Name: 622-76-4|1-Phenyl-1-butyne|99%
Brand: Ambeed
SKU: A523695
Price: 14.0 USD
Availability: InStock
Rating: 96 (22 reviews)

1
[ 622-76-4 ]
[ 64454-37-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ammonium peroxydisulfate; potassium iodide In water at 60℃; for 12h; Schlenk technique; Green chemistry; stereoselective reaction;	Diiodination of Alkynes; General Procedures General procedure: Method A: To a 25 mL Schlenck tube were added (NH4)2S2O8 (3.0 equiv), NH4I (2.5 equiv), alkyne (0.5 mmol), and H2O (1 mL). The reaction mixture was warmed to 60 °C (oil bath) and stirred for 12 h. The mixture was cooled to r.t., and EtOAc (5 mL) and H2O (2 mL) were added. The organic layer was separated, and the aqueous phase was extracted with EtOAc (2 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give the pure sample. Method B: To a 25 mL Schlenck tube were added (NH4)2S2O8 (3.0 equiv), NH4I (2.5 equiv), alkynes (0.5 mmol), and H2O (1 mL). The reaction mixture was warmed to 60 °C (oil bath) and stirred for 12 h. The mixture was cooled to r.t., and EtOAc (5 mL) and H2O (2 mL) were added. The organic layer was separated, and the aqueous phase was extracted with EtOAc (2 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give the pure sample.
90%	With [bis(acetoxy)iodo]benzene; trimethylsulphonium iodide In water at 20℃; for 0.5h; stereospecific reaction;
90%	With ammonium iodide; Oxone In water at 20℃; for 1.5h; diastereoselective reaction;

26%	Stage #1: 1-phenyl-1-butyne With trimethylsilyl iodide In dichloromethane; toluene at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With N-iodo-succinimide In dichloromethane; toluene; acetonitrile at -78 - 20℃; for 1h; Inert atmosphere; stereoselective reaction;	15 The use of TMSI and NIS at entry 1 didn't consume all the starting 3, and afforded 16 in 26% yield as a single isomer. For entries 3 and 7, TMSI/NCS and TMSCl/NIS gave only 16 in low yields, in which the chloride atom was not installed.
	With chloroform; iodine at 100℃;

Reference： [1]Jiang, Qing; Wang, Jing-Yu; Guo, Can-Cheng [Synthesis (Germany), 2015, vol. 47, # 14, p. 2081 - 2087]
[2]Rao, Dodla S.; Reddy, Thurpu R.; Kashyap, Sudhir [Organic and Biomolecular Chemistry, 2018, vol. 16, # 9, p. 1508 - 1518]
[3]Banothu, Rammurthy; Peraka, Swamy; Kodumuri, Srujana; Chevella, Durgaiah; Gajula, Krishna Sai; Amrutham, Vasu; Yennamaneni, Divya Rohini; Nama, Narender [New Journal of Chemistry, 2018, vol. 42, # 22, p. 17879 - 17883]
[4]Ide, Masataka; Yauchi, Yuta; Shiogai, Ryo; Iwasawa, Tetsuo [Tetrahedron, 2014, vol. 70, # 45, p. 8532 - 8538]
[5]Peratoner [Gazzetta Chimica Italiana, 1892, vol. 22 II, p. 69]

2
[ 1004-22-4 ]
[ 80-40-0 ]
[ 622-76-4 ]

Reference： [1]Journal of the American Chemical Society,1938,vol. 60,p. 1882
[2]Annales de Chimie (Cachan, France),1931,vol. <10>16,p. 396
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1930,vol. 191,p. 855
[3]Annales de Chimie (Cachan, France),1931,vol. <10>16,p. 396
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1930,vol. 191,p. 855
[4]Journal of the American Chemical Society,1938,vol. 60,p. 1882
[5]Bulletin of the Chemical Society of Japan,1974,vol. 47,p. 2663 - 2671

3
[ 622-76-4 ]
[ 63318-10-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-iodo-succinimide; acetic acid; lithium chloride In dichloromethane at 20℃; for 24h; regiospecific reaction;	2. General procedure for iodochlorination of alkynes General procedure: A 10 mL glass vial with a screw cap was charged with alkynes (0.2 mmol), NIS (0.3 mmol, 1.5equiv.), LiCl (0.4 mmol, 2 equiv.) and a solvent mixture of DCM (0.5 mL) and HOAc (0.5 mL).The reaction mixture was stirred at rt for 24 h. Upon completion, the reaction mixture was quenched with saturated NaCl solution and was extracted with EtOAc, the combined organic layers were dried with anhydrous Na2SO4, and the solvent was removed in vacuum. The residue was purified by flash silica gel column chromatography (eluted with hexanes and ethyl acetate) to give the desired products.
	With iodine; copper dichloride In acetonitrile

Reference： [1]Hammond, Gerald B.; Liu, Shiwen; Xu, Bo; Yang, Yi; Yang, Yuhao; Zeng, Xiaojun [Chem, 2020, vol. 6, # 4, p. 1018 - 1031]
[2]Uemura,S. et al. [Journal of the Chemical Society. Perkin transactions I, 1977, p. 676 - 680]

4
[ 622-76-4 ]
[ 66255-85-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride; Oxone In N,N-dimethyl-formamide at 20 - 25℃; for 2h;
59%	With trichloroisocyanuric acid; water In acetone at 20℃;
34%	With dipotassium peroxodisulfate; sodium chloride In water at 60℃; for 12h; Schlenk technique; Green chemistry;	General procedure for the synthesis of α,α-dihaloacetophenones via K2S2O8-mediated oxy-1,1-dihalogenation of alkynes (2a-2m, 3a-3j) General procedure: To a 25 ml Schlenck tube were added K2S2O8 (2.5 equiv.), NaX (2.0 equiv.), alkynes (0.5 mmol) and H2O (1 mL). The reaction mixture was warmed to 60 °C (oil bath) and stirred for 12 h. The reaction was cooled to room temperature,and ethyl actate (5 mL) and water (2 mL) were added. The organic layer was separated,and the aqueous phase was extracted with ethyl actate (10mL x 2). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated.The residue was purified by column chromatography to give desired product.

Reference： [1]Kim, Kye Kwang; Kim, Jae Nyoung; Kim, Kyoung Mahn; Kim, Hyoung Rae; Ryu, Eung K. [Chemistry Letters, 1992, # 4, p. 603 - 604]
[2]Hiegel, Gene A.; Bayne, Christopher D.; Ridley, Brendt [Synthetic Communications, 2003, vol. 33, # 12, p. 1997 - 2002]
[3]Wang, Jing-Yu; Jiang, Qing; Guo, Can-Cheng [Synthetic Communications, 2014, vol. 44, # 21, p. 3130 - 3138]

5
[ 622-76-4 ]
[ 495-40-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With water In neat (no solvent) at 100℃; for 22h; Green chemistry; regioselective reaction;	General procedure for hydration of alkynes General procedure: Reactions were performed in a magnetically stirred round bot-tomed flask fitted with a condenser and placed in a temperature controlled oil bath. Zeolite (H) (100 mg) was added to the well stirred solution of alkyne (2 mmol) and H2O (8 mmol) and the reac-tion mixture was allowed to stir at 100 °C. After disappearance of the alkyne (monitored by TLC) or after an appropriate time, the reaction mixture was cooled to room temperature, diluted with ethyl acetate. The catalyst was separated by filtration and the removal of solvent in vacuo yielded residue. and it was further puri-fied by column chromatography using silica gel (100-200 mesh) to afford pure products. All the products were identified on the basisof H1 and C13NMR spectral data.
92%	With iron(III) chloride; water; silver(I) triflimide In 1,4-dioxane at 95℃; for 60h; regioselective reaction;
92%	With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 25℃; for 45h; Sealed tube; regioselective reaction;

88%	With tropylium tetrafluoroborate; water; acetic acid at 130℃; for 48h; Inert atmosphere;
87%	With p-toluenesulfonic acid monohydrate; acetic acid In dichloromethane at 80℃; for 20h; Sealed tube;	General procedures for alkyne hydration General procedure: The corresponding alkyne (1 mmol) was added to a solution of p-toluenesulfonic acidmonohydrate (1 mmol, 0.190 g), acetic acid (0.5 mL) in CH2Cl2 (1.0 mL). Thereaction was then sealed and stirred at the indicated temperature (oC) and for theindicated amount of times (h) in Table 2. After completion, saturated aqueousNaHCO3 (10 mL) was added to quench the reaction and then extracted with CH2Cl2(10 mL×3). The organic layer was dried over Na2SO4 and concentrated in vacuo. Theresidue was purified by column chromatography to give the pure product. Forsubstrates 1j. 1l, 1n, 1p and 1q, DCE was used as solvent in consideration ofoperation convenience.
81%	With indium(III) triflate; water; toluene-4-sulfonic acid In 1,2-dichloro-ethane for 14h; Sealed tube; Reflux; regioselective reaction;	6.20 4.2 General procedure for the hydration of alkynes 1a-1n and 1p-1t General procedure: The reaction mixture of In(OTf)3 (11.2 mg, 2 mol %), PTSA (57.1 mg, 30 mol %), DCE (2.0 mL), alkynes 1a-1n or 1p-1t (1.0 mmol) and water (0.2 mL) in a 10 mL flask or in a 10 mL sealed tube was stirred at reflux and monitored periodically by TLC. Upon completion, DCE was removed under reduced pressure using an aspirator, and then the residue was purified by flash chromatography (PE/EA) on silica gel to afford corresponding carbonyl compounds 2a-2n or 2p-2t.
79%	With water In 1,4-dioxane at 80 - 120℃; regioselective reaction;
66%	With phosphoric acid; boron trifluoride In acetonitrile; benzene at 60 - 70℃; for 1h;
20%	With Ag₃STA; water at 100℃; for 14h; neat (no solvent); regioselective reaction;
	With graphene oxide at 100℃; for 24h;
88 %Chromat.	With iron(III) chloride; water; silver(I) triflimide In 1,4-dioxane-d8 at 120℃; for 20h; regioselective reaction;
	Multi-step reaction with 2 steps 1: dibromamine-T; water / acetone / 0.17 h 2: water; potassium iodide; sodium sulfite / acetone / 20 °C
	With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 40℃; for 48h; Inert atmosphere;
	With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 40℃; for 48h;

Reference： [1]Mameda, Naresh; Peraka, Swamy; Marri, Mahender Reddy; Kodumuri, Srujana; Chevella, Durgaiah; Gutta, Naresh; Nama, Narender [Applied Catalysis A: General, 2015, vol. 505, p. 213 - 216]
[2]Cabrero-Antonino, Jose R.; Leyva-Perez, Antonio; Corma, Avelino [Chemistry - A European Journal, 2012, vol. 18, # 35, p. 11107 - 11114]
[3]Liu, Wenbo; Wang, Haining; Li, Chao-Jun [Organic Letters, 2016, vol. 18, # 9, p. 2184 - 2187]
[4]Oss, Giulia; Ho, Junming; Nguyen, Thanh Vinh [European Journal of Organic Chemistry, 2018, vol. 2018, # 29, p. 3974 - 3981]
[5]Liu, Haixuan; Wei, Yunyang; Cai, Chun [Synlett, 2016, vol. 27, # 16, p. 2378 - 2383]
[6]Gao, Qi; Li, Shenyan; Pan, Yingming; Xu, Yanli; Wang, Hengshan [Tetrahedron, 2013, vol. 69, # 19, p. 3775 - 3781]
[7]Cabrero-Antonino, Jose R.; Tejeda-Serrano, María; Quesada, Manuel; Vidal-Moya, Jose A.; Leyva-Pérez, Antonio; Corma, Avelino [Chemical Science, 2016, vol. 8, # 1, p. 689 - 696]
[8]Pourzal, Ali-A.; Bonnet, Peter-H. [Monatshefte fur Chemie, 1983, vol. 114, p. 809 - 812]
[9]Location in patent: experimental part Venkateswara Rao; Sai Prasad; Lingaiah [Green Chemistry, 2012, vol. 14, # 5, p. 1507 - 1514]
[10]Dreyer, Daniel R.; Jia, Hong-Peng; Bielawski, Christopher W. [Angewandte Chemie - International Edition, 2010, vol. 49, # 38, p. 6813 - 6816]
[11]Cabrero-Antonino, Jose R.; Leyva-Perez, Antonio; Corma, Avelino [Chemistry - A European Journal, 2013, vol. 19, # 26, p. 8627 - 8633]
[12]Rajbongshi, Kamal Krishna; Hazarika, Debojit; Phukan, Prodeep [Tetrahedron, 2016, vol. 72, # 29, p. 4151 - 4158]
[13]Liu, Sensheng; Liu, Huan; Zhou, Haifeng; Liu, Qixing; Lv, Jinliang [Organic Letters, 2018, vol. 20, # 4, p. 1110 - 1113]
[14]Liu, Huan; Liu, Sensheng; Zhou, Haifeng; Liu, Qixing; Wang, Chunqin [RSC Advances, 2018, vol. 8, # 27, p. 14829 - 14832]

