Cr (III), Co (II) and Na (I)) in acetonitrile-water (4:1, v/v) solution and the results obtained have marked out the sensitivity of the designed probe exclusively towards Pb(II) ions with a measured detection limit of 13 μM at 2:1 stoichiometry of o-CPT:Pb(II) complex.

Alkylphosphinites as Synthons for Stabilized Carbocations

We present a new acid-free method for the generation of carbocations based on a redox condensation reaction that enables SN1 reactions with a variety of nucleophiles. We utilize readily synthesized phosphinites that are activated by diisopropyl azodicarboxylate to form betaine structures that collapse upon adding a pronucleophile, thereby yielding reactive carbocation intermediates. We also employ this approach for the alkylation of some bioactive molecules.

Concise synthesis of: N -phosphorylated amides through three-component reactions

N-Phosphorylated amides continue to be an unparalleled asset for the development of pharmaceutical molecules, and the importance of this framework has inspired researchers to look for concise and efficient methods for the synthesis of this unit. In this work, a new strategy was developed in which a one-pot synthesis of N-phosphorylated amides was achieved by a three-component reaction with carboxylic acids, phosphorus chlorides and azides under mild reaction conditions. To our knowledge, this is the first study in which this framework was constructed through a multicomponent reaction, which is innovative, efficient and economical. This journal is

NOVEL DIBENZOOXAPHOSPHININE OXIDE DERIVATIVE COMPOUNDS AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DEGENERATIVE DISEASE COMPRISING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a novel dibenzooxininin oxide derivative compound having various nitrogen-containing substituents introduced at 6-position of a dibenzooxaphosphorin oxide mononuclear, and to the use thereof. The present invention relates to a pharmaceutical composition for preventing or treating degenerative diseases and a health supplement food composition for preventing or treating degenerative diseases, comprising the dibenzooxaphosphorin oxide derivative compound of the present invention.

Synthesis, biological evaluation and molecular docking studies of novel 1,2,3-triazole-quinazolines as antiproliferative agents displaying ERK inhibitory activity

ERK1/2 inhibitors have attracted special attention concerning the ability of circumventing cases of innate or log-term acquired resistance to RAF and MEK kinase inhibitors. Based on the 4-aminoquinazoline pharmacophore of kinases, herein we describe the synthesis of 4-aminoquinazoline derivatives bearing a 1,2,3-triazole stable core to bridge different aromatic and heterocyclic rings using copper-catalysed azide-alkyne cycloaddition reaction (CuAAC) as a Click Chemistry strategy. The initial screening of twelve derivatives in tumoral cells (CAL-27, HN13, HGC-27, and BT-20) revealed that the most active in BT-20 cells (25a, IC50 24.6 μM and a SI of 3.25) contains a more polar side chain (sulfone). Furthermore, compound 25a promoted a significant release of lactate dehydrogenase (LDH), suggesting the induction of cell death by necrosis. In addition, this compound induced G0/G1 stalling in BT-20 cells, which was accompanied by a decrease in the S phase. Western blot analysis of the levels of p-STAT3, p-ERK, PARP, p53 and cleaved caspase-3 revealed p-ERK1/2 and p-STA3 were drastically decreased in BT-20 cells under 25a incubation, suggesting the involvement of these two kinases in the mechanisms underlying 25a-induced cell cycle arrest, besides loss of proliferation and viability of the breast cancer cell. Molecular docking simulations using the ERK-ulixertinib crystallographic complex showed compound 25a could potentially compete with ATP for binding to ERK in a slightly higher affinity than the reference ERK1/2 inhibitor. Further in silico analyses showed comparable toxicity and pharmacokinetic profiles for compound 25a in relation to ulixertinib.

N-pyridine-4-yl-benzamide Cdc37 inhibitor as well as derivative and application thereof

The invention discloses an N-pyridine-4-yl-benzamide Cdc37 inhibitor with a structure as shown in a general formula (I) as well as a derivative and application thereof. The compound disclosed by the invention can inhibit Cdc37 protein and downstream custo

Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.