2749-93-1

Usage

Uses

Used in Pharmaceutical Synthesis:
Benzene, 1-methyl-4-(1-propynyl)(9CI) is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to serve as a building block for the development of new drugs, contributing to advancements in medicinal chemistry.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, Benzene, 1-methyl-4-(1-propynyl)(9CI) is employed as a reactant in the synthesis of a range of organic compounds. Its versatility in undergoing various chemical reactions makes it valuable for creating complex organic molecules for different applications.
Used in Chemical Research:
Due to its distinctive properties, Benzene, 1-methyl-4-(1-propynyl)(9CI) is also used in chemical research to study reaction mechanisms, explore new synthetic pathways, and understand the behavior of similar compounds. This research can lead to the discovery of new applications and uses for Benzene, 1-methyl-4-(1-propynyl)- (9CI) and its derivatives.

InChI:InChI=1/C10H10/c1-3-4-10-7-5-9(2)6-8-10/h5-8H,1-2H3

Upstream product

• 2227-58-9 3-(4-methylphenyl)prop-2-ynoic acid 
• 917-54-4 methyllithium 
• 75-11-6 diiodomethane 
• 766-97-2 4-n-methylphenylacetylene 
• 1245898-28-5 1-(1,1-diiodoprop-1-en-2-yl)-4-methylbenzene 
• 452335-62-5 1-(1,1-dibromoprop-1-en-2-yl)-4-methylbenzene 
• 5633-34-1 (benzoylmethylene)dimethylsulfurane 
• 75159-10-3 N-(4-methylbenzylidene)-p-toluenesulfonamide 
• 75-20-7 calcium carbide 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 590-93-2 2-Butynoic acid 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 74-99-7 prop-1-yne 

Downstream Products

• 69645-19-8 C₁₂H₁₁⁽²⁾HO₂ 
• 69645-13-2 2-p-Methylphenyl-3-methyl-2-cyclopropen-1-carbonsaeuremethylester 
• 72022-41-4 1-(4-methylphenyl)-2-ferrocenylacetylene 
• 1186623-45-9 C₂₀H₂₀O₂ 
• 1174033-41-0 1,2-[(η5-cyclopentadienyl)2ZrC(4-tolyl)=C(Me)]-1,2-C2B10H10 
• 1201651-26-4 (E)-1-(4-fluoro-4,4-bis(phenylsulfonyl)but-1-enyl)-4-methylbenzene 
• 1203825-79-9 (E)-2-fluoro-1-phenyl-2-(phenylsulfonyl)-5-p-tolylpent-4-en-1-one 
• 1240423-05-5 C₂B₁₀H₁₀(C₄(C₆H₄CH₃)2(CH₃)2) 
• 56138-10-4 (2E)-2-methyl-3-(4-methylphenyl)-2-propen-1-ol 
• 156817-47-9 (Z)-2-(p-methylphenyl)-2-buten-1-ol 
• 1588773-59-4 (E)-N,N-dimethyl-2-(1-(p-tolyl)prop-1-en-2-yl)-1H-indole-1-carboxamide-1-carboxamide 
• 1588773-25-4 1-methyl-2-(p-tolyl)-3H-pyrrolo[1,2-a]indol-3-one 

Relevant academic research and scientific papers

Palladium-catalyzed allylation of tautomerizable heterocycles with alkynes

A method for the allylic amidation of tautomerizable heterocycles was developed by a palladium catalyzed allylation reaction with 100% atom economy. A series of structurally diverse N-allylic substituted heterocycles can be synthesized in good yields with high chemo-, regio-, and stereoselectivities under mild conditions.

Regio- And stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides

An electrooxidative direct difunctionalization of internal alkynes with sulfonyl hydrazides has been developed for the construction of sulfonated enethers. In this transformation, metal catalysts or stoichiometric amount of oxidants are not required and molecular nitrogen and hydrogen are the sole byproducts, providing a simple and green approach for preparing various sulfonyl tetrasubstituted alkenes. Notably, the protocol could be efficiently scaled up and the follow-up procedures of the corresponding functionalized alkenes demonstrate the practicality of the electrochemical synthesis.

