69573-41-7

Usage

Class

Aryl-azides

Uses

a. Synthetic intermediate in the production of organic materials
b. Used in the production of pharmaceuticals
c. Used in the production of agrochemicals

Potential Applications

a. Click chemistry reactions
b. Development of new drugs and materials

Hazardous Nature

Potentially hazardous chemical

Safety Measures

Should be handled with appropriate safety measures

Upstream product

• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 24070-52-8 4-bromo-1-phenyl-1-butanone 
• 935-64-8 1-phenyl-1-cyclobutanol 
• 6249-80-5 1-phenylbut-3-en-1-one 

Downstream Products

• 700-91-4 2-phenyl-1-pyrroline 
• 357443-58-4 (4-Amino-4-phenylbutyl)carbamic acid, 1,1-dimethylethyl ester 
• 1006-64-0 2-(phenyl)pyrrolidine 
• 220929-55-5 2-(diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-oxide 
• 220929-54-4 diethyl (2-phenylpyrrolidin-2-yl)phosphonate 
• 189079-82-1 4,4-Dichloro-5-phenyl-3,4-dihydro-2H-pyrrole 
• 189079-87-6 4,4-Dibromo-5-phenyl-3,4-dihydro-2H-pyrrole 
• 885060-37-7 2-(3-azido-propyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole 
• 885060-46-8 N'-(4-azido-1-phenylbutylidene)-5-chloro-2-methylbenzohydrazide 
• 950819-68-8 4-azido-2-bromo-1-phenylbutan-1-one 

Relevant academic research and scientific papers

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.

ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS

The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.

Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins

We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.

Mild Cu-Catalyzed Oxidation of Benzylic Boronic Esters to Ketones

The oxidation of benzylic boronic esters directly to the ketone is reported. This mild Cu-catalyzed method uses an ambient atmosphere of air as the terminal oxidant and is notably chemoselective. Oxidation of the C-B bond occurs selectively, even in the presence of unprotected alcohols. Initial investigation suggests the reaction proceeds through an alkylboron to Cu transmetalation, peroxide formation, and rearrangement to give the carbonyl.

Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols

A novel and regioselective approach to carbonyl-containing alkyl chlorides via silver-catalyzed ring-opening chlorination of cycloalkanols is reported. Concurrent C(sp3)-C(sp3) bond cleavage and C(sp3)-Cl bond formation efficiently occur with good yields under mild conditions, and the chlorinated products are readily transformed into other useful synthetic intermediates and drugs. The reaction features complete regioselectivity, high efficiency, and excellent practicality. (Chemical Equation Presented).

Manganese-catalyzed oxidative azidation of cyclobutanols: Regiospecific synthesis of alkyl azides by C-C bond cleavage

A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, oth

Azido carbonyl compounds as DNA cleaving agents

Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.

Pyrazole-based sulfonamide and sulfamides as potent inhibitors of mammalian 15-lipoxygenase

A series of inhibitors of mammalian 15-lipoxygenase (15-LO) based on a 3,4,5-tri-substituted pyrazole scaffold is described. Replacement of a sulfonamide functionality in the lead series with a sulfamide group resulted in improved physicochemical properties generating analogs with enhanced inhibition in cell-based and whole blood assays.

Intramolecular H-atom abstraction in γ-azido-butyrophenones: Formation of 1,5 ketyl iminyl radicals

Photolysis of γ-azidobutyrophenone derivatives yields 1,4 ketyl biradicals via intramolecular H-atom abstraction. The 1,4 ketyl biradicals expel a nitrogen molecule to form 1,5 ketyl iminyl biradicals, which decay by ring closure to form a new carbon-nitr

MITOTIC KINESIN INHIBITORS AND METHODS OF USE THEREOF

This invention relates to inhibitors of mitotic kinesins, particularly KSP, and methods for producing these inhibitors. The invention also provides pharmaceutical compositions comprising the inhibitors of the invention and methods of utilizing the inhibitors and pharmaceutical compositions in the treatment of various disorders.