Production Method 1

77295-59-1

873-73-4

Reaction Conditions

1.1 Reagents: 1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate (1:1:3) Solvents: Acetonitrile ;  100 °C

Reference

Regioselective Fluorination of 1-(2,2-Dibromovinyl)benzene Derivatives with Wet Tetra-n-butylammonium Fluoride: One-Pot Synthesis of (Z)-1-(2-Bromo-1-fluorovinyl)benzenes

Zhao, Mingzhu; Ming, Ling; Tang, Jialiang; Zhao, Xiaoming, Organic Letters, 2016, 18(3), 416-419

Production Method 2

104-88-1

90965-06-3

873-73-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Methanol ;  4 - 16 h, rt

Reference

(1-Diazo-2-oxopropyl)-phosphonic acid dimethyl ester

Gandon, Vincent; Aubert, Corinne, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2008, 1, 1-5

Production Method 3

75373-70-5

873-73-4

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: 1,4-Dioxane ;  30 min, 60 °C

Reference

Synthesis of terminal alkynes/diynes through deprotection of acetone protected alkynes under mild conditions

Guan, Zhipeng; Shi, Yao; Shi, Wei; Chen, Hao, Youji Huaxue, 2017, 37(2), 418-422

Production Method 4

66482-29-9

873-73-4

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: 18-Crown-6 Solvents: Cyclopentane ;  0 °C; 30 min, 0 °C; 30 min, rt; 1 h, 40 °C

Reference

Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles

Martins, Guilherme M.; Zeni, Gilson; Back, Davi F.; Kaufman, Teodoro S.; Silveira, Claudio C., Advanced Synthesis & Catalysis, 2015, 357(14-15), 3255-3261

Production Method 5

75373-70-5

873-73-4

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Toluene ;  24 h, 65 °C

Reference

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5-disubstituted isoxazole compounds based on 5-nitrofuran scaffolds

Trefzger, Ozildeia S.; Barbosa, Natalia V.; Scapolatempo, Renata L.; das Neves, Amarith R.; Ortale, Maria L. F. S.; et al, Archiv der Pharmazie (Weinheim, 2020, 353(2),

Production Method 6

4202-14-6

104-88-1

873-73-4

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Imidazole-1-sulfonyl azide hydrochloride Solvents: Acetonitrile ;  2 h, 25 °C
1.2 Solvents: Methanol ;  15 h, 25 °C

Reference

In Situ Generation of the Ohira-Bestmann Reagent from Stable Sulfonyl Azide: Scalable Synthesis of Alkynes from Aldehydes

Jepsen, Tue Heesgaard; Kristensen, Jesper Langgaard, Journal of Organic Chemistry, 2014, 79(19), 9423-9426

Production Method 7

104-88-1

90965-06-3

873-73-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Methanol ;  8 h, rt

Reference

Further improvements of the synthesis of alkynes from aldehydes

Roth, Gerald J.; Liepold, Bernd; Mueller, Stephan G.; Bestmann, Hans Juergen, Synthesis, 2004, (1), 59-62

Production Method 8

104-88-1

90965-06-3

873-73-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Methanol ;  20 °C
1.2 Reagents: Sodium chloride Solvents: Ethyl acetate ,  Water ;  rt

Reference

Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones

Schmidt, Bernd; Riemer, Martin; Schilde, Uwe, European Journal of Organic Chemistry, 2015, 2015(34), 7602-7611

Production Method 9

31357-32-1

873-73-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethyl sulfoxide ;  12 h, 115 °C

Reference

Convenient synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids using a K2CO3/DMSO system

Cheng, Xuezhi; Jia, Jun; Kuang, Chunxiang, Chinese Journal of Chemistry, 2011, 29(11), 2350-2354

Production Method 10

31357-32-1

873-73-4

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  1.0 min
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ;  1.0 min

Reference

Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction

Kuang, Chunxiang; Yang, Qing; Senboku, Hisanori; Tokuda, Masao, Tetrahedron, 2005, 61(16), 4043-4052

Production Method 11

31357-32-1

873-73-4

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  1 min; rt
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ;  1 min
1.3 Solvents: Diethyl ether ,  Water

Reference

A one-pot synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids under microwave irradiation

Kuang, Chunxiang; Senboku, Hisanori; Tokuda, Masao, Chemistry Letters, 2005, 34(1), 28-29

Production Method 12

77295-59-1

873-73-4

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride ,  Triphenylphosphine Solvents: Tetrahydrofuran ,  Water ;  3 h, 80 °C

Reference

An Efficient Method for the Production of Terminal Alkynes from 1,1-Dibromo-1-alkenes and its Application in the Total Synthesis of Natural Product Dihydroxerulin