Enantioselective Addition of α-Nitroesters to Alkynes

By using Rh–H catalysis, we couple α-nitroesters and alkynes to prepare α-amino-acid precursors. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a RhIII–π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α-disubstituted α-amino esters.

Rh-Catalyzed Asymmetric Hydrogenation of α,β- and β,β-Disubstituted Unsaturated Boronate Esters

A highly enantioselective hydrogenation of α,β-unsaturated boronate esters catalyzed by Rh-(S)-DTBM-Segphos complex has been developed. Both (Z)-α,β- and β,β-disubstituted substrates can be successfully hydrogenated to afford chiral boronates with excellent enantioselectivities, up to 98 % ee. Furthermore, the obtained chiral boronate esters, as important versatile synthetic intermediates are successfully transformed to the corresponding chiral alcohols, amines and other important derivatives with maintained enantioselectivities.

Palladium-catalyzed methylation of terminal alkynes

In this communication, a palladium-catalyzed procedure for the methylation of terminal alkynes has been developed. With N,N,N-trimethylbenzenaminium trifluoromethanesulfonate as the methyl source, various desired products were obtained in moderate to good yields. Both aromatic and aliphatic alkynes are applicable.

Direct Synthesis of 1-Arylprop-1-ynes with Calcium Carbide as an Acetylene Source

A simple method is described for the synthesis of 1-arylprop-1-ynes directly from aromatic aldehyde p -tosylhydrazones by using calcium carbide as an acetylene source. The salient features of this protocol are its use of a readily available and easily handled source of acetylene, its operational simplicity, its high yield, and its broad substrate scope.

Facile Access to Diverse Libraries of Internal Alkynes via Sequential Iododediazoniation/Decarboxylative Sonogashira Reaction in Imidazolium ILs without Ligand or Additive

Convenient access to diverse libraries of internal alkynes via decarboxylative Sonogashira reaction of alkynyl-carboxylic acids with iodoarenes, employing imidazolium-ILs as solvent, along with piperidine-appended imidazolium [PAIM][NTf2] as task-specific basic IL is demonstrated, without the need for any ligand or additive. The feasibility to perform these reactions by sequential one-pot iododediazoniation/decarboxylative Sonogashira reaction is also shown, and the scope of the methods is underscored by providing 29 examples. The potential for recycling and reuse of the IL solvent is also examined.

Blue Light Induced Difluoroalkylation of Alkynes and Alkenes

The difluoroalkylation of alkynes and alkenes by direct photoexcitation of ethyl difluoroiodoacetate is described. Under catalyst- and oxidant-free conditions, iododifluoroalkylation and hydrodifluoroalkylation products were generated from alkynes, and difluoroalkylation products were prepared from alkenes. This methodology provides a streamlined access to difluoroalkylated organic compounds starting from simple alkynes or alkenes.

A Pd-catalyzed domino Larock annulation/dearomative Heck reaction

A palladium-catalyzed domino Larock annulation/dearomative Heck reaction is developed, which delivers a range of tetracyclic indoline derivatives in moderate to excellent yields through a Larock annulation of N-bromobenzoyl o-iodoanilines with alkynes and a subsequent intramolecular dearomative Heck reaction. This protocol provides a straightforward route to structurally diverse indolines from readily available starting materials by forming two new rings and three chemical bonds in a single step.

Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex

The molybdenum and tungsten complexes M2(OR)6 (Mo2F6, M = Mo, R = C(CF3)2Me; W2F3, M = W, R = OC(CF3)Me2) were synthesized as bimetallic congeners of the highly active alkyne metathesis catalysts [MesC-M{OC(CF3)nMe3-n}] (MoF6, M = Mo, n = 2; WF3, M = W, n = 1; Mes = 2,4,6-trimethylphenyl). The corresponding benzylidyne complex [PhC-W{OC(CF3)Me2}] (WPhF3) was prepared by cleaving the W-W bond in W2F3 with 1-phenyl-1-propyne. The catalytic alkyne metathesis activity of these metal complexes was determined in the self-metathesis, ring-closing alkyne metathesis and cross-metathesis of internal and terminal alkynes, revealing an almost equally high metathesis activity for the bimetallic tungsten complex W2F3 and the alkylidyne complex WPhF3. In contrast, Mo2F6 displayed no significant activity in alkyne metathesis.