139416-71-0

Basic information

• Product Name: Benzenemethanol, a-ethynyl-2-methyl-
• Synonyms: 1-(o-tolyl)-2-propyn-1-ol;1-o-tolyl-2-propyn-1-ol;1-(o-methylphenyl)-2-propyn-1-ol;1-(ortho-tolyl)-2-propyn-1-ol;1-o-Tolyl-prop-2-yn-1-ol
• CAS NO: 139416-71-0
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Mol File: 139416-71-0.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-ethynyl-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-ethynyl-2-methyl-(139416-71-0)
• EPA Substance Registry System: Benzenemethanol, a-ethynyl-2-methyl-(139416-71-0)

Safety Data

• Hazardous Substances Data: 139416-71-0(Hazardous Substances Data)

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 1066-54-2 trimethylsilylacetylene 
• 4039-82-1 Benzyl propargyl ether 

Downstream Products

• 82158-24-5 o-methylphenyl(benzofuran-2-yl)methanol 
• 1262149-04-1 2-oxo-1-o-tolylpropyl acetate 
• 4549-82-0 (E)-2-methylcinnamaldehyde 
• 1446099-78-0 (E)-3-(dimethyl(phenyl)silyl)-1-(o-tolyl)prop-2-en-1-ol 

Relevant articles and documents

Allenylidene Induced 1,2-Metalate Rearrangement of Indole-Boronates: Diastereoselective Access to Highly Substituted Indolines

A process to achieve 1,2-metalate rearrangements of indole boronate as a way to access substituted indolines in high diastereoselectivities is presented. The reaction involves the generation of a Cu–allenylidene, which is sufficiently electrophilic to induce the 1,2-metalate rearrangement. The scope of the reaction is evaluated as well as further transformations of the product.

Enantioselective Propargylation of Polyols and Desymmetrization of meso 1,2-Diols by Copper/Borinic Acid Dual Catalysis

A copper/borinic acid dual catalytic reaction enabled the enantioselective propargylation of aliphatic polyols. Readily available reagents and catalysts were used in this transformation, which displayed good to excellent chemo- and stereoselectivity for a broad array of substrates. The method was also applicable to the desymmetrization of meso 1,2-diols to furnish products with three stereogenic centers and a terminal alkyne group in one operation.

Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes

A photoinitiated anti-hydropentafluorosulfanylation of terminal alkynes using SF5Cl and (TMS)3SiH as the hydrogen atom donor is reported. This transformation generates selectively (Z)-(1-alken-1-yl)pentafluoro-λ6-sulfanes

Multisubstituted pyrazole synthesis via [3?+?2] cycloaddition/rearrangement/N[sbnd]H insertion cascade reaction of α-diazoesters and ynones

The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)3 as the catalyst are described. A series of 4-substituted pyrazoles were obtained via [3 + 2] cycloaddition, 1,5-ester shift, 1,3-H shift, and N[sbnd]H insertion process. Deuterium labelling experiments, kinetic studies and control experiments were carried out for the rationalization of the mechanism.

Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines

In this paper, a palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with azomethine imines has successfully been developed under mild reaction conditions, affording biologically interesting tetrahydropyrazoloisoquinoline derivatives in high to excellent yields and with excellent stereoselectivity. The reaction follows a tandem [3+2] cycloaddition/allylation/elimination of AcOH pathway. Allenyl carbinol acetates also reacted well with in situ generated azomethine imine under cocatalysis of Ag(i)/Pd(0) catalysts in a similar reaction pathway.

Phosphorous acid promoted isomerization of propargyl alcohols to α,β-unsaturated carbonyl compounds

A metal-free and two-phase protocol for the Meyer-Schuster isomerization of propargyl alcohols to the corresponding α,β-unsaturated carbonyl compounds has been achieved in the presence of stoichiometric phosphorous acid aqueous solution, which produces the desired products in high yields with excellent stereoselectivity. Compared with the traditional methods, the procedure features broad scope of the substrates, mild conditions, and easy separation, providing an appealing alternative to the Meyer-Schuster reaction.

One-Pot, Three-Step Synthesis of Cyclopropylboronic Acid Pinacol Esters from Synthetically Tractable Propargylic Silyl Ethers

Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient one-pot procedure. Terminal acetylenes undergo a Schwartz's reagent catalyzed hydroboration; subsequent addition of further Schwartz's reage

Synthesis of Vinyl-, Allyl-, and 2-Boryl Allylboronates via a Highly Selective Copper-Catalyzed Borylation of Propargylic Alcohols

An efficient methodology for the synthesis of vinyl-, allyl-, and (E)-2-boryl allylboronates from propargylic alcohols via Cu-catalyzed borylation under mild conditions is reported. In the presence of commercially available Cu(OAc)2 or Cu(acac)2 and Xantphos, the reaction affords the desired products in up to 92% yield with a broad substrate scope (43 examples). Isolation of an allenyl boronate as the reaction intermediate suggests that an insertion-elimination-type reaction, followed by borylcupration, is involved in the borylation of propargylic alcohols.

Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes

The development of a gold(III) catalyzed direct enantioconvergent 1,5-enyne cycloisomerization and kinetic resolution reaction is described. The transformation results in highly enantioenriched bicyclo[3.1.0]hexenes at all levels of conversion, with no racemization or symmetrization taking place during the course of the reaction, and simultaneously affords optically enriched 1,5-enynes. This report marks the first highly enantioselective transformation catalyzed by a well-defined cationic gold(III) catalyst and demonstrates the unique potential of gold(III) complexes in enantioselective catalysis.

Styrene as 4π-Component in Zn(II)-Catalyzed Intermolecular Diels-Alder/Ene Tandem Reaction

A mild Zn-catalyzed intermolecular Diels-Alder/ene tandem reaction with styrene as a 4π-component is reported. A variety of dihydronaphthalene products could be prepared in moderate to good yields. Moreover, a combination of DFT calculations and experiments was performed to further understand the mechanism of this unique tandem reaction.