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Chemical Structure| 6829-40-9
Chemical Structure| 6829-40-9
Structure of 6829-40-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6829-40-9 ]

CAS No. :6829-40-9 MDL No. :MFCD00130009
Formula : C7H13NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 175.18 Pubchem ID :-
Synonyms :

Safety of [ 6829-40-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P301+P310-P311 UN#:2811
Hazard Statements:H301+H311+H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6829-40-9 ]

* 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 [ 6829-40-9 ]
  • Downstream synthetic route of [ 6829-40-9 ]

[ 6829-40-9 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 6829-40-9 ]
  • [ 643-79-8 ]
  • [ 50458-79-2 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 6, p. 1017 - 1020
[2] Molecules, 2002, vol. 7, # 2, p. 252 - 263
[3] Synlett, 2001, # 11, p. 1703 - 1706
  • 2
  • [ 6829-40-9 ]
  • [ 13984-53-7 ]
  • [ 2386-37-0 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5598 - 5604
  • 3
  • [ 6829-40-9 ]
  • [ 108-24-7 ]
  • [ 1068-90-2 ]
Reference: [1] Journal of the American Chemical Society, 1944, vol. 66, p. 350
[2] Monatshefte fuer Chemie, 1953, vol. 84, p. 595,604
[3] Journal of Organic Chemistry, 1985, vol. 50, # 26, p. 5598 - 5604
[4] Organic Letters, 2003, vol. 5, # 22, p. 4187 - 4190
  • 4
  • [ 6829-40-9 ]
  • [ 78-39-7 ]
  • [ 1068-90-2 ]
YieldReaction ConditionsOperation in experiment
87% for 2 h; Reflux In a 250 mL round bottom flask, to 4 g (18.90 mmol) of diethylaminomalonate hydrochloride 5 were added 9.43 mL (0.885 g mL−1) of triethylorthoacetate, and the reaction mixture was refluxed for 2 h (oil bath). In the meantime, the colourless solution became yellow-brown. At the end, the solution was concentrated in a rotary evaporator giving a light yellow oily product.
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 62, p. 486 - 497
  • 5
  • [ 6829-40-9 ]
  • [ 75-36-5 ]
  • [ 1068-90-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1931, vol. <4>49, p. 42
[2] Bulletin de la Societe Chimique de France, 1931, vol. <4> 49, p. 47
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1928, vol. 186, p. 1361,1362[4] Bulletin de la Societe Chimique de France, 1928, vol. <4> 43, p. 933
[5] Chemistry of Heterocyclic Compounds, 1996, vol. 32, # 8, p. 960 - 970
[6] European Journal of Organic Chemistry, 2009, # 21, p. 3619 - 3627
  • 6
  • [ 3051-27-2 ]
  • [ 6829-40-9 ]
  • [ 31894-56-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1970, vol. 18, p. 1414 - 1425
  • 7
  • [ 6829-40-9 ]
  • [ 62009-47-6 ]
YieldReaction ConditionsOperation in experiment
100% With ammonia In methanol at 80℃; Diethylaminomalonate Aminomalondiamide 2-Carbamido-3-hydroxypynazine To an aqueous solution of diethylaminomalonate (hydrochloride form) was added sodium hydrogenocarbonate (pH> 7). After extraction, the organic phase was evaporated under reduced pressure and treated with an ammoniacal solution of methanol at 80°C overnight to give aminomalondiamide quantitatively. This compound was used for next step without purification and dissolved in water. To that solution was added glyoxal sodium bisulfite hemihydrate, this reaction mixture was stirred at 90°C for 3h, and then made basic with 58percent NH4OH. Then, 30percent H2O2 was added dropwise with rapid stirring to the cold solution (0°C) [J. Med. Chem. 1983, 26, 283-86, J. Heterocyclic Chem. 1979, 16, 193]. The reaction mixture was <n="131"/>allowed to warm at room temperature and the desired 2-hydroxy-3- carboxamidopyrazine precipitated. The solid was collected (63percent yield) and part of it recrystallized.
87% With ammonium chloride In water at 100℃; for 2 h; 17.5 g of 2-aminomalonate ethyl ester and 22 g of a 50percent ammonium chloride aqueous solution were weighed and heated under reflux at 100 °C for 2 hours. After the reaction was completed, the mixture was filtered, and dried by hot air at 60 degrees for 8 hours.Get white 10.2g2-aminomalonamide in a yield of 87percent.
49% With ammonia In methanol at 60℃; for 19 h; Inert atmosphere To diethyl 2-aminomalonate [3] (8.16 g; 46.6 mmol) prepared above, 2 M ammonia in methanol (233 ml; 466 mmol) was added and heated at 60°C for 19 hours under an argon atmosphere.
The reaction solvent was removed under reduced pressure to give crude 2-aminomalonamide as pale yellow powders.
The yellow colored impurities were removed by solid-liquid extraction with methanol (100 ml) by use of a Soxhlet extractor at 90°C for 21 hours under an argon atmosphere.
The nearly colorless residue in the extraction thimble was recrystallized from water to give colorless 2-aminomalonamide (2.65 g; 22.6 mmol; yield 49percent).
1H-NMR (400 MHz, DMSO-d6): δ 7.38 (2H, brs), 7.23 (2H, brs), 3.73. (1H, s), 2.13 (2H, s).
13C-NMR (100 MHz, DMSO-d6): δ 172.0 (2C), 58.2 (1C).
melting point: 192°C
Reference: [1] Patent: WO2007/144686, 2007, A1, . Location in patent: Page/Page column 129-130
[2] Patent: CN108250104, 2018, A, . Location in patent: Paragraph 0016; 0017; 0018; 0019
[3] Patent: EP2196460, 2010, A1, . Location in patent: Page/Page column 5; 6
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 78,79, 80
  • 8
  • [ 6829-40-9 ]
  • [ 24424-99-5 ]
  • [ 102831-44-7 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine In dichloromethane at 20℃; Cooling with ice Ice bath,Amino malonic acid diethyl ester (17.5 g, 0.1 mol)And triethylamine (20 g, 0.2 mol)250 ml of dichloromethane,Di-tert-butyl dicarbonate (26 g, 0.12 mil) was added to a three-necked flask, gradually raised to room temperature and stirred at that temperature,TLC monitoring reaction ends. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with dichloromethane (200 ml of X). The resulting organic phase was dried over anhydrous magnesium sulfate,Concentrated to give diethyl 2-Boc-aminomalonic acid as a colorless oil27g (yield 98percent)
95% With triethylamine In dichloromethane EXAMPLE 48
Diethyl 2-t-butoxycarbonylamino malonate
A solution of diethyl 2-aminomalonate (5 g, 23.6 mmol) and (Boc)2O (5.65 g, 25.96 mmol) in CH2Cl2 (50 mL) was treated slowly with Et3N (2.43 g, 24 mmol) for 10 minutes.
After stirring 3 h at room temperature, the reaction was washed twice with water, dried and concentrated to give 6.16 g (95percent) of the title compound.
1H-NMR (500 MHz, CDCl3) δ5.54 (d, J=7.3 Hz, 1H), 4.93 (d, J=7.8 Hz, 1H), 4.26 (m, 4H), 1.44 (s, 9H), 1.29 (t, J=6.9 Hz, 6H).
3 g With triethylamine In ethanol at 35℃; for 4 h; Step 1 : 2-tert-butoxycarbonyl amino malonate, Diethyl aminomalonate (21.2g) and ethanol (80.0 ml) were added to a flask at room temperature, (t-Boc)2 ( 24 g) in ethanol (20.0 ml) was added dropwise to the mixture, then triethylamine (14 ml) was added. The reaction mixture was heated to and maintained at 35 °C for 4 hours. After the reaction was complete, the reaction mixture was concentrated, then ethyl acetate (60.0 ml) was added to the reaction mass, washed with water two times, then separated the ethyl acetate layer, concentrated to obtain 2 - tert-butyl ethyl malonate oxycarbonylamino as a pale yellow oil: 3.0 g.
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 15, p. 2910 - 2913
[2] Patent: CN106946724, 2017, A, . Location in patent: Paragraph 0027; 0028; 0034; 0040
[3] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 12, p. 3973 - 3979
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 9, p. 2909 - 2922
[5] Patent: US2003/65176, 2003, A1,
[6] Patent: WO2013/163892, 2013, A1, . Location in patent: Page/Page column 13
  • 9
  • [ 6829-40-9 ]
  • [ 94-05-3 ]
  • [ 853058-40-9 ]
Reference: [1] Patent: US6693193, 2004, B1, . Location in patent: Page column 14
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 218 - 222
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