1251832-81-1

Basic information

• Product Name: (2 - (4 - chlorobenzene) acetylene) benzaldehyde
• Synonyms: (2 - (4 - chlorobenzene) acetylene) benzaldehyde;2-((4-chlorophenyl)ethynyl)benzaldehyde
• CAS NO: 1251832-81-1
• Molecular Formula: C₁₅H₉ClO
• Molecular Weight: 240.68436
• EINECS: -0
• Mol File: 1251832-81-1.mol

Chemical Properties

• Boiling Point: 393.5±27.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (2 - (4 - chlorobenzene) acetylene) benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (2 - (4 - chlorobenzene) acetylene) benzaldehyde(1251832-81-1)
• EPA Substance Registry System: (2 - (4 - chlorobenzene) acetylene) benzaldehyde(1251832-81-1)

Safety Data

• Hazardous Substances Data: 1251832-81-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2 (4 chlorobenzene) acetylene) benzaldehyde is used as an intermediate in the synthesis of other organic compounds. Its unique structure allows it to be a versatile building block for creating a wide range of chemical products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (2 (4 chlorobenzene) acetylene) benzaldehyde is used as a key component in the development of various drugs. Its properties make it suitable for the creation of new medicinal compounds with potential therapeutic benefits.
Used in Dye Manufacturing:
(2 (4 chlorobenzene) acetylene) benzaldehyde is utilized in the production of dyes due to its chemical structure and properties. It contributes to the color and stability of the dyes, making it an important component in this industry.
Used in Fragrance Industry:
Due to its strong and distinct odor, (2 (4 chlorobenzene) acetylene) benzaldehyde is used in the fragrance industry to create various scent profiles for perfumes, colognes, and other scented products.
Used in Organic Electronic Devices:
(2 (4 chlorobenzene) acetylene) benzaldehyde has been studied for its potential use in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs), due to its electronic and optical properties. Its unique characteristics make it a promising candidate for advancing the field of organic electronics.

Upstream product

• 38846-64-9 2-ethynylbenzaldehyde 
• 637-87-6 1-Chloro-4-iodobenzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 31357-32-1 α,β-dibromo-p-chlorohydrocinnamic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 66482-30-2 (Z)-1-bromo-2-(4-chlorophenyl)ethylene 
• 873-73-4 4-n-chlorophenylacetylene 
• 26260-02-6 2-iodobenzaldehyde 

Downstream Products

• 1286747-86-1 C₁₅H₁₀ClNO 
• 1588973-14-1 C₂₀H₁₇ClO₂ 
• 1588971-91-8 3'-(4-chlorophenyl)-3,4,4'-triiodo-5,5-dimethyl-5H-spiro[furan-2,1'-isochromene] 
• 1588972-64-8 1-(2-((4-chlorophenyl)ethynyl)phenyl)-4-hydroxy-4-methylpent-2-yn-1-one 
• 62827-72-9 3-(p-chlorophenyl)-1H-isochromen-1-one 

Relevant articles and documents

Engaging 1,7-diynes in a photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade toward β-gem-dihalovinyl carbonyls

A new and general photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade of 1,7-diynes with alkyl halides such as BrCCl3and CBr4was reported for the first time, and used to produce 65 hitherto unreported β-gem-dihalovinyl ketones/aldehydes with moderate to excellent yields in a highly regioselective manner. This reaction tolerates a wide scope of substrates, which offers a green and efficient entry to fabricate synthetically important β-gem-dihalovinyl carbonyl scaffolds. Notably, the late-stage application of these resulting β-gem-dihalovinyl carbonyls shows high and unique reactivity profiles and demonstrates the versatility of their derivatization.