6
[ 622-76-4 ]
[ 1817-57-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tert.-butylhydroperoxide; C₄₈H₇₂O₁₂Rh₂ In ethyl acetate at 40℃; for 24h; Sealed tube;	4.4. General procedure for propargyl oxidation General procedure: A 10 mL tube equipped with a stir bar was charged with sub- strate (2.0 mmol) and Rh 2 (5- t Bu-esp) 2 (1.7 mg, 0.0020 mmol), then sealed by a rubber plug with a needle, followed by the addition of T-HYDRO (1.44 mL, 20 mmol) via syringe. The tube was placed in 40 °C oil bath for 24 h. After cooling to room temperature, sat- urated sodium thiosulfate solution was added to quench the re- action. The mixture was extracted with ethyl acetate (3 ×5 mL) and washed with water (2 ×10 mL). The ethyl acetate layer was separated and dried over Na 2 SO 4 . After evaporation of the solvent, the residue was purified by flash column chromatography (ethyl acetate/hexane) to give the desired products.4.4.1. henylbut-3-yn-2-one ( 2b ) [15] The general procedure was followed, and flash chromatography (n-hexane/EtOAc = 60/1) afforded 236 mg (82% yield). Colorless oil. TLC: R f = 0.43(n-hexane/EtOAc = 30/1). 1 H NMR (400 MHz, CDCl 3 ) 7.59 -7.54 (m, 2H), 7.48 -7.42 (m, 1H), 7.40 -7.34 (m, 2H), 2.45 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) 184.65, 133.07, 130.79, 128.67, 119.88, 90.34, 88.29, 32.78.
71%	With tert.-butylhydroperoxide; [copper(II)(salqu)] In acetonitrile at 70℃; for 4h;	Representative procedure: General procedure: 2-quinoxalinol salen (1 mol %) was added to a round bottom flask (25 mL), followed by CH3CN (10 mL), alkyne (0.5 mmol), and dropwise addition TBHP (4 equiv). The reaction was heated to 70 °C and stirred for 4 hr. The solvent was then evaporated under reduced pressure and the product was purified by flash column chromatography on silica gel (95:5 hex/EtOAc) to afford a clear or yellow oil.
62%	With tert.-butylhydroperoxide; FePcS-SiO₂ In chlorobenzene; <i>tert</i>-butyl alcohol at 40℃; for 24h;

56%	With tert.-butylhydroperoxide; toluene-4-sulfonic acid In benzene for 18h; Ambient temperature;
29%	With tert.-butylhydroperoxide; bis-(tributyltin oxide) dioxochromium(VI) In benzene at 60℃; for 8h;
	With tert.-butylhydroperoxide In <i>tert</i>-butyl alcohol at 40℃; for 24h;
	Multi-step reaction with 2 steps 1: CuCl / benzene 2: 100 percent / tetrabutylammonium chloride; tert-butyl hydroperoxide; 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt / Na₂CO₃; CuCl₂*2H₂O / H₂O / 24 h / 20 °C
	Multi-step reaction with 2 steps 1: tetrabutylammonium chloride; 2,2'-biquinoline-4,4'dicarboxylic acid dipotassium salt; Na₂CO₃ / CUCl₂2H₂O / H₂O / 24 h / 20 °C 2: 100 percent / tetrabutylammonium chloride; tert-butyl hydroperoxide; 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt / Na₂CO₃; CuCl₂2H₂O / H₂O / 24 h / 20 °C
42.6 %Chromat.	With tert.-butylhydroperoxide; C₃H₇NO*C₃₁H₃₁Cl₄Fe₂N₇O₃ In acetonitrile at 60℃; for 1h;

Reference： [1]Ning, Yangbo; Tan, Jiantao; Wang, Zhifan; Wang, Yuanhua [Journal of Organometallic Chemistry, 2021, vol. 954-955]
[2]Black, Clayton C.; Gorden, Anne E.V. [Tetrahedron Letters, 2018, vol. 59, # 9, p. 803 - 806]
[3]Perollier, Celine; Pergrale-Mejean, Corinne; Sorokin, Alexander B. [New Journal of Chemistry, 2005, vol. 29, # 11, p. 1400 - 1403]
[4]Muzart, Jacques; Piva, Olivier [Tetrahedron Letters, 1988, vol. 29, # 19, p. 2321 - 2324]
[5]Muzart, Jacques [Synthetic Communications, 1989, vol. 19, # 11-12, p. 2061 - 2068]
[6]Perollier, Celine; Sorokin, Alexander B. [Chemical Communications, 2002, # 14, p. 1548 - 1549]
[7]Nait Ajjou, Abdelaziz; Ferguson, Gabriel [Tetrahedron Letters, 2006, vol. 47, # 22, p. 3719 - 3722]
[8]Nait Ajjou, Abdelaziz; Ferguson, Gabriel [Tetrahedron Letters, 2006, vol. 47, # 22, p. 3719 - 3722]
[9]Location in patent: experimental part Khattar, Raghvi; Hundal; Mathur, Pavan [Inorganica Chimica Acta, 2012, vol. 390, p. 129 - 134]

7
[ 75-03-6 ]
[ 536-74-3 ]
[ 622-76-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: ethyl iodide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -78 - 20℃;
80%	With nickel(II) ferrite; potassium carbonate In water at 100℃; for 5h;	2.2. General procedure for the Sonogashira reaction General procedure: In a round-bottom flask equipped with a condenser for refluxingand a magnetic stirring bar, aryl/alkyl halide (1 mmol), phenylacetylene (1 mmol), K2CO3 (1.1 mmol), nickel ferrite nanoparticles(0.05 mmol) and water (3 ml) were added and heated at 100 °Cunder air atmosphere. The mixture was vigorously stirred underthese reaction conditions and its completion was monitored byTLC (EtOAc-n-hexane, 25:75).In each case, after completion of the reaction, the mixturewas dilutedwith diethyl ether and water. The organic layer was washed withbrine, dried over MgSO4, and concentrated under reduced pressureusing a rotary evaporator. The residue was purified by recrystallizationfrom ethanol and water.
75%	Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -40 - 20℃; for 0.333333h; Inert atmosphere; Stage #3: ethyl iodide In tetrahydrofuran for 8h; Inert atmosphere; Reflux;

70%	With potassium hydroxide In benzene at 80℃; for 1.33333h;
66%	Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -40 - 20℃; for 0.833333h; Inert atmosphere; Stage #2: ethyl iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 66℃; for 8h; Inert atmosphere;
	With dibenzo-18-crown-6; sodium 1.) benzene, 2.) 60 - 80 deg C, 5h; Yield given. Multistep reaction;

Reference： [1]Location in patent: scheme or table Zhao, Jinbo; Liu, Yu; He, Qiwen; Li, Yuxue; Ma, Shengming [Chemistry - A European Journal, 2009, vol. 15, # 42, p. 11361 - 11372]
[2]Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Rezvani, Hamid Reza [Catalysis Communications, 2015, vol. 60, p. 82 - 87]
[3]Ting, Chun-Ming; Hsu, Yi-Ling; Liu, Rai-Shung [Chemical Communications, 2012, vol. 48, # 52, p. 6577 - 6579]
[4]Lissel, Manfred [Tetrahedron Letters, 1985, vol. 26, # 15, p. 1843 - 1844]
[5]Zhang, Yang; Torker, Sebastian; Sigrist, Michel; Bregović, Nikola; Dydio, Paweł [Journal of the American Chemical Society, 2020, vol. 142, # 42, p. 18251 - 18265]
[6]Tarasova, O. A.; Amosova, S. V.; Trofimov, B. A [Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 8, p. 1566][Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 8, p. 1765]

8
[ 622-76-4 ]
[ 1007-32-5 ]
[ 495-40-9 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 669 - 672
[2]Organometallics,2016,vol. 35,p. 1658 - 1666
[3]Journal of Organic Chemistry,1997,vol. 62,p. 669 - 672
[4]Journal of Organometallic Chemistry,2011,vol. 696,p. 7 - 11
[5]Journal of the American Chemical Society,2005,vol. 127,p. 5766 - 5767
[6]Journal of the American Chemical Society,2009,vol. 131,p. 448 - 449
[7]Chemistry - A European Journal,2013,vol. 19,p. 8627 - 8633
[8]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9830 - 9836
[9]European Journal of Organic Chemistry,2018,vol. 2018,p. 1136 - 1140
[10]Organometallics,2018,vol. 37,p. 3588 - 3597
[11]European Journal of Organic Chemistry,2018,vol. 2018,p. 5304 - 5311
[12]Molecular catalysis,2019,vol. 469,p. 144 - 154

9
[ 3347-62-4 ]
[ 91-20-3 ]
[ 622-76-4 ]
[ 767-59-9 ]
[ 767-60-2 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 8188 - 8191

10
[ 622-76-4 ]
[ 69298-48-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With bromine; 1-n-butyl-3-methylimidazolim bromide at 20℃;
89%	With N-Bromosuccinimide In tetrahydrofuran at 80℃; for 1h; Inert atmosphere;	General procedure for products 3 (Table 2) General procedure: To a mixture of alkyne 1 (0.5 mmol) and N-halosuccinimide 2 (1.5 mmol), tetrahydrofuran (THF, 2.0 mL) was added under nitrogen at room temperature. The reaction temperature was raised to 80 °C for 1 h. The temperature of the reaction was cooled to room temperature. The resulting reaction solution was evaporated in vacuo to afford the crude products. NMR yields were determined by 1H NMR using dibromomethane as an internal standard. Solvent was evaporated, and the residue was purified by flash column chromatography on silica gel with petroleum ether as an eluent.
83%	With copper(ll) bromide In acetonitrile at 20℃; for 4h; Molecular sieve; stereoselective reaction;

61%	With N-Bromosuccinimide; acetic acid; lithium bromide In dichloromethane at 0℃; for 24h; regioselective reaction;	8. General procedure for dibromination General procedure: A 10 mL glass vial with a screw cap was charged with alkynes (0.2 mmol), NBS (0.24 mmol, 1.2equiv.), LiBr (0.24 mmol, 1.2equiv.) and a solvent mixture of DCM (0.5 mL) and HOAc (0.5 mL).The reaction mixture was stirred at 0 for 24 h. Upon completion, the reaction mixture was quenched with saturated NaCl solution and was extracted with EtOAc, the combined organic layers were dried with anhydrous Na2SO4 and the solvent was removed in vacuum. The residue was purified by flash column chromatography on silica gel (eluted with hexanes and ethyl acetate).
	With bromine; 1-n-butyl-3-methylimidazolim bromide In 1,2-dichloro-ethane at 25℃;

Reference： [1]Chiappe, Cinzia; Capraro, Dario; Conte, Valeria; Pieraccini, Daniela [Organic Letters, 2001, vol. 3, # 7, p. 1061 - 1063]
[2]Liu, Jinhua; Li, Wenjuan; Wang, Chao; Li, Yao; Li, Zhiping [Tetrahedron Letters, 2011, vol. 52, # 33, p. 4320 - 4323]
[3]Xiang, Jiannan; Yuan, Rui; Wang, Ruijia; Yi, Niannian; Lu, Linghui; Zou, Huaxu; He, Weimin [Journal of Organic Chemistry, 2014, vol. 79, # 23, p. 11378 - 11382]
[4]Hammond, Gerald B.; Liu, Shiwen; Xu, Bo; Yang, Yi; Yang, Yuhao; Zeng, Xiaojun [Chem, 2020, vol. 6, # 4, p. 1018 - 1031]
[5]Chiappe, Cinzia; Conte, Valeria; Pieraccini, Daniela [European Journal of Organic Chemistry, 2002, # 16, p. 2831 - 2837]

11
[ 622-76-4 ]
[ 122-78-1 ]
[ 101735-32-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With iron(III) chloride In 1,2-dichloro-ethane at 18 - 26℃; for 2h; regioselective reaction;	4.3. General procedure for the synthesis of naphthalene and phenanthrene derivatives General procedure: To a mixture of alkyne and aldehyde in 1,2-DCE was added anhydrous FeCl3. The solution was stirred at room temperature until the alkyne disappeared detected by TLC. Then the solvent was evaporated and the residue was subjected to chromatography directly eluting with petro ether to afford the corresponding product.
65%	With gallium(III) trichloride; water In dichloromethane Heating;

Reference： [1]Location in patent: experimental part Bu, Xiuli; Hong, Longcheng; Liu, Ruiting; Hong, Jianquan; Zhang, Zhengxing; Zhou, Xigeng [Tetrahedron, 2012, vol. 68, # 38, p. 7960 - 7965]
[2]Viswanathan, Ganapathy S.; Wang, Mingwen; Li, Chao-Jun [Angewandte Chemie - International Edition, 2002, vol. 41, # 12, p. 2138 - 2141]

12
[ 96-09-3 ]
[ 622-76-4 ]
[ 101735-32-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With p-toluenesulfonyl chloride; methyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 110℃; for 16h; Inert atmosphere; Sealed tube; regioselective reaction;	General procedures for synthesis of products 3 General procedure: General procedures for synthesis of products 3: A sealed tube was charged with diphenylacetylene (0.3 mmol) and tosyl chloride (0.33 mmol) stirred in dichloroethane (0.5 mL) for a while to completely dissolve, and then aryl epoxy (0.36 mmol) and MeOTf (0.015 mmol) added. The reaction mixture was stirred at 110 °C under nitrogen atmosphere for indicated time. After completion, the crude product was diluted with dichloromethane (10 mL) and concentrated under reduced pressure. The crude product was subjected to column chromatography on silica gel (petroleum ether/ethyl acetate: 100/1) to obtain the corresponding product
54%	With gallium(III) trichloride In dichloromethane Heating;