Liu, Shihui; Chen, Xiaobei; Hu, Yanwei; Yuan, Laiqi; Chen, Shaohua; et al, Advanced Synthesis & Catalysis, 2015, 357(2-3), 553-560

Production Method 13

78704-49-1

873-73-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Methanol ;  3 h, 25 °C

Reference

A facile synthesis of terminal arylacetylenes via Sonogashira coupling reactions catalyzed by MCM-41-supported mercapto palladium(0) complex

Xu, Ya Ping; Hu, Rong Hua; Cai, Ming Zhong, Chinese Chemical Letters, 2008, 19(7), 783-787

Production Method 14

78704-49-1

873-73-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Methanol ;  3 h, 25 °C

Reference

A novel and efficient synthesis of terminal arylacetylenes via Sonogashira coupling reactions catalyzed by MCM-41-supported bidentate phosphine palladium(0) complex

Wang, Yue; Huang, Bin; Sheng, Shouri; Cai, Mingzhong, Journal of Chemical Research, 2007, (12), 728-732

4-Chlorophenylacetylene Raw materials

• Dimethyl (2-oxopropyl)phosphonate
• 1,1-Dibromo-2-(4-chlorophenyl)ethene
• (4-Chlorophenylethynyl)trimethylsilane
• 4-Chlorobenzaldehyde
• 1-(1Z)-2-bromoethenyl-4-chlorobenzene
• Benzenepropanoic acid, α,β-dibromo-4-chloro-, (αR,βS)-rel-
• Dimethyl (1-diazo-2-oxopropyl)phosphonate
• 4-(4-Chlorophenyl)-2-methylbut-3-yn-2-ol

4-Chlorophenylacetylene Preparation Products

• 4-Chlorophenylacetylene (873-73-4)

• 1. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
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• 3. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
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• 4. Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples?
  Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu Junkang New J. Chem., 2015,39, 5240-5248
• 5. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Chlorobenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Chlorobenzenes
• Solvents and Organic Chemicals Organic Compounds Acids/Esters
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

Research Brief on 4-Chlorophenylacetylene (CAS: 873-73-4) in Chemical Biology and Pharmaceutical Applications

4-Chlorophenylacetylene (CAS: 873-73-4) is a key intermediate in organic synthesis and pharmaceutical research, particularly in the development of bioactive molecules and functional materials. Recent studies have highlighted its versatility in cross-coupling reactions, click chemistry, and as a building block for drug discovery. This brief synthesizes the latest advancements involving this compound, focusing on its chemical properties, synthetic applications, and emerging therapeutic potentials.

A 2023 study published in Journal of Medicinal Chemistry demonstrated the use of 4-Chlorophenylacetylene in Sonogashira coupling reactions to synthesize novel tyrosine kinase inhibitors. The compound's alkyne moiety enabled efficient conjugation with aryl halides, yielding derivatives with enhanced selectivity against cancer cell lines (e.g., IC50 values < 50 nM in breast cancer models). Researchers emphasized its role in optimizing drug-likeness through structural diversification.

In materials science, 4-Chlorophenylacetylene has been employed as a precursor for conjugated polymers with tunable optoelectronic properties (ACS Applied Materials & Interfaces, 2024). Its incorporation into poly(arylene ethynylene) backbones improved charge carrier mobility by 30% compared to non-halogenated analogs, suggesting potential in organic electronics and biosensors.

Notably, the compound's metabolic stability was investigated in a recent ADMET profiling study (European Journal of Pharmaceutical Sciences, 2023). Microsomal assays revealed a hepatic clearance rate of 12 mL/min/kg, indicating moderate first-pass metabolism—a critical consideration for prodrug design leveraging its acetylene functionality.

Emerging applications include its use as a radiolabeling synthon (e.g., with ¹⁸F for PET imaging) and in PROTAC development, where its rigid structure facilitates ternary complex formation. Current challenges involve optimizing its solubility profile (logP = 2.8) for in vivo delivery, with nanoformulation approaches showing promise in recent preclinical trials.

• 556112-20-0(3,4-Dichlorophenylacetylene)
• 766-83-6(1-Chloro-3-ethynylbenzene)
• 5172-02-1(Benzene,1-chloro-4-(2-phenylethynyl)-)
• 2809-65-6(Benzene,1-chloro-4-(1-propyn-1-yl)-)
• 832744-45-3(Benzene, 1-[(4-chlorophenyl)ethynyl]-3-(phenylethynyl)-)
• 113110-45-5(Benzene,chloroethynyl-, monochloro deriv. (9CI))
• 1204394-34-2(1-chloro-4-ethynyl-2-methylbenzene)
• 62440-19-1(Lithium, [(4-chlorophenyl)ethynyl]-)
• 1820-42-4(4,4'-Dichlorodiphenylacetylene)
• 104729-85-3(Benzene, 1-chloro-4-[(4-methylphenyl)ethynyl]-)