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[ CAS No. 6294-89-9 ] {[proInfo.proName]}

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Chemical Structure| 6294-89-9
Chemical Structure| 6294-89-9
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Product Details of [ 6294-89-9 ]

CAS No. :6294-89-9 MDL No. :MFCD00007594
Formula : C2H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WFJRIDQGVSJLLH-UHFFFAOYSA-N
M.W : 90.08 Pubchem ID :80519
Synonyms :

Calculated chemistry of [ 6294-89-9 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 18.91
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.56
Log Po/w (XLOGP3) : -0.8
Log Po/w (WLOGP) : -0.78
Log Po/w (MLOGP) : -1.0
Log Po/w (SILICOS-IT) : -1.39
Consensus Log Po/w : -0.68

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.24
Solubility : 156.0 mg/ml ; 1.73 mol/l
Class : Highly soluble
Log S (Ali) : -0.07
Solubility : 76.3 mg/ml ; 0.846 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.45
Solubility : 253.0 mg/ml ; 2.81 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 6294-89-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 UN#:2811
Hazard Statements:H301+H311+H331-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6294-89-9 ]

* 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 [ 6294-89-9 ]
  • Downstream synthetic route of [ 6294-89-9 ]

[ 6294-89-9 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 616-38-6 ]
  • [ 6294-89-9 ]
YieldReaction ConditionsOperation in experiment
94% at 20 - 50℃; for 24.5 h; A mixture of dimethyl carbonate (1, 45.0 g, 0.50 mol) and hydrazine hydrate (29.4 mL, 0.48 mol) was added into a 250 mL round-bottom flask equipped with a condenser. The reaction mixture was heated to 50 °C, stirred for 30 min, and then stirred at room temperature for 24 h. Water, methanol, and excess dimethyl carbonate were distilled off under reduced pressure. After dryness, a white crystal (2) (42.3 g) was obtained with a yield of 94percent, mp 69-70 °C.1H NMR (300 MHz, CDCl3): δ 3.73 (s, 3H, CH3-O), 3.77 (d, 2H,J=1.85Hz, -NH2), 6.09 (s, 1H, -NH).
94% With hydrazine hydrate In ethanol at 20 - 50℃; for 24.5 h; A mixture of dimethyl carbonate (1, 45.0 g, 0.50 mol) and hydrazine hydrate (29.4 mL, 0.48 mol) was added into a 250 mL round-bottom flask equipped with a condenser. The reaction mixture was heated to 50 °C, stirred for 30 min, and then stirred at room temperature for 24 h. Water, methanol, and excess dimethyl carbonate were distilled off under reduced pressure. After dryness, a white crystal (2) (42.3 g) was obtained with a yield of 94percent, mp 69-70 °C. 1H NMR (300 MHz, CDCl3): δ 3.73 (s, 3H, CH3 -O), 3.77 (d, 2H, J=1.85 Hz, -NH2), 6.09 (s, 1H, -NH).
91% With hydrazine hydrate In neat (no solvent) at 50 - 70℃; for 5 h; Green chemistry Hydrazine hydrate (80percent, 188 mL, 3 mol) was added dropwise to a solution of dimethyl carbonate (281 mL, 3.3 mol) over 1 h at 50 °C. On the completion of addition, the mixture was stirred at 70 °C for 4 h. Then the mixture was cooled to 0 °C. The precipitate was collected by filtration, washed with petroleum ether and dried to give compound 3 as a white solid; yield 246 g (91percent); m.p. 68–69 °C (lit.29 69–70 °C); 1H NMR (600 MHz, CDCl3): δ 6.10 (br, 1H), 3.77–3.73 (m, 5H).
70.6% for 5 h; Reflux In a 25 mL two-necked flask, 3 mL (35.6 mmol) of dimethyl carbonate and 0.85 mL (17.5 mmol) of hydrazine hydrate (80percent) were added, 0.2 g of zinc powder was added as a catalyst,Heated to reflux 5h, hot filtered to remove zinc powder,Excess dimethyl carbonate was distilled off at atmospheric pressure, the remaining liquid was cooled with cold water to stand, needle crystallization precipitated, dried to give a white solid 1.11g, a yield of 70.6percent.

Reference: [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 10, p. 4279 - 4286
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8172 - 8175[3] Angew. Chem., 2014, vol. 126, # 31, p. 8311 - 8314,4
[4] Chinese Chemical Letters, 2017, vol. 28, # 2, p. 372 - 376
[5] Chinese Chemical Letters, 2017, vol. 28, # 6, p. 1238 - 1242
[6] Journal of Chemical Research, 2018, vol. 42, # 8, p. 434 - 438
[7] Patent: CN105130895, 2017, B, . Location in patent: Paragraph 0027; 0032-0034
[8] Chemische Berichte, 1914, vol. 47, p. 2188
[9] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 94
[10] Synthetic Communications, 2006, vol. 36, # 18, p. 2613 - 2619
[11] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 2909 - 2914
[12] Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 10, p. 2024 - 2029
[13] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10299 - 10302[14] Angew. Chem., 2015, vol. 127, p. 10438 - 10441,4
  • 2
  • [ 616-38-6 ]
  • [ 6294-89-9 ]
  • [ 497-18-7 ]
Reference: [1] Journal of Chemical Research, 2018, vol. 42, # 8, p. 434 - 438
  • 3
  • [ 7803-57-8 ]
  • [ 616-38-6 ]
  • [ 6294-89-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 5, p. 1579 - 1583
  • 4
  • [ 14442-53-6 ]
  • [ 6294-89-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1912, vol. 31, p. 20
  • 5
  • [ 79-22-1 ]
  • [ 6294-89-9 ]
Reference: [1] Chemische Berichte, 1911, vol. 44, p. 3022
  • 6
  • [ 76529-39-0 ]
  • [ 6294-89-9 ]
  • [ 1666-13-3 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 2, p. 309 - 311[2] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 2, p. 345 - 347
  • 7
  • [ 14442-53-6 ]
  • [ 64-19-7 ]
  • [ 6294-89-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1912, vol. 31, p. 20
  • 8
  • [ 6294-89-9 ]
  • [ 100-51-6 ]
  • [ 5331-43-1 ]
Reference: [1] Journal of Combinatorial Chemistry, 2010, vol. 12, # 1, p. 69 - 74
  • 9
  • [ 6294-89-9 ]
  • [ 105434-90-0 ]
YieldReaction ConditionsOperation in experiment
39.3%
Stage #1: With hydrogenchloride In ethanol; water at 20℃; for 0.25 h;
Stage #2: at 20℃;
Stage #3: With potassium carbonate In methanol; water at 60℃; for 4 h; Heating / reflux
A 10 L three-necked flask is equipped with mechanical stirrer, reflux condenser and nitrogen inlet. To ethyl 3-cyano-2-oxopropionate sodium salt ("NaCOPE") (653.18 g; 4.0 mol), 585 mL of water, 3.6 L of ethanol and 350 mL of hydrochloric acid (12N; 4.2 mol) are added. The resulting suspension is stirred at RT for 15 min. Then, methyl hydrazino formiate (356.0 g; 3.95 mol) is added as a solid material. A slightly exothermic reaction occurs. After the mixture is stirred at RT for 6 h, another portion of methyl hydrazino formiate (12.0 g; 133.7 mmol) is added and the orange suspension is stirred at RT over night. Then potassium carbonate (K2CO3, 300.0 g; 2.17 mol) is added, followed by 250 mL of water. The internal temperature rises to 60° C. and a vigorous evolution of gas starts. The mixture is heated at reflux for four hours. After cooling to RT, the alcohol is evaporated to yield a red paste, which is taken up in 1 L of water and 3 L of ethyl acetate. The aqueous phase is extracted with another 500 mL portion of ethyl acetate. The organic extracts are washed with brine and dried over sodium sulfate (Na2SO4). After filtration the solvent is evaporated to yield 330 g of a brown paste. This crude product is mixed with 1 L of ether to give a light brown solid, which is separated from an orange liquid phase by filtration. The solid is dried under vacuum to yield 229.12 g (7). The liquid phase is evaporated; the residue is taken up in 250 mL of ether and cooled to -30° C. to yield another 15.09 g of 7. The total yield of 7 is 244.21 g (1.57 mol; 39.3percent). Physical characteristics are as follows: 1H-NMR (DMSO): δ (ppm) 1.26, 4.21, 5.0, 5.76, 12.12.
Reference: [1] Patent: US2008/32998, 2008, A1, . Location in patent: Page/Page column 20
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