129575-56-0

Basic information

• Product Name: (R)-α-methylbenzyl azide
• Synonyms: (R)-α-methylbenzyl azide
• CAS NO: 129575-56-0
• Molecular Weight: 147.18
• Mol File: 129575-56-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (R)-α-methylbenzyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-α-methylbenzyl azide(129575-56-0)
• EPA Substance Registry System: (R)-α-methylbenzyl azide(129575-56-0)

Safety Data

• Hazardous Substances Data: 129575-56-0(Hazardous Substances Data)

Upstream product

• 3756-41-0 (S)-(1-chloroethyl)benzene 
• 92543-26-5 (S)-(-)-Phpophorsaeure-diethylester-(1-phenylethylester) 
• 209863-91-2 (S)-N,N-1,2-benzenedisulfonyl-1-phenylethylamine 
• 32366-25-9 1-azidoethylbenzene 
• 536-74-3 phenylacetylene 
• 1517-69-7 (R)-1-phenylethanol 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 492-37-5 hydratropic acid 
• 33122-25-7 tert-butyl 2-phenylpropaneperoxoate 
• 25236-63-9 1-phenylethyl mesylate 
• 1445-91-6 (S)-1-phenylethanol 
• 98-85-1 1-Phenylethanol 

Downstream Products

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 1198399-51-7 C₁₉H₂₈N₄O₂ 
• 1198399-49-3 C₂₃H₂₈N₄O₂ 
• 1255942-91-6 tert-butyl (S)-4-methyl-1-oxo-1-((1-((R)-1-phenylethyl)-1H-1,2,3-triazol-4-yl)methylamino)pentan-2-ylcarbamate 
• 1277179-78-8 (2S,3R)-2-ethyl 3-methyl 1-((R)-1-phenylethyl)aziridine-2,3-dicarboxylate 
• 1277179-82-4 C₁₅H₁₉N₃O₄ 
• 1277179-83-5 C₁₅H₁₉N₃O₄ 
• 1277179-79-9 (2R,3S)-2-ethyl 3-methyl 1-((R)-1-phenylethyl)aziridine-2,3-dicarboxylate 
• 1277179-85-7 C₁₅H₁₉N₃O₄ 
• 1277179-84-6 C₁₅H₁₉N₃O₄ 
• 1277179-77-7 C₁₅H₁₉N₃O₄ 
• 1277179-75-5 C₁₅H₁₉N₃O₄ 
• 1277179-74-4 C₁₅H₁₉N₃O₄ 
• 1277179-76-6 C₁₅H₁₉N₃O₄ 

Relevant articles and documents

A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm

A facile and efficient method for one-pot conversion of alcohols into azides using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of NaN3, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DMF affording the corresponding alkyl azides in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1° > 2° > 3°.

Iron-Catalyzed Asymmetric Decarboxylative Azidation

The first iron-catalyzed asymmetric azidation of benzylic peresters has been reported with trimethylsilyl azide (TMSN3) as the azido source. Hydrocarbon radicals that lack of strong interactions were capable to be enantioselectively azidated. The reaction features good functional group tolerance, high yields, and mild conditions. The chiral benzylic azides can further be used in click reaction, phosphoramidation, and reductive amination, which demonstrate the synthetic values of this reaction.

Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: Synthesis of 4-haloisoxazoles and 5-halotriazoles

(Cyclopentadienyl)(cyclooctadiene) ruthenium(II) chloride [CpRuCl(cod)] catalyzes the reaction between nitrile oxides and electronically deficient 1-choro-, 1-bromo-, and 1-iodoalkynes leading to 4-haloisoxazoles. Organic azides are also suitable 1,3-dipoles, resulting in 5-halo-1,2,3-triazoles. These air-tolerant reactions can be performed at room temperature with 1.25 equivalents of the respective 1,3-dipole relative to the alkyne component. Reactive 1-haloalkynes include propiolic amides, esters, ketones, and phosphonates. Post-functionalization of the halogenated azole products can be accomplished by using palladium-catalyzed cross-coupling reactions and by manipulation of reactive amide groups. The lack of catalysis observed with [Cp RuCl(cod)] (Cp=pentamethylcyclopentadienyl) is attributed to steric demands of the Cp* (η5-C5Me5) ligand in comparison to the parent Cp (η5-C5H5). This hypothesis is supported by the poor reactivity of [(η5-C 5Me4CF3)RuCl(cod)], which serves as a an isosteric mimic of Cp* and as an isoelectronic analogue of Cp.

A Lewis acid mediated schmidt reaction of benzylic azide: Synthesis of sterically crowded aromatic tertiary amines

An efficient one-pot synthesis of sterically hindered aromatic tertiary amines through Lewis acid induced intermolecular Schmidt reaction of benzylic azides is described. In the presence of EtAlCl2, benzylic azide underwent a smooth Schmidt reaction to give the corresponding iminium ion, which, upon reduction with NaBH4 in situ, afforded the tertiary amine. The effects of substituents on the aromatic ring and the steric effects of the alkyl side chain have also been studied.