Name: 764-93-2|1-Decyne|98%
Brand: Ambeed
SKU: A303052
Rating: 93 (26 reviews)

1
[ 764-93-2 ]
[ 34683-73-3 ]
[ 24471-13-4 ]

Reference： [1]Chemische Berichte,1963,vol. 96,p. 3370 - 3373

2
[ 764-93-2 ]
[ 34683-73-3 ]
[ 29747-19-1 ]

Reference： [1]Chemische Berichte,1963,vol. 96,p. 3370 - 3373

3
[ 50-00-0 ]
[ 764-93-2 ]
[ 34683-71-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 1-decyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
93%	With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C to r.t., overnight;
80%	Stage #1: 1-decyne With n-butyllithium In tetrahydrofuran; hexane at -78 - 21℃; for 1h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 21℃; for 1h; Inert atmosphere;

78%	With n-butyllithium In N,N,N,N,N,N-hexamethylphosphoric triamide
77%	Stage #1: 1-decyne With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran at 20℃; Inert atmosphere;
72%	Stage #1: 1-decyne With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;	Undec-2-yn-1-ol (SI5). To a -78 °C solution of 1-decyne (1.0 mL, 5.55 mmol) in THF(18 mL) was added n-BuLi (2.5 mol/L in hexanes, 2.44 mL, 6.10 mmol) and the mixturewas stirred at -78 °C for 30 minutes, and then at room temperature for 30 minutes. Thesolution was brought back to -78 °C and paraformaldehyde (183 mg, 6.10 mmol) wasadded. The mixture was stirred at room temperature for 2 hours, after which saturatedNaHCO3 was added. The mixture was extracted with Et2O (3x), washed with brine, driedover Na2SO4 and concentrated in vacuo. The desired compound (669 mg, 72%) wasisolated as a colorless oil by flash chromatography using 5% EtOAc/hexanes.Spectroscopic data was in agreement with the literature.3
70%	Stage #1: 1-decyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.5h; Stage #2: formaldehyd In tetrahydrofuran at 20℃; for 16h;
68%	With n-butyllithium
	With n-Butyl chloride; lithium 1.) THF, sonication, 2.) THF, sonication, 4 h; Yield given. Multistep reaction;
	Stage #1: 1-decyne With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: formaldehyd

Reference： [1]Manjón-Mata, Inés; Quirós, M. Teresa; Buñuel, Elena; Cárdenas, Diego J. [Advanced Synthesis and Catalysis, 2020, vol. 362, # 1, p. 146 - 151]
[2]Cabezas, Jorge A.; Oehlschlager, Allan C. [Synthesis, 1999, # 1, p. 107 - 111]
[3]Hamel, Jean-Denys; Hayashi, Tatsuru; Cloutier, Mélissa; Savoie, Paul R.; Thibeault, Olivier; Beaudoin, Meggan; Paquin, Jean-François [Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9830 - 9836]
[4]Menger; Yamasaki [Journal of the American Chemical Society, 1993, vol. 115, # 9, p. 3840 - 3841]
[5]Domingo-Legarda, Pablo; Soler-Yanes, Rita; Quirós-López, M. Teresa; Buñuel, Elena; Cárdenas, Diego J. [European Journal of Organic Chemistry, 2018, vol. 2018, # 35, p. 4900 - 4904]
[6]Hamel, Jean-Denys; Beaudoin, Meggan; Cloutier, Mélissa; Paquin, Jean-François [Synlett, 2017, vol. 28, # 20, p. 2823 - 2828]
[7]Yang, Chun-Hua; Fan, Huihui; Li, Huimin; Hou, Shenyin; Sun, Xiangkun; Luo, Donghao; Zhang, Yinchao; Yang, Zhantao; Chang, Junbiao [Organic Letters, 2019, vol. 21, # 23, p. 9438 - 9441]
[8]Rychnovsky, Scott D.; Kim, Jinsoo [Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2659 - 2660]
[9]Fortes; Garrote [Synthetic Communications, 1993, vol. 23, # 20, p. 2869 - 2877]
[10]Pereira, Alban R.; Cabezas, Jorge A. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2594 - 2597]

4
[ 764-93-2 ]
[ 507-63-1 ]
[ 335-67-1 ]
[ 113999-61-4 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 2350 - 2352

5
[ 764-93-2 ]
[ 355-43-1 ]
[ 307-24-4 ]
[ 120464-27-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 2350 - 2352

6
[ 764-93-2 ]
[ 82632-80-2 ]
[ 125594-11-8 ]

Reference： [1]Angewandte Chemie,1990,vol. 102,p. 200 - 202

7
[ 764-93-2 ]
[ 201230-82-2 ]
[ 10568-44-2 ]
[ 118799-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;

Reference： [1]Buchwald, Stephen L.; Wannamaker, M. Woods; Watson, Brett T. [Journal of the American Chemical Society, 1989, vol. 111, # 2, p. 776 - 777]

8
[ 764-93-2 ]
[ 35109-88-7 ]
[ 100647-74-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 1h;

Reference： [1]Matsuda; Shinozaki; Yamaguchi; Homma; Nomoto; Miyasaka; Watanabe; Abiru [Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 241 - 252]

9
[ 764-93-2 ]
[ 693-54-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With water; at 59.84℃; for 24.0h;Ionic liquid;	Hydration Reaction-In a typical procedure, a solution of phenyl acetylene (1.0 mmol) was mixed with water (3.0 mmol) and BAILs (1.0 mmol). The reaction mixture was stirred for 10 h at 333 K. The reaction mixture was then diluted with H2O and extracted with chloroform and dried over anhydrous Na2SO4. The reaction mixture was analyzed using gas chromatography (Yonglin 6100; BP-5; 30 m × 0.25 mm × 0.25 mum). The products were identified by GC-MS (Shimadzu QP-5000; 30 m long, 0.25 mm i.d., with a 0.25-mum-thick capillary column, DB-1) and authentic samples obtained from Aldrich.Aqueous portion of the reaction mixture was evaporated to remove the water. Residue was washed three-four times with diethyl ether to remove any organic impurity. Finally, ionic liquid portion was dried under vacuum at 353 K for 4 h. The recovered ionic liquid was used in the recycling experiments.
78%	With water; In neat (no solvent); at 100℃; for 24.0h;Green chemistry;	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.
78%	With Perfluorooctanesulfonic acid; C8AgF17O3S*H2O; In water; at 100℃; for 8.0h;Darkness;	General procedure: To the mixture of phenylacetylene (1 mmol), water (3.0 mL),silver perfluorooctanesulfonate (5 mol%) and perfluorooctane sulfonateacid (2 mol%) was added. The mixture was stirred at 100 Cfor 8 h. The solution was extracted with n-hexane (diethyl ether)(3 5 mL), the combined extract was dried with anhydrous MgSO4. The rest of the solution was used for the next cycle of reaction. Theextraction solvent was removed and the crude product was separatedby column chromatography to give the pure sample.

37%Chromat.

With sulfuric acid; C18H15CoN2O10S2(2-)*2Na(1+); water; In methanol; at 80℃; for 20.0h;Schlenk technique;

General procedure: The 10 mL schlenk tube was charged with phenylacetylene (0.5 mmol, 51 mg), methanol (0.625 mL), catalyst (10 mumol, 2.0%), and then H2SO4 (10 mumol, 2.0%) dissolved in H2O (2.2mmol, 0.04 mL). The mixture was heated to 80 C and at it for 20 h in a closed tube with a magnetic stirring bar. The progres sof the reaction was monitored using TLC and GC-MS. After the reaction, the mixture was cooled to room temperature, and CH2Cl2 (5 mL) and water (5 mL) were added to the mixture.The aqueous and organic layers were separated, and the aqueous phase was extracted with CH2Cl2 (5 mL 3). The combined organic extracts were washed with a saturated NaCl solution,dried over Na2SO4, and concentrated under reduced pressure. Then the product acetophenone was obtained.

Reference： [1]Green Chemistry,2015,vol. 17,p. 532 - 537
[2]Advanced Synthesis and Catalysis,2016,vol. 358,p. 4106 - 4113
[3]Journal of the American Chemical Society,2013,vol. 135,p. 50 - 53
[4]Journal of the American Chemical Society,2011,vol. 133,p. 11632 - 11640
[5]Journal of Molecular Catalysis A: Chemical,2011,vol. 336,p. 1 - 7
[6]Tetrahedron Letters,2010,vol. 51,p. 4281 - 4283
[7]Synlett,2005,p. 3091 - 3094
[8]Chemistry - A European Journal,2011,vol. 17,p. 1261 - 1267
[9]Chemical Communications,2012,vol. 48,p. 434 - 436
[10]Tetrahedron Letters,2012,vol. 53,p. 3245 - 3249
[11]European Journal of Organic Chemistry,2019,vol. 2019,p. 5540 - 5548
[12]Applied Catalysis A: General,2015,vol. 505,p. 213 - 216
[13]Journal of Organometallic Chemistry,2015,vol. 799-800,p. 122 - 127
[14]Catalysis science and technology,2016,vol. 6,p. 7029 - 7032
[15]Organic Letters,2016,vol. 18,p. 2184 - 2187
[16]ChemCatChem,2014,vol. 6,p. 1612 - 1616
[17]Journal of Organic Chemistry,1982,vol. 47,p. 3331 - 3333
[18]Angewandte Chemie - International Edition,2010,vol. 49,p. 6813 - 6816
[19]Green Chemistry,2012,vol. 14,p. 1507 - 1514
[20]Chemical Communications,2015,vol. 51,p. 11896 - 11898
[21]Chinese Journal of Catalysis,2014,vol. 35,p. 1695 - 1700
[22]Angewandte Chemie - International Edition,2016,vol. 55,p. 13739 - 13743
Angew. Chem.,2016,vol. 128,p. 13943 - 13947,5

10
[ 764-93-2 ]
[ 3017-67-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetraethylammonium bromide; hydrogen bromide In dichloromethane for 2h; Ambient temperature;
88%	With boron tribromide In dichloromethane Inert atmosphere;
85%	With 1,1-dibromomethane In <i>N</i>,<i>N</i>-dimethyl-aniline at 120℃; for 12h; Inert atmosphere; Schlenk technique;	2. General procedure General procedure: Terminal alkynes(0.5 mmol), dibromomethane (2.5 mmol), N,N-dimethylaniline (1.5 mmol) wereplaced in a Schlenk tube (10 mL), and the mixture was stirred at 120 °C for 12 h. Then, the mixture was cooledto room temperature, washed with saturated Na2CO3solution. The crude product was extracted with ethyl acetate three times. Theorganic layer was dried over anhydrous Na2SO4, andconcentrated under reduced pressure. The residue was purified by columnchromatography on silica gel and eluted with petroleum to afford the analyticallypure products.

71%	Stage #1: 1-decyne With 9-bromo-9-bora-bicyclo[3.3.1]nonane In dichloromethane at 0℃; for 3h; Stage #2: With acetic acid In dichloromethane for 1h; Stage #3: With sodium hydroxide; dihydrogen peroxide In dichloromethane at 20℃; for 0.5h;
41%	With <i>N</i>,<i>N</i>-dimethyl-aniline; 1,1-dibromomethane at 120℃; for 12h; Schlenk technique;
	With acetic acid; 9-bromo-9-bora-bicyclo[3.3.1]nonane 1.) CH₂Cl₂, 0 deg C, 3 h; Yield given. Multistep reaction;
	With tetraethylammonium bromide; hydrogen bromide In dichloromethane

Reference： [1]Al Dulayymi, Juma'a R.; Baird, Mark S.; Simpson, Michael J.; Nyman, Susan; Port, Gordon R. [Tetrahedron, 1996, vol. 52, # 38, p. 12509 - 12520]
[2]Crossley, Steven W. M.; Barabé, Francis; Shenvi, Ryan A. [Journal of the American Chemical Society, 2014, vol. 136, # 48, p. 16788 - 16791]
[3]Chen, Xiuling; Chen, Tieqiao; Xiang, Yuqiang; Zhou, Yongbo; Han, Daoqing; Han, Li-Biao; Yin, Shuang-Feng [Tetrahedron Letters, 2014, vol. 55, # 33, p. 4572 - 4575]
[4]Dalili, Shadi; Yudin, Andrei K. [Organic Letters, 2005, vol. 7, # 6, p. 1161 - 1164]
[5]Chang, Dalu; Gu, Yang; Shen, Qilong [Chemistry - A European Journal, 2015, vol. 21, # 16, p. 6074 - 6078]
[6]Hara, Shoji; Dojo, Hidetaka; Takinami, Satoru; Suzuki, Akira [Tetrahedron Letters, 1983, vol. 24, # 7, p. 731 - 734]
[7]Ando, Tetsu; Ohno, Ryuta; Ikemoto, Kazuhisa; Yamamoto, Masanobu [Journal of Agricultural and Food Chemistry, 1996, vol. 44, # 10, p. 3350 - 3354]

