1820-42-4|1,2-Bis(4-chlorophenyl)ethyne| Ambeed

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1
[ 1820-42-4 ]
[ 544-92-3 ]
[ 5216-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-methyl-pyrrolidin-2-one

Reference： [1]Weis,C.D. [Helvetica Chimica Acta, 1966, vol. 49, p. 234 - 243]

2
[ 41468-28-4 ]
[ 532-11-6 ]
[ 1820-42-4 ]
[ 81385-69-5 ]

Reference： [1]Liebigs Annalen der Chemie,1982,p. 315 - 341

3
[ 637-87-6 ]
[ 1066-54-2 ]
[ 1820-42-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 20℃; for 18h;
96%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 18h; Inert atmosphere;
94%	With pyrrolidine; tetrabutylammomium bromide In water at 100℃; for 6h;

91%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 60℃; for 18h; Inert atmosphere;
89%	Stage #1: 1-Chloro-4-iodobenzene; trimethylsilylacetylene With potassium carbonate In methanol; acetonitrile at 40℃; Stage #2: 1-Chloro-4-iodobenzene In methanol; acetonitrile at 40℃;	2.2 General procedure for synthesis of diarylacetylenes General procedure: 4-Iodoanisole (1mmol), TMSA (1.1mmol) and K2CO3 (2mmol) were added to a freshly prepared solution of PdNPs (5mL) in a 25mL round bottomed flask fitted with stopper. Then, the reaction mixture was stirred at 40°C. The reaction progress was monitored by TLC, until complete consumption of aryl iodide. To the reaction mixture containing in situ formed 4-ethynylanisole the next batch of aryliodide (1mmol) was added and the reaction mixture was further allowed to stir until complete consumption of the arylacetylene. In this manner the targeted unsymmetrical diarylacetylene was formed. The detailed procedure is provided in the Supp. Info. Detailed procedure for synthesis of symmetrical diarylacetylenes is also mentioned in SI.
87%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; benzene at 60℃; Inert atmosphere; Sealed tube;
85%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; acetonitrile at 60℃; for 48h; Inert atmosphere;	2.5. Synthesis of 1,2-bis(4-chlorophenyl)ethyne To 500 mL ask, equipped with a magnetic stirrer and a rubberseptum, was charged with 1.26 g (1.80 mmol) of PdCl2(PPh3)2, 1.14 g(5.85 mmol) of CuI, 42.9 g (180 mmol) of 1-chloro-4-iodobenzene.The ask was purged with dry nitrogen. DBU (72.0 mL), thrime-thylsilyethynylene (13.8 mL), distilled water (1.30 mL), and aceto-nitrile (250 mL) were then added by syringe. The reaction ask wascovered in aluminum foil and was stirred at 60C for 48 h. Thereaction mixture was poured into 500 mL of distilled water. Theprecipitate was ltered and washed with distilled water. The pureproduct was obtained by recrystallization from chloroform in 85%yield (18.9 g). Purity: 99.63% (HPLC). Found: C, 67.9%; H, 3.09%. Anal.Calcd for C14H8Cl2: C, 68.04%; H, 3.26%. FT-IR (KBr, cm1): 1908.5,1492.5 (CC), 1396.3, 1088.9, 1011.2, 825.6, 656.9.1H NMR(500 MHz, CDCl3): d 7.44 (d, J 8.6 Hz, 1H), 7.32 (d, J 8.6 Hz, 1H).13C NMR (126 MHz, CDCl3): d 134.54 (s), 132.80 (s), 128.77 (s),121.45 (s), 89.18 (s).
57%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; benzene at 20℃; Inert atmosphere; Darkness;
50%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 120℃; Microwave irradiation;
	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 60℃; Inert atmosphere; Darkness;
	Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; benzene at 20 - 80℃; for 18h; Inert atmosphere; Darkness;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 18h; Inert atmosphere; Schlenk technique; Darkness;	Synthesis of 1,2-bis(4-bromophenyl)ethyne is representative General procedure: PdCl2(PPh3)2 (168mg, 0.24 mmol, 6.0 mol%), CuI (76 mg, 0.40 mmol, 10 mol%) and 1-bromo-4-iodobenzene (1.1 g, 4.0 mmol) were added into a 50-mL 2-neck round-bottom flaskwith a magnetic stirring bar. The flask was evacuated and refilled with N2 gasfollowing the usual Schlenk technique. Dry toluene (20 mL) was added while stirring.N2-sparged DBU (3.6 mL, 24 mmol, 6.0 equiv), trimethylsilylacetylene (0.28 mL, 2.0mmol, 1.0 equiv) and distilled water (29 μL, 1.6 mmol, 40 mol%) were addedconsecutively. The reaction flask was wrapped with aluminum foil and stirred at roomtemperature for 18 h. The reaction was quenched with water (20 mL) and extractedwith diethyl ether (20 mL). The organic layer was washed with 10% aqueous HCl (3 15 mL), brine (20 mL), dried over Na2SO4, gravity-filtered and the solvent removedin vacuo. The crude product was purified by silica gel column chromatography inhexane and concentrated in vacuo to obtain 1b in 34% (229 mg, 0.68 mmol) yield aswhite crystals.1
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 60℃; for 18h; Inert atmosphere; Darkness;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 60℃; for 18h; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 60 - 80℃; for 24h; Sealed tube; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water; toluene at 20℃; for 18h; Inert atmosphere; Sealed tube;

Reference： [1]Mio, Matthew J; Kopel, Lucas C; Braun, Julia B; Gadzikwa, Tendai L; Hull, Kami L; Brisbois, Ronald G; Markworth, Christopher J; Grieco, Paul A [Organic letters, 2002, vol. 4, # 19, p. 3199 - 3202]
[2]Rakshit, Souvik; Patureau, Frederic W.; Glorius, Frank [Journal of the American Chemical Society, 2010, vol. 132, # 28, p. 9585 - 9587]
[3]Gil-Molto, Juan; Najera, Carmen [Advanced Synthesis and Catalysis, 2006, vol. 348, # 14, p. 1874 - 1882]
[4]Li, Dong-Kun; Zhang, Bo; Ye, Qi; Deng, Wei; Xu, Zheng-Yang [Organometallics, 2022, vol. 41, # 4, p. 441 - 449]
[5]Mandali, Pavan Kumar; Chand, Dillip Kumar [Catalysis Communications, 2014, vol. 47, p. 40 - 44]
[6]Prusty, Namrata; Banjare, Shyam Kumar; Mohanty, Smruti Ranjan; Nanda, Tanmayee; Yadav, Komal; Ravikumar, Ponneri C. [Organic Letters, 2021, vol. 23, # 23, p. 9041 - 9046]
[7]Cheng, Shengli; Yuan, Kuanyu; Wang, Xin; Han, Jianhua; Jian, Xigao; Wang, Jinyan [Polymer, 2017, vol. 115, p. 224 - 231]
[8]Guo, Wusheng; Pleixats, Roser; Shafir, Alexandr; Parella, Teodor [Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 89 - 99]
[9]Hou, Duen-Ren; Kuan, Ting-Chun; Li, Yu-Kai; Lee, Richmond; Huang, Kuo-Wei [Tetrahedron, 2010, vol. 66, # 48, p. 9415 - 9420]
[10]Pu, Xiaotao; Qi, Xiangbing; Ready, Joseph M. [Journal of the American Chemical Society, 2009, vol. 131, # 30, p. 10364 - 10365]
[11]Wei, Chu-Hung; Mannathan, Subramaniyan; Cheng, Chien-Hong [Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 6942 - 6944]
[12]Location in patent: body text Ji, Yining; Verdaguer, Xavier; Riera, Antoni [Chemistry - A European Journal, 2011, vol. 17, # 14, p. 3942 - 3948]
[13]Ramesh; Guntreddi, Tirumaleswararao; Sahoo, Akhila K. [European Journal of Organic Chemistry, 2017, vol. 2017, # 30, p. 4405 - 4413]
[14]Yip, Shu Jan; Yoshidomi, Tetsushi; Murakami, Kei; Itami, Kenichiro [Chemistry Letters, 2018, vol. 47, # 3, p. 329 - 331]
[15]Zhou, Bo; Lu, Ailan; Shao, Changdong; Liang, Xinda; Zhang, Yanghui [Chemical Communications, 2018, vol. 54, # 75, p. 10598 - 10601]
[16]Xu, Hua-Jin; Kang, Yan-Shang; Shi, Hang; Zhang, Ping; Chen, You-Ke; Zhang, Bing; Liu, Zhi-Qiang; Zhao, Jing; Sun, Wei-Yin; Yu, Jin-Quan; Lu, Yi [Journal of the American Chemical Society, 2019, vol. 141, # 1, p. 76 - 79]
[17]Raju, Selvam; Hsiao, Huan-Chang; Thirupathi, Selvakumar; Chen, Pei-Ling; Chuang, Shih-Ching [Advanced Synthesis and Catalysis, 2019, vol. 361, # 4, p. 683 - 689]
[18]Cheng, Jie; Chu, Haoke; Guo, Yin-Long; Yang, Junfeng; Zhang, Junliang [Angewandte Chemie - International Edition, 2020, vol. 59, # 49, p. 21991 - 21996][Angew. Chem., 2020, vol. 132, # 49, p. 22175 - 22180,6]

4
[ 637-87-6 ]
[ 1066-54-2 ]
[ 1820-42-4 ]
[ 78704-49-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 77 % Chromat. 2: 11 % Chromat.	With pyrrolidine; tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one at 110℃; for 2h;

Reference： [1]Alonso, Diego A.; Nájera, Carmen; Pacheco, Ma. Carmen [Advanced Synthesis and Catalysis, 2003, vol. 345, # 9-10, p. 1146 - 1158]

5
[ 106-39-8 ]
[ 14630-40-1 ]
[ 1820-42-4 ]
[ 78704-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one at 100℃; for 7h; Title compound not separated from byproducts;
1: 53 % Chromat. 2: 8 % Chromat.	With pyrrolidine; tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one at 110℃; for 5h;

Reference： [1]Gil-Molto, Juan; Najera, Carmen [Advanced Synthesis and Catalysis, 2006, vol. 348, # 14, p. 1874 - 1882]
[2]Alonso, Diego A.; Nájera, Carmen; Pacheco, Ma. Carmen [Advanced Synthesis and Catalysis, 2003, vol. 345, # 9-10, p. 1146 - 1158]

6
[ 637-87-6 ]
[ 14630-40-1 ]
[ 1820-42-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrabutylammomium bromide In water at 25℃; for 120h;
57%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; triethylamine In N,N-dimethyl-formamide at 70℃; for 8h; Inert atmosphere;
88 % Chromat.	With pyrrolidine; copper(l) iodide In 1-methyl-pyrrolidin-2-one at 110℃; for 6h;

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 18h; Inert atmosphere; Cooling with ice;

Representative procedure for the preparation of alkynes General procedure: A 50 mL three-necked flask was dried under vacuum and then purged with dry N2. Under N2 atmosphere, the flask was charged with PdCl2(PPh3)2 (100.8 mg, 6 mol %), CuI (91.2 mg, 10 mol %), 4-iodoanisole (4.8 mmol, 1.0 equiv.) and dry benzene (25 mL). While stirring, nitrogen-sparged DBU (4.3 mL, 6.0 equiv.) was added by syringe. Then ice-chilled trimethylsilylethynylene (0.34 mL, 0.5 equiv.) was added, followed immediately by distilled water (35 L, 40 mol%). The reaction was stirred vigorously for 18 h. Then the mixture was partitioned in ethyl ether and water. The organic layer was washed with 10 % HCl, saturated aqueous NaCl, dried over anhydrous Na2SO4. Concentration under reduced pressure and purification of the crude product by flash chromatograph to afford the product 2d in 66% yield. The yields of the alkynes are ranging from 66% to 86% and all the alkynes are known compounds.

Reference： [1]Gil-Molto, Juan; Najera, Carmen [Advanced Synthesis and Catalysis, 2006, vol. 348, # 14, p. 1874 - 1882]
[2]Schmidt, Bernd; Berger, Rene; Kelling, Alexandra; Schilde, Uwe [Chemistry - A European Journal, 2011, vol. 17, # 25, p. 7032 - 7040]
[3]Alonso, Diego A.; Nájera, Carmen; Pacheco, Ma. Carmen [Advanced Synthesis and Catalysis, 2003, vol. 345, # 9-10, p. 1146 - 1158]
[4]Zhou, Feng; Han, Xiuling; Lu, Xiyan [Tetrahedron Letters, 2011, vol. 52, # 36, p. 4681 - 4685]

7
[ 26305-75-9 ]
sodium 1-{(1R,2S,5R)-menthoxycarbonyl}-2-methyl-4-phenyl-1,3-cyclopentadienide [ No CAS ]
[ 1820-42-4 ]
1-{(1R,2S,5R)-menthoxycarbonyl}-2-methyl-4-phenyl-1,3-cyclopentadiene Co (C₄(C₆H₄-4Cl)4) [ No CAS ]
1-{(1R,2S,5R)-menthoxycarbonyl}-2-methyl-4-phenyl-1,3-cyclopentadiene Co (C₄(C₆H₄-4Cl)4) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1994,vol. 473,p. 303 - 312

8
[ 26305-75-9 ]
[ 1820-42-4 ]
[ 33320-28-4 ]
[ 939044-78-7 ]

Reference： [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 2216 - 2226

9
[ 1820-42-4 ]
[ 1126-00-7 ]
[ 1037289-16-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With 1,2,3,4-tetraphenylcyclopentadiene; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 80℃; for 6h;
79%	With 1,2,3,4-tetraphenylcyclopentadiene; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; regioselective reaction;

