105058-42-2

Usage

Type of compound

Hydrocarbon derivative

Structure

Two propynyl groups attached to a benzene ring at the 1 and 4 positions

Common uses

a. Monomer in the production of polymeric materials
b. Organic synthesis
c. Building block for various industrial chemicals

Physical state

Flammable liquid

Odor

Characteristic aromatic

Safety precautions

Handle with caution due to potential hazards

Upstream product

• 624-38-4 para-diiodobenzene 
• 6224-95-9 diphenyl(1-propynyl)phosphine oxide 
• 75-20-7 calcium carbide 
• 935-14-8 1,4-diethynylbenzene 
• 5633-34-1 (benzoylmethylene)dimethylsulfurane 
• 74-88-4 methyl iodide 

Downstream Products

• 1587661-05-9 1,1'-(1,4-phenylene)bis(propane-1,2-dione) 

Relevant academic research and scientific papers

Synthesis of diarylenynes by olefination of 1-arylpropyne with arylaldehyde and their optical properties

A new synthetic protocol of 1-arylpropyne was developed by taking advantage of 1-(diphenylphosphoryl)propyne as propyne equivalent in Sonogashira coupling: consecutive subjection of phosphorylpropyne to t-BuOK and to aryl halides in the presence of Pd and Cu catalysts afforded the corresponding 1-arylpropynes. The following olefination of the 1-arylpropyne with aldehyde provided the corresponding diarylenyne. When the enynes thus obtained were irradiated with UV light, they showed strong emission in organic solvents and in the solid states. In solution, Ph2N-substituted enynes exhibited remarkable solvatofluorochromism, and Lippert–Mataga plot analysis demonstrated that they undergo the larger polarization in the excited states than in the ground states.

An approach to benzophosphole oxides through silver- or manganese-mediated dehydrogenative annulation involving C - C and C - P bond formation

Benzophosphole construction was achieved through the AgI- mediated dehydrogenative annulation of phenylphosphine oxides with internal alkynes in a process involving C - C and C - P bond formation. A wide range of asymmetrical phenylacetylenes could be employed and the reactions proceeded with perfect regioselectivity. Moreover, the annulation could be conducted even at room temperature when a MnIII promoter was used in place of Ag I. Copyright

Dimeric molecular clips based on glycoluril

Glycoluril dimers 4a and 4b were prepared and successfully transformed to glycoluril dimeric clips 7a and 7b. 1H NMR spectroscopy was used to reveal that the dimeric clip 7b with methyl substituents in its structure exists as a mixture of two distinct conformers in D2O at ambient temperature, while 7a possesses only one stable conformer under the same conditions due to its bulky phenyl substituents. The coalescence temperatures for 7b and its precursor 5b were determined. Both dimeric clips 7a and 7b formed complexes with methylviologen in D2O in which each of two clip-binding sites was occupied by one molecule of the guest. Thus, this study uncovers possible use of glycoluril dimers 4a and 4b as general building blocks for glycoluril-based supramolecular host molecules with two binding sites in their structure.

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.

Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates

Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.

Palladium-catalyzed methylation of alkynyl C(sp)-H bonds with dimethyl sulfonium ylides

A novel palladium-catalyzed methylation protocol for the synthesis of methyl-functionalized internal alkynes has been established. This methylation method is achieved through a C(sp)-C(sp3) bond formation process and represents a new synthetic application of sulfonium ylides.

Encapsulation-induced remarkable stability of a hydrogen-bonded heterocapsule

Remarkably enhanced stability of the self-assembled hydrogen-bonded heterocapsule 1×2 by the encapsulation of 1,4-bis(1-propynyl)benzene 3 a was found with Ka=1.14×109 M-1 in CDCl3 and Ka2=1.59×108 M-2 in CD3OD/CDCl3 (10 % v/v) at 298 K. The formation of 3 a(1×2) was enthalpically driven (ΔH°0 and ΔS°0) and there was a unique inflection point in the correlation between ΔH° versus ΔS° as a function of polar solvent content. The ab initio calculations revealed that favorable guest-capsule dispersion and electrostatic interactions between the acetylenic parts (triple bonds) of 3 a and the aromatic inner space of 1×2, as well as less structural deformation of 1×2 upon encapsulation of 3 a, play important roles in the remarkable stability of 3 a(1×2). Copyright