Reference： [1]Zou, Song; Zhang, Zeyu; Chen, Chao; Xi, Chanjuan [Chinese Chemical Letters, 2022, vol. 33, # 6, p. 3021 - 3025]
[2]Viswanathan, Ganapathy S.; Li, Chao-Jun [Synlett, 2002, # 9, p. 1553 - 1555]

13
[ 622-76-4 ]
[ 3457-55-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 1-phenyl-1-butyne With sodium periodate; C₂₂H₂₃N₇Ru⁽²⁺⁾F₆P^(1-)CF₃O₃S^(1-) In water; acetone at 20℃; for 1.5h; Stage #2: With sodium sulfite In dichloromethane; water for 0.166667h;	2.5. General procedure for the catalytic studies General procedure: Substrate (0.4 mmol) in 1 mL of acetone and catalyst (0.5 mol%)were taken in a round bottom flask. 2 mL of acetone and 2 mL of H2Owere added to it. NaIO4 (213 mg, 1.0 mmol) was dissolved in 1 mL ofH2O and transferred to the reaction mixture. The reaction mixture wasstirred at room temperature for∼15 min-240 min. After this time,Na2SO3 (2.0 mmol) was added to the reaction mixture followed byaddition of 2 mL of DCM and 3 mL of H2O. The reaction mixture wasfurther stirred for 10 min. A GC standard (ethylbenzene or mesityleneor stilbene or acetophenone) was added as a reference and the reactionmixture was again stirred for 5 min. It was then transferred to a separatingfunnel with the help of 3 mL of H2O and 8 mL of DCM. Theorganic layer was separated and aqueous layer was again extracted with5 mL of DCM (2 times). The combined organic layer was washed with20 mL of brine solution. Products and unreacted substrates were analyzedby GCMS. The yields were calculated by GC analyses.
77%	With potassium permanganate; iron(III) chloride In acetone at -78℃; for 15h;
76%	Stage #1: 1-phenyl-1-butyne With potassium permanganate; sodium hydrogencarbonate; magnesium sulfate In water; acetone at 0℃; for 4h; Stage #2: With sulfuric acid; sodium nitrite In water; acetone for 0.333333h;

75%	With Iodine monochloride; silver nitrate In acetonitrile at 20℃; for 4h;
70%	With dipotassium peroxodisulfate; oxygen In water; acetonitrile at 60℃; for 8h; Sealed tube;
64%	With sodium periodate; C₅₄H₄₅ClN₉Ru₂⁽³⁺⁾2Cl^(1-)Br^(1-) In water; acetone at 20℃;
62%	With diphenyl diselenide; water; bis-[(trifluoroacetoxy)iodo]benzene In tetrahydrofuran at 40℃; for 14h;
54%	With sodium periodate; C₂₃H₂₄ClN₄Ru⁽¹⁺⁾*Br^(1-) In water; acetone at 20℃;
37%	With N-iodo-succinimide; water In acetonitrile at 70℃; for 10h;
15%	With [bis(acetoxy)iodo]benzene; copper(II) bis(trifluoromethanesulfonate); acetic acid at 20℃; for 12h;
73 %Chromat.	With sodium periodate; C₅₄H₄₅ClN₉OsRu⁽³⁺⁾*3F₆P^(1-) In water; acetone at 20℃; for 3h;

Reference： [1]Gupta, Suraj K.; Mandal, Tanmoy; Gangber, Tejaswinee; Singh, Vivek; Choudhury, Joyanta [Inorganica Chimica Acta, 2020, vol. 500]
[2]Lai, Sheng; Lee, Donald G. [Tetrahedron, 2002, vol. 58, # 49, p. 9879 - 9887]
[3]Porcu, Stefania; Luridiana, Alberto; Martis, Alberto; Frongia, Angelo; Sarais, Giorgia; Aitken, David J.; Boddaert, Thomas; Guillot, Regis; Secci, Francesco [Chemical Communications, 2018, vol. 54, # 96, p. 13547 - 13550]
[4]Yang, Wen; Chen, Yu; Yao, Yongqi; Yang, Xin; Lin, Qifu; Yang, Dingqiao [Journal of Organic Chemistry, 2019, vol. 84, # 17, p. 11080 - 11090]
[5]Shen, Duyi; Wang, Hongyan; Zheng, Yanan; Zhu, Xinjing; Gong, Peiwei; Wang, Bin; You, Jinmao; Zhao, Yulei; Chao, Mianran [Journal of Organic Chemistry, 2021, vol. 86, # 7, p. 5354 - 5361]
[6]Gupta, Suraj K.; Choudhury, Joyanta [Chemical Communications, 2016, vol. 52, # 16, p. 3384 - 3387]
[7]Location in patent: experimental part Tingoli, Marco; Mazzella, Mauro; Panunzi, Barbara; Tuzi, Angela [European Journal of Organic Chemistry, 2011, # 2, p. 399 - 404]
[8]Gupta, Suraj K.; Sahoo, Sandeep K.; Choudhury, Joyanta [Organometallics, 2016, vol. 35, # 15, p. 2462 - 2466]
[9]Location in patent: experimental part Niu, Mingyu; Fu, Hua; Jiang, Yuyang; Zhao, Yufen [Synthesis, 2008, # 18, p. 2879 - 2882]
[10]Xia, Xiao-Feng; Gu, Zhen; Liu, Wentao; Wang, Ningning; Wang, Haijun; Xia, Yongmei; Gao, Haiyan; Liu, Xiang [Organic and Biomolecular Chemistry, 2014, vol. 12, # 48, p. 9909 - 9913]
[11]Zhou, Wei; Li, Hongji; Wang, Lei [Organic Letters, 2012, vol. 14, # 17, p. 4594 - 4597]
[12]Mandal, Tanmoy; Singh, Vivek; Choudhury, Joyanta [Chemistry - An Asian Journal, 2019, vol. 14, # 24, p. 4774 - 4779]

14
[ 622-76-4 ]
[ 4873-09-0 ]
1,3-diethyl-5-methyl-2,4-diphenylbenzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5961 - 5966

15
[ 622-76-4 ]
[ 530-47-2 ]
2-ethyl-1,3-diphenyl-1H-indole [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 9541 - 9544

16
[ 622-76-4 ]
[ 2170-08-3 ]
Dimethyl-phenylethynyl-{(E)-2-phenyl-3-[1-phenyl-meth-(E)-ylidene]-pent-1-enyl}-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: dimethylbis(phenylethynyl)silane With n-butyllithium; zirconocene dichloride In tetrahydrofuran at 50℃; for 3h; Stage #2: 1-phenyl-1-butyne In tetrahydrofuran at 50℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran

Reference： [1]Yu, Tao; Sun, Xiaohua; Wang, Congyang; Deng, Liang; Xi, Zhenfeng [Chemistry - A European Journal, 2005, vol. 11, # 6, p. 1895 - 1902]

17
[ 622-76-4 ]
[ 2170-08-3 ]
1,1-Dimethyl-4-phenyl-2-[1-phenyl-2-[1-phenyl-meth-(E)-ylidene]-but-(E)-ylidene]-1,2-dihydro-silete [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: dimethylbis(phenylethynyl)silane With n-butyllithium; zirconocene dichloride In tetrahydrofuran at 50℃; for 3h; Stage #2: 1-phenyl-1-butyne In tetrahydrofuran for 6h; Heating; Stage #3: With hydrogenchloride In tetrahydrofuran

Reference： [1]Yu, Tao; Sun, Xiaohua; Wang, Congyang; Deng, Liang; Xi, Zhenfeng [Chemistry - A European Journal, 2005, vol. 11, # 6, p. 1895 - 1902]

18
[ 622-76-4 ]
[ 159087-46-4 ]
(E)-1-(trimethylsilyl)-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-3-en-1-yne [ No CAS ]
(Z)-1-(trimethylsilyl)-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-3-en-1-yne [ No CAS ]
C₂₁H₃₁BO₂Si [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 14438 - 14439

19
[ 67-56-1 ]
[ 201230-82-2 ]
[ 622-76-4 ]
[ 4873-09-0 ]
3-ethyl-5-(methoxycarbonyl)methyl-2-phenyl-2-cyclopentenone [ No CAS ]

Reference： [1]Synthesis,2006,p. 3003 - 3008

20
[ 622-76-4 ]
[ 444-14-4 ]
C₁₆H₁₄BrF₂N [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 769 - 777

21
[ 300-57-2 ]
[ 622-76-4 ]
C₁₉H₂₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With zinc(II) iodide; zinc In dichloromethane at 25℃; for 16h;

Reference： [1]Hilt, Gerhard; Treutwein, Jonas [Angewandte Chemie - International Edition, 2007, vol. 46, # 44, p. 8500 - 8502]

22
[ 592-41-6 ]
[ 622-76-4 ]
C₁₆H₂₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With zinc(II) iodide; zinc In dichloromethane at 25℃; for 16h;

Reference： [1]Hilt, Gerhard; Treutwein, Jonas [Angewandte Chemie - International Edition, 2007, vol. 46, # 44, p. 8500 - 8502]

23
[ 111-66-0 ]
[ 622-76-4 ]
C₁₈H₂₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With zinc(II) iodide; zinc In dichloromethane at 25℃; for 16h;

Reference： [1]Hilt, Gerhard; Treutwein, Jonas [Angewandte Chemie - International Edition, 2007, vol. 46, # 44, p. 8500 - 8502]

24
[ 18146-00-4 ]
[ 622-76-4 ]
[ 1001165-11-2 ]

Yield	Reaction Conditions	Operation in experiment
	With zinc(II) iodide; zinc In dichloromethane at 25℃; for 8h;

Reference： [1]Hilt, Gerhard; Treutwein, Jonas [Angewandte Chemie - International Edition, 2007, vol. 46, # 44, p. 8500 - 8502]

25
[ 622-76-4 ]
[ 93-15-2 ]
C₂₁H₂₄O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 8500 - 8502

26
[ 622-76-4 ]
[ 72824-04-5 ]
C₁₉H₂₇BO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With zinc(II) iodide; zinc In dichloromethane at 25℃; for 8h;

Reference： [1]Hilt, Gerhard; Treutwein, Jonas [Angewandte Chemie - International Edition, 2007, vol. 46, # 44, p. 8500 - 8502]

27
[ 622-76-4 ]
[ 159087-46-4 ]
(E)-1-(trimethylsilyl)-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-3-en-1-yne [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 14438 - 14439

28
[ 5437-67-2 ]
[ 622-76-4 ]
[ 1236188-96-7 ]

Yield	Reaction Conditions	Operation in experiment
28%	In 1,3,5-trimethyl-benzene at 150℃; Inert atmosphere;
	In 1,3,5-trimethyl-benzene at 150℃; for 24h;	5.5-A Example 5; 1 -(2-Bromo-4-(5 -(4-ethyl-5 -phenylisoxazol-3 -yl)- 1 ,2,4-oxadiazol-3 - yl)benzyl)azetidine-3 -carboxylic acid; 5-A. Methyl 4-ethyl-5-phenylisoxazole-3-carboxylate; [00159] A solution of but-1-ynylbenzene (404 mg, 3.11 mmol) and dimethyl nitromalonate (0.381 mL, 2.82 mmol) in mesitylene (5 mL) was heated to 150 0C for 24 h. The reaction mixture was concentrated, and the residue purified on silica gel column with hexanes/ethyl acetate (10/1) to afford methyl 4-ethyl-5-phenylisoxazole- 3-carboxylate (194 mg). The compound had an HPLC ret. time = 3.25 min. -Column: YMC S5 COMBISCREEN 4.6X50 mm; Gradient time: 4 min; Flow rate = 4 ml/min; Solvent A = 10% MeOH - 90% Water - 0.2% H3PO4; Solvent B = 90% MeOH - 10% water - 0.2% H3PO; Start % B = O; Final % B = 100. LC-MS: M+1 = 232+.

