13540-76-6

Usage

Physical appearance

Yellow crystalline solid.

Common uses

Synthesis of pharmaceuticals and organic compounds.

Chemical classification

Nitro compound (due to the presence of a nitro group (NO2) attached to a benzene ring).

Structural characteristic

Prop-2-yn-1-yl group (a carbon chain with a triple bond attached to the benzene ring).

Primary use

Building block in organic synthesis.

Reaction capability

Can undergo various chemical reactions to produce derivatives with different functional groups.

Potential applications

Production of dyes, pigments, and chemical intermediates.

Safety concerns

Hazardous due to potential toxicity and flammability; should be handled with caution.

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 13169-00-1 Methoxyallene 
• 102987-40-6 (3-(4-methoxyphenyl)prop-1-ynyl)trimethylsilane 
• 106-96-7 propargyl bromide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 65032-27-1 ethynylmagnesium chloride 
• 2746-25-0 p-Methoxybenzyl bromide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 19115-30-1 1-(4-methoxyphenyl)-2-propyn-1-ol 
• 2749-94-2 1-methoxy-4-(prop-1-yn-1-yl)benzene 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 4301-14-8 acetylenemagnesium bromide 
• 100-66-3 methoxybenzene 

Downstream Products

• 13540-78-8 1-(4-Methoxy-phenyl)-4-diaethylamino-butin-⁽²⁾ 
• 117295-77-9 1,3-bis(4'-methoxyphenyl)pent-4-yn-1-ol 
• 70041-48-4 (E)-3-(4-methoxybenzylidene)-5-phenylfuran-2(3H)-one 
• 133218-12-9 ethyl (E)-6-(4-methoxyphenyl)-4-hexyn-2-enoate 
• 25090-18-0 piperovatine 
• 134529-31-0 4-Hydroxy-4-<4-methoxy-phenyl>-2-<4-methoxy-benzyliden>-buten-(3)-saeurelacton 
• 1192570-96-9 (R)-5-(4-methoxybenzyl)-2,2,8a-trimethyl-2,3,8,8a-tetrahyhydro-1H-indolizin-7-one 
• 1192570-93-6 (R)-7-(4-methoxybenzyl)-2,2,8a-trimethyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one 
• 907959-18-6 1,3,5-tris[(4-methoxyphenyl)methyl]benzene 
• 1512850-15-5 C₃₀H₃₀O₃ 
• 116557-81-4 1-benzyl-4-(4-methoxy)phenyl-1H-1,2,3-triazole 

Relevant academic research and scientific papers

Iron-Catalyzed Vinylzincation of Terminal Alkynes

Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chemistry, and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by means of alkyne carbozincation. However, this method suffers from poor tolerance for terminal alkynes, and transformation of the newly introduced organic groups is difficult, which limits its applications. Herein, we report a method for vinylzincation of terminal alkynes catalyzed by newly developed iron catalysts bearing 1,10-phenanthroline-imine ligands. This method provides efficient access to novel organozinc reagents with a diverse array of structures and functional groups from readily available vinylzinc reagents and terminal alkynes. The method features excellent functional group tolerance (tolerated functional groups include amino, amide, cyano, ester, hydroxyl, sulfonyl, acetal, phosphono, pyridyl), a good substrate scope (suitable terminal alkynes include aryl, alkenyl, and alkyl acetylenes bearing various functional groups), and high chemoselectivity, regioselectivity, and stereoselectivity. The method could significantly improve the synthetic efficiency of various important bioactive molecules, including vitamin A. Mechanistic studies indicate that the new iron-1,10-phenanthroline-imine catalysts developed in this study have an extremely crowded reaction pocket, which promotes efficient transfer of the vinyl group to the alkynes, disfavors substitution reactions between the zinc reagent and the terminal C–H bond of the alkynes, and prevents the further reactions of the products. Our findings show that iron catalysts can be superior to other metal catalysts in terms of activity, chemoselectivity, regioselectivity, and stereoselectivity when suitable ligands are used.

Compound of dipyrrolopyridine structure Preparation method and medical application

The invention discloses a compound with a dipyrrolo-pyridine structure as well as a preparation method and medical application thereof. The compound provided by the invention has obvious inhibitory activity on JAK family proteins, is an effective JAK inhibitor, and has the prospect of being developed into drugs for inhibiting JAK and further treating diseases.

Ruthenium-Catalyzed Propargylic Reduction of Propargylic Alcohols with Hantzsch Ester

Ruthenium-catalyzed propargylic reduction of propargylic alcohols bearing a terminal alkyne moiety is accomplished by using Hantzsch ester as a nucleophilic hydride source. A variety of secondary and tertiary propargylic alcohols are reduced to the corresponding propargylic reduced products such as 1-alkynes in excellent yields. Some mechanistic studies indicate that ruthenium-allenylidene complexes may work as key reactive intermediates.

Novel multitarget inhibitors with antiangiogenic and immunomodulator properties

By means of docking studies, seventeen compounds T.1-T17 have been designed and evaluated as multitarget inhibitors of VEGFR-2 and PD-L1 proteins in order to overcome resistance phenomena offered by cancer. All these designed molecules display a urea moie

HISTONE DEMENTHYLASE INHIBITORS

The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted pyrrolopyridine derivative compounds and pharmaceutical compositions comprising said compounds. The subject com

Highly regioselective nickel-catalyzed cross-coupling of N -tosylaziridines and alkylzinc reagents

Herein, we report the first ligand-controlled, nickel-catalyzed cross-coupling of aliphatic N-tosylaziridines with aliphatic organozinc reagents. The reaction protocol displays complete regioselectivity for reaction at the less hindered C-N bond, and the products are furnished in good to excellent yield for a broad selection of substrates. Moreover, we have developed an air-stable nickel(II) chloride/ligand precatalyst that can be handled and stored outside a glovebox. In addition to increasing the activity of this catalyst system, this also greatly improves the practicality of this reaction, as the use of the very air-sensitive Ni(cod)2 is avoided. Finally, mechanistic investigations, including deuterium-labeling studies, show that the reaction proceeds with overall inversion of configuration at the terminal position of the aziridine by way of aziridine ring opening by Ni (inversion), transmetalation (retention), and reductive elimination (retention).

Enantioselective Synthesis of the Tricyclic Core of FR901483 Featuring a Rhodium-Catalyzed [2+2+2] Cycloaddition

An efficient approach to the tricyclic framework of FR901483 is described. The sequence features a [3,3]-sigmatropic rearrangement of a cyanate to an isocyanate, followed by its subsequent asymmetric rhodium-catalyzed [2+2+2] cycloaddition with a terminal

Polycyanurate networks from dehydroanethole cyclotrimers: Synthesis and characterization

Novel biobased trisphenols were obtained by palladium- and cobalt-catalyzed [2 + 2 + 2] cycloaddition of dehydroanethole isomers which were readily prepared from the natural product trans-anethole. The trisphenols were transformed into their corresponding

Biarylphosphonite gold(I) complexes as superior catalysts for oxidative cyclization of propynyl arenes into indan-2-ones

Striking gold: A series of variously functionalized propynyl arenes was smoothly converted into indan-2-ones by a new gold(I)-catalyzed oxidative cyclization process. [LAu]NTf2 (Tf=trifluoromethanesulfonyl) is a superior catalyst both in terms of yield and kinetics for the present transformation. Copyright

Synthesis of allenes via Nickel-catalyzed cross-coupling reaction of propargylic bromides with grignard reagents

We describe a convenient method for the synthesis of terminal allenes from cross-coupling of propargylic bromide with Grignard reagent. The reaction of propargylic bromide with 1.2 equivalents of Grignard reagent mediated by Ni(acac)2 (2 mol%) and Ph3P (4 mol%) in THF may produce terminal allenes in good yields and high regioselectivities at room temperature. Georg Thieme Verlag Stuttgart · New York.