Name: 136350-66-8|1-Bromo-4-(2,2-dibromoethenyl)-benzene|95%
Brand: Ambeed
SKU: A1103557
Price: 46.0 USD
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Rating: 96 (29 reviews)

1
[ 136350-66-8 ]
[ 934-94-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 15℃;
90%	With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In dichloromethane; water at 0℃; for 5h;
89%	With 1,8-diazabicyclo[5.4.0]undec-7-ene monohydrate In neat (no solvent) at 25 - 30℃; for 3h;

80%	With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 60℃; for 0.5h; Sealed tube;
	With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 60℃; for 1h;	4.2. Typical procedure for the preparation of 2-(4-bromo benzyl)benzoxazole (3a) General procedure: To a solution of 1-(2,2-dibromovinyl)-4-bromobenzene (1 mmol) in DMF (5 mL) was added TBAF·3H2O (4 mmol). The mixture was stirred at 60 °C for 1 h. 2-Aminophenol (1 mmol) was added and the mixture was stirred at 60 °C for 2 h. Upon completion, the reaction mixture was cooled to room temperature and diluted with diethyl ether (60 mL). The organic phase was washed with brine, dried, filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel with ethyl acetate/hexane (3-5%) to give 3a. Other 2-benzyl benzoxazoles (3b-e) and 2-benzylbenzothiazoles (5a-e) were prepared in a similar manner.
1.82 g	With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In dichloromethane; water at 0℃; Schlenk technique; Inert atmosphere;
	With potassium phosphate In N,N-dimethyl-formamide at 90℃; for 4h; Inert atmosphere; Schlenk technique;

Reference： [1]Ratovelomanana, Victorin; Rollin, Yolande; Gebehenne, Catherine; Gosmini, Corinne; Perichon, Jacques [Tetrahedron Letters, 1994, vol. 35, # 27, p. 4777 - 4780]
[2]Chen, Xiao Yun; Wang, Long; Frings, Marcus; Bolm, Carsten [Organic Letters, 2014, vol. 16, # 14, p. 3796 - 3799]
[3]Krishna Moodapelly, Shiva; Sharma, Gangavaram V. M.; Ramana Doddi, Venkata [Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1535 - 1540]
[4]Liu, Shihui; Chen, Xiaobei; Hu, Yanwei; Yuan, Laiqi; Chen, Shaohua; Wu, Ping; Wang, Wei; Zhang, Shilei; Zhang, Wei [Advanced Synthesis and Catalysis, 2015, vol. 357, # 2-3, p. 553 - 560]
[5]Location in patent: experimental part Fan, Xuesen; He, Yan; Zhang, Xinying; Guo, Shenghai; Wang, Yangyang [Tetrahedron, 2011, vol. 67, # 34, p. 6369 - 6374]
[6]Feng, Yi-Si; Xu, Zhong-Qiu; Mao, Long; Zhang, Feng-Feng; Xu, Hua-Jian [Organic Letters, 2013, vol. 15, # 7, p. 1472 - 1475]
[7]Rao, Maddali L. N.; Islam, Sk Shamim; Dasgupta, Priyabrata [RSC Advances, 2015, vol. 5, # 95, p. 78090 - 78098]

2
[ 558-13-4 ]
[ 57477-93-7 ]
bis-(4-bromo-benzylidene)-hydrazine [ No CAS ]
[ 136350-66-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(I) chloride; ammonium hydroxide In dimethyl sulfoxide at 20℃; for 4h;

Reference： [1]Shastin; Korotchenko; Nenajdenko; Balenkova [Synthesis, 2001, # 14, p. 2081 - 2084]

3
[ 558-13-4 ]
[ 1122-91-4 ]
[ 136350-66-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: carbon tetrabromide With [3-(diphenylphosphino)phenyl](triphenyl)phosphonium perchlorate; zinc powder In dichloromethane for 0.5h; Heating; Stage #2: 4-bromo-benzaldehyde In dichloromethane at 20℃; for 6h;
96%	With triphenylphosphine In dichloromethane at 0℃; for 1.33h; Inert atmosphere;	1-Bromo-4-ethynylbenzene (1c) According to the reported method, 3 the title compound 1c was prepared from 4-bromobenzaldehyde as follows. Under an argon atmosphere, a solution of Ph3P (12.6 g, 48.0 mmol) in CH2Cl2 (10 mL) was added to a stirred solution of 4-bromobenzaldehyde (3.73 g, 20.2 mmol) and CBr4 (7.98 g, 24.1 mmol) in CH2Cl2 (25 mL) over 20 min at 0 °C. After 1 h the resultant mixture was quenched with water (30 mL) and extracted with CH2Cl2 (3 × 10 mL). The combined organic layer was washed with brine, dried over MgSO4, and evaporated under reduced pressure. Purification of the residue by silica gel column chromatography (hexane) gave 1-bromo-4-(2,2-dibromoethenyl)benzene as bright yellow liquid (6.66 g, 19.5 mmol, 96%).
95%	With triphenylphosphine In dichloromethane at 0℃; for 4h;

