622-79-7

Basic information

• Product Name: BENZYL AZIDE
• Synonyms: triazotoluene;(Azidomethyl)benzene, Pract.;Benzylazide 98%;Phenylmethyl Azide;benzyl(diazonio)azanide;diazonio(phenylmethyl)azanide;NSC 26304;α-Azidotoluene
• CAS NO: 622-79-7
• Molecular Formula: C₇H₇N₃
• Molecular Weight: 133.15
• Mol File: 622-79-7.mol
• Article Data: 287

Chemical Properties

• Melting Point: 157℃
• Boiling Point: 81-83°C 16mm
• Flash Point: 82-85°C/16mm
• Appearance: /
• Density: 1.0655
• Refractive Index: 1.5341
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in waterMiscible with ethanol and diethyl ether. Immiscible with water.
• BRN: 636825
• CAS DataBase Reference: BENZYL AZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL AZIDE(622-79-7)
• EPA Substance Registry System: BENZYL AZIDE(622-79-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 2-11-48/20/21/22-40
• Safety Statements: 15-17-33-36/37
• RIDADR: 1993
• WGK Germany: 3
• RTECS: XS6650000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 622-79-7(Hazardous Substances Data)

Usage

Description

BENZYL AZIDE is an aromatic azide compound, which is generally utilized in copper(I)-catalyzed azide-alkyne cycloaddition reactions. It is known for its ability to introduce a PhCH2N group into a molecule, making it a valuable reagent in chemical synthesis.

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 
• 86816-07-1 4-benzyloxytetrachloropyridine 
• 112157-95-6 C₁₇H₁₇N₃O₃ 
• 57294-86-7 (E)-cinnamyl azide 
• 100-39-0 benzyl bromide 
• 536-74-3 phenylacetylene 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 53772-44-4 benzyloxydiphenylphosphine 
• 780-25-6 N-benzylidene benzylamine 
• 160732-56-9 1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 4463-42-7 benzyl boronic acid 

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 
• 28798-81-4 (1-benzyl-[1,2,3]triazol-4-yl)methanol 
• 108717-96-0 1-benzyl-4-phenyl-1H-[1,2,3]triazole 
• 51118-27-5 1-benzyl-5-phenyl-1H-1,2,3-triazole 
• 20271-33-4 1-benzyl-5-amino-1,2,3-triazole-4-carboxylic acid ethyl ester 

Relevant articles and documents

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

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.

Discovery of triazolyl thalidomide derivatives as anti-fibrosis agents

Fibrosis with excessive accumulation of extracellular matrix (ECM) often causes progressive organ dysfunction and results in many inflammatory and metabolic diseases, including systemic sclerosis, pulmonary fibrosis, advanced liver disease and advanced kidney disease. The store-operated calcium entry (SOCE) pathway and the related signaling pathway were both found to be the important routes for fibrogenesis. Our aim in this study was to discover novel compounds to inhibit fibrogenesis. A number of triazolyl thalidomide derivatives were synthesized and evaluated for their anti-fibrosis activities. Compounds 7b-e, 8c-d, 10a-b and 10e inhibited intracellular Ca2+ activation and showed no cytotoxicity. Among them, 6-{4-[(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}hexanoic acid (10e) with the most potent inhibitory effect was chosen for further examination. The results revealed that compound 10e, a SOCE inhibitor, reversed the migratory ability of TGF-β1-induced myofibroblasts, dedifferentiated myofibroblasts to fibroblasts due to cytoskeleton remodeling, and restrained myofibroblast activation by targeting Orai1 and TGF-β1/SMAD2/3 signaling pathways. The in silico study indicated that compound 10e, with the appropriate lipophilic carbon chain and carboxylic acid, showed a good drug-likeness model score. Conclusively, the SOCE inhibitor, compound 10e, is used as a promising lead compound for the development of a new treatment for fibrosis. This journal is