13633-26-6

Basic information

• Product Name: Benzene, 3-buten-1-ynyl- (9CI)
• Synonyms: Benzene, 3-buten-1-ynyl- (9CI)
• CAS NO: 13633-26-6
• Molecular Formula: C₁₀H₈
• Molecular Weight: 128.17052
• Mol File: 13633-26-6.mol

Chemical Properties

• Boiling Point: 96 °C(Press: 20 Torr)
• Appearance: /
• Density: 0.948 g/cm3
• CAS DataBase Reference: Benzene, 3-buten-1-ynyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 3-buten-1-ynyl- (9CI)(13633-26-6)
• EPA Substance Registry System: Benzene, 3-buten-1-ynyl- (9CI)(13633-26-6)

Safety Data

• Hazardous Substances Data: 13633-26-6(Hazardous Substances Data)

Upstream product

• 3182-70-5 4-phenylbut-2-ynyl bromide 
• 75-21-8 oxirane 
• 6738-06-3 phenylethynylmagnesium bromide 
• 2579-22-8 Phenylpropargyl aldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 593-60-2 Vinyl bromide 
• 536-74-3 phenylacetylene 
• 75-89-8 2,2,2-trifluoroethanol 
• 85375-43-5 4-methyl-N-(4-phenylbut-3-yn-1-yl)benzenesulfonamide 
• 74752-53-7 4-propargyl-2-phenyl-Δ²-1,3,4-oxadiazolin-5-one 
• 81255-61-0 4-allenyl-2-phenyl-Δ²-1,3,4-oxadiazolin-5-one 
• 87639-40-5 4-phenyl-3-butyn-1-yl trifluoromethanesulfonate 
• 67-56-1 methanol 

Downstream Products

• 124475-74-7 2-(2-Phenylethynyl-aziridin-1-yl)-isoindole-1,3-dione 
• 214552-98-4 2-vinyl-1,3-terphenyl 
• 104-51-8 1-butylbenzene 
• 688045-37-6 (4E)-4-phenyl-2-methylhepta-4,6-dien-3-ol 
• 952115-16-1 2-hydroxy-3-phenyl-hexa-3,5-dienoic acid ethyl ester 
• 128165-62-8 3,4-epoxy-1-phenyl-3-(trimethylsilyl)-1-butyne 

Relevant articles and documents

Cobalt-catalyzed hydrohydrazination of dienes and enynes: Access to allylic and propargylic hydrazides

(Chemical Equation Presented) The cobalt-catalyzed hydrohydrazination reaction of dienes and enynes is presented. Allylic and propargylic hydrazines were obtained in synthetically useful yields (allylic amines, 60-90%; propargylic amines, 47-83%) and good chemo- and regioselectivity.

Triple-Bond Insertion Triggers Highly Regioselective 1,4-Aminomethylamination of 1,3-Enynes with Aminals Enabled by Pd-Catalyzed C-N Bond Activation

A highly chemo- and regioselective 1,4-aminomethylamination of simple enynes with aminals to allenic 1,5-diamines by taking advantage of C-N bond activation has been reported. The reaction proceeds under mild reaction conditions and can be performed under

Gold catalyzed efficient preparation of dihydrobenzofuran from 1,3-enyne and phenol

A gold catalyzed formal intermolecular [2+3] cyclo-coupling of 1,3-enynes with phenols was developed to prepare dihydrobenzofuran derivatives with the addition of 2,6-dichloropyridine N-oxide, in which, a highly ortho-selective phenol SEAr functionalizati

Radical Carbonyl Propargylation by Dual Catalysis

Carbonyl propargylation has been established as a valuable tool in the realm of carbon–carbon bond forming reactions. The 1,3-enyne moiety has been recognized as an alternative pronucleophile in the above transformation through an ionic mechanism. Herein, we report for the first time, the radical carbonyl propargylation through dual chromium/photoredox catalysis. A library of valuable homopropargylic alcohols bearing all-carbon quaternary centers could be obtained by a catalytic radical three-component coupling of 1,3-enynes, aldehydes and suitable radical precursors (41 examples). This redox-neutral multi-component reaction occurs under very mild conditions and shows high functional group tolerance. Remarkably, bench-stable, non-toxic, and inexpensive CrCl3 could be employed as a chromium source. Preliminary mechanistic investigations suggest a radical-polar crossover mechanism, which offers a complementary and novel approach towards the preparation of valuable synthetic architectures from simple chemicals.

Hydromagnesiation of 1,3-Enynes by Magnesium Hydride for Synthesis of Tri- and Tetra-substituted Allenes

A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst.

Transition metal-free formal hydro/deuteromethylthiolation of unactivated alkenes

Methylthioether is involved in the methylthiotransfer process in organisms, and therefore its functionality is of paramount importance to living organisms. Several methods for the installation of the methylthio group in small molecules have been reported previously; however, procedures starting from unactivated alkenes are rare. Herein, we report a formal hydro/deuteromethylthiolation of alkenes by using dimethyl(methylthio)sulfonium trifluoromethanesulfonate as the stimulator and sodium borohydride/deuteride as the hydrogen/deuterium source. The process represents a mild, transition metal-free and methanethiol-free route towards the synthesis of methylthioethers from unactivated alkenes. This journal is

Regioselective Access to 3-Ethylideneflavanones via Rhodium(I)-Catalyzed 1,3-Enyne Hydroacylation/Annulation Cascades

The highly efficient synthesis of 3-ethylideneflavanones through sequential rhodium(I)-catalyzed hydroacylation of terminal aryl-substituted 1,3-enynes with chelating aldehydes and annulation is described. This straightforward protocol highlights an unprecedented C3-regioselective hydroacylation of 1,3-enynes, excellent functional group compatibility, and complete atom economy. (Figure presented.).

Stereo- And Regioselective cis-Hydrophosphorylation of 1,3-Enynes Enabled by the Visible-Light Irradiation of NiCl2(PPh3)2

Described herein is a stereo- and regioselective cis-hydrophosphorylation reaction of the internal alkyne of 1,3-enynes that accesses various 1,3-dienes in good isolated yields. The visible-light irradiation of NiCl2(PPh3)2 allows the generation of highly reactive nickel(II)-phosphorus species that subsequently migrate into the internal alkyne of the 1,3-enynes and protonate the resulting vinyl nickel species, leading to various phosphinoyl 1,3-butadienes under mild reaction conditions.

Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate

The potential of (2-bromoethyl)diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)diphenylsulfonium triflate as a CH═CH2 transfer source in organic synthesis.

Fe-Catalyzed Selective Cyclopropanation of Enynes under Photochemical or Thermal Conditions

The nucleophilic Fe-complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the cyclopropanation of enynes to substituted propargyl cyclopropanes using diazoesters as carbene surrogates. The catalyst can be activated either thermally in the presence of catalytic amounts of 4-nitroanisole or under photochemical conditions. Cyclopropanation occurs selectively at the enyne moiety; alternative olefinic moieties remain intact.