85%	With triphenylphosphine In dichloromethane at 20℃; for 3h;	27.D.A Step A; 1-BROMO-4- (2. 2-DIBROMOVINVL) benzene: TETRABROMOMETHANE (21.5 g, 65.9 MMOL) was added to a cooled solution OF 4- BROMOBENZALDEHYDE (10.0 g, 54.0 MMOL) and triphenylphosphine (30.0 g, 130 MMOL) in dry methylene chloride (100 mL). Reaction mixture was stirred for 3 h at room temperature. Sub- sequently, a saturated solution of sodium hydrogencarbonate (50 mL) was added and the organic layer was washed with water (150 mL), dried with anhydrous magnesium sulfate and evaporated in vacuo. Triphenylphosphine oxide was removed from the residue by crystalliza- tion from ethyl acetate and hexane. Evaporation of the mother liquor gave 18. 4 G of an yel- lowish oil. Crude yield : 18.4 G (85%). RF (SI02, hexane) = 0.70.
85%	With triphenylphosphine In dichloromethane at 20℃; for 3h;	27.A Tetrabromomethane (21.5 g, 65.9 mmol) was added to a cooled solution of 4-bromobenzaldehyde (10.0 g, 54.0 mmol) and triphenylphosphine (30.0 g, 130 mmol) in dry methylene chloride (100 mL). Reaction mixture was stirred for 3 h at room temperature. Subsequently, a saturated solution of sodium hydrogencarbonate (50 mL) was added and the organic layer was washed with water (150 mL), dried with anhydrous magnesium sulfate and evaporated in vacuo. Triphenylphosphine oxide was removed from the residue by crystallization from ethyl acetate and hexane. Evaporation of the mother liquor gave 18.4 g of an yellowish oil. Crude yield: 18.4 g (85%). RF (SiO2, hexane) =0.70.
85%	With triphenylphosphine In dichloromethane at 20℃; for 3h;	1; A.A Example 1; (Z)-[4-[3-(4-Bromophenyl)-5-phenylpent-2-en-4-ynylsulfanyl]-2-methylphenoxy]acetic acid; General procedure (A); Step A:; 1-Bromo-4-(2,2-dibromovinyl)benzene:; Tetrabromomethane (21.5 g, 65.9 mmol) was added to a cooled solution of 4- bromobenzaldehyde (10.0 g, 54.0 mmol) and triphenylphosphine (30.0 g, 130 mmol) in dry methylene chloride (100 mL). Reaction mixture was stirred for 3 h at room temperature. Sub- sequently, a saturated solution of sodium hydrogencarbonate (50 mL) was added and the organic layer was washed with water (150 mL), dried with anhydrous magnesium sulfate and evaporated in vacuo. Triphenylphosphine oxide was removed from the residue by crystalliza- tion from ethyl acetate and hexane. Evaporation of the mother liquor gave 18.4 g of an yel- lowish oil. Crude yield: 18.4 g (85%). RF (Si02, hexane) = 0.70.
63%	With triphenylphosphine In dichloromethane at 0℃; for 5.25h; Inert atmosphere;
63%	With triphenylphosphine In dichloromethane at 0℃; Inert atmosphere;
	With triphenylphosphine In dichloromethane at 0 - 20℃;
	With triphenylphosphine In dichloromethane Inert atmosphere;
	With triphenylphosphine In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
	With triphenylphosphine In dichloromethane
	With triphenylphosphine In dichloromethane for 0.166667h; Cooling with ice;	General procedure for synthesis of 1,1-dibromoalkenes 1 General procedure: To an ice cold stirred solution of aryl aldehyde (10.0 mmol) and CBr4 (5.0 g, 15.0 mmol) in dry CH2Cl2 (80.0 mL) was added PPh3 (7.9 g, 30.0 mmol) in CH2Cl2 (70.0 mL) for 10 min. After the reaction was complete, the reaction mixture was concentrated under reduced pressure and then hexane (20.0 mL) was added to the residue. The suspended mixture was filtered to remove triphenylphosphine oxide that was washed with hexane (2 x 20.0 mL). The combined filtrates were concentrated under reduced pressure and the crude product was purified by column chromatography using hexane as the eluent to give the product 1 pure.
	With triphenylphosphine In dichloromethane at 0℃; for 1h;
	With triphenylphosphine In dichloromethane at 0℃; for 0.5h;
	Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane Stage #2: 4-bromo-benzaldehyde In dichloromethane at 20℃; for 6h;
	Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: 4-bromo-benzaldehyde In dichloromethane at 0℃; Inert atmosphere; Schlenk technique;	2. General Procedure for Synthesis of 1¹. General procedure: A To a solution of PPh3 (4.0 eq.) in CH2Cl2 (20 ml) was slowly dropped CBr4 (2.0 eq.)/CH2Cl2 (6 ml) solution at 0 °C under argon atmosphere. After being stirred for 1 h, the ketone or aldehyde (6.00 mmol) / CH2Cl2 (6 mL) solution was dropped at 0 °C and the reaction mixture was stirred overnight. To the reaction mixture was added hexane and then the precipitated solid was filtered. The eluent was concentrated under reduced pressure and the residue was purified by was purified by chromatography on SiO2 to give the corresponding gem-dibromoalkene derivative.
	Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane for 0.166667h; Cooling with ice; Stage #2: 4-bromo-benzaldehyde In dichloromethane for 3h; Cooling with ice;	2.1.4 Procedure for the Preparation of Propargyl Alcohols ((E)-6f, 6h, 6i, 6o) General procedure: The alkynes 9f, 9h, 9i, 9o were synthesized according to the literature.4 To anhydrousCH2Cl2 solution (10 mL) of carbon tetrabromide (20 mmol) was added a solution oftriphenylphosphine (40 mmol) in anhydrous CH2Cl2 (10 mL) in ice bath. The mixturewas stirred for 10 min, and a solution of aldehyde (10 mmol) in anhydrous CH2Cl2 (40 mL) was slowly added. The reaction mixture was stirred in ice bath for 3 h. The reactionwas poured into water, then, extracted three times with CH2Cl2 The combined organiclayer was washed with brine, and dried over Na2SO4. Volatile materials were removedunder reduced pressure. The residue was added to Et2O, and the resulting heterogeneoussolution was filtrated to remove triphenylphosphine oxide. The filtrate was concentratedunder reduced pressure and the residue was purified by silica-gel flash columnchromatography using n-hexane/EtOAc = 30/1 to obtain the desired 1,1-dibromo-1-alkenes.The corresponding 1,1-dibromo-1-alkene (7.00 mmol) was dissolved in dehydrated THF(10 mL), and the solution was cooled to -78 . To the solution, n-BuLi (11 mL, 17.5mmol, 1.55 M in n-hexane) was added dropwise. After being stirred for 30 min at -78 ,the reaction mixture was then allowed to stir at room temperature for 30 min. The reactionwas quenched by sat. aq. NH4Cl, and extracted three times with Et2O and dried overNa2SO4. The solvent was removed under reduced pressure. The residue was purified bysilica-gel flash column chromatography using n-hexane/EtOAc = 30/1 to obtain alkynes9f, 9h, 9i, 9o.The procedure for the preparation of 6f, 6h, 6i, 6o from alkynes 9f, 9h, 9i, 9o are similarto the above procedure 2.1.1.
	With triphenylphosphine In dichloromethane at 0℃; for 1h; Inert atmosphere;
	Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromo-benzaldehyde In dichloromethane at 0℃; for 2.08333h; Inert atmosphere;
	With triphenylphosphine In dichloromethane at 0℃; for 1.5h;
	With triphenylphosphine In dichloromethane at 0 - 20℃;
	With triphenylphosphine In dichloromethane at 0 - 20℃;	2.2 General procedure B for the synthesis of dibromoalkenes General procedure: round-bottom flask was charged with aldehyde (6.0 mmol) and CBr4 (9.0 mmol, 1.5 equiv)in DCM (50 mL) and the resulting solution was cooled to 0 °C in an ice bath. PPh3 (18.0 mmol, 3equiv) in DCM (30 mL) was added with a dropping funnel for 2 minutes at this temperature. Thereaction was monitored by TLC. After the reaction was completed, the mixture was filtered, thenfiltrate was concentrated under reduced pressure and the crude product was purified by silica gelflash column chromatography with petroleum ether to give the pure product dibromoalkenes.

