Name: 28469-92-3|1,3-Dichloro-2-vinylbenzene|98%
Brand: Ambeed
SKU: A533823
Price: 12.0 USD
Availability: InStock
Rating: 92 (32 reviews)

1
[ 28469-92-3 ]
[ 7623-19-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	General procedure A: epoxidation of styrenes General procedure: To a stirred solution of desired styrene 8 (0.03 mol, 1 equiv.) in DCM (125 mL) was slowlyadded mCPBA (0.1 mol, 2 equiv.) at 0 °C and the resulting reaction mixture was warmed to roomtemperature and stirred for 12 h. The progress of the reaction was monitored by TLC. Aftercompletion of the reaction, the reaction mixture was quenched with aqueous NaOH (3M, 100 mL)and extracted with DCM (3×50 mL). The combined organic layer was washed with brine, driedover anhydrous Na2SO4 and concentrated under reduced pressure to give a pure product (9d-9d).
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 15h;
	With perchloric acid; [(1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclotridecane)FeIII-(iodosylbenzene)]³⁺ In 2,2,2-trifluoroethanol; acetone at -60℃; for 0.166667h; Inert atmosphere; Schlenk technique;

With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 16h;

Reference： [1]Alberts, Ian; Giri, Rajan; Harding, Wayne W.; Namballa, Hari K.; Sarker, Ananta [Bioorganic and medicinal chemistry letters, 2020, vol. 30, # 16]
[2]Efange, Simon M. N.; Kamath, Ashok P.; Khare, Anil B.; Kung, Mei-Ping; Mach, Robert H.; Parsons, Stanley M. [Journal of Medicinal Chemistry, 1997, vol. 40, # 24, p. 3905 - 3914]
[3]Wang, Bin; Lee, Yong-Min; Seo, Mi Sook; Nam, Wonwoo [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11740 - 11744][Angew. Chem., 2015, vol. 127, # 40, p. 11906 - 11910,5]
[4]Verma, Vishal A.; Wang, Lan; Labadie, Sharada S.; Liang, Jun; Sellers, Benjamin D.; Wang, Jian; Dong, Liting; Wang, Qiuyue; Zhang, Shuang; Xu, Zhongya; Zhang, Yexia; Niu, Yanan; Wang, Xinxin; Wai, John; Koehler, Michael F. T.; Hu, Huiyong; Alexander, Mary Kate; Nishiyama, Mireille; Miu, Anh; Xu, Yiming; Pang, Jodie; Katakam, Anand K.; Reichelt, Michael; Austin, Cary D.; Ho, Hoangdung; Payandeh, Jian; Koth, Christopher M. [Journal of Medicinal Chemistry, 2022, vol. 65, # 5, p. 4085 - 4120]

2
[ 28469-92-3 ]
[ 371-40-4 ]
4-chloro-N-(4-fluorophenyl)-2,3-dihydroindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium <i>tert</i>-butylate In toluene at 135℃; for 36h;

Reference： [1]Beller, Matthias; Breindl, Claudia; Riermeier, Thomas H.; Eichberger, Martin; Trauthwein, Harald [Angewandte Chemie - International Edition, 1999, vol. 37, # 24, p. 3389 - 3391] Beller; Breindl; Riermeier; Tillack [Journal of Organic Chemistry, 2001, vol. 66, # 4, p. 1403 - 1412]

3
[ 28469-92-3 ]
[ 258345-73-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With bromine In chloroform at 20℃; for 0.5h;
	With bromine In tetrachloromethane at 20℃; for 2h;

Reference： [1]Cecchetti, Violetta; Tabarrini, Oriana; Sabatini, Stefano; Miao, Hua; Filipponi, Enrica; Fravolini, Arnaldo [Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 11, p. 2465 - 2471]
[2]De, Aramita; Santra, Sougata; Hajra, Alakananda; Zyryanov, Grigory V.; Majee, Adinath [Journal of Organic Chemistry, 2019, vol. 84, # 18, p. 11735 - 11740]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydrogensulfate; 4-tert-Butylcatechol at 220 - 230℃;
	Leiten des Dampfes ueber Aluminiumoxyd;

5
[ 28469-92-3 ]
(S)-1-(2,6-dichlorophenyl)ethan-1-ol [ No CAS ]
(R)-1-(2,6-dichlorophenyl)ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2,6-dichlorostyrene With benzo[1,3,2]dioxaborole In toluene at 20℃; for 2h; Stage #2: With sodium hydroxide; water; dihydrogen peroxide In toluene at 20℃; for 2h; Title compound not separated from byproducts;

Reference： [1]Doucet, Henri; Fernandez, Elena; Layzell, Timothy P.; Brown, John M. [Chemistry - A European Journal, 1999, vol. 5, # 4, p. 1320 - 1330]

6
[ 30595-79-0 ]
[ 118-69-4 ]
[ 28469-92-3 ]
[ 289058-20-4 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 4011 - 4014

7
[ 348-54-9 ]
[ 28469-92-3 ]
4-chloro-N-(2-fluorophenyl)-2,3-dihydroindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium <i>tert</i>-butylate In toluene at 135℃; for 36h;

Reference： [1]Beller; Breindl; Riermeier; Tillack [Journal of Organic Chemistry, 2001, vol. 66, # 4, p. 1403 - 1412]

8
[ 28469-92-3 ]
[ 610-49-1 ]
N-(1-anthracenyl)-4-chloro-2,3-dihydroindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With potassium <i>tert</i>-butylate In toluene at 135℃; for 36h;

Reference： [1]Beller; Breindl; Riermeier; Tillack [Journal of Organic Chemistry, 2001, vol. 66, # 4, p. 1403 - 1412]

9
[ 28469-92-3 ]
[ 36635-61-7 ]
[ 76304-48-8 ]

Yield	Reaction Conditions	Operation in experiment
48%	With sodium t-butanolate In dimethyl sulfoxide at 100℃; for 18h;

Reference： [1]Smith, Nicholas D.; Huang, Dehua; Cosford, Nicholas D. P. [Organic Letters, 2002, vol. 4, # 20, p. 3537 - 3539]

10
[ 28469-92-3 ]
[ 69226-51-3 ]
2-(2,6-dichloro-phenyl)-aziridine-1-sulfonic acid 2,2,2-trichloro-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With [bis(acetoxy)iodo]benzene; magnesium oxide In chlorobenzene at -10 - 23℃; for 8h;

Reference： [1]Guthikonda, Kiran; Wehn, Paul M.; Caliando, Brian J.; Du Bois [Tetrahedron, 2006, vol. 62, # 49, p. 11331 - 11342]

11
[ 28469-92-3 ]
[ 33512-94-6 ]
(+/-)-5-(2,6-dichlorophenyl)-3-(3-nitrophenyl)-2-isoxazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran for 3h;	6.1.4; 22 6.1.4 Synthesis of (+/-)-2,2-DICHLORO-N-[3-[5-(2,6-DICHLOROPHENYL)-3-(2-ISOXAZOLINYL)]PHENYL] ACETAMIDE (TABLE 6, Compound 37) (See Figure 22); Synthesis of (+/-)-5-(2,6-DICHLOROPHENYL)-3-(3-NITROPHENYL)-2-ISOXAZOLINE; Figure 22; Reverse 2-isoxazoline 2,6-DICHLORO-N-HYDROXYBENZENECARBOXIMIDOYL chloride (1.01 g, 4.5 mmol) and 2,2-dichloro-N- (4-ethynylphenyl) acetamide (1. 01 g, 4.42 mmol) were dissolved in anhydrous THF (40 mL) and triethylamine (1.0 mL). The mixture was stirred at room temperature for I h then heated at reflux for 4h to generate the 2,6-dichlorophenyl nitrile oxide intermediate, which reacted by a 1,3- dipolar cycloaddition reaction with 2, 2-DICHLORO-N- (4-ETHYNYLPHENYL) acetamide. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed successively with water and brine. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid was purified by column chromatography on silica gel, eluting with 8: 2 hexanes-ethyl acetate. The appropriate fractions were combined to give 2, 2-dichloro-N- [4- [3- (2, 6-dichlorophenyl) -5-isoxazolyl] phenyl] acetamide as a tan solid. NMR (300 MHz, CDC13) : 8.28 (broad s, 1H, NH), 7.88 (m, 2H), 7.72 (m, 2H), 7.44 (m, 2H), 7.36 (m, 1H), 6.62 (s, 1H), 6. 08 ppm (s, 1H). MW=416 confirmed by LC-MS, TR-20. 45 min (Method X) MH+=415-419.

Reference： [1]Current Patent Assignee: RIGEL PHARMACEUTICALS INC - WO2004/99165, 2004, A2 Location in patent: Page 54; 40/84

12
[ 28469-92-3 ]
[ 1019321-44-8 ]

Yield	Reaction Conditions	Operation in experiment
30 % Chromat.	With ammonium hydroxide; sodium hypochlorite; ammonium iodide In water at 24.84℃; for 2h;

Reference： [1]Varszegi, Csaba; Ernst, Martin; Van Laar, Frederik; Sels, Bert F.; Schwab, Ekkehard; De Vos, Dirk E. [Angewandte Chemie - International Edition, 2008, vol. 47, # 8, p. 1477 - 1480]

13
[ 28469-92-3 ]
[ 83-38-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium periodate In water; ethyl acetate; acetonitrile at 0℃; for 3.5h;
58%	With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 70℃; for 24h; Green chemistry; chemoselective reaction;

Reference： [1]Location in patent: experimental part Vijay Kumar; Prakash Reddy; Sridhar; Srinivas; Rama Rao [Synlett, 2009, # 5, p. 739 - 742]
[2]Gonzalez-De-Castro, Angela; Xiao, Jianliang [Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8206 - 8218]

14
[ 28469-92-3 ]
[ 122951-11-5 ]
[ 1159425-68-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With palladium diacetate; triethylamine; triphenylphosphine at 100℃;

Reference： [1]Shahzad, Sohail A.; Wirth, Thomas [Angewandte Chemie - International Edition, 2009, vol. 48, p. 2588 - 2591][Angew. Chem., Int. Ed., 2009, vol. 121, p. 2626 - 2628]

15
[ 74-85-1 ]
[ 19230-28-5 ]
[ 28469-92-3 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 1102 - 1110

16
[ 28469-92-3 ]
[ 23037-39-0 ]
[ 1222887-71-9 ]

Yield	Reaction Conditions	Operation in experiment
49%	With N-[menthyloxycarbonyl]-L-leucine; silver(I) acetate; palladium diacetate; lithium carbonate In Hexafluorobenzene at 80℃; for 48h;

Reference： [1]Lu, Yi; Wang, Dong-Hui; Engle, Keary M.; Yu, Jin-Quan [Journal of the American Chemical Society, 2010, vol. 132, # 16, p. 5916 - 5921]

17
[ 28469-92-3 ]
[ 657-84-1 ]
[ 1346705-02-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium periodate; acetic acid; potassium iodide In acetonitrile at 20℃; for 3h;

Reference： [1]Location in patent: experimental part Das, Biswanath; Lingaiah, Maram; Damodar, Kongara; Bhunia, Nisith [Synthesis, 2011, # 18, p. 2941 - 2944]

18
[ 28469-92-3 ]
Umemoto's reagent [ No CAS ]
[ 75-05-8 ]
[ 1431153-03-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; water at 20℃; for 4h; Inert atmosphere; UV-irradiation; Schlenk technique; regioselective reaction;

Reference： [1]Yasu, Yusuke; Koike, Takashi; Akita, Munetaka [Organic Letters, 2013, vol. 15, # 9, p. 2136 - 2139]

19
[ 201230-82-2 ]
[ 28469-92-3 ]
[ 58288-30-5 ]
N,N-dibenzyl-3-(2,6-dichlorophenyl)propanamide [ No CAS ]
C₂₃H₂₁Cl₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With palladium(II) trifluoroacetate; 1,5-bis-(diphenylphosphino)pentane; glycine ethyl ester hydrochloride In water at 120℃; for 21h; Autoclave; regioselective reaction;

Reference： [1]Zhang, Guoying; Gao, Bao; Huang, Hanmin [Angewandte Chemie - International Edition, 2015, vol. 54, # 26, p. 7657 - 7661][Angew. Chem., 2015, vol. 127, p. 7767 - 7771,5]

20
[ 28469-92-3 ]
[ 1576-35-8 ]
C₁₅H₁₃Cl₂IO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With tert.-butylhydroperoxide; iodine In tetrahydrofuran at 0 - 20℃; for 12h;

Reference： [1]Sun, Kai; Lv, Yunhe; Zhu, Zhonghong; Jiang, Yongqing; Qi, Jiejie; Wu, Hankui; Zhang, Zhiguo; Zhang, Guisheng; Wang, Xin [RSC Advances, 2015, vol. 5, # 63, p. 50701 - 50704]

21
[ 28469-92-3 ]
[ 127-65-1 ]
2-(2,6-dichlorophenyl)-1-tosylaziridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: chloramine-T With tetrabutylammonium bromide; C₁₃H₂₁N₄O₆PZr In 1,2-dichloro-ethane for 0.0833333h; Inert atmosphere; Stage #2: 1,3-dichloro-2-vinylbenzene In 1,2-dichloro-ethane at 20℃; for 16h; Inert atmosphere;
45%	In acetonitrile at 25℃; for 12h; Inert atmosphere;

Reference： [1]Pinarci, Ali A.; Daniecki, Noah; TenHoeve, Tyler M.; Dellosso, Brandon; Madiu, Rufai; Mejia, Liliana; Bektas, Seda E.; Moura-Letts, Gustavo [Chemical Communications, 2022, vol. 58, # 31, p. 4909 - 4912]
[2]Sayyad, Masthanvali; Nanaji, Yerramsetti; Ghorai, Manas K. [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12659 - 12667]

22
[ 201230-82-2 ]
[ 28469-92-3 ]
[ 103-49-1 ]
N,N-dibenzyl-3-(2,6-dichlorophenyl)propanamide [ No CAS ]
C₂₃H₂₁Cl₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With bis(η3-allyl-μ-chloropalladium(II)); hydroxylamine hydrochloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; for 24h; Autoclave;	3.1 General procedure for the hydroaminocarbonylation of amines General procedure: A mixture of alkenes 1 (1.0 mmol), amines 2 (0.5 mmol), [Pd(allyl)Cl]2 (3.7 mg,0.01 mmol), Xantphos (14.5 mg, 0.025 mmol), NH2OH·HCl (36.8 mg, 0.5 mmol), and anisole (2.0 mL) were added into a glass tube which was placed in an autoclave. Then the autoclave was purged and charged with CO at 10 atm. The reaction mixture wasstirred at 120 oC for 24 hours. After the reaction finished, the autoclave was cooled to room temperature and the pressure was carefully released. The regioselectivity were measured by GC and GC-MS. Then the corresponding reaction mixture was purified by flash column chromatography on a silica gel column (petroleum ether/ethyl acetate= 10/1 - 2/1) to give the desired products 3.

Reference： [1]Zhang, Guoying; Ji, Xiaolei; Yu, Hui; Yang, Lei; Jiao, Peng; Huang, Hanmin [Tetrahedron Letters, 2016, vol. 57, # 3, p. 383 - 386]

23
[ 28469-92-3 ]
mesityl(4-(pentafluoro-λ⁶-sulfanyl)phenyl)iodonium 4-methylbenzenesulfonate [ No CAS ]
1-(2,6-dichlorophenyl)-2-(4-(pentafluoro-λ⁶-sulfanyl)phenyl)ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With [Ru(bpy)₃](PF₆)₂; water In acetone at 20℃; for 18h; Inert atmosphere; Irradiation; Schlenk technique;	General procedures for the hydoxy(pentafluorosulfanyl)phenylation of styrenes 2 (Table 1) General procedure: A 20 mL Schlenk tube was charged with [Ru(bpy)3](PF6)2 (1.4 mg, 1.7 μmol), 1 (0.17 mmol), dryacetone (1.8 mL), water (0.2 mL), and styrene derivative 2 (0.67 mmol) under N2 atmosphere. Themixture was degassed by three freeze-pump-thaw cycles. The reaction was carried out at roomtemperature (water bath) under irradiation of visible light (placed at a distance of ~3 cm from blueLED lamp: λ = 425 ± 15 nm). After the reaction, H2O was added. The resulting mixture wasextracted with CH2Cl2, washed with H2O, dried (MgSO4), and filtered. The filtrate wasconcentrated in vacuo and the residue was purified by the chromatography or chromatography andGPC.

Reference： [1]Li, Yanjie; Koike, Takashi; Akita, Munetaka [Synlett, 2016, vol. 27, # 5, p. 736 - 740]

24
[ 7677-24-9 ]
[ 28469-92-3 ]
[ 4559-70-0 ]
2-(2,6-dichlorophenyl)-3-(diphenylphosphoryl)propanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With manganese(II) acetate; copper(I) bromide In acetonitrile at 50℃; Inert atmosphere;	14.1; 14.2; 14.3 Example 14: Synthesis of 2- (2,6-dichlorophenyl) -3-diphenoxyphosphinylpropanenitrile The reaction procedure is as follows: 2,6-dichlorostyrene and diphenylphosphine oxide as raw materials,(0.069 g, 0.4 mmol), diphenylphosphine oxide (0.162 g, 0.8 mmol), trimethylcyanosilane (0.120 g, 1.2 mmol), CuBr (0.056) was added to the reaction flask G, 0.04 mmol), manganese acetate (0.322 g, 1.2 mmol) and acetonitrile (3 mL) under argon at 50 ° C; TLC followed the reaction until complete;The crude product obtained after the completion of the reaction was separated by column chromatography (ethyl acetate: petroleum ether = 1: 1) to give the desired product (yield 84%).
79%	With copper(l) cyanide; manganese(III) triacetate dihydrate In N,N-dimethyl-formamide at 20℃; for 3h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN106432329, 2017, A Location in patent: Paragraph 0031
[2]Zhang, Pei-Zhi; Zhang, Ling; Li, Jian-An; Shoberu, Adedamola; Zou, Jian-Ping; Zhang, Wei [Organic Letters, 2017, vol. 19, # 20, p. 5537 - 5540]

25
[ 201230-82-2 ]
[ 28469-92-3 ]
[ 58288-30-5 ]
N,N-dibenzyl-3-(2,6-dichlorophenyl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With palladium(II) trifluoroacetate; 1,5-bis-(diphenylphosphino)pentane; glycine ethyl ester hydrochloride; methoxybenzene In water at 120℃; for 21h;	22 The 2, 6 - dichloro ethylene (0.8 mmol), amine acetal 2a (81.2 mg, 0.2 mmol), Pd (TFA)2(3.3 mg, 0 . 01 mmol), DPPPen (5.3 mg, 0 . 012 mmol), NH2 CH2 CO2 Me·HCl (0.04 mmol), H2 O (4 μL, 0 . 22 mmol) is added 1.0 ml anisole in, carbon monoxide (10 atm), 120 o C reaction 21 hours after stopping the reaction, of the drying solvent, ethyl acetate/petroleum ether column chromatography (1:10), get the pure product amide derivatives 3la. The product is a white solid, 98.7 mg, yield 62%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104926578, 2017, B Location in patent: Paragraph 0123-0129

26
[ 28469-92-3 ]
1-(6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)azetidin-2-one [ No CAS ]
(E)-1-(6-(2,6-dichlorostyryl)-1,2,3,4-tetrahydronaphthalen-2-yl)azetidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26 mg	With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); potassium carbonate In N,N-dimethyl-formamide at 130℃; for 1.5h; Microwave irradiation;	18.2 18.2 18.2 (E)-1-(6-(2,6-dichlorostyryl)-1,2,3,4-tetrahydronaphthalen-2-yl)azetidin-2-one A microwave tube was charged with 1-(6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)azetidin-2-one (50 mg, 0.178 mmol), acetoxy(2-(di-o-tolylphosphino)benzyl)palladium (Herrmann's Catalyst) (3.35 mg, 3.57 μmol), 2,6-dichlorostyrene (31 mg 0.178 mmol) and potassium carbonate (49.3 mg, 0.357 mmol) in DMF (1 ml), placed in a microwave and heated to 130° C. for 1.5 h. The resulting mixture was diluted with water and extracted with DCM, which was dried over MgSO4, filtrated and evaporated The residue was purified by chromatography (silica gel) affording 26 mg (E)-1-(6-(2,6-dichlorostyryl)-1,2,3,4-tetrahydronaphthalen-2-yl)azetidin-2-one as a pale white solid.

Reference： [1]Current Patent Assignee: ABBVIE INC - US2017/174672, 2017, A1 Location in patent: Paragraph 0785

27
[ 28469-92-3 ]
[ 1666-13-3 ]
[ 1576-35-8 ]
C₂₁H₁₈Cl₂O₂SSe [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With dipotassium peroxodisulfate; potassium iodide In acetonitrile at 20℃; for 12h; regioselective reaction;	General procedure: Styrene 1a (0.3 mmol), 4-methyl benzene sulfonyl hydrazine 2a (0.6 mmol), diphenyl diselenide (0.3 mmol), K2S2O8 (0.6 mmol), KI (0.2 equiv.), and CH3CN (2.0 mL) at 20 °C for 12 h (monitored by thin-layer chromatography (TLC)), quenched with water, extracted with dichloromethane (5×3 mL), and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by a shot flash silica gel column chromatography (EtOAc/petro ether=1:8)to give compound 3a as a white solid (111.1 mg, 89%).

Reference： [1]Sun, Kai; Lv, Yunhe; Shi, Zuodong; Fu, Fangfang; Zhang, Chong; Zhang, Zhiguo [Science China Chemistry, 2017, vol. 60, # 6, p. 730 - 733]

28
[ 28469-92-3 ]
[ 4559-70-0 ]
2-(2,6-dichlorophenyl)-2-hydroxyiminoethyldiphenylphosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tert.-butylnitrite; silver nitrate In ethanol; water at 20℃;	14 Example 14: Synthesis of 2-(2,6-dichlorophenyl)-2-hydroxyiminoethyldiphenylphosphine oxide Using 2,6-dichlorostyrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:(1) Add 2,6-dichlorostyrene (0.069 g, 0.4 mmol) to the reaction flask.Phosphorus phenoxide (0.162 g, 0.8 mmol),Tert-butyl nitrite (0.123 g, 1.2 mmol),Silver nitrate (0.07 g, 0.04 mmol),Water (1 mL) and ethanol (1.5 mL) were reacted at room temperature;(2) TLC tracks the reaction until complete;(3) The crude product obtained after completion of the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to give the target product (yield 71%)

Reference： [1]Current Patent Assignee: CHINASUN SPECIALTY PRODUCTS - CN107573378, 2018, A Location in patent: Paragraph 0039

29
[ 106-24-1 ]
[ 28469-92-3 ]
(E)-1,3-dichloro-2-(2-((3,7-dimethylocta-2,6-dien-1-yl)oxy)ethyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With phosphazene base-P₄-tert-butyl In hexane; m-xylene at 100℃; for 24h; Inert atmosphere;

Reference： [1]Luo, Chaosheng; Bandar, Jeffrey S. [Journal of the American Chemical Society, 2018, vol. 140, # 10, p. 3547 - 3550]

30
[ 56539-66-3 ]
[ 28469-92-3 ]
1,3-dichloro-2-(2-(3-methoxy-3-methylbutoxy)ethyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With phosphazene base-P₄-tert-butyl In hexane; m-xylene at 100℃; for 24h; Inert atmosphere;

Reference： [1]Luo, Chaosheng; Bandar, Jeffrey S. [Journal of the American Chemical Society, 2018, vol. 140, # 10, p. 3547 - 3550]

31
[ 28469-92-3 ]
[ 389573-45-9 ]
(3R,4S)-3-((2,6-dichlorophenethoxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With phosphazene base-P₄-tert-butyl In hexane; 1,3,5-trimethyl-benzene at 110℃; for 24h; Inert atmosphere;

Reference： [1]Luo, Chaosheng; Bandar, Jeffrey S. [Journal of the American Chemical Society, 2018, vol. 140, # 10, p. 3547 - 3550]

32
[ 72351-36-1 ]
[ 28469-92-3 ]
1-benzhydryl-3-((2,6-dichlorophenethoxy)methyl)azetidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With phosphazene base-P₄-tert-butyl In hexane; 1,3,5-trimethyl-benzene at 120℃; for 24h; Inert atmosphere;

Reference： [1]Luo, Chaosheng; Bandar, Jeffrey S. [Journal of the American Chemical Society, 2018, vol. 140, # 10, p. 3547 - 3550]

33
[ 2290-65-5 ]
[ 28469-92-3 ]
[ 4559-70-0 ]
diphenyl (2-(2,6-dichlorophenyl)-2-thiocyanoethyl)phosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With [2,2]bipyridinyl; manganese(II) acetate; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 30℃;	8 Example 8 Synthesis of Diphenyl (2-(2,6-Dichlorophenyl)-2-thiocyanoethyl)phosphine Oxide Using 2,6-dichlorostyrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:The reaction flask was charged with 2,6-dichlorostyrene (0.069 g, 0.4 mmol), phenoxyphosphine (0.242 g, 1.2 mmol), trimethylsilyl isothiocyanate (0.105 g, 0.08 mmol),CuCl (0.04 g, 0.04 mmol), bipyridyl (0.006 g, 0.04 mmol), manganese acetate (0.322 g, 1.2 mmol) and N-methylpyrrolidone (5 mL), reaction at 30°C;TLC tracks the reaction until it is completely over;The crude product obtained after the reaction is completed is separated by column chromatography (ethyl acetate:dichloromethane = 1:10).The target product was obtained (yield 75%).

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN107556340, 2018, A Location in patent: Paragraph 0032

34
[ 28469-92-3 ]
[ 108-24-7 ]
1-(2,6-dichlorophenyl)ethane-1,2-diyl diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With 2,2':6,2''-terpyridine; oxygen; palladium diacetate; acetic acid; bis(pinacol)diborane In acetonitrile at 90℃; for 48h; Sealed tube;

Reference： [1]Huang, Jiuzhong; Ouyang, Lu; Li, Jianxiao; Zheng, Jia; Yan, Wuxin; Wu, Wanqing; Jiang, Huanfeng [Organic Letters, 2018, vol. 20, # 17, p. 5090 - 5093]

35
[ 28469-92-3 ]
[ 4559-70-0 ]
(2-(2,6-dichlorophenyl)-2-hydroxyethyl)diphenylphosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With manganese triacetate In methanol at 30℃; for 1h;	Representative Procedure for the Preparation of β-Hydroxyphosphine oxides 3 General procedure: To a stirring solution of alkene (1.0 mmol) and diphenylphosphine oxide (2.0 mmol) in MeOH (5 mL) at 30 °C was added Mn(OAc)3 (2.0 mmol) in portions over 30 minutes. After the completion of reaction as indicated by TLC (about 30 minutes later), the mixture was cooled and the solvent was removed under vacuum. The pure product 3 was obtained by column chromatography on silica gel using petroleum ether/EtOAc/CH2Cl2 (4:1:1) as eluent.

Reference： [1]Shoberu, Adedamola; Li, Shuai-Shuai; Zhang, Guo-Yu; Li, Da-Peng; Zou, Jian-Ping [Tetrahedron, 2019, vol. 75, # 47]

36
[ 623-73-4 ]
[ 28469-92-3 ]
ethyl 5-(2,6-dichlorophenyl)-4,5-dihydroisoxazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tert.-butylnitrite; 1,1,1,3',3',3'-hexafluoro-propanol; tetrabutylammonium tetrafluoroborate In dichloromethane at 20 - 25℃; for 1h; Inert atmosphere; Electrolysis;

Reference： [1]Xiong, Mingteng; Liang, Xiao; Gao, Zhan; Lei, Aiwen; Pan, Yuanjiang [Organic Letters, 2019, vol. 21, # 23, p. 9300 - 9305]

37
[ 28469-92-3 ]
[ 107-18-6 ]
1,3-dichloro-2-{2-iodo-1-[(prop-2-en-1-yl)oxy]ethyl}benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With iodine; clinoptilolite at -5 - 20℃; regioselective reaction;	1,3-Dichloro-2-{2-iodo-1-[(prop-2-en-1-yl)oxy]-ethyl}benzene (4). A mixture of 14 g (0.25 mol) of allyl alcohol and 44.8 g (0.25 mol) of 2,6-dichlorostyrenewas cooled to -5 to 0°C, 2.6 g of clinoptilolite [(NaK)4CaAl6Si30O72] was added with vigorous stirring, and 31.5 g (0.12 mol) of finely ground crystalline iodine was then added in 1-g portions. The mixture was stirred at room temperature for 3-4 h and filtered, and the filtrate was washed with a solution of Na2S2O3 and extracted with diethyl ether. The extract was dried over CaCl2 and evaporated on a rotary evaporator, and the residue was recrystallized from an appropriate solvent. Yield 30.4 g (68%), mp 98-99°C (from EtOH). IR spectrum, ν, cm-1: 3080, 3010, 1640, 1630, 1515, 1360, 1270, 842, 560. 1H NMR spectrum, δ, ppm: 3.22 d.d and 3.51 d.d (1H each, CH2I, J = 10.3,5.8 Hz), 4.00 d.d (2H, CH2O, 3J = 5.7, 4J = 1.5 Hz),4.43 d.d (1H, CH, J = 5.8, 9.0 Hz), 5.17 d.d.t (1H,H2C=, Jcis = 10.4, 2J = 4J = 1.6 Hz), 5.26 d.d.d (1H,H2C=, Jtrans = 17.3, 2J = 4J = 1.7 Hz), 5.89 d.d.t (1H,CH=, Jcis = 10.4, 2J = 4J = 1.6, Jtrans = 17.3 Hz), 7.29 d(1H, C6H3, J = 8.8 Hz), 7.54 d.d (1H, C6H3, J = 8.8,2.7 Hz), 7.69 d.d (1H, C6H3, J = 8.8, 2.7 Hz). 13C NMR spectrum, δC, ppm: 55.3, 69.9, 80.5, 114.0, 117.4,127.8, 131.9, 133.1 (C3), 135.6 (C1), 134.9, 159.6.Found, %: C 37.41; H 3.55; Cl 19.46; I 35.58.C11H11Cl2IO. Calculated, %: C 37.01; H 3.11;Cl 19.86; I 35.55.

Reference： [1]Ezizbeyli, A. R.; Gurbanov, G. R.; Mammadbayli, E. Q.; Talybov, G. M. [Russian Journal of Organic Chemistry, 2020, vol. 56, # 1, p. 34 - 37][Zh. Org. Khim., 2020, vol. 56, # 1, p. 47 - 51,5]

38
[ 28469-92-3 ]
[ 107-18-6 ]
2-{2-bromo-1-[(prop-2-en-1-yl)oxy]ethyl}-1,3-dichlorobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.8%	With N-Bromosuccinimide at -5 - 20℃; for 3h; regioselective reaction;	2-{2-Bromo-1-[(prop-2-en-1-yl)oxy]ethyl}-1,3-dichlorobenzene (7). A mixture of 14 g (0.17 mol) of 2,6-dichlorostyrene and 10 g (0.17 mol) of allyl alcohol was cooled to -5°C, and 14 g (0.17 mol) of N-bromosuccinimide was added in portions with stirring, maintaining the temperature below 0°C. The mixture was then stirred for 3 h at room temperature, the precipitate of succinimide was filtered off, and the mixture was made alkaline by adding a solution of 15 gof sodium hydroxide in 100 mL of water, extracted with diethyl ether, and dried over CaCl2. The solvent was removed under reduced pressure. Yield 71.8%. mp 94-96°C (from EtOH). IR spectrum, ν, cm-1: 3080, 3010, 1640, 1630, 1515, 1360, 1270, 850-840, 560. 1H NMR spectrum, δ, ppm: 3.41 d.d and 3.51 d.d (1Heach, CH2Br, J = 10.3, 5.8 Hz), 4.02 d.d (2H, CH2O,3J = 5.7, 4J = 1.5 Hz), 4.42 d.d (1H, CH, J = 5.8,9.0 Hz), 5.16 d.d.t (1H, H2C=, Jcis = 10.37, 2J = 4J =1.6 Hz), 5.25 d.d.d (1H, H2C=, Jtrans = 17.3, 2J = 4J =1.7 Hz), 5.88 d.d.t (1H, CH=, Jcis = 10.4, 2J = 4J = 1.6, 7.54 d.d (1H, C6H3, J = 8.8, 2.7 Hz), 7.69 d.d (1H,C6H3, J = 8.8, 2.7 Hz). 13C NMR spectrum, δC, ppm: 55.3, 69.9, 80.5, 114.0, 117.4, 127.8, 131.9, 133.1 (C3),135.6 (C1), 134.9, 158.4. Found, %: C 42.57; H 3.54;Br 25.66; Cl 22.86. C11H11BrCl2O. Calculated, %:C 42.62; H 3.58; Br 25.77; Cl 22.87.

Reference： [1]Ezizbeyli, A. R.; Gurbanov, G. R.; Mammadbayli, E. Q.; Talybov, G. M. [Russian Journal of Organic Chemistry, 2020, vol. 56, # 1, p. 34 - 37][Zh. Org. Khim., 2020, vol. 56, # 1, p. 47 - 51,5]

39
[ 28469-92-3 ]
[ 107-19-7 ]
1,3-dichloro-2-{2-iodo-1-[(prop-2-yn-1-yl)oxy]ethyl}benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.7%	With iodine; clinoptilolite at -5 - 20℃; regioselective reaction;	1,3-Dichloro-2-{2-iodo-1-[(prop-2-en-1-yl)oxy]-ethyl}benzene (4). General procedure: A mixture of 14 g (0.25 mol) of allyl alcohol and 44.8 g (0.25 mol) of 2,6-dichlorostyrenewas cooled to -5 to 0°C, 2.6 g of clinoptilolite [(NaK)4CaAl6Si30O72] was added with vigorous stirring, and 31.5 g (0.12 mol) of finely ground crystalline iodine was then added in 1-g portions. The mixture was stirred at room temperature for 3-4 h and filtered, and the filtrate was washed with a solution of Na2S2O3 and extracted with diethyl ether. The extract was dried over CaCl2 and evaporated on a rotary evaporator, and the residue was recrystallized from an appropriate solvent. Yield 30.4 g (68%),

Reference： [1]Ezizbeyli, A. R.; Gurbanov, G. R.; Mammadbayli, E. Q.; Talybov, G. M. [Russian Journal of Organic Chemistry, 2020, vol. 56, # 1, p. 34 - 37][Zh. Org. Khim., 2020, vol. 56, # 1, p. 47 - 51,5]

40
[ 28469-92-3 ]
[ 107-19-7 ]
2-{2-bromo-1-[(prop-2-yn-1-yl)oxy]ethyl}-1,3-dichlorobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.4%	With N-Bromosuccinimide at -5 - 20℃; for 3h; regioselective reaction;	2-{2-Bromo-1-[(prop-2-en-1-yl)oxy]ethyl}-1,3-dichlorobenzene (7). General procedure: A mixture of 14 g (0.17 mol) of 2,6-dichlorostyrene and 10 g (0.17 mol) of allyl alcohol was cooled to -5°C, and 14 g (0.17 mol) of N-bromosuccinimide was added in portions with stirring, maintaining the temperature below 0°C. The mixture was then stirred for 3 h at room temperature, the precipitate of succinimide was filtered off, and the mixture was made alkaline by adding a solution of 15 gof sodium hydroxide in 100 mL of water, extracted with diethyl ether, and dried over CaCl2. The solvent was removed under reduced pressure. Yield 71.8%

Reference： [1]Ezizbeyli, A. R.; Gurbanov, G. R.; Mammadbayli, E. Q.; Talybov, G. M. [Russian Journal of Organic Chemistry, 2020, vol. 56, # 1, p. 34 - 37][Zh. Org. Khim., 2020, vol. 56, # 1, p. 47 - 51,5]

41
[ 201230-82-2 ]
[ 121-73-3 ]
[ 28469-92-3 ]
C₁₅H₁₂Cl₃NO [ No CAS ]
C₁₅H₁₂Cl₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis-(diphenylphosphino)ferrocene; potassium tetrachloropalladate(II); boric acid In tetrahydrofuran at 80℃; for 20h; Autoclave; Overall yield = 80 percent; regioselective reaction;	2.2.1 General catalytic procedure for the synthesis of branched amides (3) General procedure: Olefin (1, 0.2 mmol), nitroarene (2, 0.2 mmol), K2PdCl4 (3.3 mg, 5 mol%), dppf (5.5 mg, 5 mol%), B(OH)3 (24.8 mg, 0.4 mmol), and THF (2.5 mL) were sequentially added into an autoclave, which was then purged three times before charging with 3.5 MPa CO. The autoclave was put into the heating jacket. The solution was first stirred at 80 °C for 20 h and then cooled to room temperature; CO was released carefully once the reaction finished. Then, the solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel using pentane/ethyl acetate (4:1) as an eluent to obtain the desired branched product 3.

Reference： [1]Li, Fuwei; Shi, Lijun; Xia, Chungu; Yang, Li [Cuihua Xuebao/Chinese Journal of Catalysis, 2020, vol. 41, # 7, p. 1152 - 1160]

42
[ 95-14-7 ]
[ 28469-92-3 ]
1-(1-(2,6-dichlorophenyl)vinyl)-1H-benzo[d][1,2,3]triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With diphenyl diselenide; Selectfluor In 1,2-dimethoxyethane at 120℃;

Reference： [1]Sun, Kai; Wang, Qinlin; Wang, Xin; Wu, Lanlan; Xue, Yanru; Zhang, Bing [Chemical Communications, 2020, vol. 56, # 32, p. 4436 - 4439]

43
[ 95-14-7 ]
[ 28469-92-3 ]
2-(1-(2,6-dichlorophenyl)vinyl)-2H-benzo[d][1,2,3]triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With dipotassium peroxodisulfate; trimethylsilan; diphenyl diselenide In 1,4-dioxane at 120℃;

Reference： [1]Sun, Kai; Wang, Qinlin; Wang, Xin; Wu, Lanlan; Xue, Yanru; Zhang, Bing [Chemical Communications, 2020, vol. 56, # 32, p. 4436 - 4439]

44
[ 28469-92-3 ]
C₁₀H₁₀BrNO₂S₂ [ No CAS ]
C₁₈H₁₇Cl₂NS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With fac-tris(2-phenylpyridinato-N,C₂')iridium(III); triisopropylsilanethiol In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; Irradiation;

Reference： [1]Liu, Jige; Lu, Chenxi; Wu, Shuo; Wu, Xinxin; Wu, Zhen; Xue, Xiao-Song; Yu, Jiajia; Zhu, Chen [Angewandte Chemie - International Edition, 2020, vol. 59, # 21, p. 8195 - 8202][Angew. Chem., 2020, vol. 132, # 21, p. 8272 - 8279,8]

45
[ 28469-92-3 ]
C₁₄H₁₈BrNO₅S [ No CAS ]
C₂₂H₂₅Cl₂NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With fac-tris(2-phenylpyridinato-N,C₂')iridium(III); tert-dodecanethiol; lithium chloride In N,N-dimethyl-formamide at 20℃; for 17h; Inert atmosphere; Irradiation;

Reference： [1]Liu, Jige; Lu, Chenxi; Wu, Shuo; Wu, Xinxin; Wu, Zhen; Xue, Xiao-Song; Yu, Jiajia; Zhu, Chen [Angewandte Chemie - International Edition, 2020, vol. 59, # 21, p. 8195 - 8202][Angew. Chem., 2020, vol. 132, # 21, p. 8272 - 8279,8]

46
[ 28469-92-3 ]
(3aR,9bR)-tert-butyl 9b-((4- fluorophenyl)sulfonyl)-7-iodo-3a,4,5 ,9b-tetrahydro- 1H-benzo [e]indole-3 -carboxylate [ No CAS ]
tert-butyl (3aR,9bR)-7-((E)-2,6-dichlorostyryl)-9b-((4-fluorophenyl)sulfonyl)-1,2,3a,4,5,9b-hexahydro-3H-benzo[e]indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetrabutyl-ammonium chloride; palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In acetonitrile at 70℃; for 6h; Inert atmosphere;	2 Preparation of intermediate of 2A: tert-butyl (3aR,9bR)-7-((E)-2,6-dichlorostyryl)-9b- ((4-fluorophenyl)sulfonyl)-l,2,3a,4,5,9b-hexahydro-3H-benzo[e]indole-3-carboxylate l,3-dichloro-2-vinylbenzene (62.1 mg, 0.359 mmol), (3aR,9bR)-tert-butyl 9b-((4- fluorophenyl)sulfonyl)-7-iodo-3a,4,5,9b-tetrahydro-lH-benzo[e]indole-3(2H)- carboxylate 1A (200 mg, 0.359 mmol), Pd(OAc)2 (8.06 mg, 0.036 mmol), tri-o- tolylphosphine (21.84 mg, 0.072 mmol), DIEA (125 pi, 0.718 mmol) and tetrabutylammonium chloride (100 mg, 0.359 mmol) were combined and dissolved in acetonitrile (3.6 mL) under nitrogen at room temperature. The resulting mixture was stirred at 70 °C for 6 h. The reaction mixture was concentrated in vacuo and purified by silica gel chromatography using 0-30% EtOAc in hexanes to afford 2A (210 mg, 0.35 mmol, 97 % yield). LCMS m/z 601.8 (M+H); rt 4.25 min; Method D.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2020/231766, 2020, A1 Location in patent: Page/Page column 46-48

47
[ 28469-92-3 ]
[ 889-98-5 ]
C₁₉H₁₇Cl₂F₄NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(II) 2-ethylhexanoate; (dimethoxy)methylsilane; o-phenylenebis(diphenylphosphine) In tetrahydrofuran at 40℃; for 30h; Inert atmosphere;

Reference： [1]Fu, Bin; Li, Xiaohong; Xiong, Tao; Yuan, Xiuping; Zhang, Qian; Zhang, Qiao [Angewandte Chemie - International Edition, 2020, vol. 59, # 51, p. 23056 - 23060][Angew. Chem., 2020, vol. 132, # 51, p. 23256 - 23260,5]

48
[ 28469-92-3 ]
(E)-2-(2,6-dichlorophenyl)ethene-1-sulfonyl fluoride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; fluorosulfonylchloride In diethyl ether at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation;

Reference： [1]Nie, Xingliang; Xu, Tianxiao; Song, Jinshuai; Devaraj, Anandkumar; Zhang, Bolun; Chen, Yong; Liao, Saihu [Angewandte Chemie - International Edition, 2021, vol. 60, # 8, p. 3956 - 3960][Angew. Chem., 2021, vol. 60, # 8, p. 3956 - 3960,5]

49
[ 28469-92-3 ]
[ 1610025-95-0 ]
tert-butyl 4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With N-chloro-succinimide; sodium hydrogencarbonate In water; ethyl acetate at 65℃; for 3h;	1.G1 Step G1: Alternate preparation of tert- butyl 4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3- yl)thiazol-2-yl)piperidine-1- carboxylate To a stirred solution of tert- butyl (E)-4-(4-((hydroxyimino) methyl) thiazol-2-yl) piperidine- 1-carboxylate (3 g, 9.63 mmol) in ethyl acetate (100 mL), N-chlorosuccinimide (2.57 g, 19.27 mmol) was added followed by the addition of sodium bicarbonate (5.67 g, 67.4 mmol). To the reaction mixture, 1,3- dichloro-2-vinylbenzene (3.3 g, 19.2 mmol) and water (10 mL) were added. The reaction mixture was heated to 65 °C for 3 h, cooled to 15 °C and quenched with water. The aqueous layer was extracted twice with ethyl acetate (50 mL). The combined ethyl acetate layer was dried over anhydrous sodium sulphate, concentrated and purified by column chromatography using 30% ethyl acetate and hexane as eluent to obtain the tert- butyl 4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidine-1- carboxylate (2.9 g, 6.01 mmol, 62% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.10-7.87 (m, 1H), 7.68-7.18 (m, 3H), 6.31 (t, 11.7J H=z, 1H), 4.18- 3.64 (m, 3H), 3.58-3.51 (m, 1H), 3.31-3.21 (m, 1H), 2.88-2.80 (m, 2H), 2.16-1.84 (m, 2H), 1.59-1.51 (m, 2H), 1.42 (s, 9H) MS: m/z = 482.15 [M+1].
62%	With N-chloro-succinimide; sodium hydrogencarbonate In water; ethyl acetate at 15 - 65℃; for 3h; Further stages;	1.G1 Step Gl: Alternate preparation of tert- butyl 4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3- yl)thiazol-2-yl)piperidine-1-carboxylate To a stirred solution of tert- butyl (E)-4-(4-((hydroxyimino)methyl)thiazol-2-yl)piperidine-1-carboxylate (3 g, 9.63 mmol) in ethyl acetate (100 mL), N-chlorosuccinimide (2.57 g, 19.27 mmol) was added followed by the addition of sodium bicarbonate (5.67 g, 67.4 mmol). To the reaction mixture, 1,3- dichloro-2-vinylbenzene (3.3 g, 19.2 mmol) and water (10 mL) were added. The reaction mixture was heated to 65 °C for 3 h, cooled to 15 °C and quenched by addition of water. The aqueous layer was extracted twice with ethyl acetate (50 mL). The combined ethyl acetate layer was dried over anhydrous sodium sulphate concentrated and the obtained residue was purified by column chromatography using 30% ethyl acetate and hexane as eluent to obtain tert- butyl 4-(4-(5-(2,6-dichlorophenyl)-4,5- dihydroisoxazol-3-yl)thiazol-2-yl)piperidine-1-carboxylate (2.9 g, 6.01 mmol, 62% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.10-7.87 (m, 1H), 7.68-7.18 (m, 3H), 6.31 (t, J = 11.7 Hz, 1H), 4.18- 3.64 (m, 3H), 3.58-3.51 (m, 1H), 3.31-3.21 (m, 1H), 2.88-2.80 (m, 2H), 2.16-1.84 (m, 2H), 1.59-1.51 (m, 2H), 1.42 (s, 9H) MS: m/z = 482.15 [M+1]. MS: m/z = 482.15 [M+1].

Reference： [1]Current Patent Assignee: PI INDUSTRIES LTD - WO2021/94903, 2021, A1 Location in patent: Paragraph 47; 50
[2]Current Patent Assignee: PI INDUSTRIES LTD - WO2021/94905, 2021, A1 Location in patent: Page/Page column 55; 57-58

50
[ 28469-92-3 ]
[ 1313010-11-5 ]
tert-butyl 4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With sodium hypochlorite In tetrahydrofuran; water at 0℃; for 1h;	1.G Step G: Preparation of tert-butyl 4-(4-(5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2- yl)piperidine-1- carboxylate To a stirred solution of tert- butyl (E/Z)-4-(4-((hydroxyimino)methyl)thiazol-2-yl)piperidine-1- carboxylate (0.5 g, 1.7 mmol) in dry tetrahydrofuran (30 mL) at 0 °C, dichloro-2-vinylbenzene (0.4 g, 2.4 mmol) was added followed by addition of 4% aqueous sodium hypochlorite (6.2 mL, 5.1 mmol). The resulting reaction mixture was stirred for 1 h. The reaction was quenched with water and the aqueous layer was extracted twice with ethyl acetate (50 mL). The combined ethyl acetate layer was dried over anhydrous sodium sulphate, concentrated and purified by column chromatography using 30% ethyl acetate and hexane as eluents to obtain the tert- butyl 4-(4-(5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3- yl)thiazol-2-yl)piperidine-1- carboxylate (250 mg, 0.5 mmol, 32% yield).
32%	With sodium hypochlorite In tetrahydrofuran; water at 0℃; for 1h;	1.G Step G: Preparation of tert- butyl 4-(4-(5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2- yl)piperidine-1-carboxylate To a stirred solution of tert- butyl (E/Z)-4-(4-((hydroxyimino)methyl)thiazol-2-yl)piperidine-1- carboxylate (0.5 g, 1.7 mmol) in dry tetrahydrofuran (30 mL), dichloro-2-vinylbenzene (0.4 g, 2.4 mmol) was added at 0 °C, followed by the addition of 4% aqueous sodium hypochlorite (6.2 mL, 5.1 mmol), and the resulting nmixture was stirred for 1 h. The reaction mixture was quenched by addition of water and the aqueous layer was extracted twice with ethyl acetate (50 mL). The combined ethyl acetate layer was dried over anhydrous sodium sulphate, concentrated and the obtained residue was purified by column chromatography using 30% ethyl acetate and hexane as eluents to obtain the tert- butyl 4-(4-(5-(2,6- difluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl) piperidine- 1-carboxylate (250 mg, 0.5 mmol, 32% yield).

Reference： [1]Current Patent Assignee: PI INDUSTRIES LTD - WO2021/94903, 2021, A1 Location in patent: Page/Page column 47; 50
[2]Current Patent Assignee: PI INDUSTRIES LTD - WO2021/94905, 2021, A1 Location in patent: Page/Page column 55; 57

51
[ 28469-92-3 ]
2-(2,6-dichlorophenyl)-5-methyl-1,4-dioxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.2%	Stage #1: 2,6-dichlorostyrene With iodine; clinoptilolite; allyl alcohol at -5 - 60℃; Stage #2: With O₄₀SiW₁₂^(4-)4Na⁽¹⁺⁾19H₂O In pyridine at 60℃; for 2.5h;	General procedure for the synthesis of substituted1,4-dioxanes 7-12. General procedure: A mixture of 10.25 mmol ofallyl alcohol, 0.25 mmol of halostyrene 1-6, and 2.6 gof clinoptilolite (NaK)4CaAl6Si30O72 was cooled to -5to 0°C, and 0.12 mmol of finely powdered crystallineiodine was added with stirring. The mixture was heatedto 60°C over a period of 3-4 h, a solution of 0.02 g ofNa4SiW12O40·19H2O in 2 mL of pyridine was added,and the mixture was stirred for 2.5 h more. It was thencooled and filtered, the filtrate was washed with a solutionof Na2S2O3 and extracted with diethyl ether. Theextract was dried over Na2SO4 and evaporated underreduced pressure, and the residue was recrystallizedfrom ethanol.

Reference： [1]Talybov, G. M. [Russian Journal of Organic Chemistry, 2021, vol. 57, # 6, p. 1009 - 1011][Zh. Org. Khim., 2021, vol. 57, # 06, p. 891 - 894]

52
[ 67-56-1 ]
[ 28469-92-3 ]
C₁₃H₁₃BrO₂S [ No CAS ]
C₂₂H₂₂Cl₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium dihydrogenphosphate; fac-tris(2-phenylpyridinato-N,C₂')iridium(III) In acetonitrile at 20℃; for 70h; Irradiation; Inert atmosphere;

Reference： [1]Wei, Yunlong; Wu, Xinxin; Zhang, Hong; Zhu, Chen [Angewandte Chemie - International Edition, 2021, vol. 60, # 37, p. 20215 - 20219][Angew. Chem., 2021, vol. 133, # 37, p. 20377 - 20381]

53
[ 110-89-4 ]
[ 28469-92-3 ]
2-(2,6-dichlorophenethyl)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45 %Spectr.	With sodium (2,6-dimethylphenyl)(methyl(1-phenylethyl)carbamoyl)amide; Ta(CH<SUB>2</SUB>SiMe<SUB>3</SUB>)<SUB>3</SUB>Cl<SUB>2</SUB> In ⁽²⁾H₈-toluene at 150℃; for 20h; Inert atmosphere; regioselective reaction;

Reference： [1]Daneshmand, Pargol; Dipucchio, Rebecca C.; Ezhova, Maria B.; Lenzen, Karst E.; Schafer, Laurel L. [Journal of the American Chemical Society, 2021, vol. 143, # 29, p. 11243 - 11250]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	28469-92-3	MDL No. :	MFCD00000579
Formula :	C₈H₆Cl₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YJCVRMIJBXTMNR-UHFFFAOYSA-N
M.W :	173.04	Pubchem ID :	34254
Synonyms :

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.55
TPSA :	0.0 Å²

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.55 cm/s

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	3.95
Log Po/w (WLOGP) :	3.53
Log Po/w (MLOGP) :	4.01
Log Po/w (SILICOS-IT) :	3.88
Consensus Log Po/w :	3.56

[ CAS No. 28469-92-3 ] {[proInfo.proName]}

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[ 28469-92-3 ] Synthesis Path-Upstream 1~1

[ 28469-92-3 ] Synthesis Path-Downstream 1~53

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[ 28469-92-3 ]

Chlorides

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.78
Solubility :	0.0288 mg/ml ; 0.000166 mol/l
Class :	Soluble
Log S (Ali) :	-3.65
Solubility :	0.0387 mg/ml ; 0.000224 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.07
Solubility :	0.0147 mg/ml ; 0.0000849 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.55

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
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.
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P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
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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. 28469-92-3 ] {[proInfo.proName]}

Quality Control of [ 28469-92-3 ]

Related Doc. of [ 28469-92-3 ]

Product Details of [ 28469-92-3 ]

Calculated chemistry of [ 28469-92-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 28469-92-3 ]

Application In Synthesis of [ 28469-92-3 ]

[ 28469-92-3 ] Synthesis Path-Upstream 1~1

[ 28469-92-3 ] Synthesis Path-Downstream 1~53

Related Functional Groups of [ 28469-92-3 ]

Chlorides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 28469-92-3 ]