84702-73-8

Basic information

• Product Name: 5-azidopentan-2-one
• Synonyms: 5-azidopentan-2-one
• CAS NO: 84702-73-8
• Molecular Weight: 127.146
• Mol File: 84702-73-8.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 5-azidopentan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-azidopentan-2-one(84702-73-8)
• EPA Substance Registry System: 5-azidopentan-2-one(84702-73-8)

Safety Data

• Hazardous Substances Data: 84702-73-8(Hazardous Substances Data)

Upstream product

• 5891-21-4 5-chloro-2-pentanone 
• 13483-31-3 Acetone dimethylhydrazone 
• 42059-30-3 1-azido-2-iodoethane 
• 3884-71-7 bromo-5-pentanone-2 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 

Downstream Products

• 186303-33-3 1-(R)-(3.4-dihydroxyphenyl)-2-(1-methyl-4-azidobutylamino)ethanol oxalate salt 
• 113738-73-1 Cyclohexyl-[3-(2-methyl-[1,3]dithiolan-2-yl)-propyl]-amine; hydrochloride 
• 872-32-2 2-methyl-1H-pyrroline 

Relevant articles and documents

Convenient Cyclopentadiene Modifications for Building Versatile (Radio-)Metal Cyclopentadienyl Frameworks

The synthesis of a bifunctional cyclopentadiene-based building block, bearing an alkyl linker with a terminal chloride and an ester group is described. This building block was modified by nucleophilic substitution, leading to two new fac-[Re(CO)3]+ containing derivatives of known drug candidates for brain imaging and multi-drug resistance in cancer in as few as two steps. Furthermore, the chloride was replaced by an azide, which was subsequently coupled to phenylacetylene as a model alkyne to demonstrate its versatility for undergoing Click-type reactions. The resulting triazole was labelled with 99mTc to yield the corresponding piano-stool complex in a radiochemical purity of 86 %. The identities were confirmed by coinjection with the Re homologue.

Synthesis of Pyrrolidines by a Csp3-Csp3/Csp3-N Transition-Metal-Free Domino Reaction of Boronic Acids with γ-Azido-N-Tosylhydrazones

The reaction between γ-azido-N-tosylhydrazones and boronic acids leads to the obtention of 2,2-disubstituted pyrrolidines in a domino process that includes 1) diazoalkane formation, 2) intermolecular carboborylation of the diazocompound, and 3) intramolecular carborylation of the azide, and comprises the formation of a Csp3?Csp3 and a Csp3?N bonds on the same carbon atom. The reaction proceeds without the need of any transition-metal catalyst under microwave activation and features wide scope in both reaction partners. It can be applied to both alkyl and arylboronic acids with equal efficiency. With N-tosylhydrazones derived from 2-(2-azidoethyl)-cyclopentanone and cyclohexanone the reactions are highly diastereoselective leading to the cis-fused bicyclic systems as unique diastereoisomers. The scope of the process is illustrated by over sixty examples, including scaffolds present in natural alkaloids, and the mechanistic proposal is suppported by DFT-based computations.

A tandem reaction of 4-bromoalkyl aldehydes with sodium azide: Synthesis of 5,6,7,7a-tetrahydro-pyrrolo[1,2-d]-[1.2.3.4]oxatriazole

5,6,7,7a-Tetrahydro-pyrrolo[1,2-d]-[1.2.3.4]oxatriazoles were synthesized through a nucleophilic substitution-cycloaddition tandem reaction of 4-bromoalkyl aldehydes with sodium azide.