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Product Details of [ 132029-07-3 ]

CAS No. :132029-07-3 MDL No. :MFCD00514515
Formula : C4H2N6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PDJPUDXGFQGSRL-UHFFFAOYSA-N
M.W : 166.10 Pubchem ID :1899069
Synonyms :

Safety of [ 132029-07-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P301+P310-P321-P330-P405-P501 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 132029-07-3 ]

* 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 [ 132029-07-3 ]

[ 132029-07-3 ] Synthesis Path-Downstream   1~38

  • 1
  • 4H,7H-[1,2,5]Oxadiazolo[3,4-b]pyrazine-5,6-dione dioxime [ No CAS ]
  • [ 132029-07-3 ]
YieldReaction ConditionsOperation in experiment
85% With urea In water at 120℃; for 24h; 5 Example 5. Synthesis of Compound DFP Urea (23.6 g, 391.2 mmol) was dissolved in water (95 mL),Compound 5 (24 g, 130.4 mmol) was added with stirring and allowed to react at 120° C. for 24 h before cooling to room temperature.After leaving the refrigerator overnight, a large amount of yellow solids precipitated were filtered, washed with ice water, and dried to give compound DFP (18.5 g, 85%).
82% With sodium hydroxide
With urea
  • 2
  • [ 110-91-8 ]
  • [ 50-00-0 ]
  • [ 132029-07-3 ]
  • 4,8-Bis-morpholin-4-ylmethyl-4H,8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In methanol; water for 0.5h;
  • 4
  • [ 18997-19-8 ]
  • [ 132029-07-3 ]
  • 2,2-Dimethyl-propionic acid 8-(2,2-dimethyl-propionyloxymethyl)-8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazin-4-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide In acetonitrile for 24h; Ambient temperature;
  • 5
  • [ 506-96-7 ]
  • [ 132029-07-3 ]
  • [ 186205-18-5 ]
YieldReaction ConditionsOperation in experiment
68% With pyridine In acetonitrile at 0℃; for 2h;
  • 6
  • [ 100-39-0 ]
  • [ 132029-07-3 ]
  • [ 138589-92-1 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In acetonitrile for 24h; Ambient temperature;
  • 7
  • [ 50-00-0 ]
  • [ 106-47-8 ]
  • [ 132029-07-3 ]
  • C18H14Cl2N8O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In methanol; water
  • 8
  • [ 78-94-4 ]
  • [ 132029-07-3 ]
  • 4-[8-(3-Oxo-butyl)-8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazin-4-yl]-butan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With hydrogenchloride; hydroquinone In diethyl ether for 1h; Heating;
80% With triethylamine In 1,4-dioxane for 12h; Ambient temperature;
  • 9
  • [ 105-39-5 ]
  • [ 132029-07-3 ]
  • (8-Ethoxycarbonylmethyl-8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazin-4-yl)-acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydroxide In acetonitrile for 24h; Ambient temperature;
  • 10
  • [ 501-53-1 ]
  • [ 132029-07-3 ]
  • Bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazine-4,8-dicarboxylic acid dibenzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With pyridine In acetonitrile
  • 11
  • [ 556-61-6 ]
  • [ 132029-07-3 ]
  • 8H-Bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazine-4-carbothioic acid methylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In acetone for 2h; Heating;
  • 12
  • [ 79-22-1 ]
  • [ 132029-07-3 ]
  • Bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazine-4,8-dicarboxylic acid dimethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide In acetonitrile for 24h; Ambient temperature;
  • 13
  • [ 50-00-0 ]
  • [ 60-23-1 ]
  • [ 132029-07-3 ]
  • 2-({8-[(2-Mercapto-ethylamino)-methyl]-8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazin-4-ylmethyl}-amino)-ethanethiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In methanol; water
  • 14
  • [ 598-31-2 ]
  • [ 132029-07-3 ]
  • 1-[8-(2-Oxo-propyl)-8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazin-4-yl]-propan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With sodium hydroxide In acetonitrile for 24h; Ambient temperature;
  • 15
  • [ 132029-07-3 ]
  • [ 201025-27-6 ]
  • [ 201025-28-7 ]
YieldReaction ConditionsOperation in experiment
1: 91% 2: 4% With hydroxylaminosulfate; sodium carbonate at 70 - 75℃; for 1h;
1: 28.1% 2: 6.8% With water; sodium hydrogencarbonate; sodium carbonate; hydroxylamine-O-sulfonic acid at 70 - 75℃; for 1.5h; Synthesis of ADFP and DADFP Synthesis of ADFP and DADFP: 4-Aminodifurazano[3,4-b,e]pyrazine (ADFP) and 4,8-diaminodifurazano[3,4-b,e]pyrazine (DADFP) were synthesized by the method outlinedin Scheme-IV.To a solution of 0.5 g (0.003 mol) of 4,8-dihydrodifurazano[3,4-b,e]pyrazine (DFP) and 0.75 g (0.007 mol) ofsodium carbonate in 14.5 mL of water at 70-75 °C, we addeda solution of 1.02 g (0.008 mol) of hydroxylamino-O-sulfuricacid in 5.2 mL of water for 10 min. The pH was kept at 8-9 bythe addition of sodium bicarbonate. The mixture was kept at70-75 °C for 1.5 h and was then cooled to 15-20 °C. The precipitatewas filtered off, washed with water and acetone anddried to give 0.04 g offwhite solid 4,8-diamino-difurazano[3,4-b,e]pyrazine (DADFP) with a yield of 6.8 %. m.p.: 282.3-283.8 °C. 1H NMR (DMSO-d6, 500 MHz), d: 5.788 (s, 4H,-2NH2); 13C NMR (DMSO-d6, 125 MHz), d: 149.93; IR (KBr,nmax, cm-1), 3312, 3246 (-NH2), 1666 (C=N), 1613, 1443, 1021(furazan ring); Anal. calcd for C4H4N8O2: C 24.50, N 57.13, H2.06; found (%): C 24.41, N 57.23, H 2.01; MS (m/z): 180[M-NH2]-.During the neutralization of the above alkaline filtratesolution with hydrochloric acid, the monosubstitition productof DFP was separated. It was washed with water and dried togive 0.153 g white solid 4-aminodifurazano[3,4-b,e]pyrazine(ADFP) with a yield of 28.1 %. m.p.: 217.8-219.4 °C. 1H NMR(DMSO-d6, 500 MHz), d: 5.751 (s, 2H, -NH2), 11.913 (s, 1H,-NH); 13C NMR (DMSO-d6, 125 MHz), d: 146.89, 150.22; IR(KBr, nmax, cm-1), 3325 (-NH2), 3283 (-NH), 1654 (C=N), 1618,1445, 1003 (furazan ring); Anal. Calcd for C4H3N7O2: C 26.53,N 54.14, H 1.67; found C 26.38, N 54.21, H 1.76; MS (m/z):180 [M-H]-.
  • 16
  • [ 132029-07-3 ]
  • bisfurazano[3,4-b:3',4'-e]pyrazine biradical [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With nitric acid; trifluoroacetic anhydride at 0℃; for 1h;
92% With sodium hydroxide; chlorine In water 1.) cooling, 2.5 h, 2.) r.t., 12 h;
  • 17
  • [ 132029-07-3 ]
  • [ 106-89-8 ]
  • 4,8-Bis-oxiranylmethyl-4H,8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydroxide In acetonitrile for 24h; Ambient temperature;
  • 18
  • [ 132029-07-3 ]
  • [ 74-88-4 ]
  • 4,8-Dimethyl-4H,8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In acetonitrile for 24h; Ambient temperature;
  • 19
  • [ 88-88-0 ]
  • [ 132029-07-3 ]
  • 4,8-di(2,4,6-trinitrophenyl)difurazano[3,4-b:3',4'-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.8% Stage #1: 4H,8H-bis-furazano-[3,4-b:3′,4′-e]pyrazine With triethylamine In acetonitrile at 20℃; for 0.333333h; Stage #2: 2,4,6-trinitrochlorobenzene In acetonitrile at 20℃; for 5h;
77% With triethylamine In acetonitrile for 24h; Ambient temperature;
  • 20
  • [ 509-14-8 ]
  • [ 132029-07-3 ]
  • 4-Dinitromethyl-4H,8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium carbonate In methanol for 5h; Heating;
  • 21
  • [ 21985-89-7 ]
  • [ 132029-07-3 ]
