144924-01-6

Basic information

• Product Name: Benzenemethanol, a-(azidomethyl)-4-methoxy-
• CAS NO: 144924-01-6
• Molecular Formula: C9H11N3O2
• Molecular Weight: 193.205
• Mol File: 144924-01-6.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-(azidomethyl)-4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(azidomethyl)-4-methoxy-(144924-01-6)
• EPA Substance Registry System: Benzenemethanol, a-(azidomethyl)-4-methoxy-(144924-01-6)

Safety Data

• Hazardous Substances Data: 144924-01-6(Hazardous Substances Data)

Upstream product

• 6388-72-3 2-(4-methoxyphenyl)oxirane 
• 6595-28-4 2-azido-1-(4-methoxyphenyl)ethan-1-one 
• 2196-99-8 2-chloro-1-(4-methoxyphenyl)ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 637-69-4 4-Methoxystyrene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 6595-28-4 2-azido-1-(4-methoxyphenyl)ethan-1-one 
• 341513-45-9 (R)-β-azido-α-(4-methoxyphenyl)ethanol 
• 349642-77-9 (S)-(+)-2-azido-1-(4-methoxyphenyl)-1-ethyl acetate 
• 1489232-07-6 (-)-(R)-2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-methoxyphenyl)ethanol 
• 123-11-5 4-methoxy-benzaldehyde 
• 3755-89-3 N-(2-(4-methoxyphenyl)-2-oxoethyl)acetamide 
• 15298-28-9 N-(2-hydroxy-2-(4-methoxyphenyl)ethyl)benzamide 
• 98156-96-8 rac-2,2-dimethyl-5-(4-methoxyphenyl)oxazolidine 
• 55275-61-1 2-amino-1-(4-methoxyphenyl)ethanol 
• 50802-66-9 (S)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzamide 
• 297765-47-0 (S)-(+)-2-azido-1-(4-methoxyphenyl)-1-ethanol 
• 46084-19-9 (S)-(+)-2-amino-1-(4-methoxyphenyl)-1-ethanol 

Relevant articles and documents

Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation

A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.

Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides

A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.

A N - [2 - hydroxy -2 - (4 - methoxyphenyl) ethyl] cinnamic amide synthesis method (by machine translation)

The present invention provides a N - [2 - hydroxy - 2 - (4 - methoxyphenyl) ethyl] cinnamic amide synthesis method, the method is to methoxy acetophenone as the starting material, through chlorination reaction, azide reaction, condensation reaction by the reaction of reduction. The invention available reaction raw materials, the reaction process is simple in operation, reaction low equipment requirements, relatively mild reaction conditions, yield, the content is high, the final resulting N - [2 - hydroxy - 2 - (4 - methoxyphenyl) ethyl] cinnamide of liquid phase HPLC purity is greater than 99%. (by machine translation)

Stereoselective reduction of 2-azido-1-phenylethanone derivatives by whole cells of marine-derived fungi applied to synthesis of enantioenriched β-hydroxy-1,2,3-triazoles

Several marine-derived fungi were evaluated by the bioreduction of 2-azido-1-phenylethanone 1, and the strains A. sydowii CBMAI 935 and M. racemosus CBMAI 847 were selected for the reduction of 2-azido-1-phenylethanone derivatives 2–4. Whole cells of A. s

Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones

The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.

Mn-Catalyzed Highly Efficient Aerobic Oxidative Hydroxyazidation of Olefins: A Direct Approach to β-Azido Alcohols

(Chemical Equation Presented). An efficient Mn-catalyzed aerobic oxidative hydroxyazidation of olefins for synthesis of β-azido alcohols has been developed. The aerobic oxidative generation of azido radical employing air as the terminal oxidant is disclosed as the key process for this transformation. The reaction is appreciated by its broad substrate scope, inexpensive Mn-catalyst, high efficiency, easy operation under air, and mild conditions at room temperature. This chemistry provides a novel approach to high value-added β-azido alcohols, which are useful precursors of aziridines, β-amino alcohols, and other important N- and O-containing heterocyclic compounds. This chemistry also provides an unexpected approach to azido substituted cyclic peroxy alcohol esters. A DFT calculation indicates that Mn catalyst plays key dual roles as an efficient catalyst for the generation of azido radical and a stabilizer for peroxyl radical intermediate. Further calculation reasonably explains the proposed mechanism for the control of C-C bond cleavage or for the formation of β-azido alcohols.

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Chemoenzymatic resolution of β-azidophenylethanols by candida antarctica and their application for the synthesis of chiral benzotriazoles

As resoluc?o?es cine?ticas de (±)-β- azidofeniletano?is foram realizadas usando a lipase de Candida antarctica fornecendo os compostos enantiomericamente enriquecidos, (R)-β- azidofeniletano?is e acetato de (S)-β-azidofeniletila em bons excessos enantiome

A fast procedure for the preparation of vicinal azidoalcohols using polymer supported reagents

Several vicinal azidoalcohols were prepared in good to high yield and purity, starting from aryl α-haloketones, using reagents supported on a macroporous ion exchange resin. This is a fast and new approach to aryl azidoalcohols.

Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol

An efficient synthesis of optically active β-azido alcohols from their ketoazides by a one-pot reduction and an in situ lipase resolution protocol is described. The synthetic utility of this procedure has been illustrated by its application in the practic