Reference： [1]Umeda, Nobuyoshi; Tsurugi, Hayato; Satoh, Tetsuya; Miura, Masahiro [Angewandte Chemie - International Edition, 2008, vol. 47, # 21, p. 4019 - 4022]
[2]Location in patent: experimental part Umeda, Nobuyoshi; Hirano, Koji; Satoh, Tetsuya; Shibata, Naoto; Sato, Hirofumi; Miura, Masahiro [Journal of Organic Chemistry, 2011, vol. 76, # 1, p. 13 - 24]

10
[ 91-40-7 ]
[ 1820-42-4 ]
[ 1147304-01-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 3478 - 3483

11
[ 91-40-7 ]
[ 1820-42-4 ]
[ 1147304-32-2 ]
[ 1147304-01-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 3478 - 3483

12
[ 1820-42-4 ]
[ 244090-34-4 ]
[ 1185863-94-8 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 5639 - 5649
[2]Journal of Organic Chemistry,2009,vol. 74,p. 7481 - 7488

13
[ 1820-42-4 ]
[ 596-38-3 ]
[ 1241954-79-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,2,3,4-tetraphenylcyclopentadiene; copper(II) acetate monohydrate In o-xylene Inert atmosphere; Heating;

Reference： [1]Mochida, Satoshi; Shimizu, Masaki; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Chemistry - An Asian Journal, 2010, vol. 5, # 4, p. 847 - 851]

14
[ 1820-42-4 ]
[ 1611-83-2 ]
[ 1256971-19-3 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5462 - 5465
[2]Organic Letters,2011,vol. 13,p. 3278 - 3281

15
[ 1820-42-4 ]
[ 676578-20-4 ]
[ 1284216-17-6 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 2867 - 2874

16
[ 93-98-1 ]
[ 1820-42-4 ]
[ 1266570-08-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In o-xylene at 100℃; for 10h; Inert atmosphere; regioselective reaction;
42%	With sodium iodide dihydrate; palladium 10% on activated carbon; potassium acetate; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 36h; Schlenk technique;	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.

Reference： [1]Mochida, Satoshi; Umeda, Nobuyoshi; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Chemistry Letters, 2010, vol. 39, # 7, p. 744 - 746]
[2]Shu, Zhen; Guo, Yuntao; Li, Wei; Wang, Baiquan [Catalysis Today, 2017, vol. 297, p. 292 - 297]

17
[ 4594-71-2 ]
[ 1820-42-4 ]
C₂₄H₁₇Cl₂NO [ No CAS ]

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

18
[ 831-81-2 ]
[ 1820-42-4 ]
[ 1425513-35-4 ]

Reference： [1]Synlett,2013,vol. 24,p. 130 - 134

19
[ 1820-42-4 ]
[ 1707-03-5 ]
[ 1443465-31-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; silver(I) acetate; silver carbonate In <i>tert</i>-butyl alcohol at 90℃; for 30h;
83%	With potassium hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; silver(I) acetate; silver carbonate In <i>tert</i>-butyl alcohol for 30h;	105 Example 105 Preparation of 3,4-Bis(4-chlorophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide Example 105 Preparation of 3,4-Bis(4-chlorophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide 3,4-Bis(4-chlorophenyl)-1-phenyl-1H-2,1-benzoxaphosphinine 1-oxide (58 mg, 83%) as a target compound was obtained under the condition of 90 for 30 hours, by the same reaction as the Example 100 above, except for using bis(4-chlorophenyl)ethyne (57 mg, 0.23 mmol) instead of using diphenylacetylene of the Example 100 above. 1H NMR (400 MHz, CDCl3) δ 7.95-7.89 (m, 2H), 7.66-7.45 (m, 5H), 7.40-7.34 (m, 3H), 7.21 (d, J=8.2 Hz, 2H), 7.17-7.11 (m, 4H), 7.01 (dd, J=7.9 HZ, 4.8 Hz, 1H)
80%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; silver carbonate In 1,2-dichloro-ethane at 110℃; for 0.5h; Microwave irradiation;	15 Preparation method In a 10mL microwave reaction tube, add compound I-1 (0.3mmol), compound II-7 (0.36mmol), Ag2CO3 (0.6mmol), NaHCO3 (0.30mmol), [RhCp*Cl2]2 (0.012mmol) ), 1,2-dichloroethane (1.5 mL), the mixture was placed in a microwave reactor at 110° C. for 30 min at a microwave power of 100 w; TLC (thin layer chromatography) detected until the reaction was complete. Purification by post-treatment: cooling to room temperature, pressure concentration. The crude product is separated and purified by silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 15:12:1, and then the pure product is obtained as a brown solid, the yield: 80%.

79%	With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; silver(I) acetate In diethylene glycol dimethyl ether at 120℃; for 2h; Inert atmosphere; regioselective reaction;
61%	With chloropyridinecobaloxime(III); cesium fluoride; 9‑mesityl-10-methylacridinium perchlorate In chloroform; water at 20℃; Inert atmosphere; Irradiation; Schlenk technique;
55%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; silver carbonate In <i>tert</i>-butyl alcohol at 90℃; for 30h;

Reference： [1]Park, Youngchul; Jeon, Incheol; Shin, Seohyun; Min, Jiae; Lee, Phil Ho [Journal of Organic Chemistry, 2013, vol. 78, # 20, p. 10209 - 10220]
[2]Current Patent Assignee: KANGWON NATIONAL UNIVERSITY - US2015/344506, 2015, A1 Location in patent: Paragraph 0387-0389
[3]Current Patent Assignee: JIANGHAN UNIVERSITY - CN111995642, 2020, A Location in patent: Paragraph 0107-0110
[4]Unoh, Yuto; Hashimoto, Yuto; Takeda, Daisuke; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Organic Letters, 2013, vol. 15, # 13, p. 3258 - 3261]
[5]Qiao, Ming-Ming; Liu, Yi-Yin; Yao, Sheng; Ma, Tian-Cong; Tang, Zi-Long; Shi, De-Qing; Xiao, Wen-Jing [Journal of Organic Chemistry, 2019, vol. 84, # 11, p. 6798 - 6806]
[6]Park, Youngchul; Seo, Jungmin; Park, Sangjune; Yoo, Eun Jeong; Lee, Phil Ho [Chemistry - A European Journal, 2013, vol. 19, # 48, p. 16461 - 16468]

20
[ 873-73-4 ]
[ 637-87-6 ]
[ 1820-42-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; chlorobenzene In ethanol for 18h; Green chemistry;
79%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 10h; Inert atmosphere;
75%	With triethylamine In neat (no solvent) at 70℃; for 3h;	A typical procedure for the Sonogashira-Hagihara cross-coupling reaction General procedure: A round-bottomed flask equipped with mechanical stirring was charged by a mixtureof phenylacetylene (1.2 mmol, 0.102 g), iodobenzene (1.0 mmol, 0.203 g), triethylamine(1 mmol, 0.101 g), and catalyst (0.007 g, 2.41 mol% Co), under solventfreeconditions at 70 °C. The progress of the reaction was monitored using TLC.After completion of the reaction (4 h), the mixture was diluted with ethyl acetate.Thereafter, the mesostructured catalyst was separated by simple filtration, washedwith EtOH (3 × 10 mL), and dried at 60 °C under vacuum overnight to remove theorganic residuals and solvents for use in the next run. The crude product was thenextracted with ethyl acetate, and the combined organic layer was dried over anhydrousNa2SO4.After solvent evaporation, the residue was purified by thin-layer chromatography using n-hexane/ethyl acetate (6:1) to afford white crystals of diphenylacetylene(0.174 g, 98% yield).

40%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 6h; Inert atmosphere;
	With copper(l) iodide; [Pd2Cl2(μ-Cl)2(PPh3)2]; triethylamine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;
	With copper(l) iodide; [PdCl₂(triphenylphosphine)]2; triethylamine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;
	Stage #1: 1-Chloro-4-iodobenzene With pyrrolidine; palladium dichloride In water at 50℃; for 0.0833333h; Stage #2: 4-n-chlorophenylacetylene In water at 50℃; for 24h;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine at 25 - 40℃; for 24h; Inert atmosphere; Sealed tube;
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine In tetrahydrofuran at 40℃; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In water; benzene at 80℃;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine In tetrahydrofuran; triethylamine at 20℃; Inert atmosphere; Schlenk technique;
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;
	Stage #1: 1-Chloro-4-iodobenzene With pyrrolidine; palladium dichloride In water at 50℃; for 0.0833333h; Stage #2: 4-n-chlorophenylacetylene In water at 50℃; for 12h;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In water; benzene at 80℃;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;	Synthesis of substrates 1,2-diphenylethyne derivatives General procedure: Chapter one: A 100 mL schlenk tube was charged with iodobenzene (3.0 mmol), ethynyltrimethylsilane (3.6 mmol), PdCl2(PPh3)2 (0.15 mmol), CuI (0.15 mmol), Et3N:THF = 3:2 (10.0 mL). Then the tube was charged with nitrogen, and was stirred at room temperature for the indicated time until complete consumption of starting material as monitored by TLC analysis. After the completion of the reaction, then the reaction mxtuire was filtered and the filtrate diluted in ethyl acetate and washed with water. The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The crude product was purified by silica gel column chromatography (petroleum ether unless otherwise noted) to give the corresponding trimethyl(phenylethynyl)silanes, and used for the next reaction.
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In water; toluene at 80℃; for 18h;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Wang, Hu; Li, Li; Bai, Xing-Feng; Deng, Wen-Hui; Zheng, Zhan-Jiang; Yang, Ke-Fang; Xu, Li-Wen [Green Chemistry, 2013, vol. 15, # 9, p. 2349 - 2355]
[2]Kumar, Amrendra; Tadigoppula, Narender [Organic Letters, 2021, vol. 23, # 1, p. 8 - 12]
[3]Ghodsinia, Sara S. E.; Akhlaghinia, Batool; Jahanshahi, Roya [Research on Chemical Intermediates, 2021, vol. 47, # 8, p. 3217 - 3244]
[4]Sattler, Lars E.; Hilt, Gerhard [Chemistry - A European Journal, 2021, vol. 27, # 2, p. 605 - 608]
[5]Chen, Xuebing; Wu, Youzhi; Xu, Jinyi; Yao, Hequan; Lin, Aijun; Huang, Yue [Organic and Biomolecular Chemistry, 2015, vol. 13, # 35, p. 9186 - 9189]
[6]Yan, Hao; Wang, Haolong; Li, Xincheng; Xin, Xiaoyi; Wang, Chunxiang; Wan, Boshun [Angewandte Chemie - International Edition, 2015, vol. 54, # 36, p. 10613 - 10617][Angew. Chem., 2015, vol. 127, # 36, p. 10759 - 10763,5]
[7]Xie, Ying [Chemical Communications, 2016, vol. 52, # 83, p. 12372 - 12375]
[8]Huang, Wei; Byun, Jeehye; Rörich, Irina; Ramanan, Charusheela; Blom, Paul W. M.; Lu, Hao; Wang, Di; Caire da Silva, Lucas; Li, Run; Wang, Lei; Landfester, Katharina; Zhang, Kai A. I. [Angewandte Chemie - International Edition, 2018, vol. 57, # 27, p. 8316 - 8320][Angew. Chem., 2018, vol. 130, # 27, p. 8449 - 8453,5]
[9]Raju, Selvam; Hsiao, Huan-Chang; Thirupathi, Selvakumar; Chen, Pei-Ling; Chuang, Shih-Ching [Advanced Synthesis and Catalysis, 2019, vol. 361, # 4, p. 683 - 689]
[10]Guo, Songjin; Li, Panpan; Guan, Zhe; Cai, Libo; Chen, Siwei; Lin, Aijun; Yao, Hequan [Organic Letters, 2019, vol. 21, # 4, p. 921 - 925]
[11]Yuan, Hairui; Wang, Min; Xu, Zhenghu; Gao, Hongyin [Advanced Synthesis and Catalysis, 2019, vol. 361, # 18, p. 4386 - 4392]
[12]Li, Tongyu; Liu, Chang; Wu, Shaonan; Chen, Chen C.; Zhu, Bolin [Organic and Biomolecular Chemistry, 2019, vol. 17, # 33, p. 7679 - 7683]
[13]Yang, Qi-Liang; Xing, Yi-Kang; Wang, Xiang-Yang; Ma, Hong-Xing; Weng, Xin-Jun; Yang, Xiang; Guo, Hai-Ming; Mei, Tian-Sheng [Journal of the American Chemical Society, 2019, vol. 141, # 48, p. 18970 - 18976]
[14]Qian, Lei-Lei; Min, Xiang-Ting; Hu, Yan-Cheng; Shen, Bing-Xue; Yang, Sa-Na; Wan, Boshun; Chen, Qing-An [Chemical Communications, 2020, vol. 56, # 17, p. 2614 - 2617]
[15]Li, Ming; Yao, Tian-Yu; Sun, Sheng-Zheng; Yan, Ting-Xun; Wen, Li-Rong; Zhang, Lin-Bao [Organic and Biomolecular Chemistry, 2020, vol. 18, # 16, p. 3158 - 3163]
[16]Wu, Shaonan; Wang, Zhuo; Bao, Yinwei; Chen, Chen; Liu, Kun; Zhu, Bolin [Chemical Communications, 2020, vol. 56, # 32, p. 4408 - 4411]
[17]Deng, Guobo; Liang, Yun; Luo, Xiai; Yang, Xiumei; Yang, Yuan; Yang, Yuzhong; Zhou, Liwei [Synthesis, 2020, vol. 52, # 8, p. 1223 - 1230]
[18]He, Yuan; Liao, Xian-Zhang; Dong, Lin; Chen, Fen-Er [Organic and Biomolecular Chemistry, 2021, vol. 19, # 3, p. 561 - 567]
[19]Wang, Wei; Bao, Zhi-Peng; Qi, Xinxin; Wu, Xiao-Feng [Organic Letters, 2021, vol. 23, # 16, p. 6589 - 6593]