11
[ 764-93-2 ]
[ 66291-72-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 1-decyne With benzo[1,3,2]dioxaborole at 70℃; for 3h; Inert atmosphere; Stage #2: With bromine In dichloromethane at -10℃; for 2h; Inert atmosphere; Stage #3: With sodium hydroxide In water at 0℃; for 1.25h; stereoselective reaction;	4.3 General procedure (B) for the synthesis of (Z)-1-bromo-1-alkenes General procedure: In a typical experiment, in a 3-neck round-bottom flask, equipped with a dropping funnel and a reflux condenser, one equivalent of the corresponding alkyne and one equivalent of catecholborane were mixed, under argon. The mixture was stirred at 70°C for 3h, and afterwards cooled down at room temperature and diluted with dichloromethane (0.25mL/mmol). The solution was then cooled down at-10°C. A solution containing 2 equiv. of bromine in dichloromethane (5M) was added dropwise, over a period of one hour. The solution was then let stirring for an additional hour, at-10°C. The mixture was warmed up at 0°C, and 68mL of NaOH 2N aqueous solution were added dropwise, over a period of 15min. The reaction was let stirring for an additional hour at 0°C. The obtained solution was extracted 3 times (3×100mL) with dichloromethane and the collected organic phases washed with brine until neutral pH. The solution was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by flash chromatography or distillation.
	With bromine; sodium methylate; benzo[1,3,2]dioxaborole Yield given. Multistep reaction;
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; silver nitrate / acetone / 20 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 30 h / 0 - 20 °C / Inert atmosphere 2.2: 30 h / Inert atmosphere

Reference： [1]Fusini, Graziano; Barsanti, Davide; Angelici, Gaetano; Casotti, Gianluca; Canale, Angelo; Benelli, Giovanni; Lucchi, Andrea; Carpita, Adriano [Tetrahedron, 2018, vol. 74, # 33, p. 4381 - 4389]
[2]Millar, Jocelyn G.; Underhill, Edward W. [Journal of Organic Chemistry, 1986, vol. 51, # 24, p. 4726 - 4728]
[3]Miyakoshi, Takeru; Konno, Hiroyuki [Organic and Biomolecular Chemistry, 2019, vol. 17, # 11, p. 2896 - 2905]

12
[ 764-93-2 ]
[ 58193-44-5 ]

Yield	Reaction Conditions	Operation in experiment
94.5%	With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 2h;
94.5%	With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 2h;
93%	With carbon tetrabromide; triphenylphosphine In dichloromethane for 7h; Ambient temperature;

90%	With N-Bromosuccinimide; silver nitrate In acetone at 20℃;
85%	With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 4h; Darkness;
85%	With dibromamine-T; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.0833333h;	4.4. General procedure for synthesis of 1-bromoalkyne(5a-5l) General procedure: To a stirred solution of alkyne (1 mmol) in CH2Cl2 (3 mL), TsNBr2 (1.2 mmol) and DBU (1.2 mmol) was added. The progress of the reaction was monitored by TLC. After the completion of the reaction sodium thiosulfate (200 mg) was added to the reaction mixture and further stirred for 5 min. The reaction mixture was washed with water and extracted with ethyl acetate. The organic layer was separated and dried over Na2SO4 and concentrated in vacuo. Purification of the crude product by flash chromatography on silica gel (230-400mesh) with petroleum ether as eluent gave the desired product.
47%	With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 2h; Inert atmosphere; Darkness;
80 % Chromat.	With bis-trimethylsilanyl peroxide; copper(I) bromide In tetrahydrofuran 1) -15 deg C, 15 min 2) to r.t., total 2h;
	With potassium hydroxide; bromine In 1,4-dioxane at 20℃; for 40h;
	With N-Bromosuccinimide; silver nitrate In acetone at 20℃;

Reference： [1]Li, Lei; Rosenthal, Martin; Zhang, Heng; Hernandez, Jaime J.; Drechsler, Markus; Phan, Kim Hô; Rütten, Stephan; Zhu, Xiaomin; Ivanov, Dimitri A.; Möller, Martin [Angewandte Chemie - International Edition, 2012, vol. 51, # 46, p. 11616 - 11619][Angew. Chem., 2012, vol. 124, # 46, p. 11784 - 11787,4]
[2]Rosenthal, Martin; Li, Lei; Hernandez, Jaime J.; Zhu, Xiaomin; Ivanov, Dimitri A.; Möller, Martin [Chemistry - A European Journal, 2013, vol. 19, # 13, p. 4300 - 4307]
[3]Wagner; Heitz; Mioskowski [Tetrahedron Letters, 1990, vol. 31, # 22, p. 3141 - 3144]
[4]Miyakoshi, Takeru; Konno, Hiroyuki [Organic and Biomolecular Chemistry, 2019, vol. 17, # 11, p. 2896 - 2905]
[5]Location in patent: experimental part Zhang, Feng; Zaidi, Saheem; Haney, Kendra M.; Kellogg, Glen E.; Zhang, Yan [Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7945 - 7952]
[6]Rajbongshi, Kamal Krishna; Hazarika, Debojit; Phukan, Prodeep [Tetrahedron, 2016, vol. 72, # 29, p. 4151 - 4158]
[7]Lehnherr, Dan; Alzola, Joaquin M.; Mulzer, Catherine R.; Hein, Samuel J.; Dichtel, William R. [Journal of Organic Chemistry, 2017, vol. 82, # 4, p. 2004 - 2010]
[8]Casarini; Dembech; Reginato; Ricci; Seconi [Tetrahedron Letters, 1991, vol. 32, # 19, p. 2169 - 2170]
[9]Cho, Hyun Ju; Seo, Kyung; Lee, Cheol Ju; Yun, Hoseop; Chang, Ji Young [Journal of Materials Chemistry, 2003, vol. 13, # 5, p. 986 - 990]
[10]Bourkhis, Maroua; Gaspard, Hafida; Rullière, Pauline; de Almeida, Diana K. C.; Listunov, Dymytrii; Joly, Etienne; Abderrahim, Raoudha; de Mattos, Marcos C.; de Oliveira, Maria C. F.; Maraval, Valérie; Chauvin, Remi; Génisson, Yves [ChemMedChem, 2018, vol. 13, # 11, p. 1124 - 1130]

13
[ 764-93-2 ]
[ 20151-40-0 ]
1-(2'-bromo-4'-quinolyl)-1-decyne [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 1057 - 1060

14
[ 764-93-2 ]
[ 70557-99-2 ]
4,4,5,5-Tetramethyl-2-undec-2-ynyl-[1,3,2]dioxaborolane [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 765 - 768
[2]Monatshefte fur Chemie,2008,vol. 139,p. 241 - 249

15
[ 764-93-2 ]
[ 2217-79-0 ]
[ 62839-71-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Schwartz's reagent; tetrakis(triphenylphosphine) palladium⁽⁰⁾ 1.) THF, room temperature, 2 h, 2.) THF, room temperature, 1.5 h; Yield given. Multistep reaction;

Reference： [1]Huang, Xian; Sun, Ai-Ming [Synthetic Communications, 1998, vol. 28, # 5, p. 773 - 778]

16
[ 2700-30-3 ]
(E)-1-decenyl(phenyl)(tetrafluoroborato)-λ³-iodane [ No CAS ]
[ 764-93-2 ]
[ 112-31-2 ]
Formic acid (Z)-dec-1-enyl ester [ No CAS ]

Reference： [1]Chemical Communications,1999,p. 1363 - 1364

17
[ 764-93-2 ]
[ 872-05-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen In toluene at 20℃; for 12h; Autoclave; chemoselective reaction;
86%	With ammonium chloride; zinc In water for 16h; Heating;
80%	With palladium on activated charcoal; hydrogen In water at 25℃; for 1h;

62%	With tetra-(n-butyl)ammonium iodide; dimethyl amine; palladium dichloride In methanol at 60℃; for 2.5h; Electrochemical reaction; stereoselective reaction;	Electrochemical hydrogenation of alkynes to the Z-alkenes Electrochemical hydrogenation was carried out in three-necked round-bottomed flask (10 mL), with a graphite rod anode and a platinum disc cathode. 1 (0.80 mmol), PdCl2 (0.5 mol%, 0.7 mg), Me2NH (0.5 equiv, 0.2 mL, 2.0 M in the methonal), "Bu4NI (1.0 equiv, 295.5 mg) and MeOH (8.0 mL) were placed in a three-necked round-bottomed flask at 60 °C with a constant current of 0.1 A maintained for 2.5-5 h. The mixture was cooled to room temperature, and diluted with 20 mL of EtOAc. The organic mixture was then washed with brine, dried over anh. Na2SO4, and evaporated under vacuum. The residue was purified by flash column chromatography (n- hexane) on silica gel to provide the desired products 2.
85 % Chromat.	With isopropyl alcohol In tetrahydrofuran at 20℃; for 24h;
	With diisobutylaluminium hydride In hexane at 0 - 20℃; Inert atmosphere;
78 %Chromat.	With hydrogen In dichloromethane at 20℃; for 48h;
98 %Chromat.	With palladium on silica; hydrogen; dimethyl sulfoxide In hexane at 30℃; for 0.5h;
93 %Chromat.	With copper(II)-citrate; hexamethylenetetramine; hypophosphorous acid In water; N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere; Green chemistry; chemoselective reaction;
	With hydrogen In toluene at 139.84℃; Flow reactor;
	With Pd₀₀₀₅Pb₀₉₉₅; hydrogen In ethanol at 25℃;
96 %Chromat.	With formic acid; gold nanoparticles on rutile titania; triethylamine In acetone at 60℃; for 3h;
88 %Chromat.	With hydrogen In ethanol at 100℃; for 30h; chemoselective reaction;

Reference： [1]Mitsudome, Takato; Yamamoto, Masaaki; Maeno, Zen; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi [Journal of the American Chemical Society, 2015, vol. 137, # 42, p. 13452 - 13455]
[2]Durant, Alex; Delplancke, Jean Luc; Libert, Valery; Reisse, Jacques [European Journal of Organic Chemistry, 1999, # 11, p. 2845 - 2851]
[3]La Sorella, Giorgio; Sperni, Laura; Canton, Patrizia; Coletti, Lisa; Fabris, Fabrizio; Strukul, Giorgio; Scarso, Alessandro [Journal of Organic Chemistry, 2018, vol. 83, # 14, p. 7438 - 7446]
[4]Current Patent Assignee: INDIANA UNIVERSITY - WO2020/198464, 2020, A1 Location in patent: Page/Page column 7; 15
[5]Alonso, Francisco; Osante, Inaki; Yus, Miguel [Advanced Synthesis and Catalysis, 2006, vol. 348, # 3, p. 305 - 308]
[6]Furayama, Taniyuki; Yonehara, Mitsuhiro; Arimoto, Sho; Kobayashi, Minoru; Matsumoto, Yotaro; Uchiyama, Masanobu [Chemistry - A European Journal, 2008, vol. 14, # 33, p. 10348 - 10356]
[7]Location in patent: experimental part Polshettiwar, Vivek; Baruwati, Babita; Varma, Rajender S. [Green Chemistry, 2009, vol. 11, # 1, p. 127 - 131]
[8]Takahashi, Yusuke; Hashimoto, Norifumi; Hara, Takayoshi; Shimazu, Shogo; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi [Chemistry Letters, 2011, vol. 40, # 4, p. 405 - 407]
[9]Cao, Huanyang; Chen, Tieqiao; Zhou, Yongbo; Han, Daoqing; Yin, Shuang-Feng; Han, Li-Biao [Advanced Synthesis and Catalysis, 2014, vol. 356, # 4, p. 765 - 769]
[10]Vile, Gianvito; Wrabetz, Sabine; Floryan, Leonard; Schuster, Manfred Erwin; Girgsdies, Frank; Teschner, Detre; Perez-Ramirez, Javier [ChemCatChem, 2014, vol. 6, # 7, p. 1928 - 1934]
[11]Niu, Wenxin; Gao, Yongjun; Zhang, Weiqing; Yan, Ning; Lu, Xianmao [Angewandte Chemie - International Edition, 2015, vol. 54, # 28, p. 8271 - 8274][Angew. Chem., 2015, vol. 127, p. 8389 - 8392,4]
[12]Li, Shu-Shuang; Tao, Lei; Wang, Fu-Ze-Rong; Liu, Yong-Mei; Cao, Yong [Advanced Synthesis and Catalysis, 2016, vol. 358, # 9, p. 1410 - 1416]
[13]Fiorio, Jhonatan Luiz; Gonçalves, Renato Vitalino; Teixeira-Neto, Erico; Ortuño, Manuel A.; López, Núria; Rossi, Liane Marcia [ACS Catalysis, 2018, vol. 8, # 4, p. 3516 - 3524]

18
[ 764-93-2 ]
[ 15790-94-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With chloro-trimethyl-silane; acetic acid In tetrahydrofuran at 25℃; for 8h;

Reference： [1]Periasamy, Mariappan; Rameshkumar, Chellappan; Radhakrishnan, Ukkiramapandian; Brunet, Jean-Jacques [Journal of Organic Chemistry, 1998, vol. 63, # 15, p. 4930 - 4935]

19
[ 764-93-2 ]
[ 33775-94-9 ]
[ 370555-71-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 3h;
93%	With copper(l) iodide; triethylamine at 20℃; for 3h;

Reference： [1]Larock, Richard C; Yue, Dawei [Tetrahedron Letters, 2001, vol. 42, # 35, p. 6011 - 6013]
[2]Yue, Dawei; Larock, Richard C. [Journal of Organic Chemistry, 2002, vol. 67, # 6, p. 1905 - 1909]

20
[ 764-93-2 ]
[ 64248-56-2 ]
2-dec-1-ynyl-1,3-difluoro-benzene [ No CAS ]

Reference： [1]Synthesis,2004,p. 1281 - 1289

21
[ 764-93-2 ]
[ 13329-40-3 ]
1-octyl (4-acetophenone) acetylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 6h;
96%	With copper(l) iodide; diisopropylamine; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 16h;	1 Glyoxal synthesis step 1 is shown in FIG. 12. In a 100 mL Schlenk tube containing 46% Pd-C aerogel (110 mg, 0.47 mmol) were placed Cul (190 mg, 1 mmol), Ph3P (250 mg, 1 mmol), 4-iodoacetophenone (0.79 mmol), i-Pr2NH (0.17 mL, 1.2 mmol), deca-1-yne (8 mmol), and previously degassed dimethylformamide (DMF) (0.5 mL) under argon. This was magnetically stirred at 100° C. for a 16-h period. After cooling, the solution was removed and the catalyst was washed with DMF (3×3 mL) and recovered. The combined organic extracts were diluted in Et2O (100 mL), washed with brine (3×30 mL), dried (annh. MgSO4), and evaporated at reduced pressure. The residue (a yellow oil) was purified by preparative high pressure column chromatography (silica gel, n-hexane-EtOAc, 99.5:0.5) to give the product, 1-(4-(dec-1-ynyl)phenyl)ethanone as a yellow oil; yield: 96% 1H NMR (CDCl3): d=7.87 d,(2H), 7.53 (d, 2H), 2.55 (s, 3H), 2.03 (2H), 1.46 (2H), 1.31 (m, 10H), 0.86 (3H) 13C NMR (CDCl3): d=CH3,14.0; CH2 22.6; CH2 31.5,; CH2 29.3; CH2 28.7; CH2 28.4; CH2 28.7; CH2 18.7; C (alkyne) 100.1; C (alkyne) 78.5; CH3 29.3; C (carbonyl) 199.8; C 136.4; CH 128.4; CH 132.2; C 127.1; CH 132.2; CH 128.4
96%	With C₁₆H₂₀Cl₂N₂O₂Pd; potassium hydroxide In water; acetonitrile at 60℃; for 3h;	31. General procedure for Sonogashira coupling reaction General procedure: In a 10 mL round bottom flask, the palladium complex (0.010 mmol) was dissolved in acetonitrile (2 mL). Aryl halide (1.0 mmol), alkyne (1.2 mmol), KOH (2.00 mmol) and distilled water (2 mL) were added. The mixture was stirred at room temperature (or 60° C) for the required time. After reaction completion, the product was extracted with ethyl acetate (3x5 mL). The combined organic layers were dried with anhydrous sodium sulfate. The product was analyzed with GC and GC-MS. The product was purified using column chromatography with hexane-ethyl acetate as eluent. The characterization data were in entire agreement with the previously reported literature.32-39

92%	With potassium hydroxide; copper(l) iodide; triphenylphosphine In isopropyl alcohol at 80℃; for 5h;
80%	With aluminum oxide; potassium fluoride; triphenylphosphine for 0.15h; microwave irradiation;
93 %Chromat.	With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; silica gel for 0.333333h; Neat (no solvent); ball mill; chemoselective reaction;

Reference： [1]Wang, Lei; Yan, Jincan; Li, Pinhua; Wang, Min; Su, Caina [Journal of Chemical Research, 2005, # 2, p. 112 - 115]
[2]Current Patent Assignee: BIOLUME, INC. - US2009/81129, 2009, A1 Location in patent: Page/Page column 16; sheet 12
[3]Ibrahim, Mansur B.; Ali, Bassam El; Malik, Imran; Fettouhi, Mohammed [Tetrahedron Letters, 2016, vol. 57, # 5, p. 554 - 558]
[4]Wang, Lei; Li, Pinhua; Zhang, Yicheng [Chemical Communications, 2004, # 5, p. 514 - 515]
[5]Wang, Min; Li, Pinhua; Wang, Lei [Synthetic Communications, 2004, vol. 34, # 15, p. 2803 - 2812]
[6]Thorwirth, Rico; Stolle, Achim; Ondruschka, Bernd [Green Chemistry, 2010, vol. 12, # 6, p. 985 - 991]

22
[ 764-93-2 ]
[ 5703-26-4 ]
[ 503025-79-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With n-butyllithium In tetrahydrofuran at 20℃;

Reference： [1]Seiders II, John R.; Wang, Lijun; Floreancig, Paul E. [Journal of the American Chemical Society, 2003, vol. 125, # 9, p. 2406 - 2407]

23
[ 50-00-0 ]
[ 764-93-2 ]
[ 14489-75-9 ]
methyl-naphthalen-1-ylmethyl-undec-2-ynyl-amine [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 857 - 867

24
[ 2404-35-5 ]
[ 764-93-2 ]
dec-1-yn-1-ylcycloheptane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With copper(l) iodide; caesium carbonate In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 60℃; for 18h;

Reference： [1]Altenhoff, Gereon; Würtz, Sebastian; Glorius, Frank [Tetrahedron Letters, 2006, vol. 47, # 17, p. 2925 - 2928]

25
[ 764-93-2 ]
[ 633-70-5 ]
2,6-dibromo-9,10-bis-dec-1-ynyl-9,10-dihydro-anthracene-9,10-diol [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 785 - 788

26
[ 764-93-2 ]
[ 611-53-0 ]
5-decynyl-2'-deoxycytidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7012 - 7017

27
[ 764-93-2 ]
[ 3017-70-7 ]
2,3-dimethyltridec-2-en-4-yne [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 112 - 120

28
[ 764-93-2 ]
[ 154257-75-7 ]
3-dec-1-ynyl-2,4-difluorobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; dichloro bis(acetonitrile) palladium(II); caesium carbonate In water; acetonitrile at 100℃; for 12h;

Reference： [1]Anderson, Kevin W.; Buchwald, Stephen L. [Angewandte Chemie - International Edition, 2005, vol. 44, # 38, p. 6173 - 6177]

29
[ 764-93-2 ]
disodium decyl-1,1-bis-H-phosphinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium hypophosphite; triethyl borane; isobutyric Acid In 1,4-dioxane; methanol; hexane at 20℃; for 4h;
48%	With sodium hypophosphite In methanol at 20℃; for 2h;	1 Example 1; Preparation of Disodium 1,1-Bis-H-phosphinates in Methanol An alkyne (2 mmol) was added to a solution of NaH2PO2H2.O (5 mmol) in reagent grade methanol (10 mL). Triethylborane (1 M in hexane, 2 mmol) was then added in one portion to the stirred solution at room temperature in open container (i.e., with air). The reaction mixture rapidly became cloudy, and a white precipitate formed. After 2 hours, the mixture was filtered and the solid was washed with cold methanol or ethanol. NMR analysis of the solid at this stage generally showed at least 90% purity. If the solid was sufficiently pure (ca. 98%), it was then dried in vacuum for 24 h over P2O5. The disodium 1,1-bis-H-phosphinates are generally highly hygroscopic and obtained as white amorphous powders. The filtrate also contained unreacted NaH2PO2, and variable amounts of 1,2-bis-H-phosphinates. For certain substrates, small amounts of monoaddition products (alkenyl-H-phosphinates) may also be observed in the filtrate.
48%	With sodium hypophosphite In methanol; acetone at 20℃; for 2h;	2 Examplle 2; Preparation of Disodium 1,1-Bis-H-phosphinates in Methanol/Acetone The reaction was conducted exactly the same as in Example 1, except that methanol (10 mL) was replaced with a solution of methanol (8 mL) and acetone (2 mL). Isolated yields of the disodium 1,1-bis-H-phosphinate were improved without affecting purity.

Reference： [1]Gouault-Bironneau, Sonia; Deprele, Sylvine; Sutor, Amber; Montchamp, Jean-Luc [Organic Letters, 2005, vol. 7, # 26, p. 5909 - 5912]
[2]Current Patent Assignee: TEXAS CHRISTIAN UNIVERSITY - US2004/116673, 2004, A1 Location in patent: Page 4
[3]Current Patent Assignee: TEXAS CHRISTIAN UNIVERSITY - US2004/116673, 2004, A1 Location in patent: Page 4

30
[ 764-93-2 ]
[ 21742-00-7 ]
1-trifluoromethyl-2-undec-2-ynylbenzene [ No CAS ]

Reference： [1]Synlett,2006,p. 2941 - 2946

31
[ 764-93-2 ]
[ 21742-00-7 ]
1-trifluoromethyl-2-undeca-1,2-dienylbenzene [ No CAS ]

Reference： [1]Synlett,2006,p. 2941 - 2946

32
[ 123-29-5 ]
Al₂O₃ [ No CAS ]
[ 764-93-2 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 4142 - 4147

33
[ 764-93-2 ]
2-Bromo-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene [ No CAS ]
2-dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.2%	With copper(l) iodide; triethylamine at 130℃; for 16.0833h;	8 FIG. 17 is a reaction scheme for the synthesis of a nine-ring tetraalkylsubstituted thienothiophene according to Example 8; 2-Bromo-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5- b']dithiophene (2.16g, 4.6mmol) (106) was mixed with l-decyne(1.27g, 9.2 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol) and copper(I) iodide (0.087 g, 0.46 mmol) in triethylamine (50 mL). This mixture was bubbled with nitrogen for 5 minutes and then heated up to 130 0C under argon for 16 hours. The triethylamine was evaporated and hexane (150 mL) was added. This mixture was filtered to remove solid salts. The organic layer was washed with 1 M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel eluted with hexane to produce the target compound (2.3g, 90.2%). 1HNMR: Solvent CD2Cl2. δ 7.41 (d, IH), 7.33 (d, IH), 2.84 (t, 2H), 2.23 (t, 2H), 1.73-1.27 (m, 28H), 0.89 (m,6H).
90.2%	With copper(l) iodide; triethylamine at 130℃; for 16h;	8 2-dec-l-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5- b']dithiophene (107).; 2-Bromo-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5- b']dithiophene (2.16g, 4.6mmol) (106) was mixed with l-decyne(1.27g, 9.2mmolmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol) and copper(I) iodide (0.087 , g, 0.46 mmol) in triethylamine (50 mL). This mixture was bubbled with nitrogen for 5 minutes and then heated up to 130 0C under argon for 16 hours. The triethylamine was evaporated and hexane (150 mL) was added. This mixture was filtered to remove solid salts. The organic layer was washed with 1 M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel eluted with hexane to produce the target compound (2.3g, 90.2%). 1HNMR: Solvent CD2Cl2. δ 7.41 (d, IH), 7.33 (d, IH), 2.84 (t, 2H), 2.23 (t, 2H), 1.73-1.27 (m, 28H), 0.89 (m,6H).
90.2%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In hexane; triethylamine	8 2-dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene (107) 2-dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene (107) 2-Bromo-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene (2.16 g, 4.6 mmol) (106) is mixed with 1-decyne (1.27 g, 9.2 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol) and copper(I) iodide (0.087 g, 0.46 mmol) in triethylamine (50 mL). This mixture is bubbled with nitrogen for 5 minutes and then heated to 130° C. under argon for 16 hours. The triethylamine is evaporated and hexane (150 mL) is added. This mixture is filtered to remove solid salts. The organic layer is washed with 1M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgSO4. The solvent is removed in vacuo, and the residue is purified by chromatography on silica gel eluted with hexane to produce the target compound (2.3 g, 90.2% yield). 1HNMR (CD2Cl2): δ 7.41 (d, 1H), 7.33 (d, 1H), 2.84 (t, 2H), 2.23 (t, 2H), 1.73-1.27 (m, 28H), 0.89 (m, 6H).

90.2%

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine at 130℃; for 16h; Inert atmosphere;

8.B 2-dec-l-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5- b']dithiophene (107). 2-Bromo-3-decanyldithieno[2,3-d:2',3 '-d']thieno[3,2-b:4,5- b']dithiophene (2.16g, 4.6mmol) (106) is mixed with l -decyne(1.27g, 9.2 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol) and copper(I) iodide (0.087 g, 0.46 mmol) in triethylamine (50 mL). This mixture is bubbled with nitrogen for 5 minutes and then heated to 130 °C under argon for 16 hours. The triethylamine is evaporated and hexane (150 mL) is added. This mixture is filtered to remove solid salts. The organic layer is washed with 1 M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgS04. The solvent is removed in vacuo, and the residue is purified by chromatography on silica gel eluted with hexane to produce the target compound (2.3g, 90.2% yield). 1HNMR (CD2C12): δ 7.41 (d, 1H), 7.33 (d, 1H), 2.84 (t, 2H), 2.23 (t, 2H), 1.73-1.27 (m, 28H), 0.89 (m, 6H).