Tunable Synthesis of Indeno[1,2- c]furans and 3-Benzoylindenones via FeCl3-Catalyzed Carbene/Alkyne Metathesis Reaction of o-Alkynylbenzoyl Diazoacetates

An efficient synthesis of indeno[1,2-c]furan and 3-benzoylindenone derivatives through a FeCl3-catalyzed carbene/alkyne metathesis reaction of o-alkynylbenzoyl diazoacetates is presented. Mechanistically, the key intermediate, vinyl iron carbene, is formed by 5-exo-dig carbocyclization and terminated with a formal [3 + 2] cycloaddition or carbonylation. To the best of our knowledge, this is the first example in which FeCl3 is used as a catalyst for a carbene/alkyne metathesis reaction. Finally, derivatization reactions were carried out to showcase the value of the products.

Facile preparation of 3-aryl-4-iodoisoquinolines from N-(o-Arylethynyl)benzyl p-toluenesulfonamides with iodine and base

Treatment of N-(o-arylethynyl)benzyl p-toluenesulfonamides with molecular iodine in the presence of NaHCO3 at 60 °C, followed by the reaction with tBuOK at room temperature gave 3-aryl-4-iodoisoquinolines in good yields. 4-Iodo-3-phenylisoquinoline, which is one of the obtained 3-aryl-4-iodoisoquinolines, was further transformed into isoquinoline derivatives smoothly. The present approach is a novel one-pot method for the preparation of 3-aryl-4-iodoisoquinolines from N-(o-arylethynyl)benzyl p-toluenesulfonamides under transition-metal-free conditions.

Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property

A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.

Modular synthesis of 3-substituted isocoumarinsviasilver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes

A method involving silver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen as the terminal oxidant and the source of endocyclic oxygen. Mechanistic studies suggest the involvement of a free-radical pathway.

Radical Cascade Bicyclization/Aromatization of 1,7-Enynes with 1,3-Dicarbonyl Compounds towards 2,3-Dihydro-1H-cyclopenta[a]naphthalenes

An Ag-catalyzed radical cascade bicyclization/aromatization of C-linked 1,7-enynes with 1,3-dicarbonyls has been achieved, providing a step- and atom-economy approach for the construction of 2,3-dihydro-1H-cyclopenta[a]naphthalenes, an important structural scaffold existed in biologically active compounds. From this transformation, structurally diverse 2,3-dihydro-1H-cyclopenta[a]naphthalenes were obtained in moderate to good yields with high regioselectivity. Moreover, the further product derivatizations were also exemplified. (Figure presented.).

Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds

An efficient asymmetric tandem reaction of o-alkynylbenzaldehydes, amines, and diazo compounds catalyzed by chiral silver imidodiphosphate has been established. Chiral 1,2-dihydroisoquinoline analogues have a tertiary stereocenter at the C1 position, and substituents at the C3 position are available with up to 97% yields and 98% ee. These products can be elaborated into the corresponding β-aminophosphonates or PARP1-inhibitor analogues.

Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.

Catalytic asymmetric three-component reaction of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate

An efficient enantioselective synthesis of cyclic α-aminophosphonates via multicomponent reactions of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate has been developed with the use of a chiral silver spirocyclic phosphate as the catalyst. This protocol provides straightforward access to a series of chiral C1-phosphonylated 1,2-dihydroisoquinoline derivatives with high yields (up to 99%) and high enantioselectivities (up to 94% ee) for a broad substrate scope. The products could be further transformed into densely functionalized compounds and corresponding α-aminophosphonic acids.

Synthesis of organoselenyl isoquinolinium imidesviairon(iii) chloride-mediated tandem cyclization/selenation ofN′-(2-alkynylbenzylidene)hydrazides and diselenides

This report describes the synthesis of organoselenyl isoquinolinium imides through a tandem cyclization betweenN′-(2-alkynylbenzylidene)hydrazides and diselenides. The reaction was carried out at room temperature under an ambient atmosphere using cheap iron(iii) chloride as the metallic source. The strategy shows good tolerance to a broad range ofN′-(2-alkynylbenzylidene)hydrazides and diselenides, and forms C-N and C-Se bonds in one step. The obtained product is further transformed into a bioactiveH-pyrazolo[5,1-a]isoquinoline skeleton easilyviaa silver catalyzed [3 + 2] cycloaddition.