Benzyl azide

Base Information

• Chemical Name: Benzyl azide
• CAS No.: 622-79-7
• Molecular Formula: C7H7 N3
• Molecular Weight: 133.153
• Hs Code.: 2929909090
• European Community (EC) Number: 680-691-9
• NSC Number: 26304
• UNII: HFD57Z7J9J
• DSSTox Substance ID: DTXSID90211244
• Nikkaji Number: J54.457D
• Wikidata: Q13438697
• ChEMBL ID: CHEMBL3236190
• Mol file: 622-79-7.mol

Synonyms:Benzyl azide;(Azidomethyl)benzene;622-79-7;Benzylazide;Benzene, (azidomethyl)-;azidomethylbenzene;alpha-Azidotoluene;Toluene, .alpha.-azido-;Benzene, azidomethyl-;Benzyl Azide, Pract.;Triazotoluene;azidomethyl-benzene;NSC 26304;.alpha.-Azidotoluene;CCRIS 8029;UNII-HFD57Z7J9J;TOLUENE, alpha-AZIDO-;BRN 1907583;HFD57Z7J9J;CHEMBL3236190;MFCD00013836;NSC-26304;4-05-00-00877 (Beilstein Handbook Reference);a-Azidotoluene;(azidomethyl) benzene;Toluene, alpha-triazo-;Bn-N3;WLN: NNNR B1;(Azidomethyl)benzene, Pract.;LCZC2717;SCHEMBL13437571;Benzene, (azidomethyl)- (9CI);DTXSID90211244;AMY19781;NSC26304;BDBM50573332;STL192368;AKOS005166902;FS-5590;LS-154017;FT-0604862;EN300-82312;10.14272/UDLLFLQFQMACJB-UHFFFAOYSA-N.1;doi:10.14272/UDLLFLQFQMACJB-UHFFFAOYSA-N.1;Q13438697;F1905-6985

Chemical Property of Benzyl azide

Chemical Property:

• Melting Point: 157℃
• Refractive Index: 1.5341
• Boiling Point: 81-83°C 16mm
• Flash Point: 82-85°C/16mm
• PSA: 49.75000
• Density: 1.0655
• LogP: 1.94966
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in waterMiscible with ethanol and diethyl ether. Immiscible with water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 133.063997236
• Heavy Atom Count: 10
• Complexity: 132

Purity/Quality:

97% ^*data from raw suppliers

Benzyl azide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 2-11-48/20/21/22-40
• Safety Statements: 15-17-33-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN=[N+]=[N-]
• General Description: Benzyl azide is a versatile reagent used in azide-alkyne cycloaddition reactions, such as the iridium-catalyzed synthesis of fully substituted 1,2,3-triazoles from internal thioalkynes, where it demonstrates high efficiency and regioselectivity under mild conditions. It also serves as a substrate in p-toluenesulfonic acid-mediated cycloadditions with nitroolefins, yielding 1,2,3-triazole derivatives, though structural corrections in product identification highlight the need for careful characterization in such reactions. Its compatibility with various functional groups and solvents makes it valuable in organic synthesis and materials science.

Technology Process of Benzyl azide

There total 66 articles about Benzyl azide 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%

benzyl chloride (100-44-7) → benzyl azide (622-79-7)

Guidance literature:

With azide ion; highly branchedpolyacrylamide-APTMAI; In water; toluene; at 20 - 70 ℃; for 0.5h;

DOI:10.1007/s13738-012-0214-0

Reference yield: 100.0%

benzyl mesylate (55791-06-5) → benzyl azide (622-79-7)

Guidance literature:

With sodium azide; In DMF (N,N-dimethyl-formamide); for 12h;

Reference yield: 100.0%

benzyl bromide (100-39-0) → benzyl azide (622-79-7)

Guidance literature:

With sodium azide; In various solvent(s); for 168h; Ambient temperature;

DOI:10.1021/ja00202a034

upstream raw materials:

benzyl chloride

iodomethylbenzene

toluene

benzylamine

Downstream raw materials:

1-(phenylmethyl)-1H-1,2,3-triazole-4-carboxaldehyde

N-benzyl-N'-methyl-triazene

1,3'-dibenzyl-5,5'-bis-(1-hydroxy-cyclohexyl)-1H,3'H-[4,4']bi[1,2,3]triazolyl

2,4,6-triphenyl-1,3,5-triazine

Refernces

Iridium-catalyzed intermolecular azide-alkyne cycloaddition of internal thioalkynes under mild conditions

10.1002/anie.201309855

This research presents the first iridium-catalyzed azide-alkyne cycloaddition (IrAAC) of electron-rich internal thioalkynes, aiming to develop a mild and efficient method for synthesizing fully substituted 1,2,3-triazoles. The study demonstrates that using [{Ir(cod)Cl}2] as a catalyst allows for high efficiency and regioselectivity under mild conditions, compatible with various solvents and functional groups. The process successfully utilizes thioalkynes and azides, such as benzyl azide, in dichloromethane solvent, yielding triazole products with excellent yields. The findings highlight the advantages of IrAAC over traditional copper- and ruthenium-catalyzed methods, paving the way for broader applications in organic synthesis and materials science.

Erratum: Correction to p -toluenesulfonic acid mediated 1,3-dipolar cycloaddition of nitroolefins with NaN₃ for synthesis of 4-Aryl- NH -1,2,3-triazoles (Organic Letters (2014) 16:21 (5728-5731) DOI: 10.1021/ol5027975)

10.1021/ol503621y

The research aimed to correct an error in the previously reported synthesis of 4-aryl-NH1,2,3-triazoles. The original manuscript incorrectly identified compound 4a as 1-benzyl-4-phenyl-1,2,3-triazole, but upon re-examination of the NMR data, it was corrected to 1-benzyl-5-phenyl-1,2,3-triazole. The study concluded that the p-TsOH-mediated cycloaddition process was effective, yielding 1-benzyl-5-phenyl-1,2,3-triazole 4a in 60% yield when benzyl azide was used as the substrate. The authors apologized for the mistakes and provided corrected supporting information, including revised structure and X-ray data (CIF) for compound 4a.