Name: 13484-50-9|Perchloropyrazine|97%
Brand: Ambeed
SKU: A1003613
Price: 62.0 USD
Availability: InStock
Rating: 90 (30 reviews)

1
[ 290-37-9 ]
[ 13484-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With water; chlorine at 375℃;

Reference： [1]Current Patent Assignee: PFIZER INC - US2442473, 1946, A

2
[ 13484-50-9 ]
[ 443770-31-8 ]
[ 134654-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In various solvent(s) at 56℃; for 14h;

Reference： [1]Moran, John R.; Ericson, John L.; Dalcanale, Enrico; Bryant, Judi A.; Knobler, Carolyn B.; Cram, Donald J. [Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5707 - 5714]

3
[ 13484-50-9 ]
[ 141-97-9 ]
[ 86538-71-8 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium hydride In tetrahydrofuran at 60℃; for 6h;

Reference： [1]Tong, Y. C.; Kerlinger, H. O. [Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 365 - 368]

4
[ 13484-50-9 ]
[ 141-97-9 ]
[ 86538-70-7 ]

Yield	Reaction Conditions	Operation in experiment
10%	With sodium hydride In tetrahydrofuran r.t., overnight;

Reference： [1]Tong, Y. C.; Kerlinger, H. O. [Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 365 - 368]

5
[ 13484-50-9 ]
[ 118655-57-5 ]
[ 134733-07-6 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 24h;

Reference： [1]Cram, Donald J.; Choi, Heung-Jin; Bryant, Judi A.; Knobler, Carolyn B. [Journal of the American Chemical Society, 1992, vol. 114, # 20, p. 7748 - 7765]

6
[ 13484-50-9 ]
[ 138233-39-3 ]
[ 134654-34-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	With caesium carbonate In various solvent(s) at 30 - 50℃; for 96h;

Reference： [1]Moran, John R.; Ericson, John L.; Dalcanale, Enrico; Bryant, Judi A.; Knobler, Carolyn B.; Cram, Donald J. [Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5707 - 5714]

7
[ 13484-50-9 ]
[ 135269-76-0 ]
[ 134654-35-6 ]

Yield	Reaction Conditions	Operation in experiment
1.2%	With caesium carbonate In various solvent(s) at 25 - 50℃; for 168h;

Reference： [1]Moran, John R.; Ericson, John L.; Dalcanale, Enrico; Bryant, Judi A.; Knobler, Carolyn B.; Cram, Donald J. [Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5707 - 5714]

8
[ 13484-50-9 ]
[ 134731-88-7 ]
[ 134733-07-6 ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 24h;

Reference： [1]Moran, John R.; Ericson, John L.; Dalcanale, Enrico; Bryant, Judi A.; Knobler, Carolyn B.; Cram, Donald J. [Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5707 - 5714]

9
[ 13484-50-9 ]
[ 2235-46-3 ]
[ 86538-72-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium hydride In tetrahydrofuran at 60℃; for 6h;

Reference： [1]Tong, Y. C.; Kerlinger, H. O. [Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 365 - 368]

10
[ 13484-50-9 ]
[ 109-77-3 ]
[ 86538-68-3 ]

Yield	Reaction Conditions	Operation in experiment
84.5%	With sodium hydride In tetrahydrofuran for 20h; Heating;

Reference： [1]Tong, Y. C.; Kerlinger, H. O. [Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 365 - 368]

11
[ 13484-50-9 ]
[ 105-53-3 ]
ethyl α-(carboethoxy)-3,5,6-trichloropyrazineacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium hydride In tetrahydrofuran for 20h; Heating;

Reference： [1]Tong, Y. C.; Kerlinger, H. O. [Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 365 - 368]

12
[ 20074-67-3 ]
[ 13484-50-9 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 398 - 404

13
[ 13484-50-9 ]
[ 159435-37-7 ]
2-(4,5-Dimethyl-1,3-dithiole-2-ylidene)-5,6-dichloro-(1,3)-dithiolo<4,5-b>pyrazine [ No CAS ]

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

Reference： [1]Lahlil, Khalid; Moradpour, Alec; Merienne, Claude; Bowlas, Christopher [Journal of Organic Chemistry, 1994, vol. 59, # 26, p. 8030 - 8033]

14
[ 13484-50-9 ]
[ 159435-37-7 ]
2,6-Bis(4,5-dimethyl-1,3-dithiole-2-ylidene)bis-1,3-dithiolo<4,5-b:4',5'-e>pyrazine [ No CAS ]

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

Reference： [1]Lahlil, Khalid; Moradpour, Alec; Merienne, Claude; Bowlas, Christopher [Journal of Organic Chemistry, 1994, vol. 59, # 26, p. 8030 - 8033]

15
[ 13484-50-9 ]
[ 159435-38-8 ]
2,6-Bis(4,5-dihexyl-1,3-dithiole-2-ylidene)bis-1,3-dithiolo<4,5-b:4',5'-e>pyrazine [ No CAS ]

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

Reference： [1]Lahlil, Khalid; Moradpour, Alec; Merienne, Claude; Bowlas, Christopher [Journal of Organic Chemistry, 1994, vol. 59, # 26, p. 8030 - 8033]

16
[ 13484-50-9 ]
[ 159435-37-7 ]
[ 74-88-4 ]
2-(4,5-Dimethyl-1,3-dithiole-2-ylidene)-5-chloro-6-(methylthio)-(1,3)-dithiolo<4,5-b>pyrazine [ No CAS ]

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

Reference： [1]Lahlil, Khalid; Moradpour, Alec; Merienne, Claude; Bowlas, Christopher [Journal of Organic Chemistry, 1994, vol. 59, # 26, p. 8030 - 8033]

17
[ 13484-50-9 ]
2,5-diamino-3,6-dichloropyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phtalimide; hydrazine 1.) dimethylformamide, 323 K, 16 h; 2.) water; Multistep reaction;

Reference： [1]Barclay, Tosha M.; Cordes, A. Wallace; Oakley, Richard T.; Preuss, Kathryn E.; Zhang, Hongzhou [Acta Crystallographica, Section C: Crystal Structure Communications, 1998, vol. 54, # 7, p. 1018 - 1019]

Yield	Reaction Conditions	Operation in experiment
	Rk. mit Kaliumfluorid;
	Rk. m. konz. wss. NH3 (Druckgefaess, 115grad, 2.5h) liefert fast ausschliesslich Aminotrichlorpyrazin;
	Rk. m. konz. wss. NH3 (Druckgefaess, 120grad, 14h) liefert 2,3-Diamino-5,6-dichlorpyrazin u. 2,6-Diamino-3,5-dichlorpyrazin (etwas geringere Menge);

	Rk. m. KF zu Tetrafluoropyrazin;
	Rk. mit H2SO4 /CF3COOH/ H2O2;

Yield	Reaction Conditions	Operation in experiment
		Further examples of vicinal halo or halonitro heterocycles include: ... 4-nitro-2,4,6-trichloropyrimidine Pentafluoropyridine Tetrachloropyrazine 2,3-dichloro-5,6-dicarbomethoxypyrazine ...

20
[ 13484-50-9 ]
[ 109-77-3 ]
2-(3,5,6-trichloro-1<i>H</i>-pyrazin-2-ylidene)-malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 20 - 50℃; for 1h;

Reference： [1]Yudin; Aronova; Sheremetev; Averkiev; Antipin [Mendeleev Communications, 2001, vol. 11, # 4, p. 152 - 153]

21
[ 13484-50-9 ]
[ 55233-37-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In 1,4-dioxane; ethanol; water	3,5,6-trichloro-2-hydrazinopyrazine 3,5,6-trichloro-2-hydrazinopyrazine A solution was prepared by dissolving 21.8 grams of tetrachloropyrazine in 100 milliliters of dioxane. The solution was diluted with 250 milliliters of ethanol and 15 milliliters of hydrazine hydrate was slowly added thereto. The temperature rose from 23°C to 37°C. The solution was held, with stirring, at 23°C for 20 minutes and the 3,5,6-trichloro-2-hydrazinopyrazine product was isolated by pouring the reaction mixture in water and filtering off the solid product. The product melted at 167°-168°C and was recovered in a yield of 20.2 grams (94 percent of theoretical).

Reference： [1]Current Patent Assignee: DOW INC - US3976644, 1976, A

22
monomethyl-amino-ethanol [ No CAS ]
[ 13484-50-9 ]
[ 63880-11-5 ]
[ 63880-12-6 ]

Yield	Reaction Conditions	Operation in experiment
27%	With sodium In ethanol	2 6,7-Dichloro-3,4-dihydro-4-methyl-2H-pyrazino(2,3-b)(1,4)oxazine EXAMPLE 2 6,7-Dichloro-3,4-dihydro-4-methyl-2H-pyrazino(2,3-b)(1,4)oxazine The crude product from the reaction of tetrachloropyrazine (10.8 g, 0.05 mol) and methylaminoethanol (3.7 g, 0.05 mol) in Example 1 above was dissolved in absolute ethanol and small pieces of sodium (1.2 g, 0.05 mol) were added. After stirring overnight the ethanol was evaporated and the solid residue was washed with water, filtered, and dried on a porous plate to a weight of 7 g. The solid was recrystallized from ethanol and isopropyl alcohol (IPA) to give 4 g (27% yield) of a white solid, m.p. 170°-2°. Anal. Calcd. for C7 H7 Cl2 N3 O: C, 38.21; H, 3.21; N, 19.10. Found: C, 38.25; H, 3.44; N, 19.24.

Reference： [1]Current Patent Assignee: DOW INC - US4029657, 1977, A

23
[ 13484-50-9 ]
[ 23502-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water	I 3,5,6-Trichloro-2-methylthiopyrazine STR5 EXAMPLE I 3,5,6-Trichloro-2-methylthiopyrazine STR5 A solution was prepared by dissolving 25 grams (0.115 mole) of tetrachloropyrazine in 300 milliliters of methanol. To this solution was added over a 90 minute period, a solution of 115 milliliters of ~1.0 molar sodium mercaptide in methanol. The temperature was maintained below 20° C during the addition. The reaction mixture was stirred at room temperature overnight and thereafter poured into 400 milliliters of water. The precipitate which formed was removed by filtration and recrystallized from hexane. The 3,5,6-trichloro-2-methylthiopyrazine product was recovered in a yield of 7.11 grams, 27 percent of theoretical, and melted at 45°-47° C.

Reference： [1]Current Patent Assignee: DOW INC - US4101546, 1978, A

24
[ 106-57-0 ]
[ 13484-50-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: Glycine anhydride With phosphorus pentachloride; trichlorophosphate Stage #2: With chlorine at 120℃; for 1h;	1 Preparation of 2,3,5,6-tetrachloropyrazine. EXAMPLE 1 Preparation of 2,3,5,6-tetrachloropyrazine. Into a round bottom flask was added 2,5-diketopiperazine. To the reaction was added phosphorus oxychloride and phosphorus pentachloride. After stirring for a few minutes, chlorine gas was added. The reaction was warmed to 120° C. After stirring for a period of 1 hour, the reaction was deemed complete. The reaction was worked up and the 2,3,5,6-tetrachloropyrazine was isolated in 92% yield.
63%	With phosphorus pentachloride; trichlorophosphate at 60 - 200℃; for 23h; Inert atmosphere;
35%	With phosphorus pentachloride; trichlorophosphate at 60℃; for 48h;	32 2,3,5,6-tetrachloropyrazine To a 500 ml round bottom flask was added 200 ml of phosphorus oxychloride, then phosphorus pentachloride (145.6 g, 700 mmol) was added, and stirring was carried out to give a pale yellow turbidity. Glycine anhydride (11.4 g, 100 mmol) was added, and the mixture was heated to 60 ° C for 48 h. More than phosphorus oxychloride and phosphorus pentachloride are removed by distillation, and phosphorus oxychloride is distilled off at 150 ° C. Phosphorus pentachloride is sublimed into the condenser at 220 ° C, and heating is continued until there is no more distillate. The heating was stopped, the temperature was allowed to stand at room temperature, and the product was left open overnight (to facilitate the sublimation of residual phosphorus pentachloride) to obtain a colorless transparent oil, which was slowly added dropwise to ice water, three times with petroleum ether, and then subjected to column chromatography. A white solid of 7525 mg was obtained in a yield of 35.0%.

	With phosphorus pentachloride; trichlorophosphate at 60℃; for 48h;
	With phosphorus pentachloride; trichlorophosphate at 120℃;
	With phosphorus pentachloride; trichlorophosphate at 120℃;
	With phosphorus pentachloride; trichlorophosphate at 60℃;	2.4.1 Synthesis of precursors Precursors were synthesized according to the reported routes [1,43]. As shown in Scheme 1 , tetrachloropyrazine was synthesized through chlorination of 2,5-dioxopiperazine by phosphorus pentachloride in phosphorus oxychloride at 60 °C. Tetra[(trimethylsilyl)ethynyl] pyrazine (TEP-TMS) was synthesized through Negishi reaction where tetrachloropyrazine reacted with [(triethylsilyl)ethynyl] zinc chloride catalyzed by Pd(PPh3)4 in newly distilled THF under 80 °C for 2 days. Crude products were purified through column chromatography and characterized through mass spectrum (MS) and nuclear magnetic resonance spectrum (NMR).

Reference： [1]Current Patent Assignee: WEAVER LABS - US2021/355090, 2021, A1 Location in patent: Paragraph 007; 0325
[2]Oda, Susumu; Shimizu, Takeshi; Katayama, Takazumi; Yoshikawa, Hirofumi; Hatakeyama, Takuji [Organic Letters, 2019]
[3]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN108929280, 2018, A Location in patent: Paragraph 0139; 0141; 0142
[4]Fleischhauer, Jan; Zahn, Stefan; Beckert, Rainer; Grummt, Ulrich-Walter; Birckner, Eckhard; Goerls, Helmar [Chemistry - A European Journal, 2012, vol. 18, # 15, p. 4549 - 4557]
[5]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]
[6]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]
[7]He, Feng; He, Jingyi; Li, Yongjun; Li, Yuliang; Shen, Han; Xue, Yurui [Applied Catalysis A: General, 2021, vol. 623]

25
[ 13484-50-9 ]
[ 534-85-0 ]
[ 1145685-43-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-trimethyl-pyridine at 120 - 130℃; Sealed tube; Inert atmosphere;

Reference： [1]Fleischhauer, Jan; Zahn, Stefan; Beckert, Rainer; Grummt, Ulrich-Walter; Birckner, Eckhard; Goerls, Helmar [Chemistry - A European Journal, 2012, vol. 18, # 15, p. 4549 - 4557]

26
[ 13484-50-9 ]
[ 534-85-0 ]
[ 1145685-44-4 ]
[ 1379772-00-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 20% 2: 3%	With 2,4,6-trimethyl-pyridine at 120 - 140℃; for 120h; Sealed tube; Inert atmosphere;

Reference： [1]Fleischhauer, Jan; Zahn, Stefan; Beckert, Rainer; Grummt, Ulrich-Walter; Birckner, Eckhard; Goerls, Helmar [Chemistry - A European Journal, 2012, vol. 18, # 15, p. 4549 - 4557]

27
[ 13484-50-9 ]
[ 534-85-0 ]
[ 1379772-00-5 ]

Yield	Reaction Conditions	Operation in experiment
11%	With 2,4,6-trimethyl-pyridine at 160℃; for 72h; Sealed tube; Inert atmosphere;

Reference： [1]Fleischhauer, Jan; Zahn, Stefan; Beckert, Rainer; Grummt, Ulrich-Walter; Birckner, Eckhard; Goerls, Helmar [Chemistry - A European Journal, 2012, vol. 18, # 15, p. 4549 - 4557]

28
[ 13484-50-9 ]
N,N′-bis(2-pyridyl)benzene-1,2-diamine [ No CAS ]
[ 1568337-36-9 ]

Yield	Reaction Conditions	Operation in experiment
59%	With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 16h;

Reference： [1]Pochorovski, Igor; Milic, Jovana; Kolarski, Dusan; Gropp, Cornelius; Schweizer, W. Bernd; Diederich, Francois [Journal of the American Chemical Society, 2014, vol. 136, # 10, p. 3852 - 3858]

29
[ 13484-50-9 ]
[ 2156-04-9 ]
2,3,5,6-tetrakis(4-vinylphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In toluene; at 100℃; for 18h;Schlenk technique; Inert atmosphere;	General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Tetrahedron,2015,vol. 71,p. 6803 - 6812

30
[ 13484-50-9 ]
[ 10365-98-7 ]
2,3,5,6-tetrakis(3-methoxyphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

31
[ 13484-50-9 ]
[ 16419-60-6 ]
2,3,5,6-tetra-o-tolylpyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

32
[ 13484-50-9 ]
[ 107099-99-0 ]
2,3,5,6-tetrakis(2,5-dimethoxyphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

33
[ 13484-50-9 ]
[ 150255-96-2 ]
2,3,5,6-tetrakis(3-cyanophenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

34
[ 13484-50-9 ]
[ 6783-05-7 ]
2,3,5,6-tetra((E)-styryl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium phosphate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; catacxium A In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	6.1.17. Synthesis of tetraalkenylpyrazines. General procedure: An argon-flushed glass pressure tube was charged with Pd(dba)2 (0.005 mmol, 2 mol %), CataCXium A (0.01 mmol, 4 mol %), 2 (54.4 mg, 0.25 mmol), the appropriate alkenylboronic acid or pinacol ester (2 mmol, 8.0 equiv), K3PO4 (2 mmol, 8.0 equiv) and anhydrous 1,4-dioxane (4 mL). The tube was sealed with a Teflon cap and the reaction mixture was stirred at 100°C for 20 h. Resulting mixture was cooled down to room temperature, diluted with water and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated. After, the crude residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent. Gained solids in the end, were washed with cold hexane to give pure orange coloured products.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

35
[ 13484-50-9 ]
[ 72316-17-7 ]
2,3,5,6-tetrakis((E)-4-methylstyryl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium phosphate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; catacxium A In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	6.1.17. Synthesis of tetraalkenylpyrazines. General procedure: An argon-flushed glass pressure tube was charged with Pd(dba)2 (0.005 mmol, 2 mol %), CataCXium A (0.01 mmol, 4 mol %), 2 (54.4 mg, 0.25 mmol), the appropriate alkenylboronic acid or pinacol ester (2 mmol, 8.0 equiv), K3PO4 (2 mmol, 8.0 equiv) and anhydrous 1,4-dioxane (4 mL). The tube was sealed with a Teflon cap and the reaction mixture was stirred at 100°C for 20 h. Resulting mixture was cooled down to room temperature, diluted with water and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated. After, the crude residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent. Gained solids in the end, were washed with cold hexane to give pure orange coloured products.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

36
[ 13484-50-9 ]
[ 460748-43-0 ]
2,3,5,6-tetrakis((E)-4-fluorostyryl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; catacxium A In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	6.1.17. Synthesis of tetraalkenylpyrazines. General procedure: An argon-flushed glass pressure tube was charged with Pd(dba)2 (0.005 mmol, 2 mol %), CataCXium A (0.01 mmol, 4 mol %), 2 (54.4 mg, 0.25 mmol), the appropriate alkenylboronic acid or pinacol ester (2 mmol, 8.0 equiv), K3PO4 (2 mmol, 8.0 equiv) and anhydrous 1,4-dioxane (4 mL). The tube was sealed with a Teflon cap and the reaction mixture was stirred at 100°C for 20 h. Resulting mixture was cooled down to room temperature, diluted with water and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated. After, the crude residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent. Gained solids in the end, were washed with cold hexane to give pure orange coloured products.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

37
[ 13484-50-9 ]
[ 72316-18-8 ]
2,3,5,6-tetrakis((E)-4-methoxystyryl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium phosphate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; catacxium A In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	6.1.17. Synthesis of tetraalkenylpyrazines. General procedure: An argon-flushed glass pressure tube was charged with Pd(dba)2 (0.005 mmol, 2 mol %), CataCXium A (0.01 mmol, 4 mol %), 2 (54.4 mg, 0.25 mmol), the appropriate alkenylboronic acid or pinacol ester (2 mmol, 8.0 equiv), K3PO4 (2 mmol, 8.0 equiv) and anhydrous 1,4-dioxane (4 mL). The tube was sealed with a Teflon cap and the reaction mixture was stirred at 100°C for 20 h. Resulting mixture was cooled down to room temperature, diluted with water and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated. After, the crude residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent. Gained solids in the end, were washed with cold hexane to give pure orange coloured products.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

38
[ 13484-50-9 ]
[ 1421061-31-5 ]
2,3,5,6-tetrakis((E)-3-methylstyryl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium phosphate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; catacxium A In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	6.1.17. Synthesis of tetraalkenylpyrazines. General procedure: An argon-flushed glass pressure tube was charged with Pd(dba)2 (0.005 mmol, 2 mol %), CataCXium A (0.01 mmol, 4 mol %), 2 (54.4 mg, 0.25 mmol), the appropriate alkenylboronic acid or pinacol ester (2 mmol, 8.0 equiv), K3PO4 (2 mmol, 8.0 equiv) and anhydrous 1,4-dioxane (4 mL). The tube was sealed with a Teflon cap and the reaction mixture was stirred at 100°C for 20 h. Resulting mixture was cooled down to room temperature, diluted with water and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated. After, the crude residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent. Gained solids in the end, were washed with cold hexane to give pure orange coloured products.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

39
[ 13484-50-9 ]
[ 98-80-6 ]
[ 642-04-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

40
[ 13484-50-9 ]
[ 128796-39-4 ]
2,3,5,6-tetrakis(4-(trifluoromethyl)phenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

41
[ 13484-50-9 ]
[ 5720-05-8 ]
2,3,5,6-tetrakis(4-methylphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

42
[ 13484-50-9 ]
[ 16152-51-5 ]
2,3,5,6-tetrakis(4-isopropylphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

43
[ 13484-50-9 ]
[ 5720-07-0 ]
[ 21885-49-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

44
[ 13484-50-9 ]
[ 1423-26-3 ]
2,3,5,6-tetrakis(3-(trifluoromethyl)phenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

45
[ 13484-50-9 ]
[ 63139-21-9 ]
2,3,5,6-tetrakis(4-ethylphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

46
[ 13484-50-9 ]
[ 1765-93-1 ]
2,3,5,6-tetrakis(4-fluorophenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

47
[ 13484-50-9 ]
[ 172975-69-8 ]
2,3,5,6-tetrakis(3,5-dimethylphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

48
[ 13484-50-9 ]
[ 17933-03-8 ]
2,3,5,6-tetra-m-tolylpyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

49
[ 13484-50-9 ]
[ 153624-46-5 ]
2,3,5,6-tetrakis(4-isopropoxyphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

50
[ 13484-50-9 ]
[ 536-74-3 ]
2,3,5,6-tetrakis(phenylethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

51
[ 13484-50-9 ]
[ 766-97-2 ]
2,3,5,6-tetrakis(p-tolylethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

52
[ 13484-50-9 ]
[ 766-47-2 ]
2,3,5,6-tetrakis(o-tolylethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

53
[ 13484-50-9 ]
[ 766-82-5 ]
2,3,5,6-tetrakis(m-tolylethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

54
[ 13484-50-9 ]
[ 74331-69-4 ]
2,3,5,6-tetrakis((4-methoxy-2-methylphenyl)ethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

55
[ 13484-50-9 ]
[ 772-38-3 ]
2,3,5,6-tetrakis((4-(tert-butyl)phenyl)ethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

56
[ 13484-50-9 ]
[ 693-02-7 ]
2,3,5,6-tetra(hex-1-yn-1-yl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

57
[ 13484-50-9 ]
[ 89343-06-6 ]
2,3,5,6-tetrakis((triisopropylsilyl)ethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

58
[ 13484-50-9 ]
[ 79887-09-5 ]
2,3,5,6-tetrakis((4-butylphenyl)ethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

59
[ 13484-50-9 ]
[ 74331-70-7 ]
2,3,5,6-tetrakis((2,5-dimethylphenyl)ethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

60
[ 13484-50-9 ]
[ 40307-11-7 ]
2,3,5,6-tetrakis((4-ethylphenyl)ethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

61
[ 13484-50-9 ]
[ 62452-73-7 ]
2,3,5,6-tetrakis((4-propylphenyl)ethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

62
[ 13484-50-9 ]
[ 86-74-8 ]
C₅₂H₃₂N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.6%	Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice; Stage #2: tetrachloropyrazine In N,N-dimethyl-formamide at 60℃; for 15h; Inert atmosphere;	2 Synthesis of derivative M2 1.35 g (8.08 mmol) of carbazole was added to a 250 ml three-necked flask, Then, 100 mL of N,N-dimethylformamide was added as a reaction solvent, Stirred for 10 min on a magnetic stirrer. under ice bath conditions, 0.39 g (16.16 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 0.40 g (1.84 mmol) of 2,3,5,6-tetrachloropyrazine was dissolved in 20 ml of N,N-dimethylformamide was added dropwise to the reaction system. After completion of the addition, the reaction was carried out at 60 °C for 15 hours under nitrogen atmosphere. After the reaction, The reaction solution was poured into 150 ml of dilute hydrochloric acid at a concentration of 10% Decompression pumping, washing, drying, The crude product was treated with petroleum ether and ethyl acetate (PE:EA=10:1) As the mobile phase column chromatography washed impurities, And then washed with pure dichloromethane (DCM) to give 0.96 g of a yellow solid, Yield 70.6%.

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN106243091, 2016, A Location in patent: Paragraph 0017

63
[ 13484-50-9 ]
[ 37500-95-1 ]
C₈₄H₉₆N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.3%	Stage #1: 3,6-di(tert-butyl)-9H-carbazole With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice; Stage #2: tetrachloropyrazine In N,N-dimethyl-formamide at 60℃; for 15h; Inert atmosphere;	4 Synthesis of derivative M4 2.82 g (10.10 mmol) of 3,6-di-tert-butylcarbazole was added to a 250 ml three-necked flask, Then, 150 mL of N,N-dimethylformamide was added as a reaction solvent and stirred for 10 min on a magnetic stirrer. Under ice-cooling, 0.49 g (20.19 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 0.50 g (2.30 mmol) of 2,3,5,6-tetrachloropyrazine was dissolved in 20 ml of N,N-dimethylformamide, Was added dropwise to the reaction system, after the addition, nitrogen protection, 60 °C reaction 15h. After completion of the reaction, the reaction solution was poured into 150 ml of dilute hydrochloric acid at a concentration of 10%, and after decompression, Washed, dried, crude petroleum ether and dichloromethane (PE:DCM=35:1) The mobile phase was purified by column chromatography to give 2.15 g of a yellow solid in 79.3% yield.

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN106243091, 2016, A Location in patent: Paragraph 0019

64
[ 419536-33-7 ]
[ 13484-50-9 ]
2,3,5,6-tetrakis(4-(9H-carbazol-9-yl)phenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.7%	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In ethanol; toluene at 80℃; for 20h; Inert atmosphere;	6 Synthesis of derivative M6 Weigh 1.0 g (3.48 mmol) of intermediate 2, 0.13 g (0.58 mmol) of 2,3,5,6-tetrachloropyrazine, 7.4 g (34.8 mmol) of tripotassium phosphate, 0.014 g (0.012 mmol) of tetrakis(triphenylphosphine)palladium in a 100 ml dry two-necked flask, Add 50 mL (toluene:ethanol=5:1) as the reaction solvent, under nitrogen, Heated to 80 °C for 20 hours. After the reaction, The reaction solution was extracted with dichloromethane (50 mL x 3) after solvent extraction, The extracts were combined and dried over anhydrous magnesium sulfate, dried to dry the solvent and dried. The crude product was treated with petroleum ether and dichloromethane (PE:DCM=15:1) And the residue was purified by column chromatography to obtain 0.54 g of a white crystalline powder, Yield 89.7%.

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN106243091, 2016, A Location in patent: Paragraph 0021

65
[ 13484-50-9 ]
(4-(10H-phenoxyazine-10-yl)phenyl)boronic acid [ No CAS ]
C₇₆H₄₈N₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.5%	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In ethanol; toluene at 80℃; for 20h; Inert atmosphere;	8 Synthesis of derivative M8 Weigh 0.5 g (1.60 mmol) of intermediate 4, 0.06 g (0.28 mmol) of 2,3,5,6-tetrachloropyrazine, 3.4 g (16.0 mmol) of tripotassium phosphate, 0.01 g (0.008 mmol) of tetrakis(triphenylphosphine)palladium in a 50 ml dry two-necked flask, Add 25 mL (toluene:ethanol=5:1) as the reaction solvent, under nitrogen, Heated to 80 °C for 20 hours. After the reaction, The reaction solution was extracted with dichloromethane (25 mL x 3) after solvent extraction, The extracts were combined and dried over anhydrous magnesium sulfate, dried to dry the solvent and dried. The crude product was treated with petroleum ether and dichloromethane (PE:DCM=15:1) And the residue was purified by column chromatography to obtain 0.28 g of a yellow crystalline powder, Yield 90.5%.

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN106243091, 2016, A Location in patent: Paragraph 0023

66
[ 13484-50-9 ]
[4-(9,9-dimethyl-9,10dihydroaciridin-10-yl)phenyl]boronic acid [ No CAS ]
C₈₈H₇₂N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In ethanol; toluene at 80℃; for 20h; Inert atmosphere;	10 Synthesis of derivative M10 Weigh 0.4 g (1.22 mmol) of intermediate 6, 0.044 g (0.20 mmol) of 2,4,5,6-tetrachloropyrimidine, 2.6 g (12.2 mmol) of tripotassium phosphate, 0.007 g (0.006 mmol) of tetrakis(triphenylphosphine)palladium in 100 ml dried two-necked flask was charged with 50 mL (toluene:ethanol=5:1) as a reaction solvent, under nitrogen, and heated to 80 °C for 20 hours. After completion of the reaction, the solvent was extracted under reduced pressure and dichloromethane (25 mL x 3) The reaction solution was extracted and the extracts were combined and dried over anhydrous magnesium sulfate. The solvent was dried, drying. The crude product was treated with petroleum ether and dichloromethane (PE:DCM=15:1) and the residue was purified by column chromatography to obtain 0.23 g of yellow crystalline powder, Yield 92.1%.

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN106243091, 2016, A Location in patent: Paragraph 0025

67
[ 13484-50-9 ]
[ 13484-57-6 ]

Yield	Reaction Conditions	Operation in experiment
32.4%	With ammonium hydroxide at 120℃; for 14h; Sealed tube;	32 5,6-dichloro-2,3-diaminepyrazine: 2,3,5,6-tetrachloropyrazine (2g, 9.6mmol) was added to a 100ml glass sealed tube, 40ml of concentrated ammonia water was added, stirred, heated to 120 ° C, 14h reaction, the reaction of the starting material was completely detected by TLC, with acetic acid The ethyl ester was extracted three times, washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate,A yellow solid 535 mg was obtained in a yield of 32.4%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN108929280, 2018, A Location in patent: Paragraph 0139; 0143; 0144

68
[ 13484-50-9 ]
[ 5720-06-9 ]
[ 21798-19-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 0 - 100℃; for 24h; Inert atmosphere;

Reference： [1]Oda, Susumu; Shimizu, Takeshi; Katayama, Takazumi; Yoshikawa, Hirofumi; Hatakeyama, Takuji [Organic Letters, 2019]

69
[ 13484-50-9 ]
[ 78389-87-4 ]
tetra[(trimethylsilyl)ethynyl]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran at 80℃; for 48h;	2.4.1 Synthesis of precursors Precursors were synthesized according to the reported routes [1,43]. As shown in Scheme 1 , tetrachloropyrazine was synthesized through chlorination of 2,5-dioxopiperazine by phosphorus pentachloride in phosphorus oxychloride at 60 °C. Tetra[(trimethylsilyl)ethynyl] pyrazine (TEP-TMS) was synthesized through Negishi reaction where tetrachloropyrazine reacted with [(triethylsilyl)ethynyl] zinc chloride catalyzed by Pd(PPh3)4 in newly distilled THF under 80 °C for 2 days. Crude products were purified through column chromatography and characterized through mass spectrum (MS) and nuclear magnetic resonance spectrum (NMR).

Reference： [1]He, Feng; He, Jingyi; Li, Yongjun; Li, Yuliang; Shen, Han; Xue, Yurui [Applied Catalysis A: General, 2021, vol. 623]

70
[ 13484-50-9 ]
[ 13177-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride; tetrabutylammomium bromide In dimethyl sulfoxide at 65℃; for 4h;	2 Preparation of 2,3,5,6-tetrafluoropyrazine EXAMPLE 2 Preparation of 2,3,5,6-tetrafluoropyrazine Into a round bottom flask was added 2,3,5,6-tetrachloropyrazine and DMSO. To the reaction was added potassium fluoride (6 equiv) and tetrabutylammonium bromide (1.2 equiv). The reaction was warmed to 65° C. and stirred for 4 hours where the reaction was deemed complete. The reaction was worked up and the 2,3,5,6-tetrafluoropyrazine was isolated.

Reference： [1]Current Patent Assignee: WEAVER LABS - US2021/355090, 2021, A1 Location in patent: Paragraph 0007; 0326

71
[ 13484-50-9 ]
[ 1733-55-7 ]
[ 2861916-31-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	In 1,2-dimethylbenzene at 140℃; for 10h; Inert atmosphere;	2,3,5,6-Tetra(diphenylphosphoryl)pyrazine 2b. Under an argon atmosphere,a mixture of ethyl diphenylphosphinite (1.9 g, 8.1 mmol) and2,3,5,6-tetrachloropyrazine 1b (0.43 g, 2.0 mmol) was heated in o-xylene(10 ml) at 140 °C for 10 h. The resultant precipitate was separated byfiltration, washed with dry diethyl ether, and dried under reducedpressure. Yield 1.25 g (74%), mp 320 °C, off-white powder. Compounds2a,c were obtained similarly from 2,3-dichloropyrazine 1a or2,3-dichloroquinoxaline 2c (2 mmol) and Ph2POEt (4.1 mmol) in yields of 57 and 83%, respectively.

Reference： [1]Smirnova, Ekaterina V.; Artyushin, Oleg I.; Vologzhanina, Anna V.; Turanov, Aleksandr N.; Karandashev, Vasilii K.; Brel, Valery K. [Mendeleev Communications, 2022, vol. 32, # 5, p. 664 - 666]

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

CAS No. :	13484-50-9	MDL No. :	MFCD18447725
Formula :	C₄Cl₄N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OSISQXHQGOYLNG-UHFFFAOYSA-N
M.W :	217.87	Pubchem ID :	311820
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501	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.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 13484-50-9 ] {[proInfo.proName]}

Quality Control of [ 13484-50-9 ]

Related Doc. of [ 13484-50-9 ]

Product Details of [ 13484-50-9 ]

Safety of [ 13484-50-9 ]

Application In Synthesis of [ 13484-50-9 ]

[ 13484-50-9 ] Synthesis Path-Downstream 1~71

Related Functional Groups of
[ 13484-50-9 ]

Chlorides

Related Parent Nucleus of
[ 13484-50-9 ]

Pyrazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 13484-50-9 ] {[proInfo.proName]}

Quality Control of [ 13484-50-9 ]

Related Doc. of [ 13484-50-9 ]

Product Details of [ 13484-50-9 ]

Safety of [ 13484-50-9 ]

Application In Synthesis of [ 13484-50-9 ]

[ 13484-50-9 ] Synthesis Path-Downstream 1~71

Related Functional Groups of [ 13484-50-9 ]

Chlorides

Related Parent Nucleus of [ 13484-50-9 ]

Pyrazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 13484-50-9 ]

Related Parent Nucleus of
[ 13484-50-9 ]