Reference： [1]Current Patent Assignee: CORNING INC - WO2008/106019, 2008, A2 Location in patent: Page/Page column 4; 38-39; Sheet 13/16
[2]Current Patent Assignee: CORNING INC - WO2006/31893, 2006, A2 Location in patent: Page/Page column 36-37
[3]Current Patent Assignee: CORNING INC - US2013/109821, 2013, A1 Location in patent: Page/Page column
[4]Current Patent Assignee: CORNING INC - WO2013/66732, 2013, A1 Location in patent: Paragraph 00161

34
[ 764-93-2 ]
[ 105931-73-5 ]
4-n-decyl-3-fluorobromobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; triethylamine	39.1 Example 39 (1) In 150 ml of triethylamine, within nitrogen atmosphere, 10.0 g of 1-bromo-3-fluoro-4-iodobenzene and 4.6 g of 1-decyne were reacted for 8 hours at the room temperature in the presence of 18 mg of cuprous iodide(I) and 72 mg of dichlorobistriphenylphosphine palladium(II). After reaction, the triethyl amine was removed and the product was extracted with hexane. The hexane phase was washed with 1N-hydrochloric acid and then with water, followed by removing the hexane. The resulting liquid was dissolved in 200 ml of ethanol and hydrogenated using platinum dioxide. After confirming that no absorption of hydrogen was observed, the catalyst was removed, followed by removing the ethanol to obtain 8.9 g of 4-n-decyl-3-fluorobromobenzene.
	With copper(I) iodide In ethanol; dichlorobis(triphenylphosphine)palladium[II]; triethylamine	49.1 Example 49 (1) In 150 ml of triethylamine, within nitrogen atmosphere, 10.0 g of 1-bromo-3-fluoro-4-iodobenzene and 4.6 g of 1-decyne were reacted for 8 hours at the room temperature in the presence of 72 mg of dichlorobistriphenylphosphine palladium(II) and 18 mg of cuprous iodide (I), followed by removing the triethylamine. The product was extracted with hexane. The hexane layer was washed with 1N-hydrochloric acid and then with water, and the hexane was removed. The product was dissolved in 200 ml of ethanol, and hydrogenated using 0.3 g of platinum dioxide. After confirming that no absorption of hydrogen was observed, the catalyst was removed by filtration, followed by removing the ethanol to obtain 8.8 g of 4-n-decyl-3-fluorobromobenzene.

Reference： [1]Current Patent Assignee: SANYO CHEMICAL INDUSTRIES LTD - EP518636, 1992, A1
[2]Current Patent Assignee: SANYO CHEMICAL INDUSTRIES LTD - EP518636, 1992, A1

35
[ 764-93-2 ]
[ 17955-46-3 ]
[ 489470-69-1 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2004,vol. 214,p. 33 - 44
[2]Chemical Communications,2002,p. 1884 - 1885
[3]Chemical Communications,2002,p. 1884 - 1885
[4]Journal of Molecular Catalysis A: Chemical,2004,vol. 214,p. 33 - 44
[5]Journal of Molecular Catalysis A: Chemical,2004,vol. 214,p. 33 - 44

36
[ 494804-05-6 ]
[ 764-93-2 ]
[ 201230-82-2 ]
[ 28407-51-4 ]
(CO)6Rh₂(C(O)C₁₀H₁₈) [ No CAS ]

Reference： [1]Organometallics,1999,vol. 18,p. 3457 - 3467

37
[ 764-93-2 ]
[ 622-79-7 ]
[ 478555-29-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(l) iodide; 1-decylimidazole at 25℃; for 2h; neat (no solvent);
98%	With bis(triphenylphosphine)copper(I) nitrate at 25℃; for 1h; Neat (no solvent);
98%	With C₃₉H₄₄ClCuN₂⁽¹⁺⁾ In neat (no solvent) at 25℃; for 0.75h; Schlenk technique; Inert atmosphere;

97%	With copper; triethylamine In benzene-d6 at 40℃; for 66h; Inert atmosphere; regioselective reaction;
96%	Stage #1: 1-decyne With TiO₂ supported copper hydroxide In toluene at 60℃; Inert atmosphere; Stage #2: benzyl azide In toluene at 60℃; for 0.166667h; Inert atmosphere; regioselective reaction;
95%	With [Cu(phen)(PPh₃)2]NO₃ at 40℃; for 0.333333h; Neat (no solvent); air;
91%	With 2-{4-[(dimethylamino)methyl]-1,2,3-triazol-1-yl}cyclohexan-1-ol; copper(II) sulfate; sodium L-ascorbate In ethanol; water at 30℃; for 24h;	3.1 Procedure of the substrate selectivity study General procedure: To examine the substrate selectivity of AMTC and compare its efficiency to that of TBTA and THPTA, we applied a synthetic protocol, using the CuSO4 - sodium ascorbate catalytic system, with 1 mol% of both reagents and 2:1 water : ethanol mixture as solvent. The syntheses were performed on a 100 mg scale (100 mg of each azide was reacted with 1.05 equivalent of the alkyne), the time was 24 hours and the temperature was kept constant at 30°C. Upon completion, ethanol was evaporated under reduced pressure, the residue was diluted with water and extracted with dichloromethane. The combined organic layers were washed with 5% hydrochloric acid (to remove the ligand) and twice with water, dried with MgSO4 and evaporated. The crude product obtained after evaporation of the organic solvent was analyzed with HPLC-MS.This protocol was carried out for 11 substrate sets, the structures are given in Table 1. For each set, five reactions were performed: with no ligand, with 1 mol% and 2 mol% of AMTC, and with 1 mol% of TBTA and THPTA. The reactions for each substrate set were performed in standardized, constant-temperature conditions to ensure comparability. The results are plotted in Figure 1, which shows the percentage yield increases over the ligand-free reaction.
90%	With triethylamine In tetrahydrofuran at 65℃; for 0.5h; Inert atmosphere; regioselective reaction;
88%	With (tetra-n-butylammonium)[γ-H2SiW10O36Cu2(μ-1,1-N3)2] In acetonitrile at 59.84℃; for 18h; Inert atmosphere;
87%	With [2,2]bipyridinyl; copper(II) ferrite; triethylamine In ethyl acetate at 20℃; for 72h; regiospecific reaction;
85%	With copper(II) 12-tungstophosphoric acid salt; triethylamine In 1,4-dioxane at 25℃; for 0.5h;
84%	With [(t-Bu)4N]4[γ-H2SiW10O36Cu2(μ-1,1-N3)2] In acetonitrile at 60℃; for 27h; regioselective reaction;
80%	With Amberlyst A-21*copper(I) iodide In dichloromethane at 20℃; for 12h; Automated synthesizer; Combinatorial reaction / High throughput screening (HTS); regioselective reaction;
80%	With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 24h;	4.2.2. Preparation of compounds 4,8-32 General procedure: A typical experimental procedure for the preparation of these compounds from the corresponding commercially available alkynes is described below. To a solution of alkyne (1.0 eq) with azide (1.2 eq) in tBuOH/H2O (1/1), were added CuSO4 (0.2 eq), AscNa (0.4 eq) at room temperature. The reaction mixture was stirred at rt for 24 h, then H2O was added and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated under reduced pressure. The desired product was purified by flash chromatography (EtOAc/petroleum ether).

Reference： [1]Asano, Keisuke; Matsubara, Seijiro [Organic Letters, 2010, vol. 12, # 21, p. 4988 - 4991]
[2]Wang, Dong; Li, Na; Zhao, Mingming; Shi, Weilin; Ma, Chaowei; Chen, Baohua [Green Chemistry, 2010, vol. 12, # 12, p. 2120 - 2123]
[3]Sau, Samaresh Chandra; Roy, Sudipta Raha; Sen, Tamal K.; Mullangi, Dinesh; Mandal, Swadhin K. [Advanced Synthesis and Catalysis, 2013, vol. 355, # 14-15, p. 2982 - 2991]
[4]Rance, Graham A.; Solomonsz, William A.; Khlobystov, Andrei N. [Chemical Communications, 2013, vol. 49, # 11, p. 1067 - 1069]
[5]Location in patent: experimental part Yamaguchi, Kazuya; Oishi, Takamichi; Katayama, Tatsuyori; Mizuno, Noritaka [Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10464 - 10472]
[6]Wang, Dong; Zhao, Mingming; Liu, Xiang; Chen, Yongxin; Li, Na; Chen, Baohua [Organic and Biomolecular Chemistry, 2012, vol. 10, # 2, p. 229 - 231]
[7]Szafrański, Przemysław W.; Kasza, Patryk; Cegła, Marek T. [Tetrahedron Letters, 2015, vol. 56, # 45, p. 6244 - 6247]
[8]Location in patent: experimental part Alonso, Francisco; Moglie, Yanina; Radivoy, Gabriel; Yus, Miguel [European Journal of Organic Chemistry, 2010, # 10, p. 1875 - 1884]
[9]Location in patent: experimental part Kamata, Keigo; Nakagawa, Yoshinao; Yamaguchi, Kazuya; Mizuno, Noritaka [Journal of the American Chemical Society, 2008, vol. 130, # 46, p. 15304 - 15310]
[10]Ishikawa, Shingo; Hudson, Reuben; Moores, Audrey; Li, Chao-Jun [Heterocycles, 2012, vol. 86, # 2, p. 1023 - 1030]
[11]Purnima; Sreenu; Bhasker; Nagaiah; Lingaiah; Reddy, B. V. Subba; Yadav [Chinese Journal of Chemistry, 2013, vol. 31, # 4, p. 534 - 538]
[12]Yamaguchi, Kazuya; Kotani, Miyuki; Karnata, Keigo; Mizuno, Noritaka [Chemistry Letters, 2008, vol. 37, # 12, p. 1258 - 1259]
[13]Location in patent: experimental part Jlalia, Ibtissem; Beauvineau, Claire; Beauviere, Sophie; Oenen, Esra; Aufort, Marie; Beauvineau, Aymeric; Khaba, Eihab; Herscovici, Jean; Meganem, Faouzi; Girard, Christian [Molecules, 2010, vol. 15, # 5, p. 3087 - 3120]
[14]Location in patent: experimental part Menendez, Christophe; Chollet, Aurélien; Rodriguez, Frédéric; Inard, Cyril; Pasca, Maria Rosalia; Lherbet, Christian; Baltas, Michel [European Journal of Medicinal Chemistry, 2012, vol. 52, p. 275 - 283]

38
[ 764-93-2 ]
[ 3029-32-1 ]
[ 927439-54-1 ]

Reference： [1]Journal of Materials Chemistry,2008,vol. 18,p. 1961 - 1969

39
[ 764-93-2 ]
[ 159087-46-4 ]
[ 1191100-61-4 ]
[ 1191100-47-6 ]

Reference： [1]Journal of Organometallic Chemistry,2009,vol. 694,p. 3349 - 3352

40
[ 7647-01-0 ]
[ 764-93-2 ]
[ 1291-32-3 ]
[ 998-40-3 ]
[ 159087-46-4 ]
[ 1191100-61-4 ]
[ 1191100-47-6 ]

Reference： [1]Journal of Organometallic Chemistry,2009,vol. 694,p. 3349 - 3352

41
[ 764-93-2 ]
[ 1207732-05-5 ]
[ 1207732-07-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran for 20h; Reflux; chemoselective reaction;
87%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 27h; Inert atmosphere;	Synthesis of 1,5-dichloro-2,6-di(decyne-1-yl)naphthaleneUsing 1,5-dichloro-2,6-bis(trifluoromethanesulfonyl)naphthalene synthesized as explained above, 1,5-dichloro-2,6-di(decyne-1-yl)naphthalene was synthesized through the following procedures.Under a nitrogen atmosphere, 1,5-dichloro-2,6-bis(trifluoromethanesulfonyl)naphthalene (493 mg, 1.0 mmol) and triethylamine (0.42 mg, 3.0 mmol) were dissolved in DMF (10 ml). The solution was degassed for 30 minutes.Pd(PPh3)2Cl2 (70 mg, 0.1 mmol, 10 mol %) and CuI (38 mg, 0.1 mmol, 20 mol %) as catalysts, and 1-decyne (0.54 ml, 3.0 mmol) as a reagent were added to the solution. It was stirred for 27 hours at a room temperature in order to let it reacted, and then pure water (1 ml) and 1N hydrochloric acid (1 ml) were added to terminate the reaction.The reaction solution was subjected to extraction using methylene chloride (10 ml). This extraction was performed three times through the same procedures. Thereafter, an organic phase was rinsed by a saturated saline solution (10 ml). This rinsing was performed three times through the same procedures.Water contained in the organic phase was eliminated using anhydrous magnesium sulfate, and then the solvent was distilled under a pressure reduction condition, thereby obtaining a rough product.The rough product was separated and purified through a silica-gel column chromatography (Rf=0.3) having hexane as a moving phase, thereby obtaining a white solid of 1,5-dichloro-2,6-di(decyne-1-yl)naphthalene (408 mg, yield: 87%).The reaction formula of the above-explained reaction is as follow. Various spectrum data of the obtained 1,5-dichloro-2,6-di(decyne-1-yl)naphthalene are indicated below.1H-NMR (270 MHz, CDCl3) δ0.89 (t, 6H, J=7.0, 1.23-1.71 (m, 24H, CH2), 2.53 (t, 4H, J=7.0 Hz, CH2), 7.56 (d, 2H, J=8.5 Hz, ArH), 8.13 (d, 2H, J=8.5 Hz, ArH); EIMS (70 eV) m/z=468 (M+)

Reference： [1]Location in patent: experimental part Shinamura, Shoji; Miyazaki, Eigo; Takimiya, Kazuo [Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1228 - 1234]
[2]Current Patent Assignee: HIROSHIMA UNIVERSITY - US2011/224445, 2011, A1 Location in patent: Page/Page column 17-18

42
[ 764-93-2 ]
[ 2296-23-3 ]
[ 1218818-18-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine;copper(l) iodide; palladium diacetate; CyJohnPhos; In acetonitrile; at 60℃; for 18h;	To a stirred solution of <strong>[2296-23-3]4-hydroxy-3-iodobenzonitrile</strong> (LXXX) (4.55 g, 18.57 mmol), 1-decyne (LXXXI) (2.57 g, 18.57 mmol), (2-biphenyl)dicyclohexylphosphine (0.325 g, 0.928 mmol), (or using same moles of triphenylphosphine) and triethylamine (5.64 g, 55.71 mmol) in acetonitrile (100 mL) was added palladium(II) acetate (0.208 g, 0.928 mmol) and copper(I) iodide (0.354 g, 1.86 mmol). The reaction mixture was heated to 60 C. After 18 hours, the reaction mixture was allowed to cool to room temperature and was concentrated. The residue was dissolved in ethyl acetate and washed with IN hydrochloric acid, 6N ammonium hydroxide, and brine. The organic phase was dried (magnesium sulfate), filtered, and concentrated to provide 5.29 g of a brown oil. Flash chromatography using an Isco Combiflash unit (90 g SiO2 column, 10-20% ethyl acetate/hexanes) afforded 2.62 g (55% yield) of 2- octylbenzofuran-5-carbonitrile (LXXXII) as a yellow solid: 1H NMR (CDCl3) delta 7.80 (s, 1H), 7.52-7.43 (m, 2H), 6.43 (s, 1H), 2.78 (t, J= 7.6 Hz, 2H), 1.80-1.69 (m, 2H), 1.44-1.20 (m, 10H), 0.88 (t, 7= 6.9 Hz, 3H) ppm.

Reference： [1]Patent: WO2010/33701,2010,A2 .Location in patent: Page/Page column 155-156

43
[ 764-93-2 ]
[ 33348-34-4 ]
[ 1218818-20-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With diisopropylamine In tetrahydrofuran at 20℃; for 18h;	108.1 To a stirred solution of 4-amino-3-iodobenzonitrile (LXXXIV) (7.20 g, 29.50 mmol), 1-decyne (LXXXI) (5.30 g, 38.36 mmol), and diisopropylamine (8.96 g, 88.51 mmol) in tetrahydrofuran (100 mL) was added copper(I) iodide (0.302 g, 1.59 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.557 g, 0.790 mmol). The reaction mixture was allowed to stir at room temperature. After 18 hours, the reaction mixture was diluted with ethyl acetate and washed with IN hydrochloric acid , 6N ammonium hydroxide, and brine. The organic phase was dried (magnesium sulfate), filtered, and concentrated to provide 9.62 g of a brown oil. Flash chromatography using an Isco Combiflash unit (330 g SiO2 column, 15-30% ethyl acetate/hexanes) afforded 6.51 g (87%) of 4-amino-3-(dec-1-ynyl)benzonitrile as a light brown solid: 1H NMR (CDCl3) δ 7.50 (d, J= 1.9 Hz, 1H), 7.31 (dd, J= 1.9, 8.5 Hz, 1H), 6.65 (d, J= 8.5 Hz, 1H), 4.65 (s, 2H), 2.46 (t, J= 7.1 Hz, 2H), 1.67-1.57 (m, 2H), 1.50-1.39 (m, 2H), 1.37-1.22 (m, 8H), 0.89 (t, J= 6.9 Hz, 3H) ppm.

Reference： [1]Current Patent Assignee: SANOFI - WO2010/33701, 2010, A2 Location in patent: Page/Page column 157

44
[ 764-93-2 ]
[ 80793-25-5 ]
[ 1233676-34-0 ]
C₁₈H₂₇Br [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3176 - 3178

45
[ 764-93-2 ]
[ 615-37-2 ]
1-methyl-2-dec-1-ynyl-benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(I) oxide; caesium carbonate; In N,N-dimethyl-formamide; at 135℃; for 48h;Inert atmosphere;	General procedure: A sealable vial equipped with a magnetic stir bar was charged with Cs2CO3 (652 mg, 2.0 mmol), Cu2O (14.0 mg, 0.10 mmol) under a nitrogen atmosphere. The aperture of the vial was then covered with a rubber septum. Under a nitrogen atmosphere, alkyl alkyne (4, 1.5 mmol), aryl iodide (2, 1.0 mmol) and DMF (0.5mL) were added by syringe. The septum was then replaced by a screw cap containing a Teflon-coated septum, and the reaction vessel was placed at 135 C. After stirring at this temperature for 48 h, the heterogeneous mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). The resulting solution was filtered through a pad of silica gel then washed with ethyl acetate (20 mL) and concentrated to give the crude material which was then purified by column chromatography on silica gel toyield alkyne 5.

Reference： [1]European Journal of Organic Chemistry,2010,p. 4368 - 4371
[2]Synlett,2014,vol. 25,p. 443 - 447
[3]Synthesis,2012,vol. 44,p. 1507 - 1510

46
[ 764-93-2 ]
[ 100-39-0 ]
[ 478555-29-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium azide; copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 24h;
88%	With sodium azide In water at 25℃; for 5h; Green chemistry;	General procedure for the synthesis of triazoles General procedure: To a mixture of alkyl bromide (1 mmol), alkyne (1 mmol) and NaN3 (1.1 mmol) in H2O(3 mL) was added Fe3O4(at)SiO2-dendrimer-Cu(II) catalyst (0.01 g, 0.5 mol%) and the resulting mixture was stirred at room temperature for the given time period as mentioned in Table 2. After completion of the reaction, as monitored by TLC, the catalyst was magnetically separated and washed several times with ethanol and dried under vacuum. Then, water (20 mL) was added to the resulting reaction mixture followed by extraction with ethyl acetate (2 x 10 mL). The organic layer was dried with Na2SO4 and concentrated under vacuum to give the corresponding triazole. For further purification, the product was recrystallized from ethyl acetate/n-hexane.
87%	With sodium azide; copper(I) oxide In water at 100℃; for 0.5h;	2.3 General procedure for the one-pot synthesisof mono-1,2,3-triazoles General procedure: In a 50 mL roundbottomed flask benzyl bromide (1mmol, 1 equiv.), NaN3 (1.2 mmol, 1.2 equv.), a terminalalkyne (1.2 mmol, 1.2 equv.) and 5 mg Cu2ONPs wereplaced in water (10 mL). The mixture was magneticallystirred under reflux (100 °C) for 30 min. The progress ofthe reaction was monitored by TLC or by visualinspection of the formation of solid products. Aftercompletion of the reaction, the mixture was cooled toroom temperature and the solution was decanted. To theleftover residue, ethyl acetate (2 x 9 10 mL) was added,organic material dissolved in it and catalyst was recoveredby centrifugation. The solution was evaporated todryness using a rotary evaporator, and the crude productthus obtained was purified by short column chromatographywith silica gel. The identities of the isolatedcompounds were confirmed by either matching thespectroscopic data of the compounds already reported inthe literature and unreported compounds were furtherconfirmed by recording HRMS.

83%	With sodium azide; sodium L-ascorbate In water at 70℃; for 5h;	General procedure for the one-pot CuAAC reaction General procedure: A mixture of benzyl halides (1.0 mmol), terminal alkynes (1.0 mmol), NaN3(1.2 mmol), sodium ascorbate (10 mol%), a catalytic amount of CuIICMC/CaCO3catalyst (2.0 mol% of Cu), and 3.0 mL H2O were charged into a flask. The reactionmixture was heated at 70 °C for a specific time with constant stirring. The progresswas tracked by TLC. After completion of the reaction, ethyl acetate was added tothe flask and the catalyst was filtered by suction, washed with enough ethyl acetate,and dried in vacuum for the next run. The resulting mixture was washed with brineand dried over anhydrous Na2SO4 and evaporated in vacuum using a rotary evapora-tor to obtain the crude product. The desired pure products were further purified byrecrystallization with ethanol/H2O mixed solvent.
78%	With sodium azide; copper(II) 12-tungstophosphoric acid salt; triethylamine In N,N-dimethyl-formamide at 90℃; for 10h;
74%	With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate; fipronilβ-cyclodextrin In tetrahydrofuran; methanol; water	Synthesis General procedure: Benzyl halide (1 eq.) and the appropriate alkyne (1.2 eq.) weremixed in a round-bottomed flask. Tetrahydrofuran (THF;5ml), MeOH (5ml) and distilled water (5 ml) were addedconsecutively. To this stirring solution were added β-CD(60mg, 0.02 eq.), NaAsc (240 mg, 0.2 eq.), NaN3 (230 mg,1.2 eq.) and CuSO4·5H2O (120mg, 0.2 eq.) sequentially. Thesolution was stirred until a white precipitate formed. If thesolution turned black, an additional portion of sodiumascorbate (50 mg) was added until the solution turned clearyellow. The reaction was followed by TLC. After completion,DCM (50 ml) and saturated sodium bicarbonate (NaHCO3;50ml) were added. The organic layer was separated and theaqueous phase was extracted with DCM (3 × 50 ml). Thecombined organic phase was washed with water (3 × 50 ml),dried over MgSO4, filtered off and rotated to dryness invacuo, resulting in a hot oil residue. Hexane (50 ml) wasadded to the hot oil and the supernatant was decanted into aflat bottom flask. This was repeated two times, the combinedextracts cooled at room temperature and then allowed tocrystallize at 0 to -4 °C to afford the target compound.
73%	With sodium azide In water at 90℃; for 12h; Green chemistry; regioselective reaction;

Reference： [1]Location in patent: experimental part Fletcher, James T.; Keeney, Matthew E.; Walz, Sara E. [Synthesis, 2010, # 19, p. 3339 - 3345]
[2]Sardarian, Ali Reza; Mohammadi, Fattah; Esmaeilpour, Mohsen [Research on Chemical Intermediates, 2019, vol. 45, # 3, p. 1437 - 1456]
[3]Chand, Dillip Kumar; Rai, Randhir [Journal of Chemical Sciences, 2020, vol. 132, # 1]
[4]Zhang, Mingjuan; Xu, Jinxi; Zhang, Tianzhu; Li, Yiqun [Research on Chemical Intermediates, 2021, vol. 47, # 9, p. 3883 - 3898]
[5]Purnima; Sreenu; Bhasker; Nagaiah; Lingaiah; Reddy, B. V. Subba; Yadav [Chinese Journal of Chemistry, 2013, vol. 31, # 4, p. 534 - 538]
[6]Smit, Frans J.; Seldon, Ronnett; Aucamp, Janine; Jordaan, Audrey; Warner, Digby F.; N’Da, David D. [Medicinal Chemistry Research, 2019, vol. 28, # 12, p. 2279 - 2293]
[7]Sharma, Priti; Rathod, Jayant; Singh; Kumar, Pradeep; Sasson, Yoel [Catalysis science and technology, 2018, vol. 8, # 13, p. 3246 - 3259]

47
[ 764-93-2 ]
[ 592-35-8 ]
[ 100-52-7 ]
C₂₂H₃₃NO₂ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2437 - 2440

48
[ 764-93-2 ]
[ 89424-83-9 ]
C₁₉H₂₈O₂ [ No CAS ]
C₁₉H₂₈O₂ [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 211 - 215

49
[ 764-93-2 ]
[ 31608-22-7 ]
[ 113714-67-3 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 787 - 788

50
[ 764-93-2 ]
[ 201230-82-2 ]
[ 31599-61-8 ]
[ 1273326-82-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: carbon monoxide; 3,4-dimethyliodobenzene With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.166667h; Stage #2: 1-decyne at 20℃; for 14h; Stage #3: With sodium azide; dimethyl sulfoxide at 45℃; for 36h;	14 Typical procedure for the preparation of 4,5-disubstituted-1,2,3-(NH)-triazoles (synthesis of 3a): 14 Typical procedure for the preparation of 4,5-disubstituted-1,2,3-(NH)-triazoles (synthesis of 3a): A round-bottom sidearm flask (10 mL) containing PdCl2(PPh3)2 (0.015 mmol) was subjected to the Schlenk-line procedures of evacuation and purging of CO for three cycles. Iodobenzene and 4 equiv Et3N (1.2 mmol) were successively added, and the mixture was stirred at room temperature for 10 min, then 1-hexyne (0.45 mmol) was added, continuously stirred at room temperature for 14 h. Then NaN3 (35.1 mg, 0.54 mmol) and 1 mL DMSO were added to the mixture and the reaction continued at 45 °C for 36 h. Following, to the reaction mixture was added water (2 mL), 20% HCl solution (1 mL) and extracted with ether (3 * 10 mL). The combined organic phases were washed with brine (2 * 5 mL), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was subjected to flash column chromatography with hexanes/EtOAc (5/1) as eluent to obtain the desired 3a (56.33 mg, 82% yield). All products gave satisfactory spectroscopic and analytical data.

Reference： [1]Location in patent: experimental part Li, Na; Wang, Dong; Li, Jihui; Shi, Weilin; Li, Chao; Chen, Baohua [Tetrahedron Letters, 2011, vol. 52, # 9, p. 980 - 982]

51
[ 764-93-2 ]
[ 201230-82-2 ]
[ 699-08-1 ]
[ 1273326-90-1 ]

Yield	Reaction Conditions	Operation in experiment
86%		14 Typical procedure for the preparation of 4,5-disubstituted-1,2,3-(NH)-triazoles (synthesis of 3a): A round-bottom sidearm flask (10 mL) containing PdCl2(PPh3)2 (0.015 mmol) was subjected to the Schlenk-line procedures of evacuation and purging of CO for three cycles. Iodobenzene and 4 equiv Et3N (1.2 mmol) were successively added, and the mixture was stirred at room temperature for 10 min, then 1-hexyne (0.45 mmol) was added, continuously stirred at room temperature for 14 h. Then NaN3 (35.1 mg, 0.54 mmol) and 1 mL DMSO were added to the mixture and the reaction continued at 45 C for 36 h. Following, to the reaction mixture was added water (2 mL), 20% HCl solution (1 mL) and extracted with ether (3 * 10 mL). The combined organic phases were washed with brine (2 * 5 mL), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was subjected to flash column chromatography with hexanes/EtOAc (5/1) as eluent to obtain the desired 3a (56.33 mg, 82% yield). All products gave satisfactory spectroscopic and analytical data.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 980 - 982

52
[ 764-93-2 ]
[ 115262-00-5 ]
[ 138101-02-7 ]

Yield	Reaction Conditions	Operation in experiment
84 %Spectr.	With tetrabutyl-ammonium chloride In toluene at 110℃; for 4h;

Reference： [1]Wang, Fei; Zhang, Wei; Zhu, Jieming; Li, Huaifeng; Huang, Kuo-Wei; Hu, Jinbo [Chemical Communications, 2011, vol. 47, # 8, p. 2411 - 2413]

53
[ 764-93-2 ]
[ 1864-94-4 ]
[ 1279110-78-9 ]
phenyl 2-undecenoate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 475 - 482

54
[ 764-93-2 ]
[ 1280178-74-6 ]
[ 1227744-15-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In N,N-dimethyl-formamide at 20℃; for 11h; Inert atmosphere; chemoselective reaction;
87%	With diisopropylamine In N,N-dimethyl-formamide at 20℃; for 27h; Inert atmosphere;	Synthesis of 2,6-dibromo-3,7-di(decyne-1-yl)naphthalene Synthesis of 2,6-dibromo-3,7-di(decyne-1-yl)naphthaleneUsing 2,6-dibromo-3,7-bis(trifluoromethanesulfonyl)naphthalene synthesized through the above-explained method, 2,6-dibromo-3,7-di(decyne-1-yl)naphthalene was synthesized through the following procedures.Under a nitrogen atmosphere, 2,6-dibromo-3,7-bis(trifluoromethanesulfonyl)naphthalene (493 mg, 1.0 mmol) was dissolved in DMF (7 ml) and diisopropylamine (0.42 ml. 3.0 mmol). The solution was degassed for 30 minutes.Pd(PPh3)2Cl2 (70 mg, 0.1 mmol, 10 mol %) and CuI (38 mg, 0.1 mmol, 20 mol %) as catalysts, and 1-decyne (0.54 ml, 3.0 mmol) as a reagent were added to the solution, and the solution was stirred for 27 hours at a room temperature in order to let it reacted. Thereafter, pure water (1 ml) and 1N hydrochloric acid (1 ml) were added, and then reaction was terminated.The reaction solution was subjected to extraction using methylene chloride (10 ml). This extraction was performed three times through the same procedures. Thereafter, an organic phase was rinsed by a saturated saline solution (10 ml). This rinsing was performed three times through the same procedures.Water contained in the organic phase was eliminated using anhydrous magnesium sulfate, and then the solvent was distilled under a pressure reduction condition, thereby obtaining a rough product.The rough product was separated and purified through a silica-gel column chromatography (Rf=0.3) having hexane as a moving phase, thereby obtaining a white solid of 2,6-dibromo-3,7-di(decyne-1-yl)naphthalene (488 mg, yield: 87%).The reaction formula of the above-explained reaction is as follow. Various spectrum data of the obtained 2,6-dibromo-3,7-di(decyne-1-yl)naphthalene are indicated below.1H-NMR (270 MHz, CDCl3) δ0.89 (t, 6H, J=7.02 Hz, CH2), 1.27-1.37 (m, 2OH, CH2), 1.61-1.72 (m, 4H, CH2), 2.51 (t, 4H, J=6.62 Hz, CH2), 7.79 (s, 2H, ArH), 7.95 (s, 2H, ArH); EIMS (70 eV) m/z=558 (M+)

Reference： [1]Location in patent: experimental part Shinamura, Shoji; Osaka, Itaru; Miyazaki, Eigo; Nakao, Akiko; Yamagishi, Masakazu; Takeya, Jun; Takimiya, Kazuo [Journal of the American Chemical Society, 2011, vol. 133, # 13, p. 5024 - 5035]
[2]Current Patent Assignee: HIROSHIMA UNIVERSITY - US2011/224445, 2011, A1 Location in patent: Page/Page column 11

55
[ 764-93-2 ]
[ 930091-76-2 ]
[ 1227744-28-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In N,N-dimethyl-formamide at 20℃; for 11h; Inert atmosphere; chemoselective reaction;
80%	With diisopropylamine In N,N-dimethyl-formamide at 20℃; for 11h; Inert atmosphere;	Synthesis of 3,6-dibromo-2,7-di(decyne-1-yl)naphthalene Synthesis of 3,6-dibromo-2,7-di(decyne-1-yl)naphthaleneUsing 3,6-dibromo-2,7-bis(trifluoromethanesulfonyl)naphthalene synthesized as explained above, 3,6-dibromo-2,7-di(decyne-1-yl)naphthalene was synthesized through the following procedures.Under a nitrogen atmosphere, 3,6-dibromo-2,7-bis(trifluoromethanesulfonyl)naphthalene (582 mg, 1.0 mmol) was dissolved in DMF (7 ml) and diisopropylamine (7 ml). The solution was degassed for 30 minutes.Pd(PPh3)2Cl2 (70 mg, 0.05 mmol, 10 mol %) and CuI (38 mg, 0.1 mmol, 20 mol %) as catalysts, and 1-decyne (0.36 ml, 2.0 mmol) as a reagent were added to the solution. The solution was stirred for 11 hours at a room temperature in order to let it reacted, and then pure water (1 ml) and 1N hydrochloric acid (1 ml) were added in order to terminate the reaction.The reaction solution was subjected to extraction using methylene chloride (5 ml). This extraction was performed three times through the same procedures. Thereafter, an organic phase was rinsed by a saturated saline solution (5 ml). This rinsing was performed three times through the same procedures.Water contained in the organic phase was eliminated using anhydrous magnesium sulfate, and then the solvent was distilled under a pressure reduction condition, thereby obtaining a rough product.The rough product was separated and purified through a silica-gel column chromatography (Rf=0.3) having hexane as a moving phase, thereby obtaining a white solid of 3,6-dibromo-2,7-di(decyne-1-yl)naphthalene (444 mg, yield: 80%).The reaction formula of the above-explained reaction is as follow. Various spectrum data of the obtained 3,6-dibromo-2,7-di(decyne-1-yl)naphthalene are indicated below.1H-NMR (270 MHz, CDCl3) δ0.89 (t, 6H, J=6.8 Hz, CH2), 1.27-1.72 (m, 24H, CH2), 2.50 (t, 4H, J=6.9 Hz, CH2), 7.81 (s, 2H, ArH), 7.93 (s, 2H, ArH), EIMS (70 eV) m/z=558 (M+)

Reference： [1]Location in patent: experimental part Shinamura, Shoji; Osaka, Itaru; Miyazaki, Eigo; Nakao, Akiko; Yamagishi, Masakazu; Takeya, Jun; Takimiya, Kazuo [Journal of the American Chemical Society, 2011, vol. 133, # 13, p. 5024 - 5035]
[2]Current Patent Assignee: HIROSHIMA UNIVERSITY - US2011/224445, 2011, A1 Location in patent: Page/Page column 13-14

56
[ 764-93-2 ]
2,6-dibromonaphthalene-1,5-diyl bis(trifluoromethanesulfonate) [ No CAS ]
[ 1227744-57-1 ]

Yield	Reaction Conditions	Operation in experiment
61%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In N,N-dimethyl-formamide at 20℃; for 11h; Inert atmosphere; chemoselective reaction;
61%	With diisopropylamine In N,N-dimethyl-formamide at 20℃; for 11h; Inert atmosphere;	Synthesis of 2,6-dibromo-1,5-di(decyne-1-yl)naphthaleneUsing 2,6-dibromo-1,5-bis(trifluoromethanesulfonyl)naphthalene synthesized as explained above, 2,6-dibromo-1,5-di(decyne-1-yl)naphthalene was synthesized through the following procedures.Under a nitrogen atmosphere, 2,6-dibromo-1,5-bis(trifluoromethanesulfonyl)naphthalene (582 mg, 1.0 mmol) was dissolved in DMF (7 ml) and diisopropylamine (7 ml). The solution was degassed for 30 minutes.Pd(PPh3)2Cl2 (70 mg, 0.05 mmol, 10 mol %) and CuI (38 mg, 0.1 mmol, 20 mol %) as catalysts, and 1-decyne (0.36 ml, 2.0 mmol) as a reagent were added to the solution. It was stirred for 11 hours at a room temperature in order to let it reacted, and then pure water (1 ml) and 1N hydrochloric acid (1 ml) were added to terminate the reaction.The reaction solution was subjected to extraction using methylene chloride (5 ml). This extraction was performed three times through the same procedures. Thereafter, an organic phase was rinsed by a saturated saline solution (5 ml). This rinsing was performed three times through the same procedures.Water contained in the organic phase was eliminated using anhydrous magnesium sulfate, and then the solvent was distilled under a pressure reduction condition, thereby obtaining a rough product.The rough product was separated and purified through a silica-gel column chromatography (Rf=0.2) having hexane as a moving phase, thereby obtaining a white solid of 2,6-dibromo-1,5-di(decyne-1-yl)naphthalene (340 mg, yield: 61%).The reaction formula of the above-explained reaction is as follow. Various spectrum data of the obtained 2,6-dibromo-1,5-di(decyne-1-yl)naphthalene are indicated below.1H-NMR (270 MHz, CDCl3) δ0.89 (t, 6H, J=7.0, 1.26-1.70 (m, 2411, CH2), 2.62 (t, 4H, J=7.3 Hz, CH2), 7.68 (d, 2H, J=9.4 Hz, ArH), 8.10 (d, 2H, J=9.4 Hz, ArH); EIMS (70 eV) m/z=558 (M+)
57%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Schlenk technique;

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Location in patent: experimental part Shinamura, Shoji; Osaka, Itaru; Miyazaki, Eigo; Nakao, Akiko; Yamagishi, Masakazu; Takeya, Jun; Takimiya, Kazuo [Journal of the American Chemical Society, 2011, vol. 133, # 13, p. 5024 - 5035]
[2]Current Patent Assignee: HIROSHIMA UNIVERSITY - US2011/224445, 2011, A1 Location in patent: Page/Page column 22
[3]Lu, Yifan; Qiao, Yanjun; Xue, Haodong; Zhou, Gang [Organic Letters, 2018, vol. 20, # 21, p. 6632 - 6635]
[4]Qiao, Yanjun; Yang, Longfei; Zhu, Jiangyu; Yan, Chuan; Chang, Dongdong; Zhang, Ning; Zhou, Gang; Zhao, Yan; Lu, Xuefeng; Liu, Yunqi [Journal of the American Chemical Society, 2021, vol. 143, # 29, p. 11088 - 11101]

57
[ 764-93-2 ]
[ 2177-70-0 ]
[ 1332500-76-1 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 14460 - 14466

58
N,N-bis(2-decyl-1-tetradecyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide [ No CAS ]
[ 764-93-2 ]
[ 909019-80-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: N,N-bis(2-decyl-1-tetradecyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide; 1-decyne With copper(l) iodide; triethylamine In toluene at 65℃; for 24h; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 100 - 110℃; for 40h;	1 ZA-VI-77 (2.2 g, 1.8 mmol) was dissolved in 50 ml toluene and 10 ml triethylamine, degassed with nitrogen for 10 min. Tetrakis(triphenylphosphine) palladium(0) (0.28 g, 0.24 mmol), copper(I) iodide (0.034 g, 0.18 mmol) and 1-decyne (1.3 ml, 7.20 mmol) were added successively. The reaction was heated at 65° C. under nitrogen for 1 day. 0.5 ml DBU was added and the reaction temperature was raised to 100° C. and stirred for 16 h. Then 0.5 ml more DBU was added and the reaction temperature was raised to 110° C. and the reaction was further stirred at this temperature for 1 day. The reaction mixture was cooled to room temperature and poured into 2 N HCl solution, extracted with dichloromethane. The solvent was removed and the residue purified by chromatography eluting with 1:3 chloroform/hexane. 1.9 g (86%) yellow solid was obtained. 1H NMR (500 MHz, CDCl3): δ(ppm): 9.32 (s, 2H), 9.10 (s, 2H), 8.25 (s, 2H), 4.42 (d, J=7.0 Hz, 4H), 3.52 (t, J=7.0 Hz, 4H), 2.15 (m, 2H), 2.00 (m, 4H), 1.63 (m, 4H), 1.55-1.0 (m, 104H), 0.91 (t, J=7.0 Hz, 6H), 0.80 (m, 12H). 13C NMR (125 MHz, CDCl3): δ(ppm): 164.9, 164.7, 141.1, 129.4, 128.7, 128.1, 127.5, 125.5, 122.1, 121.5, 121.0, 120.8, 120.7, 119.5, 45.5, 37.5, 34.0, 32.4, 32.3, 31.3, 30.64, 30.62, 30.4, 30.1, 30.07, 30.01, 29.9, 29.74, 29.70, 27.1, 23.2, 23.0, 14.6, 14.5. (11 aliphatic carbons not observed presumably due to overlapping resonances). MS (MALDI), m/z calc. for C92H139N2O4 (M+H), 1336.0808; found 1337.0807. Elemental analysis: calculated for C92H138N2O4, C, 82.70; H, 10.41; N, 2.10; found C, 82.82; H, 10.55; N, 2.21.