Reference： [1]Watterson, Scott H.; Guo, Junqing; Spergel, Steve H.; Langevine, Charles M.; Moquin, Robert V.; Shen, Ding Ren; Yarde, Melissa; Cvijic, Mary Ellen; Banas, Dana; Liu, Richard; Suchard, Suzanne J.; Gillooly, Kathleen; Taylor, Tracy; Rex-Rabe, Sandra; Shuster, David J.; McIntyre, Kim W.; Cornelius, Georgia; D'Arienzo, Celia; Marino, Anthony; Balimane, Praveen; Warrack, Bethanne; Salter-Cid, Luisa; McKinnon, Murray; Barrish, Joel C.; Carter, Percy H.; Pitts, William J.; Xie, Jenny; Dyckman, Alaric J. [Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2820 - 2840]
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2010/85581, 2010, A1 Location in patent: Page/Page column 70-71

29
[ 88070-48-8 ]
[ 622-76-4 ]
[ 1235479-12-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In tert-Amyl alcohol at 110℃; for 16h; regioselective reaction;
32%	With sodium iodide dihydrate; palladium 10% on activated carbon; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 36h; Schlenk technique; regioselective reaction;	3.2. General procedure General procedure: A mixture of a substituted benzamide (1) (0.3 mmol, 1.0 equiv),an alkyne (2) (0.6 mmol or 0.9 mmol, 2.0 equiv or 3.0 equiv),10% Pd/C (0.03 mmol, 10 mol%, Alfa Aesar, No. 044696, eggshell,reduced), NaI·2H2O (0.6 mmol, 2.0 equiv), Cs2CO3 (0.3 mmol, 1.0equiv), and KOAc (0.6 mmol, 2.0 equiv) was weighted in a Schlenktube equipped with a stir bar. DMF (1.0 mL) was added and themixture was stirred at 120 °C for 36 h under air. Afterwards, themixture was filtered and washed with H2O (30 mL) and extractedwith CH2Cl2 (3×30 mL). The combined organic phase was driedwith anhydrous Na2SO4. After removal of solvents under reducedpressure, the residue was absorbed to small amounts of silica. Thepurification was performed by flash column chromatography onsilica gel with EA:PE (Petroleum ether) = 1:5 or 1:10 as eluent.
	With [Cp*Rh(CH₃CN)₃](BF₄)₂; potassium carbonate In water at 110℃; for 16h; Schlenk technique; Green chemistry; regioselective reaction;

Reference： [1]Hyster, Todd K.; Rovis, Tomislav [Journal of the American Chemical Society, 2010, vol. 132, # 30, p. 10565 - 10569]
[2]Shu, Zhen; Guo, Yuntao; Li, Wei; Wang, Baiquan [Catalysis Today, 2017, vol. 297, p. 292 - 297]
[3]Upadhyay, Nitinkumar Satyadev; Thorat, Vijaykumar H.; Sato, Ryota; Annamalai, Pratheepkumar; Chuang, Shih-Ching; Cheng, Chien-Hong [Green Chemistry, 2017, vol. 19, # 14, p. 3219 - 3224]

30
[ 622-76-4 ]
[ 66498-51-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 0.333333h;	General procedure for α,α-dibromoketones using CoFe2O4SiO2 -SO3H catalyst General procedure: In a typical reaction, alkyne (1 mmol), NBS (3 mmol), and CoFe2O4SiO2-SO3H catalyst (10 wt%) were taken in a round bottom flask in acetonitrile-water mixture (30:1). The reaction mixture was placed under continuous stirring for 20 min at room temperature. The reaction was monitored using TLC from time to time to ascertain the completion of the reaction. After completion of the reaction, the catalyst was separated via magnetic decantation. The crude product was purified by flash column chromatography using 5% petroleum ether-ethyl acetate as eluent. The catalyst was magnetically separated, washed with excess of ethyl acetate, methanol and dried in oven and kept in desiccator for further use. Spectroscopic data for the some of the compounds are given below.
66%	With N-Bromosuccinimide; iron(III) chloride hexahydrate; water In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;	General procedure for products 4 (Table 3) General procedure: To a mixture of alkyne 1 (0.5 mmol), N-halosuccinimide 2 (2.0 mmol), and FeCl3·6H2O (0.025 mmol) was added water (1.0 mL) and tetrahydrofuran (THF, 2.0 mL) under nitrogen at room temperature. The reaction temperature was raised to 80 °C for 3 h. The temperature of the reaction was cooled to room temperature. The resulting reaction solution was quenched with 2 mL of saturated NaHCO3 and extracted with 15 mL of ethyl acetate for three times. The extract was dried over MgSO4. After short column chromatography, the solvent was evaporated in vacuo to afford the crude products. NMR yields were determined by 1H NMR using dibromomethane as an internal standard. Solvent was evaporated, and the residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:200) as an eluent.
52%	With dipotassium peroxodisulfate; sodium bromide In water at 60℃; for 12h; Schlenk technique; Green chemistry;	General procedure for the synthesis of α,α-dihaloacetophenones via K2S2O8-mediated oxy-1,1-dihalogenation of alkynes (2a-2m, 3a-3j) General procedure: To a 25 ml Schlenck tube were added K2S2O8 (2.5 equiv.), NaX (2.0 equiv.), alkynes (0.5 mmol) and H2O (1 mL). The reaction mixture was warmed to 60 °C (oil bath) and stirred for 12 h. The reaction was cooled to room temperature,and ethyl actate (5 mL) and water (2 mL) were added. The organic layer was separated,and the aqueous phase was extracted with ethyl actate (10mL x 2). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated.The residue was purified by column chromatography to give desired product.

With dibromamine-T; water In acetone for 0.166667h; regioselective reaction;

4.2. General procedure for synthesis of ketones (2a-2k) General procedure: To a stirred solution alkyne (1 mmol) in acetone (3 mL) and water (0.1 mL), TsNBr2 (1.5 mmol) was added. After 10 min, KI (0.6 mmol) and Na2SO3 (3 mmol) was added and stirring was continued at room temperature. After the completion of the reaction the reaction mixture was washed with water and extracted with ethyl acetate. The organic layer was dried with Na2SO4, concentrated and purified by flash chromatography on silica gel (230-400 mesh) using petroleum ethere-ethyl acetate as eluent.

Reference： [1]Dutta, Mintu Maan; Rajbongshi, Kamal Krishna; Phukan, Prodeep [Synthetic Communications, 2017, vol. 47, # 24, p. 2330 - 2341]
[2]Liu, Jinhua; Li, Wenjuan; Wang, Chao; Li, Yao; Li, Zhiping [Tetrahedron Letters, 2011, vol. 52, # 33, p. 4320 - 4323]
[3]Wang, Jing-Yu; Jiang, Qing; Guo, Can-Cheng [Synthetic Communications, 2014, vol. 44, # 21, p. 3130 - 3138]
[4]Rajbongshi, Kamal Krishna; Hazarika, Debojit; Phukan, Prodeep [Tetrahedron, 2016, vol. 72, # 29, p. 4151 - 4158]

31
[ 622-76-4 ]
[ 5973-83-1 ]
[ 1350770-35-2 ]
[ 1350770-34-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium carbonate In 2,2,2-trifluoroethanol at 45℃; regioselective reaction;

Reference： [1]Hyster, Todd K.; Rovis, Tomislav [Chemical Communications, 2011, vol. 47, # 43, p. 11846 - 11848]

32
[ 622-76-4 ]
[ 2446-51-7 ]
4-ethyl-3-phenylisoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; potassium 2,4,6-trimethylbenzoate In lithium hydroxide monohydrate at 60℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;	2.2 General Procedure for Ruthenium-CatalyzedAnnulation of N-Methoxybenzamideswith Alkynes in PEG-400/H2O General procedure: A Schlenk tube equipped with a magnetic stir bar was charged with [RuCl2(p-cymene)]2 (9.2 mg, 0.015 mmol,3 mol%), N-methoxybenzamide 1 (0.5 mmol), potassium 2,4,6-trimethylbenzoate (20.3 mg, 0.1 mmol, 20 mol%), and PEG-400 (2.0 mL). The reaction tube was evacuated and backfilled with argon (this sequence was carried out three times) and then alkyne 2 (0.75 mmol, if liquid) and water(1.0 mL) were added by syringe (alkyne that was solid at room temperature was added with the ruthenium catalyst).The reaction mixture was stirred at 60 °C for 12 h underan argon atmosphere. After being cooled to room temperature,the reaction mixture was extracted with diethyl ether(3 × 10 mL). The combined ether layer was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired isoquinolone 3.
88%	With bis[dibromido(η⁶-p-cymene)osmium(II)]; anhydrous Sodium acetate; glacial acetic acid at 60℃; for 24h;
83%	With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; potassium 2,4,6-trimethylbenzoate In lithium hydroxide monohydrate at 60℃; for 16h; Inert atmosphere;

Reference： [1]Cai, Mingzhong; Li, Jianying; Liu, Rong; Ye, Qian [Catalysis Letters, 2022]
[2]Yang, Jian; Wu, Liexin; Xu, Huiying; Gao, Hui; Zhou, Zhi; Yi, Wei [Organic Letters, 2019, vol. 21, # 24, p. 9904 - 9908]
[3]Ackermann, Lutz; Fenner, Sabine [Organic Letters, 2011, vol. 13, # 24, p. 6548 - 6551]

33
[ 622-76-4 ]
2-methyl-N-(2-pyrimidyl)aniline [ No CAS ]
[ 1355058-69-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With F₆P^(1-)2Ru⁽²⁺⁾3Cl^(1-)*2C₁₀H₁₄; copper(II) acetate monohydrate In water at 100℃; for 24h; Inert atmosphere; Green chemistry; regioselective reaction;	4.2. General procedure for the ruthenium-catalyzed oxidative annulation reaction in PEG-400/H₂O General procedure: A mixture of N-2-pyrimidyl-substituted aniline 1 (0.5 mmol), alkyne 2 (1.0 mmol), Cu(OAc)2H2O (1.0 mmol), [Ru2Cl3(p-cymene)2][PF6] (0.015 mmol) in PEG-400 (1.2 mL) and H2O (0.8 mL) was stirred at 100 °C under Ar for 24 h until complete consumption of starting material as judged by TLC. After being cooled to room temperature, the mixture was extracted three times with light petroleum ether (3 x 10 mL). The combined ether phase was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired products 3.
89%	With potassium hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; sodium acetate In water; isopropyl alcohol Electrochemical reaction; Reflux; Inert atmosphere;
77%	With potassium hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper(II) acetate monohydrate In water at 100℃; for 22h; Inert atmosphere; regioselective reaction;

Reference： [1]Liao, Yang; Wei, Ting; Yan, Tao; Cai, Mingzhong [Tetrahedron, 2017, vol. 73, # 9, p. 1238 - 1246]
[2]Xu, Fan; Li, Yan-Jie; Huang, Chong; Xu, Hai-Chao [ACS Catalysis, 2018, vol. 8, # 5, p. 3820 - 3824]
[3]Ackermann, Lutz; Lygin, Alexander V. [Organic Letters, 2012, vol. 14, # 3, p. 764 - 767]

34
[ 622-76-4 ]
[ 104-09-6 ]
[ 1394846-87-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With iron(III) chloride In 1,2-dichloro-ethane at 18 - 26℃; for 2h; regioselective reaction;	4.3. General procedure for the synthesis of naphthalene and phenanthrene derivatives General procedure: To a mixture of alkyne and aldehyde in 1,2-DCE was added anhydrous FeCl3. The solution was stirred at room temperature until the alkyne disappeared detected by TLC. Then the solvent was evaporated and the residue was subjected to chromatography directly eluting with petro ether to afford the corresponding product.

Reference： [1]Location in patent: experimental part Bu, Xiuli; Hong, Longcheng; Liu, Ruiting; Hong, Jianquan; Zhang, Zhengxing; Zhou, Xigeng [Tetrahedron, 2012, vol. 68, # 38, p. 7960 - 7965]

35
[ 622-76-4 ]
[ 4251-65-4 ]
[ 1394846-76-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With iron(III) chloride; In 1,2-dichloro-ethane; at 18 - 26℃; for 2h;	General procedure: To a mixture of alkyne and aldehyde in 1,2-DCE was added anhydrous FeCl3. The solution was stirred at room temperature until the alkyne disappeared detected by TLC. Then the solvent was evaporated and the residue was subjected to chromatography directly eluting with petro ether to afford the corresponding product.

Reference： [1]Tetrahedron,2012,vol. 68,p. 7960 - 7965

36
[ 622-76-4 ]
[ 43017-75-0 ]
[ 1394847-08-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With iron(III) chloride In 1,2-dichloro-ethane at 18 - 26℃; for 2h; regioselective reaction;	4.3. General procedure for the synthesis of naphthalene and phenanthrene derivatives General procedure: To a mixture of alkyne and aldehyde in 1,2-DCE was added anhydrous FeCl3. The solution was stirred at room temperature until the alkyne disappeared detected by TLC. Then the solvent was evaporated and the residue was subjected to chromatography directly eluting with petro ether to afford the corresponding product.