Reference： [1]Poupon, Jean-Christophe; Boezio, Alessandro A.; Charette, Andre B. [Angewandte Chemie - International Edition, 2006, vol. 45, # 9, p. 1415 - 1420]
[2]Kumaki, Wataru; Kinoshita, Hidenori; Miura, Katsukiyo [Tetrahedron, 2022, vol. 110]
[3]Ma, Xiaoshen; Herzon, Seth B. [Journal of Organic Chemistry, 2016, vol. 81, # 19, p. 8673 - 8695]
[4]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2004/37776, 2004, A2 Location in patent: Page 71-72
[5]Current Patent Assignee: VTV THERAPEUTICS INC. - US2005/70583, 2005, A1 Location in patent: Page/Page column 38
[6]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2005/105725, 2005, A1 Location in patent: Page/Page column 41-42
[7]Chen, Xiao Yun; Wang, Long; Frings, Marcus; Bolm, Carsten [Organic Letters, 2014, vol. 16, # 14, p. 3796 - 3799]
[8]Morri, Ashok Kumar; Thummala, Yadagiri; Doddi, Venkata Ramana [Organic Letters, 2015, vol. 17, # 18, p. 4640 - 4643]
[9]Yang, Yiwen; Kuang, Chunxiang; Jin, Hui; Yang, Qing [Synthesis, 2011, # 21, p. 3447 - 3452]
[10]Liu, Liu; Wang, Yulei; Zeng, Zhiping; Xu, Pengxiang; Gao, Yuxing; Yin, Yingwu; Zhao, Yufen [Advanced Synthesis and Catalysis, 2013, vol. 355, # 4, p. 659 - 666]
[11]Li, Huan; Zhang, Zhikun; Shangguan, Xianghang; Huang, Shan; Chen, Jun; Zhang, Yan; Wang, Jianbo [Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11921 - 11925][Angew. Chem., 2014, vol. 126, # 44, p. 12115 - 12119,5]
[12]Tokimizu, Yusuke; Wieteck, Marcel; Rudolph, Matthias; Oishi, Shinya; Fujii, Nobutaka; Hashmi, A. Stephen K.; Ohno, Hiroaki [Organic Letters, 2015, vol. 17, # 3, p. 604 - 607]
[13]Webber, Rodrigo; Peglow, Thiago J.; Nobre, Patrick C.; Barcellos, Angelita M.; Roehrs, Juliano A.; Schumacher, Ricardo F.; Perin, Gelson [Tetrahedron Letters, 2016, vol. 57, # 37, p. 4128 - 4132]
[14]Singh, Radhey M.; Nandini, Durgesh; Bharadwaj, Kishor Chandra; Gupta, Tanu; Singh, Raj Pal [Organic and Biomolecular Chemistry, 2017, vol. 15, # 47, p. 9979 - 9982]
[15]Yang, Dongdong; Shan, Lihong; Xu, Ze-Feng; Li, Chuan-Ying [Organic and Biomolecular Chemistry, 2018, vol. 16, # 9, p. 1461 - 1464]
[16]Meng, Mengting; Wang, Guofang; Yang, Liangfeng; Cheng, Kai; Qi, Chenze [Advanced Synthesis and Catalysis, 2018, vol. 360, # 6, p. 1218 - 1231]
[17]Sun, Wencheng; Teng, Qiaoling; Cheng, Dongping; Li, Xiaonian; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 3]
[18]Kozuma, Akane; Komatsuki, Keiichi; Saito, Kodai; Yamada, Tohru [Chemistry Letters, 2020, vol. 49, # 1, p. 60 - 63]
[19]Chen, Haifeng; Gong, Hegui; Yao, Ken; Ye, Yang [Organic Letters, 2020]
[20]Liang, Hao; He, Xiaobo; Zhang, Yaqi; Chen, Bin; Ouyang, Jia-Sheng; Li, Yongsu; Pan, Bendu; Subba Reddy, Chitreddy V.; Chan, Wesley Ting Kwok; Qiu, Liqin [Chemical Communications, 2020, vol. 56, # 77, p. 11429 - 11432]
[21]Zhao, Jiangui; Zheng, Xueli; Tao, Shaokun; Zhu, Yuxin; Yi, Jiwei; Tang, Songbai; Li, Ruixiang; Chen, Hua; Fu, Haiyan; Yuan, Maolin [Organic Letters, 2021, vol. 23, # 15, p. 6067 - 6072]
[22]Li, Sifan; Wang, Yu; Wu, Zibo; Shi, Weiliang; Lei, Yibo; Davies, Paul W.; Shu, Wei [Organic Letters, 2021, vol. 23, # 18, p. 7209 - 7214]
[23]Huang, Shenlin; Zhang, Yingyin; Zheng, Yu; Zhu, Baolong [Journal of Organometallic Chemistry, 2022, vol. 965-966]

4
2-(4-bromophenyl)-1,1-bis(trimethylsilyl)ethene [ No CAS ]
[ 136350-66-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-Bromosuccinimide In acetonitrile at 20℃; for 4h;

Reference： [1]Pawluć, Piotr; Hreczycho, Grzegorz; Walkowiak, Jȩdrzej; Marciniec, Bogdan [Synlett, 2007, # 13, p. 2061 - 2064]

5
[ 50-00-0 ]
[ 136350-66-8 ]
[ 37614-58-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 1-bromo-4-(2,2-dibromovinyl)benzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Stage #2: formaldehyd In tetrahydrofuran at -78 - 20℃; for 3h;	27.D.B Step B, 3-(4-BROMOPHENEL) PROP-2-VN-1-OL The above bromo derivative (8.0 g, 23 MMOL) was dissolved in dry tetrahydrofuran (120 mL) and cooled TO-78°C under inert atmosphere. 2M Solution of lithium diisopropyla- mide in tetrahydrofuran (38 mL, 75 MMOL) was added dropwise to the reaction mixture and it was stirred for 2 h under cooling. Finely powdered paraformaldehyde (7.0 g, 230 MMOL) was added to the mixture and it was stirred for further 3 h warming up the reaction mixture slowly to the room temperature. Brine (50 mL) was added and the mixture was extracted with ether (4X50 mL). The collected organic layers were dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo. The residue was pre-purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 1: 0-3: 1) and the obtained crude product was fur- ther purified by crystallization from ethyl acetate and hexane yielding 3.0 G of the desired product. Yield : 3.0 G (66%). RF = 0. 10 (SIO2, HEXANE/ETHYL acetate 9: 1). 'H NMR spectrum (250 MHz, CDC13) : 7.24-7. 49 (m, 4 H); 4.48 (s, 2 H).
66%	Stage #1: 1-bromo-4-(2,2-dibromovinyl)benzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Stage #2: formaldehyd In tetrahydrofuran at 20℃; for 3h;	27.B The above bromo derivative (8.0 9, 23 mmol) was dissolved in dry tetrahydrofuran (120 mL) and cooled to -78° C. under inert atmosphere. 2M Solution of lithium diisopropylamide in tetrahydrofuran (38 mL, 75 mmol) was added dropwise to the reaction mixture and it was stirred for 2 h under cooling. Finely powdered paraformaldehyde (7.0 g, 230 mmol) was added to the mixture and it was stirred for further 3 h warming up the reaction mixture slowly to the room temperature. Brine (50 mL) was added and the mixture was extracted with ether (4×50 mL). The collected organic layers were dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo. The residue was pre-purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 1:0-3:1) and the obtained crude product was further purified by crystallization from ethyl acetate and hexane yielding 3.0 g of the desired product. Yield: 3.0 g (66%). RF=0.10 (SiO2, hexane/ethyl acetate 9: 1). 1H NMR spectrum (250 MHz, CDCl3): 7.24-7.49 (m, 4 H); 4.48 (s, 2 H).
66%	Stage #1: 1-bromo-4-(2,2-dibromovinyl)benzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Stage #2: formaldehyd In tetrahydrofuran at -78 - 20℃; for 3h;	1; A.B Step B:; 3-(4-Bromophenyl)prop-2-yn-1-ol:; 1-Bromo-4-(2,2-dibromovinyl)benzene (8.0 g, 23 mmol) was dissolved in dry tetra- hydrofuran (120 mL) and cooled to -78°C under inert atmosphere. 2M Solution of lithium diisopropylamide in tetrahydrofuran (38 mL, 75 mmol) was added dropwise to the reaction mixture and it was stirred for 2 h under cooling. Finely powdered paraformaldehyde (7.0 g, 230 mmol) was added to the mixture and it was stirred for further 3 h warming up the reac- tion mixture slowly to the room temperature. Brine (50 mL) was added and the mixture was extracted with ether (4x50 mL). The collected organic layers were dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo. The residue was pre-purified by column chromatography (silica gel Fluka 60, hexane/ethyl acetate 1:0 - 3:1) and the obtained crude product was further purified by crystallization from ethyl acetate and hexane yielding 3.0 g of the desired product. Yield: 3.0 g (66%). RF = 0.10 (Si02, hexane/ethyl acetate 9 : 1 ). ¹H NMR spectrum (250 MHz, CDCI3, On): 7.24 - 7.49 (m, 4 H) ; 4.48 (s, 2 H).

Reference： [1]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2004/37776, 2004, A2 Location in patent: Page 72
[2]Current Patent Assignee: VTV THERAPEUTICS INC. - US2005/70583, 2005, A1 Location in patent: Page/Page column 38; 39
[3]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2005/105725, 2005, A1 Location in patent: Page/Page column 42

6
[ 134469-07-1 ]
[ 136350-66-8 ]
[ 21547-85-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; tetrabutyl ammonium fluoride; N,N`-dimethylethylenediamine In water; N,N-dimethyl-formamide at 65℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Xu, Hui; Zhang, Yin; Huang, Jianqiang; Chen, Wanzhi [Organic Letters, 2010, vol. 12, # 16, p. 3704 - 3707]

7
[ 136350-66-8 ]
[ 766-96-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With caesium carbonate; dimethyl sulfoxide at 115℃; for 12h;
90%	With tetrabutyl ammonium fluoride; water; triphenylphosphine In tetrahydrofuran at 80℃; for 2.5h; Sealed tube;
76%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25 - 30℃; for 16h;

75%	With Succinimide; potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Schlenk technique; Inert atmosphere;	General procedure for terminal alkynes preparation: General procedure: To an oven-dried Schlenk tube, 1,1-dibromoalkene (1 equiv), succinimide (2 equiv), K2CO3 (6 equiv) were added along with dry DMSO (3 mL). This mixture was stirred at 90°C for 2h. After that, the mixture was cooled to room temperature and extracted with ethyl acetate (30mL) and washed with water (10mL) followed by brine solution (10mL). The organic extract was dried over dry MgSO4 and concentrated. The pure product was obtained by silica gel column chromatography using ethyl acetate/hexane as eluent.
30%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 16h;	1-Bromo-4-ethynylbenzene (1c) DBU (11.6 mL, 78.0 mmol) was dropwise added to a stirred solution of 1-bromo-4-(2,2-dibromoethenyl)benzene (6.65 g, 19.5 mmol) in anhydrous CH3CN (38 mL) over 10 min at room temperature. After 16 h the reaction mixture was cooled to 15 °C and quenched by dropwise addition of HCl (5 M in H2O, 10 mL) over 15 min. After additional stirring for 5 min, the resultant mixture was extracted with EtOAc/hexane (1:1, 2 × 10 mL). The combined organic layer was washed with water (10 mL), dried over anhydrous K2CO3, and evaporated under reduced pressure. Purification ofthe residue by silica gel column chromatography (hexane) gave 1c as white crystal (1.06 g, 5.83 mmol,30%).
	With hydrogenchloride; caesium carbonate In dimethyl sulfoxide at 20 - 125℃; for 12h;
	With sodiumsulfide nonahydrate In dimethyl sulfoxide at 40℃; for 18h;
	Stage #1: 1-bromo-4-(2,2-dibromovinyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: With methanol In tetrahydrofuran for 1h;
	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	2.1.4 Procedure for the Preparation of Propargyl Alcohols ((E)-6f, 6h, 6i, 6o) General procedure: The alkynes 9f, 9h, 9i, 9o were synthesized according to the literature.4 To anhydrousCH2Cl2 solution (10 mL) of carbon tetrabromide (20 mmol) was added a solution oftriphenylphosphine (40 mmol) in anhydrous CH2Cl2 (10 mL) in ice bath. The mixturewas stirred for 10 min, and a solution of aldehyde (10 mmol) in anhydrous CH2Cl2 (40 mL) was slowly added. The reaction mixture was stirred in ice bath for 3 h. The reactionwas poured into water, then, extracted three times with CH2Cl2 The combined organiclayer was washed with brine, and dried over Na2SO4. Volatile materials were removedunder reduced pressure. The residue was added to Et2O, and the resulting heterogeneoussolution was filtrated to remove triphenylphosphine oxide. The filtrate was concentratedunder reduced pressure and the residue was purified by silica-gel flash columnchromatography using n-hexane/EtOAc = 30/1 to obtain the desired 1,1-dibromo-1-alkenes.The corresponding 1,1-dibromo-1-alkene (7.00 mmol) was dissolved in dehydrated THF(10 mL), and the solution was cooled to -78 . To the solution, n-BuLi (11 mL, 17.5mmol, 1.55 M in n-hexane) was added dropwise. After being stirred for 30 min at -78 ,the reaction mixture was then allowed to stir at room temperature for 30 min. The reactionwas quenched by sat. aq. NH4Cl, and extracted three times with Et2O and dried overNa2SO4. The solvent was removed under reduced pressure. The residue was purified bysilica-gel flash column chromatography using n-hexane/EtOAc = 30/1 to obtain alkynes9f, 9h, 9i, 9o.The procedure for the preparation of 6f, 6h, 6i, 6o from alkynes 9f, 9h, 9i, 9o are similarto the above procedure 2.1.1.
	With caesium carbonate In dimethyl sulfoxide at 115℃; for 18h; Inert atmosphere;

Reference： [1]Location in patent: scheme or table Zhao, Ming; Kuang, Chunxiang; Yang, Qing; Cheng, Xuezhi [Tetrahedron Letters, 2011, vol. 52, # 9, p. 992 - 994]
[2]Liu, Shihui; Chen, Xiaobei; Hu, Yanwei; Yuan, Laiqi; Chen, Shaohua; Wu, Ping; Wang, Wei; Zhang, Shilei; Zhang, Wei [Advanced Synthesis and Catalysis, 2015, vol. 357, # 2-3, p. 553 - 560]
[3]Morri, Ashok Kumar; Thummala, Yadagiri; Doddi, Venkata Ramana [Organic Letters, 2015, vol. 17, # 18, p. 4640 - 4643]
[4]Rao, Maddali L.N.; Shamim Islam, Sk [Tetrahedron Letters, 2021, vol. 71]
[5]Kumaki, Wataru; Kinoshita, Hidenori; Miura, Katsukiyo [Tetrahedron, 2022, vol. 110]
[6]Xu, Wenjing; Zhang, Wensheng; Zhang, Fei [Heterocyclic Communications, 2016, vol. 22, # 3, p. 165 - 167]
[7]Singh, Radhey M.; Nandini, Durgesh; Bharadwaj, Kishor Chandra; Gupta, Tanu; Singh, Raj Pal [Organic and Biomolecular Chemistry, 2017, vol. 15, # 47, p. 9979 - 9982]
[8]Yang, Dongdong; Shan, Lihong; Xu, Ze-Feng; Li, Chuan-Ying [Organic and Biomolecular Chemistry, 2018, vol. 16, # 9, p. 1461 - 1464]
[9]Kozuma, Akane; Komatsuki, Keiichi; Saito, Kodai; Yamada, Tohru [Chemistry Letters, 2020, vol. 49, # 1, p. 60 - 63]
[10]Liang, Hao; He, Xiaobo; Zhang, Yaqi; Chen, Bin; Ouyang, Jia-Sheng; Li, Yongsu; Pan, Bendu; Subba Reddy, Chitreddy V.; Chan, Wesley Ting Kwok; Qiu, Liqin [Chemical Communications, 2020, vol. 56, # 77, p. 11429 - 11432]

8
[ 5720-05-8 ]
[ 136350-66-8 ]
[ 1242257-68-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With C₁₇H₁₅ClN₇Pd⁽¹⁺⁾*F₆P^(1-); potassium carbonate In water at 100℃; for 12h;

Reference： [1]Location in patent: experimental part Gu, Shaojin; Xu, Hui; Zhang, Na; Chen, Wanzhi [Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1677 - 1686]

9
[ 136350-66-8 ]
[ 98-80-6 ]
[ 18648-66-3 ]

Reference： [1]Chemistry - An Asian Journal,2010,vol. 5,p. 1677 - 1686

10
[ 504-29-0 ]
[ 136350-66-8 ]
[ 1338248-68-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium hydrogencarbonate In N,N-dimethyl-formamide at 120℃; for 48h;
73%	With potassium fluoride In N,N-dimethyl-formamide at 20 - 130℃; for 12.1667h; Inert atmosphere; regioselective reaction;

Reference： [1]Wu, Zhiqing; Pan, Yinyin; Zhou, Xiangge [Synthesis, 2011, # 14, p. 2255 - 2260]
[2]Liu, Guoping; Cong, Xuefeng; He, Jiaheng; Luo, Shunzhong; Wu, Di; Lan, Jingbo [Journal of Chemical Research, 2012, vol. 36, # 12, p. 687 - 690]

11
[ 136350-66-8 ]
[ 959-88-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 3-nitropyridine; caesium carbonate In dimethyl sulfoxide at 120℃; for 12h; regioselective reaction;	. General experimental procedure for the synthesis of 1,3 diynes 2a-c, e-g, i-k, o using (2,2-dibromovinyl)arenes 4a-j. General procedure: A 10 mL reaction vial was charged with a (2,2-dibromovinyl)arenes 4a-j (1.0 mmol), cesium carbonate (1.0 mmol), DMSO (1 mL) and 10 mol% 3-nitopyridine. The reaction vial was then heated at 120 °C for 12 h. After completion of the reaction (progress was monitored by TLC; SiO2, Hexane/EtOAc = 9.5:0.5), the mixture was diluted with ethyl acetate (15 mL) and water (20 mL) and extracted with ethyl acetate (3 × 10 mL). The combined organic layer was washed with brine (3 × 10 mL) and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and the remaining residue was purified by column chromatography over silica gel using hexane / ethyl acetate (9.5:0.5) as an eluent to obtain the desired products 2a-c, e-g, i-k, o in high yields.
41%	With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 25℃;

Reference： [1]Kaldhi, Dhananjaya; Vodnala, Nagaraju; Gujjarappa, Raghuram; Kabi, Arup K.; Nayak, Subhashree; Malakar, Chandi C. [Tetrahedron Letters, 2020, vol. 61, # 16]
[2]Location in patent: experimental part Jin, Hui; Kuang, Chunxiang [Chinese Journal of Chemistry, 2011, vol. 29, # 3, p. 592 - 594]

12
[ 106-45-6 ]
[ 136350-66-8 ]
[ 1350729-52-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 25℃; for 0.0833333h; Sealed tube;

Reference： [1]Jin, Hui; Yang, Yiwen; Kuang, Chunxiang; Yang, Qing [Synlett, 2011, # 19, p. 2886 - 2890]

13
[ 127-08-2 ]
[ 136350-66-8 ]
[ 7500-37-0 ]

Reference： [1]Chinese Chemical Letters,2011,vol. 22,p. 571 - 574

14
[ 136350-66-8 ]
[ 5301-98-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) iodide; sodium azide; potassium carbonate; sodium L-ascorbate In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Wang, Xiaokun; Kuang, Chunxiang; Yang, Qing [European Journal of Organic Chemistry, 2012, # 2, p. 424 - 428]

15
[ 136350-66-8 ]
[ 1420041-17-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrabutyl ammonium fluoride In toluene at 100℃; for 1.5h; Sealed tube; regioselective reaction;

Reference： [1]Zhao, Mingzhu; Ming, Ling; Tang, Jialiang; Zhao, Xiaoming [Organic Letters, 2016, vol. 18, # 3, p. 416 - 419]

16
[ 1027941-92-9 ]
[ 136350-66-8 ]
2-((4-bromophenyl)ethynyl)-3-phenylindolizin-1-yl pivalate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 1-bromo-4-(2,2-dibromovinyl)benzene With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 3-phenyl-1-(pyridin-2-yl)prop-2-yn-1-yl pivalate With copper(l) chloride In dimethyl sulfoxide; butan-1-ol at 20℃; for 0.333333h;

Reference： [1]Oh, Kyung Hwan; Kim, Seong Min; Park, Sun Young; Park, Jin Kyoon [Organic Letters, 2016, vol. 18, # 9, p. 2204 - 2207]

17
[ 1666-13-3 ]
[ 136350-66-8 ]
(E)-1-bromo-1-(phenylselanyl)-2-(4-bromophenyl)ethene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: diphenyl diselenide With sodium tetrahydroborate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromo-4-(2,2-dibromovinyl)benzene at 50℃; for 0.5h; Inert atmosphere; stereoselective reaction;	General procedure for synthesis of (E)-1-bromo-1-arylselenoalkenes 3 General procedure: To a solution of diaryl diselenide 2 (0.25 mmol) in PEG-400 (1.0 mL) under Ar atmosphere, NaBH4 (0.029 g, 0.75 mmol) was added at room temperature and the mixture was stirred for 30 min. Then, the 1,1-dibromoalkene 1 (0.5 mmol) was added and the temperature was slowly raised to 50 °C. The reaction progress was monitored by TLC. After the time indicated in Table 2, the reaction mixture was quenched with water (10.0 mL) and extracted with ethyl acetate (3 x 15.0 mL). The organic phase was separated, dried with MgSO4 and the solvent was evaporated under reduced pressure. The product was isolated by column chromatography using silica gel 60 Å (0.060-0.200 mm-Across) and hexane as eluent.

Reference： [1]Webber, Rodrigo; Peglow, Thiago J.; Nobre, Patrick C.; Barcellos, Angelita M.; Roehrs, Juliano A.; Schumacher, Ricardo F.; Perin, Gelson [Tetrahedron Letters, 2016, vol. 57, # 37, p. 4128 - 4132]

18
[ 136350-66-8 ]
(E)-1-bromo-4-(2-bromovinyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With 2Na⁽¹⁺⁾*C₁₂H₃₀B₂O₆Te^(2-) at 20℃; for 1h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: triethylamine; Dimethyl phosphite / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere 2: sodium hydroxide / isopropyl alcohol / 1.5 h / Inert atmosphere; Reflux
	Multi-step reaction with 2 steps 1: phosphonic acid diethyl ester; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: sodium hydroxide / isopropyl alcohol / Reflux

Reference： [1]Perin, Gelson; Barcellos, Angelita M.; Peglow, Thiago J.; Nobre, Patrick C.; Cargnelutti, Roberta; Lenardão, Eder J.; Marini, Francesca; Santi, Claudio [RSC Advances, 2016, vol. 6, # 105, p. 103657 - 103661]
[2]Chen, Haifeng; Gong, Hegui; Yao, Ken; Ye, Yang [Organic Letters, 2020]
[3]Zhao, Jiangui; Zheng, Xueli; Tao, Shaokun; Zhu, Yuxin; Yi, Jiwei; Tang, Songbai; Li, Ruixiang; Chen, Hua; Fu, Haiyan; Yuan, Maolin [Organic Letters, 2021, vol. 23, # 15, p. 6067 - 6072]

19
[ 67-56-1 ]
[ 136350-66-8 ]
[ 41841-16-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylsilane; cyclohexa-1,4-diene; oxygen; cobalt acetylacetonate In nonane at 24℃;

Reference： [1]Ma, Xiaoshen; Herzon, Seth B. [Journal of Organic Chemistry, 2016, vol. 81, # 19, p. 8673 - 8695]

20
[ 1115-70-4 ]
[ 136350-66-8 ]
6-(4-bromobenzyl)-N<SUP>2</SUP>,N<SUP>2</SUP>-dimethyl-1,3,5-triazine-2,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium phosphate; copper(l) iodide; indan-1,2,3-trione hydrate In 1,4-dioxane at 110℃; for 12h; Sealed tube;

Reference： [1]Zhang, Chen; Ban, Meng-Tao; Zhu, Kai; Zhang, Li-Yu; Luo, Zhen-Yu; Guo, Shun-Na; Cui, Dong-Mei; Zhang, Yu [Organic Letters, 2017, vol. 19, # 15, p. 3947 - 3949]

21
[ 3731-59-7 ]
[ 136350-66-8 ]
4-(4-bromobenzyl)-6-morpholino-1,3,5-triazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With copper(I) oxide; potassium phosphate; indan-1,2,3-trione hydrate In 1,4-dioxane at 110℃; for 12h; Sealed tube;

Reference： [1]Zhang, Chen; Ban, Meng-Tao; Zhu, Kai; Zhang, Li-Yu; Luo, Zhen-Yu; Guo, Shun-Na; Cui, Dong-Mei; Zhang, Yu [Organic Letters, 2017, vol. 19, # 15, p. 3947 - 3949]

22
[ 141-97-9 ]
[ 136350-66-8 ]
[ 111787-85-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium acetate; caesium carbonate; silver carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 12h; Inert atmosphere;	Synthesis of ethyl 5-aryl-2-methylfuran-3-carboxylate3a-h (General method). General procedure: Cs2CO3 (179 mg, 0.55 mmol),KOAc (49 mg, 0.50 mmol), and Ag2CO3(138 mg, 0.50 mmol)were added sequentially to a stirred solution of dibromide1a-h (0.25 mmol) and ethyl acetoacetate (2) (98 mg,0.75 mmol) in DMF (6 ml) at room temperature. Then thereaction mixture was stirred at 120°C under N2 for 12 h.After the completion of the reaction (TLC control, EtOAc-petroleum ether, 1:10), it was quenched with aqueous 1 MHCl solution (15 ml) and filtered. Then the filtrate wasextracted with EtOAc (3×5 ml), the combined organicextracts were washed with brine (15 ml) and H2O (2×10 ml),dried (Na2SO4), and concentrated under reduced pressure.The crude product was purified by column chromatographyon silica gel (EtOAc-petroleum ether, 1:10) to affordproducts 3a-h. All the known compounds gave satisfactoryspectroscopic values which are analogous to spectroscopicdata reported in the literature.

Reference： [1]Zhang, Wensheng; Xu, Wenjing [Chemistry of Heterocyclic Compounds, 2017, vol. 53, # 5, p. 615 - 617][Khim. Geterotsikl. Soedin., 2017, vol. 53, # 5, p. 615 - 617,3]

23
[ 109902-31-0 ]
[ 136350-66-8 ]
(Z)-5-(4-bromobenzylidene)-3,3-dimethyl-1-(pyridin-2-ylmethyl)pyrrolidin-2-one [ No CAS ]
(E)-5-(4-bromobenzylidene)-3,3-dimethyl-1-(pyridin-2-ylmethyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 36% 2: 30%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate In 1,4-dioxane at 140℃; for 24h; Schlenk technique; Sealed tube; Overall yield = 66 %;	General procedure for Pd-catalyzed 2-pyridylmethyl-directedβ-C(sp3)-H activation and cyclization of aliphatic amides withgem-dibromoolefins General procedure: A 25 mL Schlenk tube was charged with amide 1 (0.5 mmol), gem-dibromoolefin 2(1.0 mmol), Pd2(dba)3 (0.025 mmol), K2CO3 (1.0 mmol) and 1,4-dioxane (2 mL). Thetube was sealed under air atmosphere. The reaction mixture was stirred in an oil bathat 140 C for 24 h. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate, filtered through Celite, and the filtrate was concentrated.The crude residue was purified through a silica gel column (eluent: petroleumether/acetone = 5/1, v/v) to give pure 3 or 4.

Reference： [1]Zhou, Danni; Wang, Chunxia; Li, Mingliang; Long, Zheng; Lan, Jingbo [Chinese Chemical Letters, 2018, vol. 29, # 1, p. 191 - 193]

24
[ 591-50-4 ]
[ 136350-66-8 ]
[ 13667-12-4 ]

Yield	Reaction Conditions	Operation in experiment
49%		General procedure: A mixture of gem-dibromoalkene 1 (0.68 mmol), Cs2CO3 (2.4 mmol) and DMSO (2 ml) was stirred at 115oC for 15 h. After 1 was completely consumed, iodobenzene (0.4 mmol) and Pd/C (5 mol%) were addedand the reaction was deaerated with nitrogen gas and stirred at 80 oC for 25 h. After finished, the reactionwas cooled down to room temperature and diluted with ethyl acetate and water for extraction. Thecombined organic phase from three time extraction was dried over anhydrous MgSO4. After removal ofthe solvent, the residue was subjected to column chromatography on silica gel to obtain alkyne 3 in highpurity.

Reference： [1]Synlett,2018,vol. 29,p. 209 - 214

25
[ 136350-66-8 ]
[ 778641-02-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With Ir(ppy)<SUB>2</SUB>(bpy); N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 36h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;	3. General Procedure for Synthesis of 2. General procedure: An 25 mL oven-dried Schlenk tube was equipped with a stirring bar and Ir(ppy)2(bpy)PF6 (0.004mmol, 1 mol%). The Schlenk tube was degassed by using standard Schlenk techniques with an oil pump. Then 1,1-dibromoalkenes 1 (0.4mmol), iPr2NEt ( 1.2mmol, 3 eq.) and DCE (4 mL) were injected into the reaction tube. The reaction mixture was placed at a distance of about 5 cm from a blue LEDs and stirred at room temperature for 36h. The reaction mixture was diluted with DCM (30 mL) and 0.1 M HCL solution (2 x 20mL). The layers were separated. The aqueous layer was extracted with DCM (2 x 30 mL). The combined organic layers were washed with H2O (2 x 10 mL) and then were dried over Na2SO4. Afterwards, the organic solution was concentrated under reduced pressure using a rotary evaporator and purification was done by column chromatography on silica gel (200-300 mesh) with petroleum ether as the eluent to give the pure product 2.
	With triethylamine; Dimethyl phosphite In N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere;
	With triethylamine; phosphonic acid diethyl ester In N,N-dimethyl-formamide at 0 - 20℃;

Reference： [1]Sun, Wencheng; Teng, Qiaoling; Cheng, Dongping; Li, Xiaonian; Xu, Xiaoliang [Tetrahedron Letters, 2020, vol. 61, # 3]
[2]Chen, Haifeng; Gong, Hegui; Yao, Ken; Ye, Yang [Organic Letters, 2020]
[3]Zhao, Jiangui; Zheng, Xueli; Tao, Shaokun; Zhu, Yuxin; Yi, Jiwei; Tang, Songbai; Li, Ruixiang; Chen, Hua; Fu, Haiyan; Yuan, Maolin [Organic Letters, 2021, vol. 23, # 15, p. 6067 - 6072]

26
[ 286-20-4 ]
[ 136350-66-8 ]
2-((4-bromophenyl)ethynylselanyl)cyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With selenium; copper(l) iodide; 1,10-Phenanthroline; tetra-(n-butyl)ammonium iodide; sodium hydroxide In water at 50℃; for 24h;	4 Synthesis of 2-(4-bromophenylethynylselenyl) cyclohexanol compound At room temperature, the cyclohexene oxide (1.2mmol, 3equiv), Elemental selenium (1.2mmol, 3equiv), 1-(2,2-Dibromovinyl) 4-bromobenzene (0.4 mmol, 1 equiv), Cuprous iodide (0.08mmol, 0.2equiv), 1,10-phenanthroline (0.08mmol, 0.2equiv), Tetrabutylammonium iodide (1.2mmol, 3equiv), Sodium hydroxide (1.2mmol, 3equiv) and 2mL water were added to the reaction tube, Tighten it with a Teflon stopper, Stir at 50°C reaction temperature for 24h. After the reaction, the reaction mixture was cooled, Then add ethyl acetate to dilute, Transfer the diluted solution to the separatory funnel, Extract with saturated brine, separate the water phase and the organic phase, Then extract the aqueous phase 3 times with ethyl acetate, combine the organic phases, Add 5g of anhydrous sodium sulfate and let stand for 30min, Wash the filter cake 3 times with 5mL ethyl acetate each time, and then spin off the solvent. The product was separated by column chromatography (eluent: petroleum ether: diethyl ether = 98: 2), The product is a white liquid, The yield was 69%, and the weight of the product was 99 mg.

Reference： [1]Current Patent Assignee: WENZHOU MEDICAL UNIVERSITY - CN112010795, 2020, A Location in patent: Paragraph 0064-0073

27
[ 120-72-9 ]
[ 136350-66-8 ]
C₁₆H₁₀BrN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium phosphate; copper(l) iodide; tetrabutylammomium bromide In N,N-dimethyl-formamide at 110℃; for 6h; Schlenk technique; Inert atmosphere;

Reference： [1]Rao, Maddali L. N.; Islam, Sk Shamim; Dasgupta, Priyabrata [Organic and Biomolecular Chemistry, 2021, vol. 19, # 36, p. 7855 - 7860]

28
[ 1576-37-0 ]
[ 136350-66-8 ]
N-benzyl-N-((4-bromophenyl)ethynyl)-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With Cupric sulfate; N,N,N,N,-tetramethylethylenediamine; potassium hydroxide In water monomer at 60℃; for 8h;	III General Procedure D for the Synthesis of Ynamides inWater General procedure: To an oven-dried 4 mL vial, N-nucleophile (0.2 mmol, 1 equiv) was added followed byCuSO4•5H2O (0.02 mmol, 10 mol%), KOH (0.8 mmol, 4 equiv), 2 wt.% APGS-2000-M/H2O (0.4mL, 0.5 M), dibromoalkenes (0.3 mmol, 1.5 equiv), and DMEDA (0.04 mmol, 20 mol%). Theresulting mixture was stirred at 60 °C for 8 h. Upon the completion monitored by TLC, thereaction was cooled to room temperature and extracted with ethyl acetate, combined the organic layers then concentrated under reduced pressure. The crude product was further purified by flashcolumn chromatography with a 5% ethyl acetate in petroleum ether to afford the desired product.

Reference： [1]Huang, Shenlin; Zhang, Yingyin; Zheng, Yu; Zhu, Baolong [Journal of Organometallic Chemistry, 2022, vol. 965-966]

29
[ 1007-47-2 ]
[ 136350-66-8 ]
C₂₄H₁₅Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tripotassium phosphate tribasic; palladium diacetate; 1,2-(diphenylphosphino)ethane In tetrahydrofuran at 60℃; for 6h; Inert atmosphere;

Reference： [1]Jia, Xiao-Ying; Li, Qing-Han; Wu, Chuan; Wu, Kun; Zhou, Lin [RSC Advances, 2022, vol. 12, # 21, p. 13314 - 13318]

30
[ 1638189-19-1 ]
[ 136350-66-8 ]
C₂₆H₁₉Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tripotassium phosphate tribasic; palladium diacetate; 1,2-(diphenylphosphino)ethane In tetrahydrofuran at 60℃; for 6h; Inert atmosphere;

Reference： [1]Jia, Xiao-Ying; Li, Qing-Han; Wu, Chuan; Wu, Kun; Zhou, Lin [RSC Advances, 2022, vol. 12, # 21, p. 13314 - 13318]

31
[ 136350-66-8 ]
C₁₀H₁₀AlF [ No CAS ]
C₂₄H₁₃BrF₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tripotassium phosphate tribasic; palladium diacetate; 1,2-(diphenylphosphino)ethane In tetrahydrofuran at 60℃; for 6h; Inert atmosphere;

Reference： [1]Jia, Xiao-Ying; Li, Qing-Han; Wu, Chuan; Wu, Kun; Zhou, Lin [RSC Advances, 2022, vol. 12, # 21, p. 13314 - 13318]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	136350-66-8	MDL No. :	MFCD00273344
Formula :	C₈H₅Br₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	340.84 g/mol	Pubchem ID :	-
Synonyms :

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 136350-66-8 ]

Quality Control of [ 136350-66-8 ]

Related Doc. of [ 136350-66-8 ]

Product Details of [ 136350-66-8 ]

Safety of [ 136350-66-8 ]

Application In Synthesis of [ 136350-66-8 ]

[ 136350-66-8 ] Synthesis Path-Upstream 1~2

[ 136350-66-8 ] Synthesis Path-Downstream 1~31

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry