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[ CAS No. 866751-49-7 ] {[proInfo.proName]}

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Chemical Structure| 866751-49-7
Chemical Structure| 866751-49-7
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Product Details of [ 866751-49-7 ]

CAS No. :866751-49-7 MDL No. :MFCD17018339
Formula : C8H13N3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 151.21 Pubchem ID :-
Synonyms :

Safety of [ 866751-49-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3259
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 866751-49-7 ]

* 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 [ 866751-49-7 ]

[ 866751-49-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 866751-49-7 ]
  • [ 5538-51-2 ]
  • [ 1128045-91-9 ]
YieldReaction ConditionsOperation in experiment
46% With pyridine In chloroform at 0 - 20℃; for 2h; General Procedure for the Preparation of LigustrazinylAmides (8a-8l, Method A of Scheme 1), Example of N-((3,5,6-trimethylpyrazin-2-yl)methyl)benzamide (8a) General procedure: A solution of 2-aminemethyl-3,5,6-trimethylpyrazine (7)(0.755 g, 0.005 mol) and pyridine (0.4 g, 0.0055 mol) in chloroform (30 mL), benzoyl chloride (0.0775 g, 0.0055 mol) was added drop by drop at 0 °C. After 2 h of stirring at room temperature, the mixture was washed with water (3 x 30 mL). The organic phase was dried over anhydrous sodium sulfate and the solvent evaporated in vacuo. The residue was purified by flash column chromatography and then recrystallized from ethanol to afford 8a
  • 2
  • [ 2345-34-8 ]
  • [ 866751-49-7 ]
  • [ 1128046-28-5 ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: 4-acetyloxy-benzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 5h; Stage #2: 1‐(3,5,6‐trimethylpyrazin‐2‐yl)methanamine In tetrahydrofuran at 20℃; General Procedure for the Preparation of LigustrazinylAmides (8m-8u, Method B in Scheme 1). Example of (E)-3-(2,5-dimethoxyphenyl)-N-((3,5,6-trimethylpyr-azin-2-yl) methyl) Acrylamide (8m) General procedure: A mixture of 2,5-dimethoxylcinnamic acid (1.04 g, 0.005 mol), HOBt (0.73 g, 0.0055 mol) and DCC (1.12 g, 0.0055 mol) in anhydrous THF (20 mL) was stirred at 0 °C for 5 h, and then the solids were filtered off. A solution of 2-aminemethyl-3,5,6-trimethylpyrazine (7) (0.755 g, 0.005 mol) in anhydrous THF (15 mL) was then added to the filtrate. After the mixture was stirred at room temperature overnight, the solvent was evaporated in vacuo and the residue was poured into ethyl acetate and washed with saturated sodium bicarbonate, 50% citric acid and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. The crude product was purified by recrystallisation from 90-95% ethanol.
  • 3
  • [ 1124-11-4 ]
  • [ 866751-49-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dihydrogen peroxide; acetic acid 2.1: acetic anhydride 3.1: thionyl chloride / dichloromethane / 2.5 h / 0 - 20 °C 4.1: ethanol; N,N-dimethyl-formamide / 1.5 h / 80 °C 4.2: 2.5 h / Reflux
Multi-step reaction with 5 steps 1: dihydrogen peroxide; acetic acid 2: acetic anhydride 3: thionyl chloride / dichloromethane / 2.5 h / 0 - 20 °C 4: ethanol; N,N-dimethyl-formamide / 1.5 h / 80 °C 5: hydrazine hydrate / ethanol / 2.5 h / Reflux
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / tetrachloromethane / 1 h / 95 °C / Irradiation 2: acetonitrile / 2 h / 85 °C 3: hydrazine hydrate / ethanol / 5 h / 90 °C
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / tetrachloromethane / 2 h / 95 °C 2: acetonitrile / 2 h / 85 °C 3: hydrazine hydrate / ethanol / 5 h / 90 °C
Multi-step reaction with 3 steps 1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 10 h / 75 °C / Irradiation 2: sodium iodide / N,N-dimethyl-formamide / 1.5 h / 95 °C 3: hydrazine hydrate / ethanol / 5 h / 85 °C
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Reflux 2: N,N-dimethyl-formamide; ethanol / 2 h / 80 °C 3: hydrazine hydrate / ethanol / 2 h / Reflux
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 10 h / Irradiation; Reflux 2: sodium iodide / N,N-dimethyl-formamide / 2 h / 95 °C 3: hydrazine hydrate / ethanol / 2 h / Reflux
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; Benzoyl bromide / tetrachloromethane / 10 h / Irradiation; Reflux 2: sodium iodide / N,N-dimethyl-formamide / 2 h / 95 °C 3: hydrazine hydrate / ethanol / 2 h / Reflux