Reference： [1]Location in patent: experimental part Bu, Xiuli; Hong, Longcheng; Liu, Ruiting; Hong, Jianquan; Zhang, Zhengxing; Zhou, Xigeng [Tetrahedron, 2012, vol. 68, # 38, p. 7960 - 7965]

37
[ 4594-71-2 ]
[ 622-76-4 ]
C₂₀H₁₉NO [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4166 - 4169

38
[ 1003-31-2 ]
[ 622-76-4 ]
[ 58109-40-3 ]
3-ethyl-4-phenyl-2-(thiophen-2-yl)quinoline [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 5323 - 5327
Angew. Chem.,2013,vol. 125,p. 5431 - 5435,5

39
[ 622-76-4 ]
[ 66003-76-7 ]
[ 16282-16-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2096 - 2099

40
[ 622-76-4 ]
[ 614-14-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 1-phenyl-1-butyne With formic acid; toluene-4-sulfonic acid In water at 100℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: With chloro-(pentamethylcyclopentadienyl)-{5-methoxy-2-{1-[(4-methoxyphenyl)imino-N]ethyl}phenyl-C}-iridium(lll); water; sodium formate at 20 - 80℃; for 14h;
	Multi-step reaction with 2 steps 1: trifluorormethanesulfonic acid; water / 2,2,2-trifluoroethanol / 48 h / 40 °C / Inert atmosphere 2: sodium tetrahydroborate; methanol / 20 °C

Reference： [1]Li, Jia; Wang, Chao; Xue, Dong; Wei, Yawen; Xiao, Jianliang [Green Chemistry, 2013, vol. 15, # 10, p. 2685 - 2689]
[2]Liu, Sensheng; Liu, Huan; Zhou, Haifeng; Liu, Qixing; Lv, Jinliang [Organic Letters, 2018, vol. 20, # 4, p. 1110 - 1113]

41
[ 622-76-4 ]
[ 107-18-6 ]
[ 1555862-36-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1-(carboxymethyl)-3-methylimidazolium chloride; hydrogenchloride; palladium dichloride In water at 20℃; for 30h; diastereoselective reaction;	4.2 General procedure for the synthesis of 1,4-dienes General procedure: A mixture of alkynes 1 (0.5 mmol), 2 (0.6 mmol), palladium chloride (3.2 mg, 3 mol %), ionic liquid (0.5 mL), HX (0.25 mL) in a test tube (10 mL) equipped with a magnetic stirring bar. The mixture was stirred under the atmosphere of air at room temperature. After the reaction was completed, 10 mL ethyl acetate (3×10 mL) was added into the tube. The combined organic layers were washed with brine to neutral, dried over MgSO4, and concentrated in vacuum. Purification of the residue on a preparative TLC afforded the desired products. Residual ionic liquid obtained after the workup was stirred with diethyl ether (2×10 mL) for 15 min, and the ethereal layer was decanted. The ionic liquid was then directly used for the next runs without further dry and reused for up to five runs.

Reference： [1]Li, Jianxiao; Yang, Shaorong; Wu, Wanqing; Qi, Chaorong; Deng, Zhongxian; Jiang, Huanfeng [Tetrahedron, 2014, vol. 70, # 7, p. 1516 - 1523]

42
[ 622-76-4 ]
[ 657-84-1 ]
[ 1574533-08-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 100℃; for 36h;	General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%):

Reference： [1]Tetrahedron,2014,vol. 70,p. 1984 - 1990

43
[ 622-76-4 ]
[ 657-84-1 ]
[ 445378-01-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h;	General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1

Reference： [1]Tetrahedron,2014,vol. 70,p. 1984 - 1990

44
[ 574-66-3 ]
[ 622-76-4 ]
[ 1523451-60-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With palladium diacetate; trifluoroacetic acid; zinc dibromide In 1,4-dioxane; chlorobenzene at 120℃; for 5h;	General Procedure A: Synthesis of isoquinoline oxides General procedure: A solution of oxime (0.3 mmol), alkyne (0.45 mmol), Pd(OAc)2 (10 mol%), ZnBr2(0.3 mmol), TFA (0.06 mmol) in PhCl : dioxane = 2 : 1 (1.5 mL) was heated at 120 °C under air. The reaction was monitored by TLC. After the reaction was completed, thereaction mixture was cooled down to room temperature. The mixture was washed with sat. aq NaHCO3 (15 mL) to neutralize acid. The aqueous layers were extracted with ethyl acetate (15 mL x 3). The combined organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to provide the crude product. The crude product was purified by flash column chromatography on silica gel.

Reference： [1]Li, Bingyao; Jiao, Pingxuan; Zhong, Hongban; Huang, Jianhui [Synlett, 2013, vol. 24, # 18, p. 2431 - 2436]

45
[ 622-76-4 ]
[ 673485-54-6 ]
[ 1610537-61-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; acetic acid at 120℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Qian, Zhen-Chao; Zhou, Jun; Li, Bo; Hu, Fang; Shi, Bing-Feng [Organic and Biomolecular Chemistry, 2014, vol. 12, # 22, p. 3594 - 3597]

46
[ 885-77-8 ]
[ 622-76-4 ]
[ 1616470-98-4 ]
[ 1616470-99-5 ]

Yield	Reaction Conditions	Operation in experiment
82 % de	With tetrafluoroboric acid In ethylene dibromide at 55℃; Overall yield = 45 %;	2. General Procedure for the Synthesis of fluoroalkenes General procedure: To a stirred solution of alcohol (0.5 mmol) andfluoroboric acid (0.75mmol)in DBE (2.0 mL) was added alkyne (0.6 mmol). The mixture was heated at 55°C andstirred for 8-10 h. Upon completion of the reaction, the solvent was removed by rotary evaporation to provide rawproduct, which waspurified on silica gel to afford themixture of E/Z isomers.

Reference： [1]Yan, Xiao-Wei; Zhang, Qiang; Wei, Wei; Ji, Jian-Xin [Tetrahedron Letters, 2014, vol. 55, # 28, p. 3750 - 3752]

47
[ 622-76-4 ]
(E)-(1-bromo-2-iodobut-1-en-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 1-phenyl-1-butyne With trimethylsilyl bromide In dichloromethane; toluene at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With N-iodo-succinimide In dichloromethane; toluene; acetonitrile at -78 - 20℃; for 1h; Inert atmosphere; stereoselective reaction;	3 4.3. General procedure of (E)-3-(1-bromo-2-iodobut-1-en-1-yl)-1,6-dibutylpyrene 2, for Scheme 3 General procedure: Under an argon atmosphere, to a solution of 1 (366 mg, 1.0 mmol) in anhydrous toluene (4 mL) at 78°C was added TMSBr (1.5 mL of 1 M in dichloromethane) dropwise over 5 min, and the mixture was stirred for 5 min. Then, NIS (337 mg, 1.5 mmol) in acetonitrile was slowly added over 5 min, and the cooling-bath was removed to warm to room temperature. After additional stirring for 1 h, the reaction was quenched at 0°C with saturated aqueous sodium thiosulfate, and stirred for 10 min, and warmed to ambient temperature. The aqueous phase was extracted with toluene (15 mLx3), and the combined organic phases were washed with brine (30 mL), and then dried with sodium sulfate, and concentrated to give 589 mg of crude products. Purification by silica gel column chromatography (eluent: hexane) afforded 443 mg of 2 in 77% yield as a yellow solid material. Analytical data are listed in the section below. 4.3.3. (E)-(1-Bromo-2-iodobut-1-en-1-yl)benzene (4). 81% yield (98:2, 2.45 g); a pale red oil; 1H NMR (400 MHz, CDCl3) 7.39-7.29 (m, 5H), 2.87 (q, J=7.4 Hz, 2H), 1.19 (t, J=7.4 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) 144.1, 129.4, 128.9, 128.6, 117.1, 103.9, 39.6, 13.3 ppm; MS (EI) m/z: 336 (M+), 257 ([M-Br]+); IR (neat): 3054, 2969, 2930, 2871, 1593, 1487, 1455, 1441 cm-1; Anal. Calcd for C10H10BrI: C, 35.64; H, 2.99. Found: C, 35.66; H, 2.79; HRMS (DI) calcd for C10H10BrI: 335.9011, found 335.9029.
81%	Stage #1: 1-phenyl-1-butyne With trimethylsilyl bromide In dichloromethane; toluene at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: With N-iodo-succinimide In dichloromethane; toluene at 20℃; for 1h; Inert atmosphere;	2 Synthesis of (E) -bromoiodoalkene (I) represented by the chemical formula (1) General procedure: Under an argon atmosphere, a solution of alkyne (II) (366 mg, 1.0 mmol) represented by the chemical formula (12) in anhydrous toluene ) Solution (-78 ° C.) was added dropwise a 1 M methylene chloride solution of TMSBr (1.5 mL) for 5 minutes and the mixture was stirred for 5 minutes. Next, a solution of N-iodosuccinimide (NIS: 337 mg, 1.5 mmol) in acetonito Ril solution (1.5 mL) was added over 5 minutes, the cooling bath was removed and warmed to room temperature. The starting alkyne (II) disappeared immediately after the addition of iodosuccinimide and became one spot on TLC. After further stirring for 1 hour, a saturated aqueous solution of sodium thiosulfate was added and the reaction was terminated at 0 ° C. The mixture was stirred for 10 minutes and then warmed to room temperature.Toluene (15 mL × 3) was added to extract the aqueous layer. The organic layer was washed with brine (30 mL), then dried with Na 2 SO 4 and concentrated to give a crude product (589 mg). The crude product was confirmed to be an isomer ratio of 94: 6 on the 1 H NMR spectrum. The isomer ratio is (E) -bromoiodoalkene (I) in which the positions of Br and I are reversed with respect to (E) -bromoiodoalkene (I) represented by chemical formula (1) It was 6. This was purified by silica gel column chromatography (eluent: hexane) to obtain (E) -bromoiodoalkene (I) represented by chemical formula (1) as a yellowish white solid (215 mg, yield 77%) . The isomer ratio was 94: 6, unchanged from that before purification. The structure around the double bond was obtained by X-ray crystal structure analysis of the single crystal of the obtained product, and it was found that it is (E) -1-bromo-2-iodovinyl compound.In Example 2 and Comparative Examples 1 to 3, a commercially available asymmetric alkyne 1-phenyl-1-butyne was tested for iodobromination. In Example 2, iodobromination was performed on 1-phenyl-1-butyne by the same method as in Example 1 to obtain (E) -bromoiodoalkene represented by the chemical formula (2) I) as a pale red oil having 2.45 g (yield 77%). The isomer ratio was 98: 2 which was the same as before purification. In addition, no unreacted 1-phenyl-1-butyne remained. In Example 2, (E) -bromoiodoalkene (I) could be obtained on a gram scale.
75%	With N-iodo-succinimide; acetic acid; lithium bromide In dichloromethane at 0℃; for 24h; regioselective reaction;	7. General procedure for iodobromination General procedure: A 10 mL glass vial with a screw cap was charged with alkynes (0.2 mmol), NIS (0.3 mmol, 1.5equiv.), LiBr (0.4 mmol, 2 equiv) and a solvent mixture of DCM (0.5 mL) and HOAc (0.5 mL).The reaction mixture was stirred at 0 for 24 h. Upon completion, the reaction mixture was quenched with saturated NaCl solution and was extracted with EtOAc, the combined organic layers were dried with anhydrous Na2SO4 and the solvent was removed in vacuum. The residue was purified by flash column chromatography on silica gel (eluted with hexanes and ethyl acetate).

Reference： [1]Ide, Masataka; Yauchi, Yuta; Shiogai, Ryo; Iwasawa, Tetsuo [Tetrahedron, 2014, vol. 70, # 45, p. 8532 - 8538]
[2]Current Patent Assignee: RYUKOKU UNIVERSITY - JP2016/30731, 2016, A Location in patent: Paragraph 0043; 0045; 0048
[3]Hammond, Gerald B.; Liu, Shiwen; Xu, Bo; Yang, Yi; Yang, Yuhao; Zeng, Xiaojun [Chem, 2020, vol. 6, # 4, p. 1018 - 1031]

48
[ 5378-52-9 ]
[ 622-76-4 ]
4-ethyl-3-phenylquinolin-2-amine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 11541 - 11548

49
[ 5378-52-9 ]
[ 622-76-4 ]
5-ethyl-2,4-diphenylimidazo[1,2-a]quinoline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 11541 - 11548

50
[ 622-76-4 ]
[ 5973-83-1 ]
[ 1350770-34-1 ]
C₁₇H₁₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium carbonate at 45℃;

Reference： [1]Hyster, Todd K.; Rovis, Tomislav [Chemical Communications, 2015, vol. 51, # 26, p. 5778 - 5778]

51
[ 28281-76-7 ]
[ 622-76-4 ]
[ 1416562-06-5 ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 9972 - 9974

52
[ 622-76-4 ]
[ 369-57-3 ]
[ 16282-16-9 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 4808 - 4813
Angew. Chem.,2016,vol. 128,p. 54888 - 54893

53
[ 622-76-4 ]
[ 6625-74-7 ]
(E)-N-(2-(1-phenylbut-1-en-2-yl)phenyl)pivalamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 12h; Inert atmosphere; Sealed tube; regioselective reaction;	VI. General procedure for hydroarylation reaction General procedure: To a screw-cap vial was added AgSbF6 (8 mol%), [RhCp*Cl2]2 (1 mol%), Cu(OAc)2·H2O (10 mol%) and pivalimide (0.2 mmol) are weighed into the vial open to air (if a solid, the alkyne is added at this point). 1,2-DCE (1 mL) and alkyne (1 equiv.) if a liquid are added via syringe and the reaction is sealed with a plastic screw-cap lid and placed in a pre-heated (80 °C) block under nitrogen atmosphere. The reaction is stirred for 12 hours and then cooled to room temperature and checked by TLC. The reaction is filtered over celite, washing with ether or dichloromethane into a 50 mL round-bottom flask. The solvent is removed and the residue was purified by flash column chromatography on silica gel with ethyl acetate and pet.ether as the solvent (typically 5% ethyl acetate in pet. ether).