Reference： [1]Current Patent Assignee: GEORGIA INSTITUTE OF TECHNOLOGY - US8039625, 2011, B2 Location in patent: Page/Page column 29

59
[ 764-93-2 ]
[ 909019-74-5 ]
[ 909019-82-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; triethylamine In toluene at 65℃; for 22h; Inert atmosphere;	1 1,7-Bisbromo-N,N'-(3,4,5-tridodecylbenzyl)-3,4,9,10-tetracarboxylic diimide (1.02 g, 0.56 mmol) was suspended in 35 ml toluene and 3.5 ml triethylamine, degassed with nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium(0) (0.064 g, 0.055 mmol), copper(I) iodide (0.012 g, 0.063 mmol) and 1-decyne (0.4 ml, 2.20 mmol) were added successively. The reaction was heated at 65° C. under nitrogen for 22 h and poured into 2 N HCl solution. The solvent was removed and the residue purified by chromatography eluting with 2:1 chloroform/hexane, 0.94 g (87%) red solid was obtained. 1H NMR (500 MHz, CDCl3): δ(ppm): 10.05 (d, J=8.5 Hz, 2H), 8.72 (s, 2H), 8.59 (d, J=8.5 Hz, 2H), 6.79 (s, 4H), 5.27 (s, 4H), 3.95 (t, J=6.5 Hz, 8H), 3.87 (t, J=6.5 Hz, 4H), 2.62 (t, J=7.0 Hz, 4H), 1.8-1.6 (m, 16H), 1.53 (m, 4H), 1.5-1.1 (m, 124H), 0.85 (m, 24H). 13C NMR (125 MHz, CDCl3): δ(ppm): 163.3, 163.1, 153.0, 138.2, 137.8, 134.3, 133.9, 132.0, 130.4, 127.5, 127.2, 127.0, 122.8, 121.8, 121.0, 108.1, 101.5, 82.2, 73.4, 69.1, 43.9, 31.9, 31.8, 30.3, 29.73, 29.70, 29.65, 29.61, 29.46, 29.44, 29.36, 29.23, 29.21, 29.13, 28.3, 26.1, 22.7, 22.6, 20.3, 14.1. (11 aliphatic carbons not observed presumably due to overlapping resonances). MS (MALDI), m/z, calc. for C130H198N2O10 1947.5038; found 1947.5046. Elemental analysis: calculated for C130H198N2O10, C, 80.11; H, 10.24; N, 1.44; found C, 80.25; H, 10.26; N, 1.46.

Reference： [1]Current Patent Assignee: GEORGIA INSTITUTE OF TECHNOLOGY - US8039625, 2011, B2 Location in patent: Page/Page column 30

60
[ 764-93-2 ]
[ 633-70-5 ]
[ 880496-19-5 ]

Reference： [1]Journal of Nanoscience and Nanotechnology,2011,vol. 11,p. 4648 - 4657

61
[ 764-93-2 ]
[ 111-83-1 ]
[ 35365-59-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 1-decyne With n-butyllithium In tetrahydrofuran; hexane at -78 - -60℃; for 0.5h; Stage #2: 1-bromo-octane With sodium iodide In tetrahydrofuran; hexane for 18h; Reflux;	6(c) 6(c) Synthesis of 9-octadecyne 1-decyne (15 g, 0.108 mol) was dissolved in anhydrous tetrahydrofuran (250 mL) and cooled to -78° C. under argon. n-butyl lithium (2.5 M in hexane, 39.2 mL, 0.098 mol) was added dropwise, maintaining the reaction temperature After cooling to 0° C., the reaction was quenched by addition of saturated ammonium chloride solution. The mixture was diluted with water (50 mL) and ethyl acetate (200 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2*). The combined organics were washed with water (200 mL), brine (200 mL) then dried (Na2SO4) and filtered. Concentration of the filtrate in vacuo gave 9-octadecyne as an orange oil (25.1 g, 93%). 1H NMR (300 MHz, CDCl3) 2.18-2.10 (m, 4H), 1.55-1.15 (m, 24H), 0.85 (m, 6H).
83%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 96h;
42.6%	Stage #1: 1-decyne With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 2h; Stage #2: 1-bromo-octane In tetrahydrofuran at 25 - 60℃;	5 Example 5 Synthesis of octadec-9-yne ake a 250 ml two-necked flask, pump for 3 times, and add dec-1-yne (8.29 g, 60 mmol).60 ml of water-free THF was taken with a syringe and poured into a two-necked flask.Stir at -10 ° C for 10 min,LDA was added dropwise at -10 ° C for 2 h.In this process, the solution turns from pale yellow to a turbid white-yellow solution.The viscosity of the solution becomes large and the solution is white and viscous.Add 1-bromooctane (17.38 g, 90 mmol),Add 20ml of anhydrous THF solvent and return to room temperature.Reheat to 60 ° C reaction,After heating, the solution turned yellow-green and the viscosity decreased. Reacted overnight,The solution turned pale yellow and slightly cloudy.Extracted with PE, washed 3 times with water, distilled under reduced pressure, and removed at 70 ° C,Use PE as an eluent to pass the column,A colorless transparent liquid was obtained with a yield of 10.65 g and a yield of 42.6%.

25%

Stage #1: 1-decyne With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: 1-bromo-octane In tetrahydrofuran; hexane at 0 - 60℃; for 12h;

Reference： [1]Current Patent Assignee: NEUDRIVE - US2019/131533, 2019, A1 Location in patent: Paragraph 0634-0636
[2]Rode, Katharina; Ramadas Narasimhamurthy, Poorva; Rieger, Rene; Krätzschmar, Felix; Breder, Alexander [European Journal of Organic Chemistry, 2021, vol. 2021, # 11, p. 1720 - 1725]
[3]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN108117563, 2018, A Location in patent: Paragraph 0044; 0045; 0046
[4]Location in patent: experimental part Wu, Jhong-Sian; Lin, Chung-Te; Wang, Chien-Lung; Cheng, Yen-Ju; Hsu, Chain-Shu [Chemistry of Materials, 2012, vol. 24, # 12, p. 2391 - 2399]

62
[ 764-93-2 ]
[ 295328-85-7 ]
[ 100-52-7 ]
[ 1376191-10-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2932 - 2935

63
[ 764-93-2 ]
[ 22348-32-9 ]
[ 100-52-7 ]
[ 27694-89-9 ]
[ 27694-89-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2932 - 2935

64
[ 764-93-2 ]
[ 22348-32-9 ]
[ 100-52-7 ]
[ 27694-89-9 ]
[ 1376191-72-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2254 - 2257
[2]Organic Letters,2012,vol. 14,p. 2932 - 2935

65
[ 764-93-2 ]
[ 1006-64-0 ]
[ 100-52-7 ]
[ 1376191-20-6 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2932 - 2935

66
[ 764-93-2 ]
[ 50672-84-9 ]
[ 1402908-91-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 3Intermediate 164-[(1E)-dec-1-en-1-yl]-1-naphthaldehyde To a solution of 1-decyne (1378 g, 12.89 mmol) in THF (40 mL) at RT was added catecholborane (1M in THF, 21 mL, 21 mmol) with stirring. After heating to reflux for 3.5 h, the reaction mixture was cooled to RT, 4-bromonaphthalene-1-carboxaldehyde (CAS 50672-84-9) (2.0 g, 8.51 mmol) and tetrakis(triphenylphosphine)palladium(0) (893 mg, 0.77 mmol) were added. After the reaction mixture was stirred for 20 min at RT, Na2CO3 (2M solution, 12.9 mL) was added and heated to reflux for 16 h with stirring. The mixture was cooled to RT, quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water, brine, and dried over magnesium sulfate. The resulting product was purified by MPLC (hexanes) to afford 353 mg of Intermediate 16 as yellow solid.1H NMR (600 MHz, CDCl3) delta 10.31 (s, 1H), 9.29 (dd, J=0.59, 8.51 Hz, 1H), 8.17 (d, J=8.22 Hz, 1H), 7.86 (d, J=7.34 Hz, 1H), 7.63-7.67 (m, 2H), 7.57 (ddd, J=1.32, 6.97, 8.44 Hz, 1H), 7.11 (d, J=15.55 Hz, 1H), 6.36 (dt, J=7.04, 15.55 Hz, 1H), 2.34 (tdd, J=1.61, 7.04, 7.41 Hz, 2H), 1.55 (dt, J=7.30, 14.97 Hz, 2H), 1.24-1.42 (m, 10H), 0.89 (t, J=7.30 Hz, 3H)

Reference： [1]Patent: US2012/264715,2012,A1 .Location in patent: Page/Page column 14

67
[ 764-93-2 ]
[ 188813-09-4 ]
[ 1393877-86-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 7392 - 7400

68
[ 764-93-2 ]
[ 188813-09-4 ]
[ 1393877-87-6 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 7392 - 7400

69
[ 764-93-2 ]
[ 37529-30-9 ]

Reference： [1]Chemistry Letters,2012,vol. 41,p. 1566 - 1568

70
[ 764-93-2 ]
[ 2267-25-6 ]
[ 1418136-98-7 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 568 - 581

71
[ 764-93-2 ]
[ 42923-79-5 ]
[ 100-52-7 ]
2-benzyl-1-(dec-1-yn-1-yl)-7-nitro-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5928 - 5931

72
[ 764-93-2 ]
[ 856596-02-6 ]
[ 1560768-76-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium(0); sodium carbonate; In N,N-dimethyl-formamide; at 110.0℃; for 1.0h;Inert atmosphere; Schlenk technique;	140 mg (1.0 mmol) of <strong>[856596-02-6]2-mercapto-5-pyrimidinecarbaldehyde</strong>,278 mg (2.0 mmol) of 1-decyne 15 mg (2%) of triphen ylphosphine palladium acetate,540 mg (3.0 mmol) cuprous iodide,530 mg (5.0 mmol) of sodium carbonate was added to the Schlenk tube under a nitrogen atmosphere,Under nitrogen atmosphere, 4.0 ml of N, N-dimethylformamide was added,The reaction was stirred at 110 C for 1 hour. After the reaction is over,Separation and purification can yield 65% separation yield of 2- (1-decynyl) -5-pyrimidine formaldehyde.After completion of the reaction, separation and purification gave a yield of 2-(1-decynyl)-5-pyrimidinecarbaldehydein 65% yield.

Reference： [1]Organic Letters,2014,vol. 16,p. 1282 - 1285
[2]RSC Advances,2016,vol. 6,p. 65775 - 65778
[3]Patent: CN105732245,2016,A .Location in patent: Page/Page column 5; 6

73
[ 764-93-2 ]
[ 1439-36-7 ]
[ 593-08-8 ]

Reference： [1]Nature Chemistry,2014,vol. 6,p. 22 - 27

74
[ 274-87-3 ]
[ 764-93-2 ]
[ 1612226-52-4 ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 6204 - 6223

75
[ 764-93-2 ]
[ 13865-19-5 ]
N-methylcamphanylpiperazine [ No CAS ]
C₂₈H₄₈N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(I) bromide; In toluene; at 25℃; for 24h;	To a stirred suspension of chiral piperazine 1 or 2 (0.210 g,1 mmol), CuBr (0.014 g, 0.1 mmol), and 1-alkyne 3 (1.1 mmol) in toluene (3 mL), freshly distilled aldehyde 4 (1 mmol) was addedat 25 C. The contents were stirred at 25 C for 24 h. Toluene was then removed after which water (5 mL) and DCM (15 mL) were added. The DCM layer was washed with saturated NaCl solution, dried (Na2SO4), and concentrated. The residue was purified by column chromatography using hexane and ethyl acetate (9:1) as eluent to isolate the propargyl amines 6. 4.1.22 4-(4,5,9,9-Tetramethyl-octahydro-5,8-methano-quinazolin-1-yl)-tetradec-5-ynoic acid methyl ester 6ng Brown liquid; Rf = 0.6 (silica gel, hexane/EtOAc 90:10); yield: 0.412 g, 93%, [alpha]D25 = -45.5(c 0.62, CHCl3); IR(neat) 2947, 2931, 2854, 1655, 1473, 1391, 1358, 1249, 1090, 1002, 936, 843, 772 cm-1; 1H NMR (400 MHz, CDCl3, delta ppm) 3.64 (s, 3H), 3.59-3.57 (t, J = 8.0 Hz, 1H), 2.83-2.80 (m, 2H), 2.74-2.71 (m, 1H), 2.58-2.54 (m, 1H), 2.41-2.38 (t, J = 12.0 Hz, 2H), 2.26 (s, 3H), 1.86-1.81 (q, J = 20.0 Hz, 6H), 1.67-1.59 (m, 2H), 1.48-1.38 (m, 5H), 1.27 (s, 9H), 1.22 (s, 3H), 0.97 (s, 3H), 0.88-0.85 (t, J = 20.0 Hz, 4H), 0.75 (s, 3H); 13C NMR (100 MHz, CDCl3, delta ppm) 174.0, 84.8, 78.1, 64.7, 54.4, 52.9, 51.4, 50.0, 48.3, 47.8, 47.0, 41.7, 37.1, 31.8, 30.7, 29.3, 29.0, 28.7, 25.9, 22.6, 22.0, 20.7, 18.5, 14.4, 14.1; HRMS (ESI): m/z calcd for C28H48N2O2: 444.3716, [M+H+]; found: 445.3785.

