[ CAS No. 43015-44-7 ] {[proInfo.proName]}

Name: 43015-44-7|3,6-Dimethylpyrazine-2,5-dicarboxylic acid|98%
Brand: Ambeed
SKU: A733553
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Product Details of [ 43015-44-7 ]

CAS No. :	43015-44-7	MDL No. :	MFCD18449241
Formula :	C₈H₈N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FTVHHZKDJQVMCP-UHFFFAOYSA-N
M.W :	196.16	Pubchem ID :	22407722
Synonyms :

Safety of [ 43015-44-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 43015-44-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 43015-44-7 ]

[ 43015-44-7 ] Synthesis Path-Downstream 1~31

1
[ 18903-30-5 ]
[ 43015-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; water

Reference： [1]Oeconomides [Chemische Berichte, 1886, vol. 19, p. 2524] Kalischer [Chemische Berichte, 1895, vol. 28, p. 1518]

2
[ 43015-44-7 ]
[ 15719-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	at 200 - 201℃;

Reference： [1]Wleuegel [Chemische Berichte, 1882, vol. 15, p. 1051]

3
[ 160601-81-0 ]
[ 43015-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	With cis-nitrous acid

Reference： [1]Gastaldi; Princivalle [Gazzetta Chimica Italiana, 1928, vol. 58, p. 416][Gazzetta Chimica Italiana, 1929, vol. 59, p. 753]

4
[ 43015-44-7 ]
[ 209667-81-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride for 2h; Heating;
	With thionyl chloride Reflux;	3,6-dimethyl-2,5-pyrazinedicarboxylic acid chloride (6). 196 mg (1 mmol) of 5 and 2 mL of SOCl2 were refluxed for overnight. Excess SOCl2 was removed in vacuo and the residue was directly used in the next reaction.
	With thionyl chloride Reflux;

With thionyl chloride for 6h; Reflux;

1.2 (2) Synthesis of Compound (VII) Compound (V, tetramethylpyrazine) with a mass concentration of 10%The potassium permanganate aqueous solution is oxidized for 4 hours, then hot filtered.The filter cake is washed with warm water.The combined filtrates were concentrated by rotary evaporation.After cooling to room temperature, adjust the pH to 3 with concentrated sulfuric acid.The filter cake was filtered by suction for about 6 hours.Obtaining the compound (VI, 3,6-dimethyl-2,5-pyrazinedicarboxylic acid);Adding SOCl2 to compound (VI),Heating and refluxing for about 6h,Excess SOCl2 is removed by vacuum filtration,Finally obtaining a pale yellow solid compound (VII,3,6-dimethyl-2,5-pyrazinedicarboxylic acid chloride)

Reference： [1]Brunner, Henri; Störiko, Reinhard; Rominger, Frank [European Journal of Inorganic Chemistry, 1998, vol. 6, p. 771 - 781]
[2]Huang, Yao-Dong; Tu, Wei; Yuan, Yu-Qin; Fan, Dong-Li [Tetrahedron, 2014, vol. 70, # 6, p. 1274 - 1282]
[3]Lai, Miao; Ji, Xiaoming; Tao, Tao; Shan, Yuanyuan; Liu, Pengfei; Zhao, Mingqin [Journal of Thermal Analysis and Calorimetry, 2017, vol. 128, # 3, p. 1627 - 1638]
[4]Current Patent Assignee: TIANJIN UNIVERSITY - CN108503598, 2018, A Location in patent: Paragraph 0042; 0048; 0049; 0050; 0051

5
[ 885-65-4 ]
[ 43015-44-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With hydrogenchloride; sodium hydroxide 1.) reflux, 30 min;

Reference： [1]Brunner, Henri; Störiko, Reinhard; Rominger, Frank [European Journal of Inorganic Chemistry, 1998, vol. 6, p. 771 - 781]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide

8
[ 617-84-5 ]
[ 43015-44-7 ]
[ 620610-33-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: N-formyldiethylamine; 2,5-dimethylpyrazine-3,6-dicarboxylic acid With trichlorophosphate at 80 - 85℃; for 12h; Stage #2: With ammonium hydroxide Further stages.;

Reference： [1]Arany, Andrea; Meth-Cohn, Otto; Berhes, Istvan; Nyerges, Miklos [Organic and Biomolecular Chemistry, 2003, vol. 1, # 12, p. 2164 - 2167]

9
[ 43015-44-7 ]
[ 68-12-2 ]
[ 620610-32-4 ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: 2,5-dimethylpyrazine-3,6-dicarboxylic acid; N,N-dimethyl-formamide With trichlorophosphate at 80 - 85℃; for 12h; Stage #2: With ammonium hydroxide Further stages.;

Reference： [1]Arany, Andrea; Meth-Cohn, Otto; Berhes, Istvan; Nyerges, Miklos [Organic and Biomolecular Chemistry, 2003, vol. 1, # 12, p. 2164 - 2167]

10
[ 43015-44-7 ]
[ 18889-09-3 ]
[ 620610-34-6 ]

Yield	Reaction Conditions	Operation in experiment
32%	Stage #1: 2,5-dimethylpyrazine-3,6-dicarboxylic acid; N,N-diallylcarboxamide With trichlorophosphate at 80 - 85℃; for 12h; Stage #2: With ammonium hydroxide Further stages.;

Reference： [1]Arany, Andrea; Meth-Cohn, Otto; Berhes, Istvan; Nyerges, Miklos [Organic and Biomolecular Chemistry, 2003, vol. 1, # 12, p. 2164 - 2167]

11
[ 43015-44-7 ]
[ 209667-82-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 99 percent / SOCl₂ / 2 h / Heating 2: NEt₃ / CH₂Cl₂ / 16 h / Ambient temperature 3: SOCl₂ / toluene / 1 h / Heating 4: NaOH / methanol / 3.5 h / Heating

Reference： [1]Brunner, Henri; Störiko, Reinhard; Rominger, Frank [European Journal of Inorganic Chemistry, 1998, vol. 6, p. 771 - 781]

12
[ 43015-44-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 99 percent / SOCl₂ / 2 h / Heating 2: NEt₃ / CH₂Cl₂ / 16 h / Ambient temperature 3: SOCl₂ / toluene / 1 h / Heating

Reference： [1]Brunner, Henri; Störiko, Reinhard; Rominger, Frank [European Journal of Inorganic Chemistry, 1998, vol. 6, p. 771 - 781]

13
[ 43015-44-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 99 percent / SOCl₂ / 2 h / Heating 2: NEt₃ / CH₂Cl₂ / 16 h / Ambient temperature

Reference： [1]Brunner, Henri; Störiko, Reinhard; Rominger, Frank [European Journal of Inorganic Chemistry, 1998, vol. 6, p. 771 - 781]

14
[ 861554-17-8 ]
[ 43015-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / 70 °C / dann auf 115grad 2: nitrous acid

Reference： [1]Gastaldi; Princivalle [Gazzetta Chimica Italiana, 1928, vol. 58, p. 416][Gazzetta Chimica Italiana, 1929, vol. 59, p. 753]

15
[ 43015-44-7 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate In 1,2-dichloro-ethane for 24h; Heating / reflux;	2 5 mmol of (PBTZ)2Ir(Cl)2Ir(PBTZ)2, 25 mmol of 3,6-dimethylpyrazine-2,5-dicarboxylic acid (2 MPy2CA), and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane, and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down to about 50° C. and filtrated. The filtrated solution was purified by using column chromatography to thereby produce (PBTZ)2Ir(2 MPy2CA)Ir(PBTZ)2 at a yield of 89%.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2008/269484, 2008, A1 Location in patent: Page/Page column 5

16
[ 43015-44-7 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In 1,2-dichloro-ethane for 24h; Heating / reflux;	5 5 mmol of (2FPpy)2Ir(Cl)2Ir(2FPpy)2, 25 mmol of 3,6-dimethyl pyrazine-2,5-dicarboxylic acid (2 MPy2CA), and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane, and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down to about 50° C., and filtrated. The filtrated solution was purified by using column chromatography to thereby produce (2FPpy)2Ir (2 MPy2CA)Ir(2FPpy)2 at a yield of 87%.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2008/269484, 2008, A1 Location in patent: Page/Page column 5

17
[ 43015-44-7 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In 1,2-dichloro-ethane for 24h; Heating / reflux;	8 5 mmol of (SPBOZ)2Ir(Cl)2Ir(SPBOZ)2, 25 mmol of 3,6-dimethylpyrazine-2,5-dicarboxylic acid (2 MPy2CA), and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane, and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down to about 50° C., and filtrated. The filtrate solution was purified by using column chromatography to thereby produce (SPBOZ)2Ir(2 MPy2CA)Ir(SPBOZ)2 at a yield of 88%.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2008/269484, 2008, A1 Location in patent: Page/Page column 6

18
[ 43015-44-7 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In 1,2-dichloro-ethane for 24h; Heating / reflux;	11 5 mmol of (DMFQ)2Ir(Cl)2Ir(DMFQ)2, 25 mmol of 3,6-dimethylpyrazine-2,5-dicarboxylic acid (2 MPy2CA) and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane, and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down to about 50° C. and filtrated. The filtrated solution was purified by using column chromatography to thereby produce (DMFQ)2Ir(2 MPy2CA)Ir(DMFQ)2 at a yield of 83%.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2008/269484, 2008, A1 Location in patent: Page/Page column 6

19
[ 1124-11-4 ]
[ 43015-44-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium permanganate In water at 70 - 90℃; for 4h;	3,6-dimethyl-2,5-pyrazinedicarboxylic acid (5). The KMnO4 (15.8 g, 0.1 mol) was added to 150 mL distilled water in the flash, added with tetramethylpyrazine 4 (2.72 g, 20 mmol) at 70 °C, then heated to 90 °C and reaction for 4 h. The mixture was filtered and the solid MnO2 cake was washed with 50 mL water. The filtrate was concentrated to 30 mL by rotary evaporation, cooled and acidified dropwise with conc. H2SO4. The crude precipitate was recrystallized from 20 mL water to obtain compound 5 in 50% yield.1H NMR (CDCl3, 300 MHz, TMS): δ = 2.85 (s, 6H, -CH3); m.p.171 °C.
	With potassium permanganate In water at 100℃;
	With potassium permanganate In water for 4h;	1.2 Compound (V, tetramethylpyrazine) with a mass concentration of 10%The potassium permanganate aqueous solution is oxidized for 4 hours, then hot filtered.The filter cake is washed with warm water.The combined filtrates were concentrated by rotary evaporation.After cooling to room temperature, adjust the pH to 3 with concentrated sulfuric acid.The filter cake was filtered by suction for about 6 hours.Obtaining the compound (VI, 3,6-dimethyl-2,5-pyrazinedicarboxylic acid);Adding SOCl2 to compound (VI),Heating and refluxing for about 6h,Excess SOCl2 is removed by vacuum filtration,Finally obtaining a pale yellow solid compound (VII,3,6-dimethyl-2,5-pyrazinedicarboxylic acid chloride)

Reference： [1]Huang, Yao-Dong; Tu, Wei; Yuan, Yu-Qin; Fan, Dong-Li [Tetrahedron, 2014, vol. 70, # 6, p. 1274 - 1282]
[2]Lai, Miao; Ji, Xiaoming; Tao, Tao; Shan, Yuanyuan; Liu, Pengfei; Zhao, Mingqin [Journal of Thermal Analysis and Calorimetry, 2017, vol. 128, # 3, p. 1627 - 1638]
[3]Current Patent Assignee: TIANJIN UNIVERSITY - CN108503598, 2018, A Location in patent: Paragraph 0042; 0048; 0049; 0050; 0051

20
[ 43015-44-7 ]
[ 1544691-31-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / Reflux 2: triethylamine / chloroform / 3 h / Inert atmosphere; Cooling with ice