21
[ 3376-24-7 ]
[ 1820-42-4 ]
[ 96286-65-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5440 - 5443

22
[ 1820-42-4 ]
[ 4559-70-0 ]
1-phenyl-2,3-di-(p-chlorophenyl)-1H-phosphindole-1-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With silver(I) acetate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;
80%	With 1-ethoxy-2-methylpyridin-1-ium tetrafluoroborate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h; Irradiation;
77%	With chloropyridinecobaloxime(III); sodium formate In dichloromethane at 60℃; for 20h; Inert atmosphere; Irradiation;

73%	With 1-ethoxy-2-methylpyridin-1-ium tetrafluoroborate; sodium hydrogencarbonate; eosin y In N,N-dimethyl-formamide at 35℃; for 48h; Irradiation; Schlenk technique; Inert atmosphere;
64%	With silver(I) acetate In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;	1-Ethoxy-2,3-diphenylphosphindole 1-Oxide (3aa); TypicalProcedure General procedure: A suspension of phosphinate 1a (85 mg, 0.50 mmol), diphenylacetylene(2a; 178 mg, 1.00 mmol), AgOAc (167.0 mg, 1.00 mmol) inDMSO (2.0 mL) was stirred under N2 atmosphere at r.t., and then at 120 C for 12 h. At r.t., the reaction mixture was diluted with H2O(10 mL) and extracted with EtOAc (3 ~ 25 mL). The combined organiclayers were dried (Na2SO4). After filtration and evaporationof the solvents in vacuo, the crude product was purified by columnchromatography on silica gel (n-hexane.EtOAc, 5:1 2:1) to afford3aa as an off-white oil; yield: 104 mg (60%).
55%	With dipotassium peroxodisulfate In acetonitrile at 90℃; for 24h; Sealed tube; Inert atmosphere;
30%	With tert.-butylhydroperoxide; ammonium hydroxide; copper(ll) sulfate pentahydrate In water; acetonitrile at 60℃; for 0.5h;

Reference： [1]Unoh, Yuto; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Angewandte Chemie - International Edition, 2013, vol. 52, # 49, p. 12975 - 12979][Angew. Chem., 2013, vol. 52-125, # 49, p. 13213 - 13217]
[2]Huang, Wei; Byun, Jeehye; Rörich, Irina; Ramanan, Charusheela; Blom, Paul W. M.; Lu, Hao; Wang, Di; Caire da Silva, Lucas; Li, Run; Wang, Lei; Landfester, Katharina; Zhang, Kai A. I. [Angewandte Chemie - International Edition, 2018, vol. 57, # 27, p. 8316 - 8320][Angew. Chem., 2018, vol. 130, # 27, p. 8449 - 8453,5]
[3]Liu, Wen-Qiang; Lei, Tao; Zhou, Shuai; Yang, Xiu-Long; Li, Jian; Chen, Bin; Sivaguru, Jayaraman; Tung, Chen-Ho; Wu, Li-Zhu [Journal of the American Chemical Society, 2019, vol. 141, # 35, p. 13941 - 13947] Liu, Wen-Qiang; Lei, Tao; Zhou, Shuai; Yang, Xiu-Long; Li, Jian; Chen, Bin; Sivaguru, Jayaraman; Tung, Chen-Ho; Wu, Li-Zhu [Journal of the American Chemical Society, 2019, vol. 141, # 35, p. 13941 - 13947]
[4]Quint, Valentin; Morlet-Savary, Fabrice; Lohier, Jean-François; Lalevée, Jacques; Gaumont, Annie-Claude; Lakhdar, Sami [Journal of the American Chemical Society, 2016, vol. 138, # 23, p. 7436 - 7441]
[5]Ma, Wenbo; Ackermann, Lutz [Synthesis, 2014, vol. 46, # 17, p. 2297 - 2304]
[6]Ma, Dumei; Chen, Weizhu; Hu, Gaobo; Zhang, Yun; Gao, Yuxing; Yin, Yingwu; Zhao, Yufen [Green Chemistry, 2016, vol. 18, # 12, p. 3522 - 3526]
[7]Zhang, Pengbo; Gao, Yuzhen; Zhang, Liangliang; Li, Zhiqiang; Liu, Yan; Tang, Guo; Zhao, Yufen [Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 138 - 142]

23
[ 1820-42-4 ]
[ 16110-98-8 ]
[ 1476744-07-6 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11427 - 11432

24
[ 1820-42-4 ]
[ 673485-54-6 ]
[ 1610537-54-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	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]

25
[ 88-61-9 ]
[ 1820-42-4 ]
3,4-bis(4-chlorophenyl)-6,8-dimethylbenzo[c][1,2]oxathiine 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In 1,4-dioxane at 100℃; for 16h; Sealed tube; Inert atmosphere; Schlenk technique;

Reference： [1]Qi, Zisong; Wang, Mei; Li, Xingwei [Chemical Communications, 2014, vol. 50, # 68, p. 9776 - 9778]

26
[ 36122-35-7 ]
[ 1820-42-4 ]
[ 1476744-07-6 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 37138 - 37141

27
[ 1820-42-4 ]
[ 114-83-0 ]
N-(2,3-bis(4-chlorophenyl)-1H-indol-1-yl)acetamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 16,p. 6176 - 6179

28
[ 1820-42-4 ]
[ 4105-21-9 ]
5,6-bis(4-chlorophenyl)naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cobalt(II) diacetate tetrahydrate In N,N-dimethyl-formamide at 110℃; for 2h; Sealed tube;	4.2. General procedure for annulation of 2-arylimidazo[1,2-a]pyridine derivatives General procedure: A 10 mL vial was charged the requisite 2-arylimidazo[1,2-a]pyridine derivatives (1.0 equiv), internal alkynes (2.0 equiv), Co(OAc)2·4H2O (1.2 equiv) and [RhCp*Cl2]2 (5 mol%) in DMF (1 mL). The vial was sealed, heated to 110 °C and stirred for 2 h. The resulting mixture was analyzed by TLC. After cooling to room temperature, the mixture was concentrated in vacuo. The products were isolated by silica gel with ethyl acetate and petroleum ether as the eluent to afford the desired products.
78%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In 1,2-dichloro-ethane at 100℃; for 12h; Sealed tube;
64%	With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; copper diacetate In toluene at 110℃; for 12h;

Reference： [1]Wang, Wei; Niu, Jun-Long; Liu, Wen-Bo; Shi, Tan-Hao; Hao, Xin-Qi; Song, Mao-Ping [Tetrahedron, 2015, vol. 71, # 42, p. 8200 - 8207]
[2]Qi, Zisong; Yu, Songjie; Li, Xingwei [Journal of Organic Chemistry, 2015, vol. 80, # 7, p. 3471 - 3479]
[3]Peng, Haibo; Yu, Jin-Tao; Jiang, Yan; Wang, Lei; Cheng, Jiang [Organic and Biomolecular Chemistry, 2015, vol. 13, # 19, p. 5354 - 5357]

29
[ 3112-85-4 ]
[ 1820-42-4 ]
(E)-1,2-bis(4-chlorophenyl)-1-(2-(methylsulfonyl)phenyl)ethene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; 1-Adamantanecarboxylic acid In chlorobenzene at 140℃; for 24h; Inert atmosphere; regioselective reaction;	4.6. Reaction of methyl phenyl sulfones 1 with alkynes 2 General procedure: To a 20 mL two-necked flask with a reflux condenser, a balloon,and a rubber cup were added methyl phenyl sulfone 1 (0.75 mmol),alkyne 2 (0.25 mmol), [Cp*Rh(MeCN)3](SbF6)2 (0.01 mmol, 8.3 mg),1-AdCOOH (0.1 mmol, 18 mg), 1-methylnaphlene (ca. 30 mg) as internal standard, and PhCl (1 mL). Then, the resulting mixture was stirred under nitrogen at 140 C for 24 h. After cooling, the reaction mixture was extracted with ethyl acetate (100 mL). The organic layer was washed by aqueous NaHCO3 (100 mL, three times) and dried over Na2SO4. After evaporation of the solvents under vacuum,product 3 was isolated by column chromatography on silica gel using hexane/ethyl acetate as eluent. Further purification by gel permeation chromatography (GPC) was performed, if needed.

Reference： [1]Nobushige, Kazunori; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Tetrahedron, 2015, vol. 71, # 37, p. 6506 - 6512]

30
[ 78704-49-1 ]
[ 1820-42-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 6 h / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 20 °C 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 20 °C / Schlenk technique; Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium carbonate / methanol; dichloromethane / 1 h / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / Inert atmosphere

Reference： [1]Chen, Xuebing; Wu, Youzhi; Xu, Jinyi; Yao, Hequan; Lin, Aijun; Huang, Yue [Organic and Biomolecular Chemistry, 2015, vol. 13, # 35, p. 9186 - 9189]
[2]Deng, Guobo; Liang, Yun; Luo, Xiai; Yang, Xiumei; Yang, Yuan; Yang, Yuzhong; Zhou, Liwei [Synthesis, 2020, vol. 52, # 8, p. 1223 - 1230]
[3]Sattler, Lars E.; Hilt, Gerhard [Chemistry - A European Journal, 2021, vol. 27, # 2, p. 605 - 608]

31
[ 42918-20-7 ]
[ 1820-42-4 ]
1,2-bis(4-chlorophenyl)-3-methylnaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With palladium(II) trifluoroacetate; caesium carbonate; glyoxal bis(N-methyl-N-phenylhydrazone) In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;

Reference： [1]Watanabe, Kohei; Mino, Takashi; Hatta, Chikako; Ito, Shisei; Sakamoto, Masami [Organic and Biomolecular Chemistry, 2015, vol. 13, # 48, p. 11645 - 11650]

32
[ 1820-42-4 ]
[ 885-91-6 ]
5,6-bis(4-chlorophenyl)-10-methylnaphtho[1',2':4,5]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cobalt(II) diacetate tetrahydrate In N,N-dimethyl-formamide at 110℃; for 2h; Sealed tube;	4.2. General procedure for annulation of 2-arylimidazo[1,2-a]pyridine derivatives General procedure: A 10 mL vial was charged the requisite 2-arylimidazo[1,2-a]pyridine derivatives (1.0 equiv), internal alkynes (2.0 equiv), Co(OAc)2·4H2O (1.2 equiv) and [RhCp*Cl2]2 (5 mol%) in DMF (1 mL). The vial was sealed, heated to 110 °C and stirred for 2 h. The resulting mixture was analyzed by TLC. After cooling to room temperature, the mixture was concentrated in vacuo. The products were isolated by silica gel with ethyl acetate and petroleum ether as the eluent to afford the desired products.

Reference： [1]Wang, Wei; Niu, Jun-Long; Liu, Wen-Bo; Shi, Tan-Hao; Hao, Xin-Qi; Song, Mao-Ping [Tetrahedron, 2015, vol. 71, # 42, p. 8200 - 8207]

33
[ 934-37-2 ]
[ 1820-42-4 ]
3,4-bis(4-chlorophenyl)-2-methylimidazo[5,1,2-cd]indolizine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 5722 - 5731

34
[ 1820-42-4 ]
[ 406207-65-6 ]
2-tert-butyl-3,4-bis(4-chlorophenyl)imidazo[5,1,2-cd]indolizine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 5722 - 5731

35
[ 13688-68-1 ]
[ 1820-42-4 ]
[ 21015-56-5 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1361 - 1364
Angew. Chem.,2016,vol. 129,p. 1381 - 1384,4

36
[ 1613-37-2 ]
[ 1820-42-4 ]
C₂₃H₁₇Cl₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.7%	With N-(tert-butoxy)-1H-pyrrole-2-carboxamide; silver(I) citrate In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere;	2 Example 2 Under inert gas protection,To the reactor was added 10 ml of N, N-dimethylformamide,And in turn added to itTo 1.5 mmol of quinoline N-oxide, 1. Ommol of the compound of formula (1_2), 0.15 mmolSilver citrate catalyst, 0.15 mmol ligand, stirring heating to 110 ° C,And the reaction was stirred at that temperature for 20 hours.After completion of the reaction, all volatiles were removed by vacuum,The product was extracted with ethyl acetate, the organic phase removed the solvent,The resulting residue was chromatographed on a 300-400 mesh silica gel column,Using petroleum ether / ethyl acetate as the eluent to give the compound of formula (11-2) above,The yield was 90.7%.

Reference： [1]Current Patent Assignee: Zhou Xiaofang - CN106966968, 2017, A Location in patent: Paragraph 0028; 0029; 0030

37
[ 1452-77-3 ]
[ 1820-42-4 ]
(Z)-N-(1,2-bis(4-chlorophenyl)vinyl)picolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With cesiumhydroxide monohydrate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; stereoselective reaction;	Cesium Hydroxide-Mediated Hydroamidation of Internal Aryl Alkynes with Amides General procedure: The reaction of diphenylacetylene (1a) with picolinamide (2a) is representative (Table 2, entry1): In a glovebox filled with nitrogen, diphenylacetylene (1a; 45 mg, 0.25 mmol), 2-picolinamide (2a;31 mg, 0.25 mmol), and CsOH•OH2 (42 mg, 0.25 mmol) were placed in a 2-mL microwave vessel(Biotage). The vessel was sealed with a cap and then taken out of the glovebox. Dimethyl sulfoxide(DMSO, 1.0 mL) was sequentially injected via a syringe. The mixture was stirred for 24 h at 120 °C.The resulting mixture was then quenched with water. The mixture was extracted with ethyl acetatethree times, and the combined organic layer was dried over anhydrous Na2SO4. After concentrationunder reduced pressure, silica gel column purification with hexane/ethyl acetate (3/1, v/v) afforded (Z)-N-(1,2-diphenylvinyl)picolinamide (3aa; 50 mg, 0.17 mmol) in 66% yield.

Reference： [1]Yamamoto, Chiaki; Hirano, Koji; Miura, Masahiro [Chemistry Letters, 2017, vol. 46, # 7, p. 1048 - 1050]

38
[ 318-54-7 ]
[ 1820-42-4 ]
2,2,2-trifluoro-1-(6,7,8,9-tetrakis(4-chlorophenyl)-3-methyl-3H-benzo[e]indol-1-yl)ethanone [ No CAS ]
C₂₅H₁₆Cl₂F₃NO [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1810 - 1818

39
[ 1820-42-4 ]
[ 42048-11-3 ]
[ 21739-93-5 ]
2,7-dichloro-9,10-bis(4-chlorophenyl)-1-methylphenanthrene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 3381 - 3385
Angew. Chem.,2018,vol. 130,p. 3439 - 3443,5

40
[ 1006-50-4 ]
[ 1820-42-4 ]
[ 13959-02-9 ]
5,6-bis(4-chlorophenyl)isoquinolino[7,8-f]quinoline [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 3381 - 3385
Angew. Chem.,2018,vol. 130,p. 3439 - 3443,5

41
[ 201230-82-2 ]
[ 2446-51-7 ]
[ 1820-42-4 ]
9-chloro-12-(4-chlorophenyl)isoindolo[2,1-b]isoquinoline-5,7-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: N-methoxybenzamide; bis(4-chlorophenyl)acetylene With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate In chlorobenzene at 60℃; for 16h; Schlenk technique; Stage #2: carbon monoxide With palladium diacetate; silver trifluoroacetate; sodium carbonate In chlorobenzene at 120℃; for 15h;	13 Example 13 According to the method described in Embodiment 1,N-methoxybenzamide 1a was sequentially added to a 15 mL schlenk reaction tube(60.4 mg, 0.4 mmol), chlorobenzene (2 mL),2e (108.2 mg, 0.44 mmol), [Cp*RhCl2] 2 (6.2 mg, 2.5 mol%), cesium acetate (23.0 mg, 0.12 mmol), placed in an oil bath at 60 ° C for heating for 16 h, after completion of the reaction, Palladium acetate (9.0 mg, 0.04 mmol), silver trifluoroacetate (176.7 mg, 0.8 mmol), sodium carbonate (21.2 mg, 0.2 mmol), vacuum three times, and then heated in a 120 ° C oil bath were added to the system. After stirring for 15 h, the reaction was quenched with EtOAc EtOAc (EtOAc)EtOAc. Filtration, concentration under reduced pressure, and separation and purification on silica gel column (eluent to a volume ratio of 10/1 in dichloromethane/ethyl acetate) afforded a yellow solid isoindole [2,1-b]isoquinolin-5. 7-Diketone 3 m (97 mg, 62%).

Reference： [1]Current Patent Assignee: HENAN NORMAL UNIVERSITY - CN108467393, 2018, A Location in patent: Paragraph 0049; 0050; 0051

42
[ 1820-42-4 ]
[ 102-04-5 ]
3-benzyl-1,2-bis(4-chlorophenyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With [RhCl₂(p-cymene)]2; potassium acetate; sodium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube;	4.2. General procedure for ruthenium-catalyzed annulation of 1,3-diphenylacetone with internal alkynes General procedure: A 25mL sealed tube was charged with 1,3-diphenylacetone 1a(0.2 mmol, 2.0 equiv), internal alkynes 2 (0.1 mmol, 1.0 equiv),[RuCl2(p-cymene)]2 (0.015 mmol, 15 mol%), KOAc (0.2 mmol, 2.0equiv), Na2CO3 (0.2 mmol, 2.0 equiv) and PhMe (0.5 mL). The vialwas evacuated and filled with N2 atmosphere, and stirred at 100 Cfor 24 h. After being cooled to room temperature, the mixture wasevaporated under reduced pressure. The residue was purified byflash column chromatography on silica gel, eluting with petroleumether to afford the desired products 3.
68%	With [RhCl₂(p-cymene)]2; potassium acetate; sodium carbonate In toluene at 100℃; for 24h; Sealed tube; Inert atmosphere;	7 Example 7 Add dibenzyl ketone (42mg, 0.2mmol) to a 25mL sealed tube with magnets,The corresponding internal alkynes (0.1 mmol),Catalyst [RuCl2(p-cymene)]2 (9mg, 15%mol),0.5mL toluene, then add dry sodium carbonate (21mg, 0.2mmol),Potassium acetate (19mg, 0.2mmol), pump nitrogen three times,React at 100°C for 24 hours,Then it is separated by column chromatography (eluent: petroleum ether) to obtain the target compound.The characterization is as follows.

Reference： [1]Gao, Jie; Zhang, Shujia; Zhang, Yuhong [Tetrahedron, 2018, vol. 74, # 43, p. 6263 - 6269]
[2]Current Patent Assignee: DALIAN UNIVERSITY - CN108033866, 2020, B Location in patent: Paragraph 0044-0047

43
[ 1820-42-4 ]
[ 1121545-24-1 ]
7,8-bis(4-chlorophenyl)benzo[4,5]cyclohepta[1,2,3-de]naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With silver (II) carbonate; palladium diacetate; tri(4-chlorophenyl)phosphine In 1,2-dichloro-ethane at 80℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Yan, Jianming; Rahman, Md. Shafiqur; Yoshikai, Naohiko [Chemistry - A European Journal, 2019, vol. 25, # 40, p. 9395 - 9399]

44
[ 1820-42-4 ]
[ 15754-60-6 ]
(Z)-1-(4,5-bis(4-chlorophenyl)-2-methylpent-4-en-2-yl)-1H-pyrazole [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 7679 - 7683

45
[ 1820-42-4 ]
[ 291514-02-8 ]
4,5-bis(4-chlorophenyl)-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]isothiazole 2,2-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With silver hexafluoroantimonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper(II) acetate monohydrate; acetic acid In 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Schlenk technique; diastereoselective reaction;

Reference： [1]Qian, Lei-Lei; Min, Xiang-Ting; Hu, Yan-Cheng; Shen, Bing-Xue; Yang, Sa-Na; Wan, Boshun; Chen, Qing-An [Chemical Communications, 2020, vol. 56, # 17, p. 2614 - 2617]

46
[ 1820-42-4 ]
[ 245368-50-7 ]
5,6-bis(4-chlorophenyl)-1,3,4,4a,5,7a-hexahydrocyclopenta[c][1,2]thiazine 2,2-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With silver hexafluoroantimonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper(II) acetate monohydrate; trifluoroacetic acid In 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Schlenk technique; diastereoselective reaction;

Reference： [1]Qian, Lei-Lei; Min, Xiang-Ting; Hu, Yan-Cheng; Shen, Bing-Xue; Yang, Sa-Na; Wan, Boshun; Chen, Qing-An [Chemical Communications, 2020, vol. 56, # 17, p. 2614 - 2617]

47
[ 1820-42-4 ]
[ 54015-96-2 ]
5,6,7,8-tetrakis(4-chlorophenyl)-3-methoxy-1-(pyridin-2-yl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium acetate In 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; Inert atmosphere;

Reference： [1]Wu, Shaonan; Wang, Zhuo; Bao, Yinwei; Chen, Chen; Liu, Kun; Zhu, Bolin [Chemical Communications, 2020, vol. 56, # 32, p. 4408 - 4411]

48
[ 1820-42-4 ]
[ 19264-68-7 ]
[ 96286-65-6 ]
[ 86-74-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With silver hexafluoroantimonate; silver orthophosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 2,6-dimethylbenzoic acid In 1,2-dichloro-ethane at 120℃; for 24h; Inert atmosphere;	Rh-Catalyzed Reaction of 9-Benzoylcarbazoles 1 with Alkynes 2. General procedure: To a 10 mL screw-cap vialwere added 9-benzoylcarbazole 1 (0.1 mmol), alkyne 2 (0.15 mmol) [Cp*RhCl2]2 (0.01 mmol, 6 mg),AgSbF6 (0.04 mmol, 14 mg), Ag3PO4 (0.01 mmol, 4 mg), 2,6-dimethylbenzoic acid (0.2 mmol, 30 mg),DCE (2 mL), and naphthalene (ca. 30 mg) as internal standard. The mixture was stirred under argon(1 atm) at 120 °C (bath temperature) for 24 h. The reaction mixture was diluted by ethyl acetate (40mL). The organic layer was washed by 1N HCl aq. (20 mL, three times) and brine (20 mL) and driedover Na2SO4. After evaporation of the solvents under vacuum, product 3 and 9H-carbazole 4 wereisolated by column chromatography on silica gel using hexane-ethyl acetate as eluent. Furtherpurification by GPC (gel permeation chromatography) was performed, if needed.

Reference： [1]Ochiai, Shiho; Sakai, Asumi; Usuki, Yoshinosuke; Kang, Bubwoong; Shinada, Tetsuro; Satoh, Tetsuya [Chemistry Letters, 2021, vol. 50, # 4]

49
[ 1820-42-4 ]
[ 86847-79-2 ]
C₃₉H₃₀Cl₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With anhydrous silver tetrafluoroborate; bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; copper (II) acetate In 1,2-dichloro-ethane at 120℃; for 24h; Autoclave; Inert atmosphere;	7 Implementation case 1Synthesis of N-(5,6,7,8-tetraphenyl-1-isoquinolineyl)neovaleramide 3a. General procedure: In a 20 ml pressure-resistant reaction tube, 35.6 mg of N- (2-pyridyl) neovaleramide (0.2 mmol), 78.4 mg of diphenylacetylene (0.44 mmol), 6.18 mg of [Cp*RhCl2]2(0.01 mmol), 13.7 mg of AgSbF6 were added to a20ml pressure-resistant reaction tube (0.04 mmol), 76.3 mg copper acetate (0.42 mmol), 2 ml of 1,2-dichloroethane, nitrogen protection sealed and placed in a heating agitator at 120 °C stirred for 24 hours. The reaction mixture was quenched, extracted, and dried in the organic phase with anhydrous sodium sulfate or anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure to obtain the residue, and the residue was separated by silica gel column chromatography (the elution solvent was petroleum ether / ethyl acetate) to give the target product 3a, yellow solid 57.5mg, yield 54%
43%	With silver hexafluoroantimonate; bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; copper (II) acetate In 1,2-dichloro-ethane at 120℃; for 24h; Inert atmosphere;	General procedure for the synthesis of Isoquinolines General procedure: 2-Aminopyridine Pivalamides 1 (0.2 mmol, 1.0 equiv), [Cp*RhCl2]2 (0.01 mmol, 5 mol%), AgSbF6 (0.04 mmol, 20 mol%), Cu(OAc)2 (0.42 mmol, 2.1 equiv), diphenylacetylene 2 (0.44 mmol, 2.2 equiv) and DCE (2 mL) were added to a 35 mL Schlenk tube. After being purged with nitrogen, the mixture was stirred at 120 °C for 24 h. Then cooled to room temperature, and quenched by adding water (2 mL). The resulting mixture was extracted with dichloromethane. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography.

Reference： [1]Current Patent Assignee: CHANGSHA TECHNOLOGY UNIV - CN114456111, 2022, A Location in patent: Paragraph 0014-0015; 0021
[2]Gan, Xiaoting; Huang, Fen; Ren, Zhijun; Li, Bo; Chen, Shaojie; Luo, Wenkun; Zhou, Jun [Tetrahedron Letters, 2022, vol. 103]

50
[ 779-30-6 ]
[ 1820-42-4 ]
11-chloro-8,9,14-tris(4-chlorophenyl)-6H-chromeno[4’,3’,4,5]pyrrolo[2,1-a]isoquinolin-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With silver hexafluoroantimonate; bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; anhydrous silver carbonate In 1,2-dichloro-benzene at 110℃; for 5h; Inert atmosphere;

Reference： [1]Michikita, Ryudai; Usuki, Yoshinosuke; Satoh, Tetsuya [European Journal of Organic Chemistry, 2022, vol. 2022, # 22]

CAS No. :	1820-42-4	MDL No. :	MFCD01861446
Formula :	C₁₄H₈Cl₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QFRLNLXZHMUYHO-UHFFFAOYSA-N
M.W :	247.12	Pubchem ID :	97372
Synonyms :

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P271-P273-P280-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P391-P403+P233-P405-P501	UN#:	3077
Hazard Statements:	H315-H318-H335-H410	Packing Group:	Ⅲ
GHS Pictogram:

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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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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.
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1820-42-4 ] {[proInfo.proName]}

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[ 1820-42-4 ] Synthesis Path-Downstream 1~50

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