873-73-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorophenylacetylene is utilized as a pharmaceutical intermediate, playing a crucial role in the synthesis of various pharmaceutical compounds. Its unique chemical properties and reactivity in Sonogashira reactions make it a valuable component in the development of new drugs and therapeutic agents.

InChI:InChI=1/C8H5Cl/c1-2-7-3-5-8(9)6-4-7/h1,3-6H

Upstream product

• 99-91-2 para-chloroacetophenone 
• 39598-55-5 (bromomethylene)triphenylphosphorane 
• 104-88-1 4-chlorobenzaldehyde 
• 637-87-6 1-Chloro-4-iodobenzene 
• 107-19-7 propargyl alcohol 
• 66482-30-2 (Z)-1-bromo-2-(4-chlorophenyl)ethylene 
• 78704-49-1 1-(4-chlorophenyl)-2-trimethylsilylacetylene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 471-25-0 Propiolic acid 
• 4131-56-0 ((4-chlorophenyl)ethynyl)triethylsilane 
• 66482-29-9 1-(2-bromovinyl)-4-chlorobenzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 23135-16-2 1,2-dibromo-1-(4-chlorophenyl)ethane 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 

Downstream Products

• 1201-88-3 (Ξ)-4,α-dichloro-β-nitro-styrene 
• 51118-06-0 1,4-bis(4-chlorophenyl)buta-1,3-diyne 
• 6178-24-1 (4-chloro-phenyl)-(4-chloro-cis-styryl)-sulfide 
• 6510-80-1 (4-chloro-phenyl)-(4-chloro-trans-styryl)-sulfide 
• 31554-58-2 3-(4-bromophenyl)-5-(4-chlorophenyl)isoxazole 
• 37614-57-6 3-(4-chlorophenyl)prop-2-yn-1-ol 
• 14688-30-3 3,5-di(p-chlorophenyl)isoxazole 
• 42866-55-7 (4-Chloro-phenyl)-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-acetaldehyde 
• 2809-65-6 4-chloro-1-propynylbenzene 
• 42289-90-7 1-Chloro-4-(4-chloro-3,3,4-trifluoro-cyclobut-1-enyl)-benzene 
• 26792-74-5 3,3-Bis-dimethylamino-1--propin-(1) 
• 25631-76-9 3-(4-Chloro-phenyl)-4,4-bis-trifluoromethyl-cyclobut-2-enone 
• 33206-26-7 6-(4-chloro-phenyl)-2-trichloromethyl-[1,3]oxazin-4-one 
• 25631-94-1 3-(4-Chloro-phenyl)-5-phenyl-6,6-bis-trifluoromethyl-cyclohexa-2,4-dienone 

Relevant academic research and scientific papers

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.

UREA, AMIDE, AND SUBSTITUTED HETEROARYL COMPOUNDS FOR CBL-B INHIBITION

Compounds of formulae (I) and (II), compositions, and methods for use in inhibiting the E3 enzyme Cbl-b in the ubiquitin proteasome pathway are disclosed. The compounds, compositions, and methods can be used to modulate the immune system, to treat diseases amenable to immune system modulation, and for treatment of cells invivo, in vitro, or ex vivo.

Facile Conversion of Molecularly Complex (Hetero)aryl Carboxylic Acids into Alkynes for Accelerated SAR Exploration

1,2,3-Triazoles are well-established bioisosteres for amides, often installed as a result of structure?activity-relationship (SAR) exploration. A straightforward approach to assess the effect of the replacement of an amide by a triazole would start from the carboxylic acid and the amine used for the formation of a given amide and convert them into the corresponding alkyne and azide for cyclization by copper-catalyzed alkyne?azide cycloaddition (CuAAC). Herein, we report a functional-group-tolerant and operationally simple decarbonylative alkynylation that allows the conversion of complex (hetero)aryl carboxylic acids into alkynes. Furthermore, the utility of this method was demonstrated in the preparation of a triazolo analog of the commercial drug moclobemide. Lastly, mechanistic investigations using labeled carboxylic acid derivatives clearly show the decarbonylative nature of this transformation.

Fritsch-Buttenberg-Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes

A series of 1-heteroatom-substituted vinyl p-tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl p-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch-Buttenberg-Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using13C-labeled sulfoxides and by using DFT calculations.

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes

The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz

Efficient Multigram Approach to Acetylenes and CF3-ynones Starting from Dichloroalkenes Prepared by Catalytic Olefination Reaction (COR)

A novel approach to terminal acetylenes based on catalytic olefination reaction COR of arylaldehydes to form dichloroalkenes followed by treatment with nBuLi was elaborated. This method is atom economical and displays high yields and effectivity. The corresponding alkynes can be prepared in up to 97 % yield. One pot procedure towards CF3-ynones was elaborated to provide these products in up to 87 % yield starting from dichloroalkenes.