  • 4
  • [ 2316-26-9 ]
  • [ 866751-49-7 ]
  • C19H23N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.3% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 12h; Round-bottomed flask were added sequentially 274.56mg (1.32mmol) 3,4- dimethoxy cinnamic acid, 4.30 mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI, 528muL (3.97mmol) triethylamine; 20mL of methylene chloride was added, the reaction was stirred at room temperature 12 h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20 mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered, and reduced pressure evaporated to dryness.The residue was separated by silica gel column white solid, yield: 86.3%,
  • 5
  • [ 866751-49-7 ]
  • [ 830-09-1 ]
  • C18H21N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.8% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; 7 Example 7: preparaton of L4 (Compound No. 4) Round-bottomed flask were added sequentially 235.84mg (1.32mmol) 4- methoxy cinnamic acid, 4.30mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI, 528 μL (3.97mmol) of triethylamine; 20mL of dichloromethane was added, the reaction mixture was stirred at room temperature 12h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20 mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered, and reduced pressure evaporated to dryness.The residue was separated by silica gel column white solid, yield: 85.8%,
  • 6
  • [ 6099-03-2 ]
  • [ 866751-49-7 ]
  • C18H21N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.1% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 12h; Round-bottomed flask were added sequentially 235.84mg (1.32mmol) 2- methoxy cinnamic acid, 4.30mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI, 528 muL (3.97mmol) of triethylamine; 20mL of dichloromethane was added, the reaction mixture was stirred at room temperature 12h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20 mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered, and reduced pressure evaporated to dryness.The residue was separated by silica gel column white solid, yield: 90.1%,
  • 7
  • [ 10538-51-9 ]
  • [ 866751-49-7 ]
  • C19H23N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.5% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; 11 Example 11: preparaton of L8 (Compound No. 8) Round-bottomed flask were added sequentially 274.56mg (1.32mmol) 2,5-dimethoxy-cinnamic acid, 4.30 mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI, 528μL (3.97mmol) triethylamine; 20mL of methylene chloride was added, the reaction was stirred at room temperature 12 h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20 mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered, and reduced pressure evaporated to dryness.The residue was separated by silica gel column white solid, yield: 88.5%,
  • 8
  • [ 33130-03-9 ]
  • [ 866751-49-7 ]
  • C20H25N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.2% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; 13 Example 13: preparaton of L10 (Compound No. 10) Round-bottomed flask were added sequentially 314.16mg (1.32mmol) 2,3,4- trimethoxy cinnamic acid, 4.30mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI, 528μL (3.97mmol) triethylamine; 20mL of methylene chloride was added, the reaction was stirred at room temperature 12 h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20 mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered, and reduced pressure evaporated to dryness.The residue was separated by silica gel column white solid, yield: 85.2%,
  • 9
  • [ 121-34-6 ]
  • [ 866751-49-7 ]
  • C16H19N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.8% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; 15 Example 15: preparaton of L12 (Compound No. 12) Round bottom flask were sequentially added 200.64mg (1.32mmol) 3- methoxy-4-hydroxybenzoic acid, 4.30mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI and 59mg (0.44mmol) HOBT; 20mL sulfate was added N, N- dimethylformamide, the reaction mixture was stirred at room temperature nitrogen for 12h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered and the filtrate evaporated to dryness.The residue was separated by silica gel column to give a white solid, yield: 81.8%,
  • 10
  • [ 866751-49-7 ]
  • [ 99-06-9 ]
  • C15H17N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.4% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; 17 Example 17: preparaton of L14 (Compound No. 14) Round bottom flask were sequentially added 182.16mg (1.32mmol) 3- hydroxybenzoic acid, 4.30mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI and 59mg (0.44mmol) HOBT; then add 20mL dried N, N- dimethylformamide, nitrogen protection reaction was stirred at room temperature 12h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered and the filtrate evaporated to dryness.The residue was separated by silica gel column to give a white solid, yield: 78.4%,
  • 11
  • [ 866751-49-7 ]
  • [ 14755-02-3 ]
  • C17H19N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.8% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h;Inert atmosphere; Round-bottomed flask were added sequentially 216.48mg (1.32mmol) 3- hydroxy cinnamic acid, 4.30mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI and 59mg (0.44mmol) HOBT; then add 20mL dried N, N- dimethylformamide, nitrogen protection reaction was stirred at room temperature 12h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered and the filtrate evaporated to dryness.The residue was separated by silica gel column as a pale yellow solid, yield: 74.8%,
  • 12
  • [ 866751-49-7 ]
  • [ 1570-05-4 ]
  • C15H17N3O3 [ No CAS ]
  • 13
  • [ 866751-49-7 ]
  • [ 1570-05-4 ]
  • C29H29N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.6% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 12h; Round-bottomed flask were added sequentially 440.88mg (1.32mmol) 16b, 4.30mL (1.33mmol) TMP-NH2The CH2Cl2Solution, 253mg (1.32mmol) EDCI and 59mg (0.44mmol) HOBT; then add 20mL dichloromethane at room temperature the reaction was stirred 12h.TLC [V (petroleum ether) :V (acetone) = 2] Detection reaction is essentially complete, the reaction was successively washed with water (2 × 20mL) and saturated brine (20 mL) wash, dried over anhydrous sodium sulfate, filtered, and reduced pressure evaporated to dryness.The residue was separated by silica gel column to give a white solid, yield: 91.6%,
  • 14
  • [ 866751-49-7 ]
  • [ 23028-17-3 ]
  • C17H21N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 18.0h; Danshensu 1.0 g (5.0 mmol) was dissolved in 15 mL of DMF, and EDC · HC1 1(6. Ommol) and1-hydroxy-benzo-triazole (HOBt)0.8g (6. Ommol),Stir at room temperature,The reaction system was cooled to 0 C with an ice-water bath,0.83 g of 2-aminomethyl-3,5,6-trimethylpyrazine prepared in Example 1 was added dropwise(5.5 mmol),Reaction at room temperature for 18h,The reaction was monitored by TLC. After the reaction of the starting material was completed, ice-salt water was added to the reaction system(8 wt% NaCl, -4 C, same below) and ethyl acetate and extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with ice-brineWashed three times, washed the organic phase of DMF, the organic phase was dried over anhydrous Na2S04, concentrated under reduced pressure, silica gel column separation (petroleum ether: Ethyl acetate = 1: 3, v / v) to give 1.08 g of pale yellow viscous product as D001 in 65% yield.
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Chemical Structure| 2828433-66-3

A1495735[ 2828433-66-3 ]

tert-Butyl 2-((3,5,6-trimethylpyrazin-2-yl)methyl)hydrazine-1-carboxylate

Reason: Derivatives