Reference： [1]Kathiravan, Subban; Nicholls, Ian A. [Tetrahedron Letters, 2017, vol. 58, # 1, p. 1 - 4]

54
[ 622-76-4 ]
[ 96468-88-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With bis(acetylacetonate)nickel(II); 1,3-dibenzylimidazolium bromide; butyl magnesium bromide In tetrahydrofuran; toluene at 60℃; for 1h; Inert atmosphere; Schlenk technique; regioselective reaction;
42%	With C₁₅H₂₃Cl₂FeN₃; ethylmagnesium bromide In tetrahydrofuran at 80℃; for 20h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;	4.9 General procedure for catalytic cyclotrimerization of alkynes General procedure: To a stirred solution of catalyst 1 in THF (1mL), alkyne (0.5mmol) and then EtMgBr (11mol%, 1M in THF) was charged in PTFE screw-capped reaction vial equipped with a stirrer bar inside the glovebox. Then, the reaction mixture was brought outside and stirred at room temperature. Progress of the reaction was monitored by GC, which indicated the completion of the reaction in specified time. The reaction mixture was quenched by exposing it to the open atmosphere. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography to provide cyclotrimerized product.

Reference： [1]Xue, Fei; Loh, Ying Kai; Song, Xiaolu; Teo, Wei Jie; Chua, J. Y. Darrence; Zhao, Jin; Hor, T. S. Andy [Chemistry - An Asian Journal, 2017, vol. 12, # 1, p. 168 - 173]
[2]Gawali, Suhas Shahaji; Gunanathan, Chidambaram [Journal of Organometallic Chemistry, 2019, vol. 881, p. 139 - 149]

55
[ 622-76-4 ]
[ 95-54-5 ]
[ 10130-25-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 1-phenyl-1-butyne With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene In dichloromethane at -78 - 0℃; Stage #2: With water; sodium hydroxide In dichloromethane at 0 - 40℃; for 12h; Stage #3: 1,2-diamino-benzene Further stages;
72%	With dibromamine-T; water; potassium carbonate In water; acetonitrile at 80℃; for 1h;	4.2. General procedure for synthesis of quinoxalines (3a-3q) General procedure: To a solution of alkyne (0.5 mmol) in a mixture of CH3CN and H2O (9:1 ratio, 3 mL), TsNBr2 (1 mmol), 1,2-diamine (0.5 mmol) and K2CO3 (2 mmol) was added and the mixture was heated at 80 °C in open air for 1 h. After completion of the reaction, water was added and the reaction mixture was extracted with EtOAc (3×25 mL). The organic layer was separated, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography using petroleum ether and ethyl acetate mixture as eluent.

Reference： [1]Zhang, Zhong; Luo, Yuzheng; Du, Hongguang; Xu, Jiaxi; Li, Pingfan [Chemical Science, 2019, vol. 10, # 19, p. 5156 - 5161]
[2]Hazarika, Debojit; Phukan, Prodeep [Tetrahedron, 2017, vol. 73, # 10, p. 1374 - 1379]

56
[ 622-76-4 ]
(2-methoxy-phenyl)-pyrimidin-2-yl-amine [ No CAS ]
3-ethyl-7-methoxy-2-phenyl-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With F₆P^(1-)2Ru⁽²⁺⁾3Cl^(1-)*2C₁₀H₁₄; copper(II) acetate monohydrate In water at 100℃; for 24h; Inert atmosphere; Green chemistry;	4.2. General procedure for the ruthenium-catalyzed oxidative annulation reaction in PEG-400/H₂O General procedure: A mixture of N-2-pyrimidyl-substituted aniline 1 (0.5 mmol), alkyne 2 (1.0 mmol), Cu(OAc)2H2O (1.0 mmol), [Ru2Cl3(p-cymene)2][PF6] (0.015 mmol) in PEG-400 (1.2 mL) and H2O (0.8 mL) was stirred at 100 °C under Ar for 24 h until complete consumption of starting material as judged by TLC. After being cooled to room temperature, the mixture was extracted three times with light petroleum ether (3 x 10 mL). The combined ether phase was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired products 3.

Reference： [1]Liao, Yang; Wei, Ting; Yan, Tao; Cai, Mingzhong [Tetrahedron, 2017, vol. 73, # 9, p. 1238 - 1246]

57
[ 622-76-4 ]
[ 64019-08-5 ]
5,7-dimethyl-3-ethyl-2-phenyl-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With F₆P^(1-)2Ru⁽²⁺⁾3Cl^(1-)*2C₁₀H₁₄; copper(II) acetate monohydrate In water at 100℃; for 24h; Inert atmosphere; Green chemistry;	4.2. General procedure for the ruthenium-catalyzed oxidative annulation reaction in PEG-400/H₂O General procedure: A mixture of N-2-pyrimidyl-substituted aniline 1 (0.5 mmol), alkyne 2 (1.0 mmol), Cu(OAc)2H2O (1.0 mmol), [Ru2Cl3(p-cymene)2][PF6] (0.015 mmol) in PEG-400 (1.2 mL) and H2O (0.8 mL) was stirred at 100 °C under Ar for 24 h until complete consumption of starting material as judged by TLC. After being cooled to room temperature, the mixture was extracted three times with light petroleum ether (3 x 10 mL). The combined ether phase was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired products 3.

Reference： [1]Liao, Yang; Wei, Ting; Yan, Tao; Cai, Mingzhong [Tetrahedron, 2017, vol. 73, # 9, p. 1238 - 1246]

58
[ 622-76-4 ]
[ 248937-32-8 ]
3-ethyl-2-phenyl-1-(pyrimidin-2-yl)-1H-benzo[g]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With F₆P^(1-)2Ru⁽²⁺⁾3Cl^(1-)*2C₁₀H₁₄; copper(II) acetate monohydrate In water at 100℃; for 24h; Inert atmosphere; Green chemistry;	4.2. General procedure for the ruthenium-catalyzed oxidative annulation reaction in PEG-400/H₂O General procedure: A mixture of N-2-pyrimidyl-substituted aniline 1 (0.5 mmol), alkyne 2 (1.0 mmol), Cu(OAc)2H2O (1.0 mmol), [Ru2Cl3(p-cymene)2][PF6] (0.015 mmol) in PEG-400 (1.2 mL) and H2O (0.8 mL) was stirred at 100 °C under Ar for 24 h until complete consumption of starting material as judged by TLC. After being cooled to room temperature, the mixture was extracted three times with light petroleum ether (3 x 10 mL). The combined ether phase was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired products 3.

Reference： [1]Liao, Yang; Wei, Ting; Yan, Tao; Cai, Mingzhong [Tetrahedron, 2017, vol. 73, # 9, p. 1238 - 1246]

59
[ 622-76-4 ]
[ 824-79-3 ]
(E)-1-((1-chloro-1-phenylbut-1-en-2-yl)sulfonyl)-4-methylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol at 80℃; for 3h; Inert atmosphere; Schlenk technique; Enzymatic reaction; stereoselective reaction;
83%	With iron(III) chloride hexahydrate In 2,2,2-trifluoroethanol at 120℃; for 3h; Inert atmosphere;	11 Synthesis Example 11 (E) -1 - ((1-chloro-phenylbutene) sulfonyl) -4-methylbenzene To the reactor was added 0.20 mmol of 1-phenyl-1-butyne, 0.30 mmol of sodium p-methylphenylsulfinate,0.40 mmol of ferric chloride hexahydrate, 2.0 mL of trifluoroethanol solvent. Heated to 120 ° C under a nitrogen atmosphere,After stirring for 3 h, the reaction was stopped, cooled to room temperature, extracted with dichloromethane, dried, and the solvent was removed by distillation under reduced pressure. The crude product was separated by column chromatography to give the desired product in 83% yield.

Reference： [1]Zeng, Kui; Chen, Lang; Chen, Yi; Liu, Yongping; Zhou, Yongbo; Au, Chak-Tong; Yin, Shuang-Feng [Advanced Synthesis and Catalysis, 2017, vol. 359, # 5, p. 841 - 847]
[2]Current Patent Assignee: HUNAN UNIVERSITY - CN106083669, 2016, A Location in patent: Paragraph 0060; 0061; 0062

60
[ 591-50-4 ]
[ 5963-77-9 ]
[ 622-76-4 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2061 - 2064
[2]Tetrahedron Letters,2017,vol. 58,p. 1413 - 1416

61
[ 1003-31-2 ]
[ 622-76-4 ]
[ 1428541-15-4 ]
3-ethyl-4,5-diphenyl-2-(thiophen-2-yl)pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4824 - 4828
Angew. Chem.,2017,vol. 129,p. 4902 - 4906,5

62
[ 622-76-4 ]
[ 59046-72-9 ]
[ 77502-10-4 ]
[ 495-40-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 37% 2: 36%	With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 200℃; for 0.5h; Microwave irradiation;	General procedure for the reaction of 2-(phenylethynyl)benzaldehyde (1) and alkynes 2 General procedure: A solution of 2-(phenylethynyl)benzaldehyde (1) (0.60 mmol, 124 mg), alkyne 2 (0.30 mmol), and TsOH.H2O(0.90 mmol, 171 mg) in ClCH2CH2Cl (2.0 mL) was treated at 200 °C for 30 min under microwave condition (Biotage INITIATOR; Allreactions were carried out under temperature-constant operation). Thereaction mixture was diluted with CHCl3 and washed with saturatedNaHCO3 (aq) and brine. The organic layer was dried over MgSO4.After removal of the solvent under reduced pressure, the residue waspurified by chromatography on SiO2 to give the naphthalene derivatives. Further purification was carried out a recyclable preparativeHPLC, if necessary. The structures of the products were assigned bytheir NMR spectra. The product was characterized by comparing itsspectral data with previous report.8a

Reference： [1]Umeda, Rui; Ikeda, Naoki; Ikeshita, Masahiro; Sumino, Keita; Nishimura, Sota; Nishiyama, Yutaka [Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 2, p. 213 - 215]

63
[ 622-76-4 ]
[ 701-49-5 ]
3-ethyl-3-benzyl-5-fluoro-N-methylisoindolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With rhenium(I) pentacarbonyl bromide; lithium tert-butoxide at 140℃; for 36h; Schlenk technique; Inert atmosphere;	2 Example 2 3-Ethyl-3-benzyl-5-fluoro-N-methylisoindolinone (Formula I-b) To a 25 mL Schlenk bottle, under N2 protection,5-fluoro-N-methylbenzamide (formula II-b) (1 mmol, 153.1 mg)1-phenyl-1-butyne (formula III-a) (1 mmol, 130 mg)Catalyst pentacarbonyl rhenium bromide (0.025 mmol, 10.2 mg),Lithium tert-butoxide (0.3 mmol, 24 mg) andSolvent anisole (4 mL),At 140 ° C,After 36 h the reaction was quenched with saturated NaHCO3 solution (10 mL)And then extracted with methylene chloride, the organic phase was combined, dried with anhydrous sodium sulfate, filtered and dried.Purification by column chromatography (eluent: petroleum ether: ethyl acetate = 5/1, v / v) gave 261 mg of the desired product (Formula I-a) in 92% yield.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Institute of Chemistry (in: CAS) - CN107151226, 2017, A Location in patent: Paragraph 0029; 0030; 0031; 0032

64
[ 622-76-4 ]
[ 97-51-8 ]
[ 149-73-5 ]
3-ethyl-2-methoxy-6-nitro-2-phenyl-2H-1-benzopyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With trifluorormethanesulfonic acid In toluene at 60℃; for 15h; Inert atmosphere; regioselective reaction;	4.2 General procedure for the synthesis of 2,3-disubstituted 2H-1-benzopyrans General procedure: To a solution of nitrosalicylaldehyde (2.0 mmol), diphenylacetylene (1.0 mmol) and trimethyl orthoformate (2.0 mmol) in toluene (5.0 mL) under nitrogen, trifluoromethanesulfonic acid (18 μL, 0.20 mmol, 20 mol%) was added. After being stirred at reflux for 15 h, methanol (5.0 mL, 0.12 mol) was added. Then the reaction mixture was quenched with H2O. The organic layer was separated and the aqueous layer was extracted with ethylacetate. The combined organic layer was washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (hexane/ethylacetate = 100: 1 to 20: 1) to afford product.

Reference： [1]Tanaka, Kenta; Sukekawa, Mayumi; Shigematsu, Yosuke; Hoshino, Yujiro; Honda, Kiyoshi [Tetrahedron, 2017, vol. 73, # 45, p. 6456 - 6464]

65
[ 24589-99-9 ]
[ 622-76-4 ]
[ 149-73-5 ]
3-ethyl-2-methoxy-6-methoxycarbonyl-2-phenyl-2H-1-benzopyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With trifluorormethanesulfonic acid In toluene at 60℃; for 15h; Inert atmosphere; regioselective reaction;	4.2 General procedure for the synthesis of 2,3-disubstituted 2H-1-benzopyrans General procedure: To a solution of nitrosalicylaldehyde (2.0 mmol), diphenylacetylene (1.0 mmol) and trimethyl orthoformate (2.0 mmol) in toluene (5.0 mL) under nitrogen, trifluoromethanesulfonic acid (18 μL, 0.20 mmol, 20 mol%) was added. After being stirred at reflux for 15 h, methanol (5.0 mL, 0.12 mol) was added. Then the reaction mixture was quenched with H2O. The organic layer was separated and the aqueous layer was extracted with ethylacetate. The combined organic layer was washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (hexane/ethylacetate = 100: 1 to 20: 1) to afford product.