Reference： [1]Tetrahedron Asymmetry,2014,vol. 25,p. 1634 - 1646

76
[ 764-93-2 ]
[ 15126-06-4 ]
methyl 2-octylbenzofuran-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; triphenylphosphine; at 60℃; for 1h;	General procedure: A freshly prepared solution of PdNPs (12.5 mL) was taken up in a 25-mL round-bottomed flask. To this solution K2CO3 (0.276 g, 2 mmol)and Ph3P (0.052 g, 0.2 mmol) were added followed by 2-iodophenol(0.22 g, 1 mmol) and phenylacetylene (0.122 g, 1.2 mmol). Then, themixture was stirred at 60 C under aerobic conditions. The reactionwas monitored by TLC until complete consumption of phenylacetylene.When the reaction was complete, the solvents were evaporatedand the residue was purified by column chromatography (hexane-EtOAc). Yields for all compounds are calculated after column chromatography.The catalyst could be recycled. The size of the PdNPs afterfour catalytic cycles was found in the range of 12-18 nm by TEM analysisindicating some agglomeration.The reactions of 2-iodophenol or <strong>[15126-06-4]methyl 4-hydroxy-3-iodobenzoate</strong>with arylacetylenes were carried out as given in the typical procedure.However, reactions using alkylacetylenes did not require theuse of Ph3P.

Reference： [1]Synthesis,2015,vol. 47,p. 1661 - 1668

77
[ 764-93-2 ]
[ 77897-23-5 ]
(S)-3-benzyl-4-((S)-9-methylnonadec-10-yn-9-yl)morpholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 987 - 999

78
[ 764-93-2 ]
[ 1122-44-7 ]
4-amino-5-decynylpyrimidine-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 22h;Inert atmosphere;	To a stirred solution of <strong>[1122-44-7]4-amino-5-iodouracil</strong> (200 mg, 0.84 mmol) in anhydrous dimethylformamide (15 mL) at room temperature in a nitrogen atmosphere were added tetrakis(triphenylphosphine)palladium (98 mg, 0.08 mmol), copper(I)iodide (32 mg, 0.17 mmol), diisopropylethylamine (0.28 mL, 1.7 mmol) and 1-decyne (0.46 mL, 2.53 mmol). The reaction mixture was stirred at room temperature. After 22 h, 10 drops of 5% of the disodium salt of EDTA/H2O were added to the reaction mixture, and the mixture was concentrated in vacuo. The residue obtained was purified on silica gel column using MeOH/CHCl3 (4:96, v/v) as an eluent to give 4. This was obtained as a solid in 47% yield; mp 240-245 C; 1H NMR (DMSO-d6): delta 0.87 (t, J = 6.6 Hz, 3H, CH3), 1.27 (t, J = 1.2 Hz, 8H, 4* CH2), 1.37 (t, J = 6.0 Hz, 2H, gamma-CH2), 1.53 (t, J = 7.2 Hz, 2H, beta-CH2), 2.39 (t, J = 7.2 Hz, 2H, alpha-CH2), 6.54 (s, 1H, NH2), 7.51 (br s, 1H, NH2), 7.57 (s, 1H, H-6), 10.75 (br s, 1H, NH); 13C NMR (DMSO-d6): delta: 14.42 (CH3), 19.50, 22.54, 28.55, 28.86, 28.98, 29.06, 31.72 (7* CH2), 44.41 (C-beta), 72.60 (C-alpha), 95.93 (C-5), 145.74 (C-6), 155.57 (C-2), 165.92 (C-4). Anal. C14H21N3O (M.W. 247.17). Calcd C 67.98, H 8.56, N 16.99. Found C 67.59, H 8.17, N 16.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 1771 - 1777

79
[ 25637-18-7 ]
[ 764-93-2 ]
[ 201230-82-2 ]
[ 93190-76-2 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 10200 - 10203

80
[ 764-93-2 ]
[ 3340-78-1 ]
C₂₅H₃₁N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(I) trifluoromethanesulfonate * 1/2 toluene; C₂₄H₄₀N₂O₃; oxygen; rose bengal In tetrahydrofuran at 0℃; for 50h; Irradiation; Green chemistry; enantioselective reaction;	4.2. Typical experimental procedure for the enantioselective CDC of N-aryltetrahydroisoquinoline with terminal alkynes by using in situ Cu(I)OTf-L₄ catalyst: General procedure: In a reaction vial, Cu(I)OTf (5 mol%), with ligand (L4) (6 mol%) were dissolved in THF and the reaction was stirred for 1 h at RT under inert conditions (Argon Atmosphere). It was then cooled to 0 °C and 2-phenyltetrahydroisoquinoline (0.1 mmol) was added followed by subsequently addition of RB (5 mol%) and phenylacetylene (0.2 mmol) under the irradiation of visible light with molecular oxygen (1 atm). The reaction was checked on TLC, eluting with hexane/dichloromethane/diethyl ether (100:60:1). When the reaction was completed, the excess solvent was evaporated by using rotary evaporator and the product was purified by chromatography on silica gel (eluting with hexane/dichloromethane/diethyl ether, 100:60:1). 1H NMR spectroscopy was used for characterization of the final product.

Reference： [1]Kumar, Gaurav; Verma, Shailesh; Ansari, Amamudin; Khan, Noor-ul H.; Kureshy, Rukhsana I. [Catalysis Communications, 2017, vol. 99, p. 94 - 99]

81
[ 764-93-2 ]
[ 22348-32-9 ]
[ 623-47-2 ]
ethyl 3-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)tridec-4-ynoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 267 - 274

82
[ 764-93-2 ]
indium(III) bromide [ No CAS ]
[ 18292-38-1 ]
C₁₄H₂₅Br₂In [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With dimethyldimethoxysilan; In dichloromethane; at 20℃; for 24h;	General procedure: alkyne 1-decyne (0.980 mmol, 0.1354 g) was added to a solution of InBr3 (0.996 mmol, 0.3530g) and methallyl trimethylsilane (2.07 mmol, 0.2654 g) in dichloromethane (1 mL). The mixture wasstirred at room temperature for 24 h. The reaction mixture was cooled to -78 C, and 0.75 M I2 in THFsolution (2 mL) was added. The resultant mixture was stirred at -78 C for 30 min. The mixture wasquenched by saturated Na2S2O3 aq (10 mL). The mixture was extracted with dichloromethane (3 × 10mL). The collected organic layer was dried over MgSO4. The solvent was evaporated, and the residuewas purified by column chromatography (hexane, column length 10 cm, diameter 26 mm silica gel)and GPC (CHCl3) to give the product (0.279 g, 89%).IR: (neat) 1650, 1457 cm-1; 1H-NMR: (400 MHz, CDCl3) 5.92 (s, 1H, 4-CHI), 4.83 (s, 1H, 1-H), 4.75 (s,1H, 1-H), 2.87 (s, 2H, 3-H2), 2.16 (t, J = 7.8 Hz, 2H, 5-H), 1.65 (s, 3H, 2-Me), 1.43-1.23 (m, 14H), 0.88 (t,J = 6.8 Hz, 3H); 13C-NMR: (100 MHz, CDCl3) 149.4 (s, C-4), 142.5 (s, C-2), 113.0 (t, C-1), 76.2 (d, 4-CHI),45.8 (t, C-3), 36.4 (t, C-5), 31.9 (t), 29.43 (t), 29.38 (t), 29.22 (t), 27.0 (t), 22.7 (t), 21.8 (q, 2-Me), 14.1 (q, C-12); HRMS: (EI, 70 eV) Calculated (C14H25I) 320.1001 (M+), Found: 320.1000

Reference： [1]Molecules,2018,vol. 23

83
indium(III) chloride [ No CAS ]
[ 764-93-2 ]
[ 18292-38-1 ]
C₁₄H₂₅Cl₂In [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	In dichloromethane; at 20℃; for 24h;	General procedure: Alkyne 1 (1 mmol) was added to a solution of InBr3 (1 mmol) and allylic silane 2 (2 mmol) indichloromethane (1 mL). The mixture was stirred at room temperature for 24 h, and then 0.75 M I2 inTHF solution (2 mL) was added at 78 C. The resultant mixture was stirred at 78 C for 30 min.The mixture was quenched by saturated Na2S2O3 aq (10 mL), and then extracted with dichloromethane(3 10 mL). The collected organic layers were dried over MgSO4, and concentrated under reducedpressure. The yield was determined by 1H-NMR using 1,1,2,2-tetrachloroethane as an internal standard.The crude product was purified by flash chromatography (spherical silica gel 60 m, 30 g, diameter2.7 cm) and GPC to give the product.

Reference： [1]Molecules,2018,vol. 23

84
[ 764-93-2 ]
[ 2101-86-2 ]
[ 1222130-95-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With tris[3,5-bis(trifluoromethyl)pyrazolato]tricopper(I) In dichloromethane at 20℃; for 12h;	3. General method III for the synthesis of triazoles General procedure: A 5 mL vial was charged with selected alkyne (1.0. mmol), p-tolyl azide (1.0 mmol),and dichloromethane (3.0 mL). {-[3,5-(CF3)2Pz]Cu}3 (1 mol%) was added to the reactionand stirred at room temperature for 12 h. The yield was calculated using 1,3,5-(trimethoxy)benzene as internal standard.
92%	With Na⁽¹⁺⁾*C₈H₁₁O₅^(1-); copper(II) sulfate In water; <i>tert</i>-butyl alcohol at 20℃; for 24h;	Synthesis of 1,4-disubstuted-1,2,3-triazoles by direct CuAAC method. General procedure: Organic azide (2.0 mmol), alkyne (2.0 mmol), CuSO4 (0.4 mmol), sodium ascorbate (0.8 mmol), tert-butanol (10 ml) and water (10 mL) were added to a 20 mL reaction vial and stirred rapidly at room temperature for 24 h. The reaction mixture was extracted with CH2Cl2 and 5% NH4OH (aq), and the organic layer separated and dried over MgSO4. Following gravity filtration volatiles were removed via rotary evaporation and the residue air dried to give the desired triazole product.

Reference： [1]Muñoz-Castro, Alvaro; Noonikara-Poyil, Anurag; Rasika Dias, H. V. [Molecules, 2022, vol. 27, # 1]
[2]Fletcher, James T.; Sobczyk, Jill M.; Gwazdacz, Sarah C.; Blanck, Aaron J. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 20, p. 3320 - 3323]

85
[ 764-93-2 ]
[ 704-41-6 ]
1-(dodeca-1,3-diyn-1-yl)-2-(trifluoromethyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,10-Phenanthroline; tetrabutylammonium dichloroaurate(I); [bis(acetoxy)iodo]benzene; In acetone; at 50℃;	General procedure: In a3 mL screwed vial, [nBu4N][AuCl2] (0.05mmol, 5%) and Phen (0.1 mmol, 10%) were addedinto the mixture of aryl alkyne (0.2 mmol, 1.0 equiv), aliphatic alkyne (0.6 mmol, 3.0 equiv.),and PIDA (0.4 mmol, 2.0 equiv) in 0.8 mL anhydrous CH3CN. The reaction was run at 50 oCand monitored by TLC. After the reaction was completed, the solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel to givedesired diyne product.

Reference： [1]Chem,2018,vol. 4,p. 1983 - 1993

86
[ 764-93-2 ]
[ 1214264-88-6 ]
(E)-1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dec-1-enyl)-2-(2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine) [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7363 - 7366

87
[ 764-93-2 ]
[ 579-72-6 ]
1-(2-(dimethylamino)phenyl)undec-2-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 1-decyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-(dimethylamino)benzaldehyde In tetrahydrofuran; hexane at -78 - -40℃; for 2.08333h; Inert atmosphere;

Reference： [1]Zhao, Shuang; Wang, Xiaoyang; Wang, Pengfei; Wang, Guangwei; Zhao, Wentao; Tang, Xiangyang; Guo, Minjie [Organic Letters, 2019, vol. 21, # 11, p. 3990 - 3993]

88
[ 764-93-2 ]
[ 88912-27-0 ]
1-(3-chloropyridin-4-yl)undec-2-yn-1-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 8731 - 8742

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	764-93-2	MDL No. :	MFCD00009576
Formula :	C₁₀H₁₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ILLHQJIJCRNRCJ-UHFFFAOYSA-N
M.W :	138.25	Pubchem ID :	12997
Synonyms :

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P240-P241-P242-P243	UN#:	3295
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 764-93-2 ] {[proInfo.proName]}

Quality Control of [ 764-93-2 ]

Related Doc. of [ 764-93-2 ]

Product Details of [ 764-93-2 ]

Safety of [ 764-93-2 ]

Application In Synthesis of [ 764-93-2 ]

[ 764-93-2 ] Synthesis Path-Upstream 1~1

[ 764-93-2 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry