2,6-Dimethylpyrazine | Pyrazines

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Quality Control of 2,6-Dimethylpyrazine Purity: 98% SDS Specification

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Product Details of 2,6-Dimethylpyrazine

CAS No. :	108-50-9
Formula :	C₆H₈N₂
M.W :	108.14
SMILES Code :	CC1=CN=CC(C)=N1
MDL No. :	MFCD00006148
InChI Key :	HJFZAYHYIWGLNL-UHFFFAOYSA-N
Pubchem ID :	7938

Safety of 2,6-Dimethylpyrazine

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H228-H302-H315-H319
Precautionary Statements:	P210-P264-P270-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Class:	4.1
UN#:	1325
Packing Group:	Ⅲ

Application In Synthesis of 2,6-Dimethylpyrazine

* 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.

Upstream synthesis route of [ 108-50-9 ]
Downstream synthetic route of [ 108-50-9 ]

[ 108-50-9 ] Synthesis Path-Upstream 1~4

1
[ 78-90-0 ]
[ 56-81-5 ]
[ 123-32-0 ]
[ 108-50-9 ]
[ 77164-93-3 ]

References: [1] Chinese Chemical Letters, 2013, vol. 24, # 8, p. 751 - 754.

2
[ 78-90-0 ]
[ 56-81-5 ]
[ 108-50-9 ]
[ 77164-93-3 ]
[ 108-49-6 ]

References: [1] Catalysis Science and Technology, 2017, vol. 7, # 15, p. 3399 - 3407.
[2] New Journal of Chemistry, 2017, vol. 41, # 18, p. 9875 - 9883.

3
[ 78-90-0 ]
[ 56-81-5 ]
[ 123-32-0 ]
[ 61892-95-3 ]
[ 108-50-9 ]
[ 77164-93-3 ]

References: [1] Chinese Chemical Letters, 2013, vol. 24, # 8, p. 751 - 754.

4
[ 78-90-0 ]
[ 56-81-5 ]
[ 108-50-9 ]
[ 77164-93-3 ]

References: [1] Catalysis Science and Technology, 2017, vol. 7, # 15, p. 3399 - 3407.

[ 108-50-9 ] Synthesis Path-Downstream 1~22

1
[ 67-56-1 ]
[ 108-50-9 ]
[ 92508-08-2 ]

References: [1]Journal of Agricultural and Food Chemistry,2000,vol. 48,p. 868 - 872.

2
[ 108-50-9 ]
[ 5521-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; In water; at 70℃;	2,6-Dimethylpyrazine (500mg, 4.60mmol) was dissolved in water (10ml), heated at 700C and KMnO4 in water (25ml) was added dropwise. The mixture was stirred and heated overnight. After cooling to room temperature the MnO2 cake was filtered and washed with water several times. The filtrate was acidified with 5M HCI solution (pH 1.5) and extracted with ethyl acetate (3 x 50ml). The residue was dried over magnesium sulphate, filtered and evaporated to afford the product (D25); MS (ES+) m/e 139 [M+H]+.

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 556 - 565.
[2]Patent: WO2006/97691,2006,A1 .Location in patent: Page/Page column 30.
[3]International Journal of Molecular Sciences,2018,vol. 19.

3
[ 108-50-9 ]
[ 38557-72-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With sulfuryl dichloride; In N,N-dimethyl-formamide; at 60℃; for 2.5h;Cooling with ice;	Example 12 [00659] Preparation of Cpd 88 H2 N 150 C / 3 days N [00660] Part 1, Step A: To a cooled solution of 2,6-dimethylpyrazine (108 g, 1.0 mol) in DMF (260 mL) on an ice/H20 bath, while stirring vigorously, was added sulfuryl chloride (270 mL, 3.3 mol). The rate of addition was controlled to maintain the reaction temperature between 40-60 C for about 2 hours. After the addition, the cooling bath was removed and the mixture was stirred for an additional 0.5 hours. LC/MS analysis of an aliquot showed <5% starting material remained. The reaction mixture was then cooled in an ice/water bath and, while maintaining the temperature below 35 C, quenched carefully with 10 M NaOH (1 L), followed by the addition of Na2C03 (solid) to pH 6. After the addition of water (800 mL), the mixture was distilled. The distillate was collected and the organics were separated. The aqueous layer was extracted with ethyl ether (100 mL x 3) and the ether extracts were combined with the organics separated previously. The combined extracts were washed with water (30 mL x 3), then brine and dried over Na2S04. After the extracts were concentrated, the residue was distilled and the product was collected as a colorless liquid, approximate boiling point: 127 C at 154 mmHg (99.1 g, 69%). 1H NMR (500 MHz, CHLOROFORM- ) delta ppm 8.05 (1H, s), 2.61 (3H, d, J=0.63 Hz), 2.50 (3H, s).
36%		First, a synthesis method of an intermediate, 2-chloro-3,5-dimethylpyrazine is described. 7.12 g of 2,6-dimethylpyrazine and 6.5 mL of dimethylformamide (abbreviation : DMF) were put in a three-neck flask equiiped with a drop funnel and a thermometer, and the inside was refluxed under a nitrogen atmosphere. 6.7 mL of sulfuric chloride was put in a drop funnel and the reaction container was soaked in an ice bath. While the reaction solution was being stirred, the sulfuric chloride was dropped in such a way that the temperature of the solution be kept 45 C +/- 5 C. After that, water was added after it was confirmed that the temperature of the solution was 40 0C or lower. After it was confirmed again that the temperature of the solution was 40 0C or lower, an aqueous sodium hydroxide was added and the pH of the solution was adjusted to 7 to 8. This solution was subjected to steam distillation. The obtained <n="82"/>solution was subjected to extraction using dichloromethane to separate an organic layer. The organic layer obtained was dried with magnesium sulfate. After the drying, the solution was filtrated. After the solvent of this solution was distilled off, the obtained residue was distilled under reduced pressure, so that an objective intermediate was obtained (clear and colorless liquid, yield of 36 %).

References: [1]Patent: WO2013/112788,2013,A1 .Location in patent: Paragraph 00660.
[2]Patent: WO2008/149828,2008,A1 .Location in patent: Page/Page column 80-81; 82.
[3]European Journal of Organic Chemistry,2005,p. 4141 - 4153.

4
[ 108-50-9 ]
[ 92508-08-2 ]

References: [1]European Journal of Organic Chemistry,2005,p. 4141 - 4153.

5
[ 134276-45-2 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 55138-74-4 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
[ 15707-34-3 ]