25837-46-1

Usage

Uses

Phenyl-d5-acetylene (CAS# 25837-46-1) is a useful isotopically labeled research compound.

Upstream product

• 5161-29-5 styrene-2,3,4,5,6-d⁵ 
• 87682-48-2 (phenyl-d5-ethynyl)trimethylsilane 
• 28077-64-7 acetophenone-d5 
• 1076-43-3 benzene-d6 
• 14132-51-5 2,3,4,5,6-pentadeuteriobenzaldehyde 
• 1401307-49-0 C₁₇H₂₁⁽²⁾H₅Si 
• 4165-57-5 bromobenzene-d5 
• 460-12-8 Butadiyne 
• 71-43-2 benzene 

Downstream Products

• 87682-48-2 (phenyl-d5-ethynyl)trimethylsilane 
• 25837-47-2 phenylacetylene-d6 
• 87682-43-7 C₂₈H₈⁽²⁾H₁₀ 
• 1262296-19-4 [Mo(CCC6D5)(dppe)(η-cycloheptatrienyl)] 
• 1449715-40-5 4-[2-(²H₅)phenylethynyl]benzaldehyde 
• 1401307-47-8 5-deutero-1,4-diphenyl-D₁₀-1H-1,2,3-triazole 
• 1401307-46-7 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D₅)-1H-1,2,3-triazol-1-yl)thymidine 
• 29822-79-5 4-(2-phenylethynyl)benzonitrile 
• 1385817-49-1 C₁₅H₄⁽²⁾H₅N 
• 28901-32-8 C₁₁H₁₁⁽²⁾H₅Si 
• 891493-41-7 C₁₀H₃⁽²⁾H₅ 

Relevant academic research and scientific papers

Ultraviolet photochemistry of diacetylene: Reactions with benzene and toluene

The reactions of metastable diacetylene with benzene and toluene are explored using a molecular beam pump-probe time-of-flight mass spectrometer. Diacetylene is laser-excited to the 210610 band of the 1Δu←X1Σ+g transition, whereupon rapid intersystem crossing occurs to the lowest triplet states. The triplet state diacetylene then reacts with either benzene or toluene as the gas mixture traverses a short reaction tube (approximately 20 μs). The reactions are quenched as the gas mixture expands into the ion source region of a time-of-flight mass spectrometer where the primary photoproducts are detected using vacuum ultraviolet (VUV) photoionization or resonant two-photon ionization (R2PI). The major products from the reaction of diacetylene and benzene have molecular formulas C8H6 and C10H6, and are identified as phenylacetylene and phenyldiacetylene using R2PI spectroscopy. The major products from metastable diacetylene's reaction with toluene are C9H8 and C11H8. The C9H8 product is confirmed as a mixture of o-, m-, and p-ethynyltoluene, with the ortho product dominating. Mechanisms for the formation of the above products are proposed based on deuterium substitution studies of the reactions. The potential importance of these reactions is discussed as they relate to hydrocarbon growth in sooting flames.

Piers′ Borane-Induced Tetramerization of Arylacetylenes

We herein report that the reaction of Piers′ borane, i. e. HB(C6F5)2, with an excess of arylacetylenes at room temperature leads to tetramerization of the acetylene and the diastereoselective formation of boryl-substituted

Cyano-Schmittel Cyclization through Base-Induced Propargyl-Allenyl Isomerization: Highly Modular Synthesis of Pyridine-Fused Aromatic Derivatives

The cyano-Schmittel cyclization of i situ-generated cyano-allenes has been carried out. The DFT calculation results suggest that the diradical pathway plays a major role in this cyclization. The reactions can be conveniently performed in a one-pot manner through cascade Sonogashira coupling of terminal cyano-ynes with organic halides, followed by base-promoted propargyl-allenyl isomerization/cyclization, leading to an efficient access to pyridine-fused polycyclic architectures. In particular, a large variety of aryl or heteroaryl rings such as furans, thiophenes and pyridines can be incorporated into the follow-up cyano-Diels-Alder reactions, highlighting the great synthetic utility of this chemistry.

METHODS FOR PREPARING DEUTERATED 1,2,3-TRIAZOLES

This disclosure relates to a method that involves reacting an azide with an alkyne in the presence of deuterated water and a copper-containing catalyst, thereby forming a deuterated 1,2,3-triazole.

Synthesis of deuterated 1,2,3-triazoles

The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl 2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D + ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.

Synthesis of deuterated 1,2,3-triazoles

The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl 2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D + ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.

Generation of nucleophilic chromium acetylides from gem-trichloroalkanes and chromium Chloride: Synthesis of propargyl alcohols

Nucleophilic mixed chromium(II) and chromium(III) acetylides are generated from the smooth reduction of primary 1,1,1-trichloroalkanes with chromium(II) chloride in the presence of an excess amount of triethylamine at room temperature. These species arise from chrornium(III) vinylidene carbenoids. It has been demonstrated that uncommon low-valent CrII acetylides are formed by C-H insertion of CrIICl2 into terminal alkynes, formed in situ through the FritschButtenberg-Wiechell (FBW) rearrangement, whereas CrIII acetylides are concomitantly generated by HCl elimination from the chromium(III) vinylidene carbenoid, Both divergent pathways result, overall, in the formation of nucleophilic acetylides. In situ trapping with electrophilic aldehydes afforded propargyl alcohols. Furthermore, deuteration experiments and the use of deuterium labeled 1,1,1-trichloroalkane substrates demonstrated the prevalence of low-valent Cr11 acetylides, potentially useful, yet highly elusive synthetic intermediates.

Competitive 1,2- and 1,5-hydrogen shifts following 2-vinylbiphenyl photocyclization

The photocyclization of 2-vinylbiphenyl and its derivatives has been proposed to occur via a two-step mechanism: photocyclization to form an unstable 8a,9-dihydro-phenanthrene intermediate, followed by exothermic unimolecular isomerization to a 9,10-dihyd

Chemically-induced discotic liquid crystals. Structural, studies with NMR spectroscopy

The use of nuclear magnetic resonance (NMR) spectrometry for the structural studies of chemically-induced discotic liquid crystals was discussed. The synthesis of the phase inductor with two deutrons in the phenyl ring was accomplished in a single step using the catalytic exchange procedure. The reaction was quenched by the addition of 5 ml D2O, the organic layer was left to evaporate and 0.38 g of the product was obtained. The degree of deuteriation was found by proton NMR to be approximately 70%.

Gas Phase Reactions of Protonated 1,3-Diphenylpropyne and Some Isomeric + Ions

Metastable (3-phenyl-2-propynyl)benzenium ions, generated by electron impact induced fragmentation from the appropriately substituted 1,4-dihydrobenzoic acid, react by loss of .CH3 and C6H6.The study of deuterated derivatives reveals that hydrogen/deuterium exchanges involving all hydrogen and deuterium atoms precede the fragmentations.The results suggest a skeletal rearrangement by electrophilic ring-closure reactions giving rise to protonated phenylindene and protonated 9,10-methano-9,10-dihydroanthracene prior to the elimination of C6H6 and .CH3, respectively.A study of isomeric + ions by collision-induced decomposition and by deuterium labelling shows that these ions interconvert by hydrogen migrations and skeletal rearrangements.