Reference： [1]Tanaka, Kenta; Sukekawa, Mayumi; Shigematsu, Yosuke; Hoshino, Yujiro; Honda, Kiyoshi [Tetrahedron, 2017, vol. 73, # 45, p. 6456 - 6464]

66
[ 5963-77-9 ]
[ 108-90-7 ]
[ 622-76-4 ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; caesium carbonate; In dimethyl sulfoxide; at 130℃; for 12h;	General procedure: Alkynyl carboxylic acid (1.0 mmol), aryl chloride (1.0 mmol), Pd(OAc)2 (3.4 mg, 0.015 mmol), L5 (17.5 mg, 0.03 mmol), Cs2CO3 (391 mg, 2.4 mmol), and DMSO (5.0 mL) were added to the reaction vial. The mixture was stirred at 130 C for 12 h, after which the mixture was extracted with Et2O and the organic layer was dried over magnesium sulfate. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography on silica gel.

Reference： [1]Bulletin of the Korean Chemical Society,2017,vol. 38,p. 1368 - 1371

67
[ 622-76-4 ]
[ 64-19-7 ]
(E)-2-iodo-1-phenylbut-1-en-1-yl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triiodoisocyanuric acid In neat (no solvent) at 20℃; for 3h;	General procedure. General procedure: In a 10 mL round bottom flask, 0.34 mmol of TXCA was added to a stirred mixture of 6 mLof solvent and the substrate (HOAc for iodinations and 1:1 (v/v) mixture of HOAc:Ac2O for the chlorination andbrominations). GC-MS analyses were carried out to evaluate the extension of the reaction and, after itscompletion; 10 mL of distilled water were added to the reaction medium, followed by addition of of 10%NaHSO3 (10 mL). The aqueous phase was then extracted with ethyl acetate (1 x 20 mL + 2 x 10 mL) and thecombined organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filteredand evaporated under vacuum (rotatory evaporator). The crude products were obtained by flashchromatography. NMR and MS analyses were carried out.

Reference： [1]Crespo, Livia T.C.; Nogueira, Geisa P.; De Mattos, Marcio C.S.; Esteves, Pierre M. [Arkivoc, 2017, vol. 2018, # 2, p. 205 - 214]

68
[ 622-76-4 ]
[ 536-60-7 ]
2-(4-isopropylbenzyl)-1-phenylbutan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With N-Bromosuccinimide; silver hexafluoroantimonate In tetrahydrofuran; 1,4-dioxane at 120℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Chun, Supill; Chung, Young Keun [Organic Letters, 2018, vol. 20, # 18, p. 5583 - 5586]

69
[ 67-56-1 ]
[ 622-76-4 ]
[ 57205-27-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate at 25℃; for 3h; UV-irradiation; Schlenk technique; Green chemistry; regioselective reaction;
76%	With 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 3h; Irradiation;	2 Example 2 The acetylenic compound and 10-methyl-9-mesityl acridinium perchlorate (Acr+-Mes, 9-mesityl-10-Methylacridinium) is added to the solvent and is exposed to visible light at a wavelength of 450 nm to 460 nm in the atmosphere at room temperature.The reaction was driven, and after 3 hours, the reaction liquid was obtained, and the reaction liquid was dried under reduced pressure at a temperature of 25 ° C and a pressure of 1.3 kPa.The concentrate was obtained; the concentrate was subjected to silica gel column chromatography (200-300 mesh silica gel, eluent was petroleum ether: ethyl acetate = 70 mL: 1(mL) gives 2,2-dimethoxy-1,2-diphenylethane-1-one (3a).Oily liquid (20.9 mg, 82%). 1H NMR (400 MHz, CDCl3) δ 8.06 (d, J = 7.2 Hz,2H), 7.62 (d, J=7.2Hz, 2H), 7.42 (t. J=7.2Hz, 1H), 7.36-7.28 (m, 5H), 3.23(s, 6H). 13C NMR (100 MHz, CDCl3) δ 195.1, 136.9, 134.3, 132.8, 130.0, 128.9,128.5, 128.1, 126.9, 103.6, 50.0. HRMS (ESI, m/z): Calculated for [C16H16O3] (M+Na)+ 279.0992, found 279.0990.Its structural formula is:Wherein: the structural formula of the acetylenic compound is: wherein Ar is a phenyl group; and R1 is a phenyl group.The molar ratio of 10-methyl-9-mesityl acridinium perchlorate to acetylenic compound was 1:67.The solvent refers to a mixture of an alcohol compound and acetonitrile in a volume ratio of 1.0 mL: 0.2 mL, and an alcoholThe compound is methanol.The ratio of the acetylenic compound to the alcohol compound was 0.1 mmol: 1.0 mL.Visible light refers to LED blue light.

Reference： [1]Lei, Wen-Long; Yang, Biao; Zhang, Qing-Bao; Yuan, Pan-Feng; Wu, Li-Zhu; Liu, Qiang [Green Chemistry, 2018, vol. 20, # 24, p. 5479 - 5483]
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN109265328, 2019, A Location in patent: Paragraph 0030-0036

70
[ 622-76-4 ]
[ 53226-42-9 ]
[ 88123-59-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: N-cyclopentylbenzamide With 2-iodopyridine; trifluoromethylsulfonic anhydride In 1,2-dichloro-ethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: 1-phenyl-1-butyne In 1,2-dichloro-ethane at 90℃; for 18h; Inert atmosphere;	4.1. General Procedure D General procedure: To a solution of amide (0.6 mmol, 3 equiv.) and 2-iodopyridine (3 equiv.) in 1,2-dichloroethane (3 mL), triflic anhydride (3 equiv.) was added at 0 °C. The reaction mixture was stirred for 15 minutes at 0 °C. The alkyne (1 equiv.) was then added and the reaction was stirred at 90 °C during 18 hours. After cooling to room temperature, the reaction was quenched with a saturated solution of NaHCO3 (3 mL) and stirred during 1 hour. Then the aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure. The crude residue was purified by flash column chromatography on Silica gel.

Reference： [1]Stopka, Tobias; Adler, Pauline; Hagn, Gerhard; Zhang, Haoqi; Tona, Veronica; Maulide, Nuno [Synthesis, 2019, vol. 51, # 1, p. 194 - 202]

71
[ 622-76-4 ]
[ 16026-77-0 ]
4-chloro-3-((4-phenylbut-3-en-2-yl)amino)phenol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3545 - 3551

72
[ 188290-36-0 ]
[ 622-76-4 ]
[ 1812-51-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 12h; Irradiation; Inert atmosphere; Schlenk technique; regioselective reaction;

Reference： [1]Song, Chunlan; Dong, Xin; Wang, Zhongjie; Liu, Kun; Chiang, Chien-Wei; Lei, Aiwen [Angewandte Chemie - International Edition, 2019, vol. 58, # 35, p. 12206 - 12210][Angew. Chem., 2019, vol. 131, p. 12334 - 12338,5]

73
[ 608-28-6 ]
[ 622-76-4 ]
1,3-dimethyl-2-(1-phenylbuta-1,2-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1-phenyl-1-butyne 0.25 mmol and N, N-dimethylformamide 1 mL were added toIn a 15 mL reaction tube, repeatedly fill 10 times with nitrogen, and stir at room temperature for 15 min.Add 0.5 mmol of water,Then placed in a reaction dish at 100 C for 16h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, the organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by thin layer chromatography to obtain 7.3mg of the target product. Color oil, 31% yield.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0056-0059

74
[ 10602-01-4 ]
[ 622-76-4 ]
2-(4-(1-phenylbuta-1,2-dien-1-yl)phenyl)-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: 1-phenyl-1-butyne With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; Schlenk technique; Inert atmosphere; Stage #2: p-bromobenzaldehyde 1,3-dioxolane With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In toluene at 60℃; for 1.5h; Schlenk technique; Inert atmosphere;

Reference： [1]Castiñeira Reis, Marta; Feringa, Ben L.; Mateos-Gil, Jaime; Mondal, Anirban [Angewandte Chemie - International Edition, 2020, vol. 59, # 20, p. 7823 - 7829][Angew. Chem., 2020, vol. 132, # 20, p. 7897 - 7903,7]

75
[ 622-76-4 ]
[ 17422-74-1 ]
3-(3-chloro-2-ethyl-1H-inden-1-yl)-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With boron trichloride In dichloromethane at 20℃; for 4h;	3-(2-Aryl-3-fluoro-1H-inden-1-yl)-4H-chromen-4-ones 6aa-6ah;General Procedure General procedure: To a mixture of carbaldehyde 3 (0.172 mmol, 1.0 equiv) and alkyne 4 (0.172 mmol, 1.0 equiv) in CH2Cl2 (2 mL) was added BF3·OEt2 (0.43 mmol, 2.5 equiv) at room temperature. The mixture was stirred for the required time (monitored by TLC). After completion of the reaction, it was quenched with a few drops of sat. Na2S2O3 solution. The solvent was removed through vacuum and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc, 4:1) to afford 6aa-6ah.

Reference： [1]Fernandes, Rodney A.; Kumari, Anupama [Synthesis, 2020, vol. 52, # 15, p. 2245 - 2258]

76
[ 622-76-4 ]
[ 17422-74-1 ]
3-(3-bromo-2-ethyl-1H-inden-1-yl)-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With boron tribromide In dichloromethane at 20℃; for 5h;	3-(2-Aryl-3-fluoro-1H-inden-1-yl)-4H-chromen-4-ones 6aa-6ah;General Procedure General procedure: To a mixture of carbaldehyde 3 (0.172 mmol, 1.0 equiv) and alkyne 4 (0.172 mmol, 1.0 equiv) in CH2Cl2 (2 mL) was added BF3·OEt2 (0.43 mmol, 2.5 equiv) at room temperature. The mixture was stirred for the required time (monitored by TLC). After completion of the reaction, it was quenched with a few drops of sat. Na2S2O3 solution. The solvent was removed through vacuum and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc, 4:1) to afford 6aa-6ah.

Reference： [1]Fernandes, Rodney A.; Kumari, Anupama [Synthesis, 2020, vol. 52, # 15, p. 2245 - 2258]

77
[ 42059-81-4 ]
[ 622-76-4 ]
3-(3-bromo-2-ethyl-1H-inden-1-yl)-6-methyl-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With boron tribromide In dichloromethane at 20℃; for 6h;	3-(2-Aryl-3-fluoro-1H-inden-1-yl)-4H-chromen-4-ones 6aa-6ah;General Procedure General procedure: To a mixture of carbaldehyde 3 (0.172 mmol, 1.0 equiv) and alkyne 4 (0.172 mmol, 1.0 equiv) in CH2Cl2 (2 mL) was added BF3·OEt2 (0.43 mmol, 2.5 equiv) at room temperature. The mixture was stirred for the required time (monitored by TLC). After completion of the reaction, it was quenched with a few drops of sat. Na2S2O3 solution. The solvent was removed through vacuum and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc, 4:1) to afford 6aa-6ah.

Reference： [1]Fernandes, Rodney A.; Kumari, Anupama [Synthesis, 2020, vol. 52, # 15, p. 2245 - 2258]

78
[ 69155-76-6 ]
[ 622-76-4 ]
3-(3-chloro-2-ethyl-1H-inden-1-yl)-6-fluoro-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With boron trichloride In dichloromethane at 20℃; for 3h;	3-(2-Aryl-3-fluoro-1H-inden-1-yl)-4H-chromen-4-ones 6aa-6ah;General Procedure General procedure: To a mixture of carbaldehyde 3 (0.172 mmol, 1.0 equiv) and alkyne 4 (0.172 mmol, 1.0 equiv) in CH2Cl2 (2 mL) was added BF3·OEt2 (0.43 mmol, 2.5 equiv) at room temperature. The mixture was stirred for the required time (monitored by TLC). After completion of the reaction, it was quenched with a few drops of sat. Na2S2O3 solution. The solvent was removed through vacuum and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc, 4:1) to afford 6aa-6ah.

Reference： [1]Fernandes, Rodney A.; Kumari, Anupama [Synthesis, 2020, vol. 52, # 15, p. 2245 - 2258]

79
[ 622-76-4 ]
[ 59046-72-9 ]
1-bromo-3-ethyl-2-phenylnaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 8h; Inert atmosphere; regioselective reaction;	4.1. General synthesis of 1-halonaphthalenes 3 General procedure: A solution of 2-(phenylethynyl)benzaldehyde (1) (0.90 mmol, 0.185 g), alkyne (0.60 mmol), Cu(OTf)2 (0.045 mmol, 0.016 g), NXS (NBS, NCS, or NIS; 0.90 mmol) in ClCH2CH2Cl (4.0 mL) was stirred at 80 °C for 8 h under a nitrogen atmosphere. The reaction mixture was diluted with CHCl3 and washed with saturated NaHCO3 aq. and brine. The organic layer was dried over MgSO4. After removal of the solvent under reduced pressure, the residue was purified by chromatography on SiO2 to give the 1-halonaphthalenes 3. Further purification was carried out a recyclable preparative HPLC, if necessary.

Reference： [1]Umeda, Rui; Ueda, Ryo; Tanaka, Taiki; Hayashi, Akitsugu; Ikeshita, Masahiro; Suzuki, Shuichi; Naota, Takeshi; Nishiyama, Yutaka [Tetrahedron, 2021, vol. 79]

80
[ 7648-30-8 ]
[ 622-76-4 ]
ethyl (E)-2,2-difluoro-3-(iodo(phenyl)methylene)pentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane In acetonitrile at 130℃; for 4h; Inert atmosphere; stereoselective reaction;	A. General procedure for Lewis acid induced difluoroalkylation of alkynes or alkenes General procedure: Under the protection of argon, K2CO3 (138 mg, 1 mmol, 2.0 equiv), alkyne or alkene (0.5 mmol), ICF2CO2Et (373 mg, 191 uL, 0.4 mmol, 3.0 equiv), solvent (CH3CN, 2 mL) wereadded sequentially to a 10 mL Schlenk tube equipped with a magnetic stir bar. The reactionwas stirred at 130 oC for 4-8 h, and cooled by a fan to keep the temperature relatively constant. The resulting solution was concentrated in vacuum and the residue was purified by chromatography on silica gel, eluting with the mixture of ethylacetate/petroleum ether to give difluoroalkylation product, the total yield of Z and E-productswas recorded in isolated yield. The Z/E ratios are determined by 19F and 1H NMR spectroscopy.
63%	With diethylzinc(II) In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere;

Reference： [1]Wu, Jianglong; Wang, Chenyu; Wang, Zhongjie; Li, Hongjun; Liu, Ruyan; Wang, Yan; Zhou, Pengsheng; Li, Dianjun; Yang, Jinhui [Synthesis, 2022, vol. 54, # 13, p. 3055 - 3068]
[2]Li, Xin; He, Songtao; Song, Qiuling [Organic Letters, 2021, vol. 23, # 8, p. 2994 - 2999]

81
[ 18742-02-4 ]
[ 622-76-4 ]
[ 73183-34-3 ]
(Z)-2-(6-(1,3-dioxolan-2-yl)-4-phenylhex-3-en-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With 4,7-Dimethyl-1,10-phenanthroline; tributylphosphine; P(p-CH₃OC₆H₄)3; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 18h; Schlenk technique; Inert atmosphere;	2.4. General procedure for carboboration of electron-rich alkynes with alkyl bromides General procedure: Alkyne (1.0 equiv, typically from 100 to 200 μmol scale) (if solid), alkyl bromide (1.5 equiv) (ifsolid), B2pin2 (1.5 equiv), CuCl (15 mol%), and tris(4-methoxyphenyl)phosphine (8 mol%) wereplaced in a Schlenck tube and purged with argon. The mixture was suspended in dry THF (0.5mL) and tributylphosphine (8 mol%) was added (alkyne and alkyl bromide were added if liquid)and stirred for 5-10 min until a clear solution was formed. Then, 4,7-dimethyl-1,10-phenanthroline(20 mol%) was added dissolved in 0.5 mL of THF, upon which a bright red color could beobserved.* Next, NaOtBu (1.6 equiv) was added, turning the solution into a dark brownsuspension, and the mixture was stirred at room temperature for 18 h under argon atmosphere.The reaction was quenched by passing the mixture through a short silica plug and washed withtert-butyl methyl ether. The resulting filtrate was concentrated in vacuo and analyzed by 1H NMRusing hexamethyldisilane as an internal standard.

Reference： [1]Carretero, Juan C.; Gómez Arrayás, Ramón; Kim-Lee, Shin-Ho; Mauleón, Pablo [Chem, 2021, vol. 7, # 8, p. 2212 - 2226]

82
[ 13287-42-8 ]
[ 622-76-4 ]
[ 73183-34-3 ]
(Z)-4,4,5,5-tetramethyl-2-(6-(oxiran-2-yl)-4-phenylhex-3-en-3-yl)-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 4,7-Dimethyl-1,10-phenanthroline; tributylphosphine; P(p-CH₃OC₆H₄)3; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 18h; Schlenk technique; Inert atmosphere;	2.4. General procedure for carboboration of electron-rich alkynes with alkyl bromides General procedure: Alkyne (1.0 equiv, typically from 100 to 200 μmol scale) (if solid), alkyl bromide (1.5 equiv) (ifsolid), B2pin2 (1.5 equiv), CuCl (15 mol%), and tris(4-methoxyphenyl)phosphine (8 mol%) wereplaced in a Schlenck tube and purged with argon. The mixture was suspended in dry THF (0.5mL) and tributylphosphine (8 mol%) was added (alkyne and alkyl bromide were added if liquid)and stirred for 5-10 min until a clear solution was formed. Then, 4,7-dimethyl-1,10-phenanthroline(20 mol%) was added dissolved in 0.5 mL of THF, upon which a bright red color could beobserved.* Next, NaOtBu (1.6 equiv) was added, turning the solution into a dark brownsuspension, and the mixture was stirred at room temperature for 18 h under argon atmosphere.The reaction was quenched by passing the mixture through a short silica plug and washed withtert-butyl methyl ether. The resulting filtrate was concentrated in vacuo and analyzed by 1H NMRusing hexamethyldisilane as an internal standard.

Reference： [1]Carretero, Juan C.; Gómez Arrayás, Ramón; Kim-Lee, Shin-Ho; Mauleón, Pablo [Chem, 2021, vol. 7, # 8, p. 2212 - 2226]

83
[ 578-66-5 ]
[ 1122-17-4 ]
[ 622-76-4 ]
C₂₂H₁₆Cl₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 8-amino quinoline; dichloromaleic acid anhydride; 1-phenyl-1-butyne for 12h; Stage #2: With silver carbonate; tris(o-methoxyphenyl)phosphine; cobalt(II) iodide In chlorobenzene at 130℃; for 24h;	3 Example 1 General procedure: The reaction is carried out in the reactor, first add acid anhydride 1a (0.5mmol, 1eq.) and amine 2a (0.55mmol, 1.1eq.), pre-stirring for 1-12 hours (here, 12 hours), and then add alkyne 3a ( 0.75mmol, 1.5eq.), cobalt iodide (0.2eq.), o-methoxytriphenylphosphine (0.3eq.), silver carbonate (1.0eq.) and 1,2-dichlorobenzene 10mL, Reacted at 130°C for 24 hours; after the reaction, the multi-substituted isoquinolinone derivative 4a was separated by column chromatography with a yield of 94%.

Reference： [1]Current Patent Assignee: Dalian Institute of Chemical Physics (in: CAS); CHINESE ACADEMY OF SCIENCES - CN113321639, 2021, A Location in patent: Paragraph 0021-0023; 0025-0026; 0029-0030

84
[ 622-76-4 ]
[ 57139-24-9 ]
C₂₁H₂₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; potassium 2,4,6-trimethylbenzoate In lithium hydroxide monohydrate at 60℃; for 12h; Schlenk technique; Inert atmosphere;	2.2 General Procedure for Ruthenium-CatalyzedAnnulation of N-Methoxybenzamideswith Alkynes in PEG-400/H2O General procedure: A Schlenk tube equipped with a magnetic stir bar was charged with [RuCl2(p-cymene)]2 (9.2 mg, 0.015 mmol,3 mol%), N-methoxybenzamide 1 (0.5 mmol), potassium 2,4,6-trimethylbenzoate (20.3 mg, 0.1 mmol, 20 mol%), and PEG-400 (2.0 mL). The reaction tube was evacuated and backfilled with argon (this sequence was carried out three times) and then alkyne 2 (0.75 mmol, if liquid) and water(1.0 mL) were added by syringe (alkyne that was solid at room temperature was added with the ruthenium catalyst).The reaction mixture was stirred at 60 °C for 12 h underan argon atmosphere. After being cooled to room temperature,the reaction mixture was extracted with diethyl ether(3 × 10 mL). The combined ether layer was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired isoquinolone 3.

Reference： [1]Cai, Mingzhong; Li, Jianying; Liu, Rong; Ye, Qian [Catalysis Letters, 2022]

85
[ 622-76-4 ]
[ 72755-09-0 ]
C₁₇H₁₄FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; potassium 2,4,6-trimethylbenzoate In lithium hydroxide monohydrate at 60℃; for 12h; Schlenk technique; Inert atmosphere;	2.2 General Procedure for Ruthenium-CatalyzedAnnulation of N-Methoxybenzamideswith Alkynes in PEG-400/H2O General procedure: A Schlenk tube equipped with a magnetic stir bar was charged with [RuCl2(p-cymene)]2 (9.2 mg, 0.015 mmol,3 mol%), N-methoxybenzamide 1 (0.5 mmol), potassium 2,4,6-trimethylbenzoate (20.3 mg, 0.1 mmol, 20 mol%), and PEG-400 (2.0 mL). The reaction tube was evacuated and backfilled with argon (this sequence was carried out three times) and then alkyne 2 (0.75 mmol, if liquid) and water(1.0 mL) were added by syringe (alkyne that was solid at room temperature was added with the ruthenium catalyst).The reaction mixture was stirred at 60 °C for 12 h underan argon atmosphere. After being cooled to room temperature,the reaction mixture was extracted with diethyl ether(3 × 10 mL). The combined ether layer was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired isoquinolone 3.

Reference： [1]Cai, Mingzhong; Li, Jianying; Liu, Rong; Ye, Qian [Catalysis Letters, 2022]

86
[ 622-76-4 ]
[ 1613-79-2 ]
C₁₇H₁₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; potassium 2,4,6-trimethylbenzoate In lithium hydroxide monohydrate at 60℃; for 12h; Schlenk technique; Inert atmosphere;	2.2 General Procedure for Ruthenium-CatalyzedAnnulation of N-Methoxybenzamideswith Alkynes in PEG-400/H2O General procedure: A Schlenk tube equipped with a magnetic stir bar was charged with [RuCl2(p-cymene)]2 (9.2 mg, 0.015 mmol,3 mol%), N-methoxybenzamide 1 (0.5 mmol), potassium 2,4,6-trimethylbenzoate (20.3 mg, 0.1 mmol, 20 mol%), and PEG-400 (2.0 mL). The reaction tube was evacuated and backfilled with argon (this sequence was carried out three times) and then alkyne 2 (0.75 mmol, if liquid) and water(1.0 mL) were added by syringe (alkyne that was solid at room temperature was added with the ruthenium catalyst).The reaction mixture was stirred at 60 °C for 12 h underan argon atmosphere. After being cooled to room temperature,the reaction mixture was extracted with diethyl ether(3 × 10 mL). The combined ether layer was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired isoquinolone 3.

Reference： [1]Cai, Mingzhong; Li, Jianying; Liu, Rong; Ye, Qian [Catalysis Letters, 2022]

87
[ 622-76-4 ]
[ 72755-11-4 ]
C₁₈H₁₇NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With di-μ-chlorobis-[(η⁶-p-cymene)chlororuthenium(II)]; potassium 2,4,6-trimethylbenzoate In lithium hydroxide monohydrate at 60℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;	2.2 General Procedure for Ruthenium-CatalyzedAnnulation of N-Methoxybenzamideswith Alkynes in PEG-400/H2O General procedure: A Schlenk tube equipped with a magnetic stir bar was charged with [RuCl2(p-cymene)]2 (9.2 mg, 0.015 mmol,3 mol%), N-methoxybenzamide 1 (0.5 mmol), potassium 2,4,6-trimethylbenzoate (20.3 mg, 0.1 mmol, 20 mol%), and PEG-400 (2.0 mL). The reaction tube was evacuated and backfilled with argon (this sequence was carried out three times) and then alkyne 2 (0.75 mmol, if liquid) and water(1.0 mL) were added by syringe (alkyne that was solid at room temperature was added with the ruthenium catalyst).The reaction mixture was stirred at 60 °C for 12 h underan argon atmosphere. After being cooled to room temperature,the reaction mixture was extracted with diethyl ether(3 × 10 mL). The combined ether layer was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (light petroleum ether-ethyl acetate) to afford the desired isoquinolone 3.

Reference： [1]Cai, Mingzhong; Li, Jianying; Liu, Rong; Ye, Qian [Catalysis Letters, 2022]

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CAS No. :	622-76-4	MDL No. :	MFCD00039945
Formula :	C₁₀H₁₀	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FFFMSANAQQVUJA-UHFFFAOYSA-N
M.W :	130.19	Pubchem ID :	69328
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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P321
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
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Disposal
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P501	Dispose of contents/container to ...
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
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Code	Phrase
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H310	Fatal in contact with skin
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 622-76-4 ] {[proInfo.proName]}

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[ 622-76-4 ] Synthesis Path-Downstream 1~87

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