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[ CAS No. 6136-93-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 6136-93-2
Chemical Structure| 6136-93-2
Chemical Structure| 6136-93-2
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Product Details of [ 6136-93-2 ]

CAS No. :6136-93-2 MDL No. :MFCD00043982
Formula : C6H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :UDELMRIGXNCYLU-UHFFFAOYSA-N
M.W : 129.16 Pubchem ID :80223
Synonyms :

Calculated chemistry of [ 6136-93-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 32.88
TPSA : 42.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 0.58
Log Po/w (WLOGP) : 0.91
Log Po/w (MLOGP) : -0.01
Log Po/w (SILICOS-IT) : 0.53
Consensus Log Po/w : 0.77

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.74
Solubility : 23.4 mg/ml ; 0.181 mol/l
Class : Very soluble
Log S (Ali) : -1.04
Solubility : 11.8 mg/ml ; 0.0911 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.04
Solubility : 11.8 mg/ml ; 0.091 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.4

Safety of [ 6136-93-2 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P280-P305+P351+P338 UN#:1993
Hazard Statements:H225-H302+H312+H332-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6136-93-2 ]

* 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 [ 6136-93-2 ]
  • Downstream synthetic route of [ 6136-93-2 ]

[ 6136-93-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 6136-93-2 ]
  • [ 645-36-3 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1988, # 1, p. 95 - 100
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 6640
  • 2
  • [ 61189-99-9 ]
  • [ 6136-93-2 ]
YieldReaction ConditionsOperation in experiment
64% With phosphorus pentoxide; triethylamine In toluene for 1 h; (ii) Diethoxyacetonitrile(See, for example, Inami, K., Shiba, T., Bull. Chem. Soc. Jpn., 1985, 58, 352.) <n="65"/>2,2-Diethoxyacetamide (7.13 g, 49.04 mmol; see step (i) above) was dissolved in toluene (50 mL), NEt3 (10.4 mL) was added followed by P2O5 (9.04 g, 64.32 mmol) and the mixture stirred for 1 h. The solvent was distilled off at atmospheric pressure, the distillation apparatus was then placed under reduced pressure and the distillation continued, the sub-title compound was collected as a clear colourless liquid (4.049 g, 64percent). B.P. = 1000C at 12-15 mmHg. vmax KBr/crn 1: 2983, 2937, 2896 υ(C-H), 2247 υ(N.ident.C), 1067 δ(C-O). δH 1H(CDCl3): 1.27 (6H, t, 2(CH3) (J=8.0Hz)), 3.73 (4H, m, 2(CH2)), 5.31 (IH, s, C-H).LREIMS: Found 130.13 (M+H) calculated for C6HnNO2 129.08
Reference: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 1, p. 352 - 360
[2] Patent: WO2008/38018, 2008, A1, . Location in patent: Page/Page column 63-64
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 2660
[4] Journal of the American Chemical Society, 1947, vol. 69, p. 2660
[5] Chemische Berichte, 1934, vol. 67, p. 1507,1511
  • 3
  • [ 122-51-0 ]
  • [ 6136-93-2 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 30, p. 6606 - 6609
  • 4
  • [ 645-36-3 ]
  • [ 6136-93-2 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 15, p. 5156 - 5159
  • 5
  • [ 7677-24-9 ]
  • [ 122-51-0 ]
  • [ 6136-93-2 ]
Reference: [1] Tetrahedron Letters, 1981, vol. 22, # 43, p. 4279 - 4280
[2] Tetrahedron, 1983, vol. 39, # 6, p. 967 - 974
  • 6
  • [ 6065-82-3 ]
  • [ 6136-93-2 ]
Reference: [1] Heterocycles, 1979, vol. 13, p. 175 - 180
[2] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 1, p. 352 - 360
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 2660
[4] Patent: WO2008/38018, 2008, A1,
  • 7
  • [ 74-90-8 ]
  • [ 122-51-0 ]
  • [ 6136-93-2 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 1338
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 1338
[3] Recueil des Travaux Chimiques des Pays-Bas, 1972, vol. 91, p. 711 - 728
  • 8
  • [ 5344-23-0 ]
  • [ 6136-93-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1988, # 1, p. 95 - 100
  • 9
  • [ 100313-60-8 ]
  • [ 1478-41-7 ]
  • [ 6136-93-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1960, vol. 635, p. 1 - 21
  • 10
  • [ 631-57-2 ]
  • [ 122-51-0 ]
  • [ 6136-93-2 ]
Reference: [1] Chemische Berichte, 1962, vol. 95, p. 1859 - 1862
  • 11
  • [ 64-17-5 ]
  • [ 71648-28-7 ]
  • [ 6136-93-2 ]
  • [ 61189-99-9 ]
  • [ 58995-69-0 ]
  • [ 6065-82-3 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 2660
  • 12
  • [ 6136-93-2 ]
  • [ 124-41-4 ]
  • [ 76742-48-8 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: at 20℃; for 4 h;
Diethoxyacetamidine hydrochloride was synthesized according to the literature method.3 To a solution of sodium methoxide (0.09 g, 1.6 mmol) in methanol (8.4 mL) was added diethoxyacetonitrile (2.00 g, 15.5 mmol) and the reaction mixture was stirred for 4 hours at room temperature. Solid carbon dioxide (0.5 g) was added and most of the methanol was evaporated. Diethyl ether was added and the sodium carbonate was removed by filtration.The filtrate was concentrated to afford methyl diethoxyacetimidate as a colorless oil (2.47 g, 99 percent yield) which was used in the next step without further purification. The oil was dissolved in methanol (4mL), ammonium chloride (0.82 g, 15.3 mmol) was added, and the resultant mixture was stirred overnight at room temperature. The mixture was filtered and the methanol was removed in vacuo. The resulting oil was cooled to -78 °C to form a solid and washed by diethyl ether (3 mL). The solid was filtered, warmed to ambient temperature and dried in vacuo to givedi ethoxyacetamidine hydrochloride (1.64 g, 58 percent, 2 steps) as a white solid. 1H NMR (400 MHz, DMSO-d6): 9.15(br, 4 H), 5.29 (s, 1H), 3.61 (q, 4 H, J = 6.8 Hz), 1.18 (t, 6 H, J = 6.8 Hz).
96% at 20℃; for 24 h; To a stirred solution of diethoxyacetonitrile (5 g, 38.75 mmol) in dry methanol (80 mL) was added 1 mL of a 20 percent solution of sodium methoxide. After the addition, the reaction mixture was stirred at RT for 24 h, quenched with solid CO2, and then concentrated. The resulting residue was diluted with water and extracted with chloroform. The organic layer was washed with brine and dried over Na2S04 to yield methyl 2,2-diethoxyacetimidate (6 g, 96 percent). XH NMR (400 MHz, DMSO-i3/4) δ (ppm): 7.95 (s, 1H),) , 4.82 (s, 1H), 3.66 (s, 3H), 3.49 (q , 4H, J = 7.2Hz); 1.16-1.13 (t, , 3H, J = 7.2Hz).
77% With methanol In acetonitrile at 20℃; for 16 h; To a solution of sodium methoxide (13.38 g, 248mmol) in MeOH (300 mL) was added dropwise 2,2-diethoxyacetonitrile(17.22 ml., 124 mmol). The resulting mixturewas stirred at rt for 16 h. The reaction was then diluted with300 mL of water and the product was extracted with 3x250mL of Et20. The combined Et20 layers were washed with100 mL ofbrine, dried over sodium sulfate, and evaporated togive the desired product as a colorless liquid (15.3 g, 95mmol, 77percent yield).
Reference: [1] Chemistry Letters, 2014, vol. 43, # 7, p. 1037 - 1039
[2] Patent: WO2011/28741, 2011, A1, . Location in patent: Page/Page column 341
[3] Journal of the American Chemical Society, 2015, vol. 137, # 18, p. 5980 - 5989
[4] Patent: JP5714745, 2015, B2, . Location in patent: Paragraph 0715; 0716
[5] Heterocycles, 1981, vol. 16, # 8, p. 1315 - 1319
[6] Patent: WO2006/18725, 2006, A1, . Location in patent: Page/Page column 225-226
[7] Patent: WO2007/125405, 2007, A2, . Location in patent: Page/Page column 17; 35-36
[8] Patent: WO2008/12622, 2008, A2, . Location in patent: Page/Page column 56
[9] Patent: WO2008/12623, 2008, A1, . Location in patent: Page/Page column 55
  • 13
  • [ 6136-93-2 ]
  • [ 76742-48-8 ]
YieldReaction ConditionsOperation in experiment
92% With carbon dioxide; sodium methylate In methanol; diethyl ether a)
To a solution of sodium methoxide (3.54 ml of a 25percent wt. solution in methanol, 15.5 mmol) in methanol (80 ml) was added diethoxyacetonitrile (215 ml, 155 mmol) and the reaction mixture stirred for 4 hours at room temperature.
Solid carbon dioxide was added and most of the methanol was removed in vacuo.
Diethyl ether (30 ml) was added and the sodium carbonate removed by filtration.
The residue was concentrated to afford methyl diethoxyacetimidate as a colourless oil (22 g, 92percent yield) which was used with no further purification.
MS (+ve ESI): 162 (M+H)+.
Reference: [1] Patent: US7235559, 2007, B1,
  • 14
  • [ 67-56-1 ]
  • [ 6136-93-2 ]
  • [ 76742-48-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5493 - 5496
[2] Journal of Organic Chemistry, 1982, vol. 47, # 11, p. 2196 - 2199
[3] Heterocycles, 1981, vol. 15, # 1, p. 301 - 304
[4] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 6, p. 1087 - 1089
  • 15
  • [ 67-56-1 ]
  • [ 6136-93-2 ]
  • [ 124-41-4 ]
  • [ 76742-48-8 ]
Reference: [1] Patent: WO2016/206101, 2016, A1, . Location in patent: Page/Page column 68; 69
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