  • 4,8-Bis(3,5-diamino-2,4,6-trinitrophenyl)difurazano[3,4-b:3',4'-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine In acetonitrile for 24h; Ambient temperature;
  • 22
  • [ 108-24-7 ]
  • [ 132029-07-3 ]
  • [ 186205-18-5 ]
YieldReaction ConditionsOperation in experiment
67% at 70 - 80℃; for 2h;
  • 23
  • [ 132029-07-3 ]
  • [ 24294-89-1 ]
YieldReaction ConditionsOperation in experiment
38% With nitric acid In acetic acid at 90℃; for 0.333333h;
  • 24
  • [ 132029-07-3 ]
  • 4,7-Dinitroso-4H,7H-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With nitric acid; sodium nitrite In acetic acid at 90 - 100℃; for 15h;
  • 25
  • [ 132029-07-3 ]
  • [ 74-88-4 ]
  • 4,8-Dimethyl-4H,8H-bis[1,2,5]oxadiazolo[3,4-b;3',4'-e]pyrazine [ No CAS ]
  • [ 212391-77-0 ]
YieldReaction ConditionsOperation in experiment
1: 18% 2: 47% With sodium hydroxide In ethanol at 60 - 70℃; for 6h;
  • 27
  • bis-(8<i>H</i>-bis[1,2,5]oxadiazolo[3,4-<i>b</i>;3',4'-<i>e</i>]pyrazin-4-yl)-diazene [ No CAS ]
  • [ 132029-07-3 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol Heating;
  • 28
  • [ 404852-17-1 ]
  • [ 132029-07-3 ]
  • [ 1391032-55-5 ]
  • [ 1391032-54-4 ]
YieldReaction ConditionsOperation in experiment
1: 29.6% 2: 16.5% With N-ethyl-N,N-diisopropylamine In chloroform for 1.5h; Reflux;
  • 29
  • [ 1161751-72-9 ]
  • [ 132029-07-3 ]
  • [ 1391032-54-4 ]
YieldReaction ConditionsOperation in experiment
0.83 g In tetrahydrofuran at 50 - 60℃; for 2h;
  • 30
  • [ 1161751-72-9 ]
  • [ 132029-07-3 ]
  • [ 1391032-55-5 ]
  • [ 1391032-54-4 ]
YieldReaction ConditionsOperation in experiment
1: 43% 2: 11%
  • 31
  • [ 97-00-7 ]
  • [ 132029-07-3 ]
  • 4,8-bis(2,4-dinitrophenyl)difurazano[3,4-b:3',4'-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.3% Stage #1: 4H,8H-bis-furazano-[3,4-b:3′,4′-e]pyrazine With triethylamine In acetonitrile at 20℃; for 0.333333h; Stage #2: 1-chloro-2,4-dinitro-benzene In acetonitrile for 8h; Reflux;
62.3% Stage #1: 4H,8H-bis-furazano-[3,4-b:3′,4′-e]pyrazine With triethylamine In acetonitrile at 25℃; for 0.333333h; Stage #2: 1-chloro-2,4-dinitro-benzene In acetonitrile at 80℃; for 8h; 1 After stirring at a temperature of 25 ° C,4H, 8H-difurazano[3,4-b: 3 ', 4'-e] pyrazine(1 g, 6 mmol) was added to anhydrous acetonitrile (15 mL)After stirring and stirring, NEt3 (1.21 g, 12 mmol) was slowly added dropwise thereto.After stirring for 20 min, 1-chloro-2,4-dinitrobenzene (2.43 g, 12 mmol) in anhydrous acetonitrile (5 mL) was slowly added thereto,The solution was heated to 80 ° C and heated for 8 hours. After cooling, the mixture was allowed to stand at -18 ° C for 24 h,Generate a lot of red crystals. The resulting crystals were washed successively with acetonitrile, hot water and methanol,Dried to give 1.87 g of 4,8-bis (2,4-dinitrophenyl)difurazano[3,4-b: 3 ', 4'-e] pyrazine,The yield was 62.3% and the purity was 98.5%.
  • 32
  • [ 132029-07-3 ]
  • C5HN5S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With pyridine; disulfur dichloride In acetonitrile at -25 - 82℃; for 4h; Inert atmosphere; 3.2. General Procedure for the Reaction of 1,2,5-Oxadiazoles with S2Cl2 and Pyridine in Acetonitrile General procedure: Sulfur monochloride (quantity, see Table 1) was added dropwise to a stirred suspension of oxadiazole6-9 (1.0 mmol) and pyridine (quantity, see Table 1) in dry acetonitrile (10 mL) under argon at -25 °C.The mixture was stirred at room temperature or heated at the temperature and for the time specified inTable 1. The precipitate was filtered and washed thoroughly with MeCN and hexane.
  • 33
  • [ 132029-07-3 ]
  • 4,8-dihydro-1,2,5-thiadiazolo[3,4-b]-1,2,5-oxadiazolo[3,4-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With pyridine; disulfur dichloride In acetonitrile at -25 - 20℃; for 20h; Inert atmosphere; 3.2. General Procedure for the Reaction of 1,2,5-Oxadiazoles with S2Cl2 and Pyridine in Acetonitrile General procedure: Sulfur monochloride (quantity, see Table 1) was added dropwise to a stirred suspension of oxadiazole6-9 (1.0 mmol) and pyridine (quantity, see Table 1) in dry acetonitrile (10 mL) under argon at -25 °C.The mixture was stirred at room temperature or heated at the temperature and for the time specified inTable 1. The precipitate was filtered and washed thoroughly with MeCN and hexane.
  • 34
  • [ 132029-07-3 ]
  • 4,8-dihydrobis([1,2,5]thiadiazolo)[3,4-b:3',4'-e]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With pyridine; disulfur dichloride In acetonitrile at -25 - 20℃; for 20h; Inert atmosphere; 3.2. General Procedure for the Reaction of 1,2,5-Oxadiazoles with S2Cl2 and Pyridine in Acetonitrile General procedure: Sulfur monochloride (quantity, see Table 1) was added dropwise to a stirred suspension of oxadiazole6-9 (1.0 mmol) and pyridine (quantity, see Table 1) in dry acetonitrile (10 mL) under argon at -25 °C.The mixture was stirred at room temperature or heated at the temperature and for the time specified inTable 1. The precipitate was filtered and washed thoroughly with MeCN and hexane.
  • 35
  • [ 132029-07-3 ]
  • [ 201025-28-7 ]
YieldReaction ConditionsOperation in experiment
34% With sodium carbonate; hydroxylamine-O-sulfonic acid In water at 75℃; for 2h; 6 Example 6. Synthesis of Compound 6 DFP (5 g, 30 mmol) and sodium carbonate (9.5 g, 90 mmol) were dissolved in 145 mL of water, heated to 75[deg.] C. and a solution of NH2OSO3H (15.3 g, 120 mmol) in water (65 mL) was added dropwise.After the completion of the dropwise addition, the pH of the system was adjusted to 8-9 with sodium carbonate. After the reaction at 75° C. for 2 hours, it was cooled to room temperature. After filtration, washing with water and acetone, drying afforded a grey diamino-substituted product 6 (2 g, 34%).
With hydroxylamine-O-sulfonic acid
  • 36
  • [ 132029-07-3 ]
  • C4N6O2(2-)*2K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With potassium hydroxide In methanol; water at 20℃; for 0.5h; 1 Example 1. Synthesis of Compound 1 DFP (3.32 g, 20.0 mmol) was dissolved in methanol (50 mL), and a solution of potassium hydroxide (2.46 g, 44.0 mmol) in water (6 mL) was added dropwise to the mixture, and the mixture was stirred at room temperature for 30 min.A large amount of yellow solid is produced.Filter, wash with methanol and acetone,Drying a yellow solid 1 (4.52 g, yield: 93%).
85.8% With potassium hydroxide In methanol; water at 10 - 20℃; for 0.5h; 4.2. Synthesis and Characterization of Energetic Materials Synthesis of 4,8-dipotassiumdifurazano[3,4-b,e]pyrazine (DFPK) To a solution of DFP (0.66 g, 5.0 mmol) inabsolute methanol (15 mL) at 10 C, a solution of potassium hydroxide (0.62 g, 11.0 mmol) in water(1.5 mL) was added portionwise. The mixture was stirred for 0.5 h at room temperature. The precipitatewas filtered o, washed with methanol and acetone, and dried to give 1.04 g yellow powder, yield 85.8%.13C-NMR (D2O, 125 MHz), : 157.02; IR (KBr) cm1: 1557 (C=N), 1532, 1381, 1341, 1011 (furazan ring),887, 774; Anal. for C4K2N6O2 (mol. wt. 242.28): Calcd: C 19.83, N 34.69; Found: C 19.78, N 33.67.
  • 37
  • [ 132029-07-3 ]
  • 1:2 cocrystal of 4H,8H-difurazano[3,4-b:3',4'-e]pyrazine and hydroxylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine In ethanol; water Heating;
  • 38
  • (5Z,6E)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6(4H,7H)-dione dioxime [ No CAS ]
  • [ 132029-07-3 ]
YieldReaction ConditionsOperation in experiment
61% With [bis(acetoxy)iodo]benzene In acetonitrile at 25℃; for 0.75h; Schlenk technique;
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