32366-25-9

Usage

Physical state

Colorless to pale yellow liquid

Odor

Sweet, floral

Uses

a. Chemical intermediate in the production of pharmaceuticals
b. Chemical intermediate in the production of dyes
c. Chemical intermediate in the production of other organic compounds
d. Potential precursor for the synthesis of azido-containing polymers and materials
e. Reagent in organic synthesis

Hazardous properties

Explosive

Safety precautions

Handle with caution due to explosive properties

InChI:InChI=1/C8H10N3/c1-7(10-11-9)8-5-3-2-4-6-8/h2-7,9H,1H3/q+1

Upstream product

• 672-65-1 (1-chloroethyl)benzene 
• 4648-54-8 trimethylsilylazide 
• 585-71-7 (1-bromoethyl)benzne 
• 93-92-5 1-phenylethyl acetate 
• 329976-80-9 potassium (1-phenylethyl)trifluoroborate 
• 4013-34-7 3-phenyl-2-oxabutane 
• 2040-37-1 benzyl 1-phenylethyl ether 
• 98-86-2 acetophenone 
• 1445-91-6 (S)-1-phenylethanol 
• 94073-86-6 (1-methoxymethoxy)ethylbenzene 
• 10604-60-1 (1-iodoethyl)benzene 
• 1524-12-5 1-phenylethyl 2,2,2-trifluoroacetate 
• 252031-74-6 tert-butyl 1-phenylethyl carbonate 
• 100-41-4 ethylbenzene 

Downstream Products

• 3480-59-9 N-(1-phenylethyl)benzamide 
• 25102-87-8 N-(α-methyl)benzylidene 1-phenylethanamine 
• 65370-31-2 bis(1-phenylethyl)methanediimine 
• 147169-48-0 (R,S)-N-(tert-butyloxycarbonyl)-α-methylbenzylamine 
• 1721-92-2 2-methyl-4-phenylquinoline 
• 618-36-0 rac-methylbenzylamine 
• 129575-56-0 (R)-α-methylbenzyl azide 
• 31002-29-6 (S)-α-azidoethylbenzene 
• 63778-17-6 1-(1-phenylethyl)-1H-1,2,3-triazole 
• 71506-76-8 2-methyl-N-(((1-phenylethyl)imino)methylene)propan-2-amine 
• 1259931-56-0 1-(1-phenyethyl)-1H-1,2,3-triazole-4,5-D₂ 
• 1309761-85-0 5-bromo-4-phenyl-1-(1-phenyl-ethyl)-1H-[1,2,3]triazole 
• 77473-29-1 1,2-dimethoxy-4-(1-phenylethyl)benzene 

Relevant academic research and scientific papers

Metal-Free Fast Azidation by Using Tetrabutylammonium Azide: Effective Synthesis of Alkyl Azides and Well-Defined Azido-End Polymethacrylates

An effective method to synthesize azido-end polymethacrylates from tetrabutylammonium azide (BNN3) in a nonpolar solvent (toluene) was developed. Several low-mass alkyl halides were reacted with BNN3 in toluene as model reactions and

ATRP, subsequent azide substitution and 'click' chemistry: Three reactions using one catalyst in one pot

This communication describes a novel and fast reaction to substitute the living chain end after Atom Transfer Radical Polymerization (ATRP) by an azide functionality. The reaction is catalyzed by the ATRP catalyst at room temperature in aqueous solution a

Facile Direct Coupling Reactions of MOM-protected Benzylic Alcohols Using Aluminum Chloride

MOM group is one of the most commonly used protecting groups for alcohols. This study describes novel direct functionalization of the MOM-protected benzylic alcohols. Preparation of allylic compounds from benzyl MOM ethers was successfully achieved by utilization of allyltrimethylsilane and AlCl3. In addition, direct azidation of benzyl MOM ethers using TMSN3 was successful carried out under AlCl3-mediated reaction conditions. These results demonstrate that this novel synthetic procedure is a promising approach to direct functionalization of MOM-protected alcohols including allylation and azidation.

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

Direct AlCl3-catalyzed transformation of benzyl THP ethers and allyl benzyl ethers

THP and allyl groups are frequently used for the protection of alcohols. In this study, novel direct transformations of benzyl THP ethers and allyl benzyl ethers, protected forms of alcohols, are reported. TMSN3 and AlCl3 were employ

Furfuryl Cation Induced Three-Component Reaction to Synthesize Triazole-Substituted Thioesters

A furfuryl cation induced three-component thioesterification reaction between thiols, 5-bromo-2-furylcarbinols and azides is reported. This metal-free method relies on the acetyl chloride/HFIP-mediated cascade formal [3+2] cycloaddition/ring-opening/thioesterification, which allows the efficient construction of a series of complex triazole-thioesters linked with an (Z)-olefin. Selenols are also suitable for this strategy. Further derivatization of thioesters highlighted the potential utility of our method.

Highly regioselective and sustainable solar click reaction: A new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide-alkyne cycloaddition reaction

The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(ii) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.

Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles

A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.

Thermal azide-Alkene cycloaddition reactions: straightforward multi-gram access to Δ2-1,2,3-Triazolines in deep eutectic solvents

The multi-gram synthesis of a wide range of 1,2,3-Triazolines via azide-Alkene cycloaddition reactions in a Deep Eutectic Solvent (DES) is reported. The role of DES in this transformation as well as the origin of the full product distribution was studied with an experimental/computational-DFT approach.

Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents

A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.