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[ CAS No. 696-23-1 ] {[proInfo.proName]}

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Chemical Structure| 696-23-1
Chemical Structure| 696-23-1
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Product Details of [ 696-23-1 ]

CAS No. :696-23-1 MDL No. :MFCD00005191
Formula : C4H5N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FFYTTYVSDVWNMY-UHFFFAOYSA-N
M.W : 127.10 Pubchem ID :12760
Synonyms :

Calculated chemistry of [ 696-23-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 32.38
TPSA : 74.5 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) : -6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.53
Log Po/w (XLOGP3) : 0.28
Log Po/w (WLOGP) : 0.63
Log Po/w (MLOGP) : 0.06
Log Po/w (SILICOS-IT) : -0.63
Consensus Log Po/w : 0.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.15
Solubility : 9.01 mg/ml ; 0.0709 mol/l
Class : Very soluble
Log S (Ali) : -1.41
Solubility : 4.99 mg/ml ; 0.0392 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.96
Solubility : 13.8 mg/ml ; 0.109 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 696-23-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 696-23-1 ]

* 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 [ 696-23-1 ]
  • Downstream synthetic route of [ 696-23-1 ]

[ 696-23-1 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 13369-83-0 ]
  • [ 696-23-1 ]
YieldReaction ConditionsOperation in experiment
89 %Chromat. With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 0.333333 h; (1) In the 5 mL micro-reaction flask,Then, 50 mg of 4-bromo-2-methyl-5-nitroimidazole prepared in Example 1 was added,Add 3 mL of methanol to completely dissolve,And then 5 mg of 10percent palladium on carbon (Pd / C) as catalyst.The reaction flask was placed on a hydrogenation apparatus to pass high purity hydrogen gas, replaced three times, the reaction pressure was adjusted to 100 mmHg,The reaction was stirred at 25 ° C for 30 min.Stop the reaction, centrifuge to remove Pd / C,The remaining liquid was evaporated under reduced pressure to give 2-methyl-5-nitroimidazole,The yield was 47percent by HPLC analysis.
Reference: [1] Patent: CN106674123, 2017, A, . Location in patent: Paragraph 0039; 0040
  • 2
  • [ 18874-52-7 ]
  • [ 696-23-1 ]
YieldReaction ConditionsOperation in experiment
47 %Chromat. With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 0.5 h; (1) In the 5 mL micro-reaction flask,Then, 50 mg of 4-bromo-2-methyl-5-nitroimidazole prepared in Example 1 was added,Add 3 mL of methanol to completely dissolve,And then 5 mg of 10percent palladium on carbon (Pd / C) as catalyst.The reaction flask was placed on a hydrogenation apparatus to pass high purity hydrogen gas, replaced three times, the reaction pressure was adjusted to 100 mmHg,The reaction was stirred at 25 ° C for 30 min.Stop the reaction, centrifuge to remove Pd / C,The remaining liquid was evaporated under reduced pressure to give 2-methyl-5-nitroimidazole,The yield was 47percent by HPLC analysis.
Reference: [1] Patent: CN106674123, 2017, A, . Location in patent: Paragraph 0037; 0038
  • 3
  • [ 693-98-1 ]
  • [ 696-23-1 ]
YieldReaction ConditionsOperation in experiment
3.8 g at 150℃; for 2 h; Take concentrated sulfuric acid 20ml and 5g sodium sulfate into a three-mouth bottle,Stir at room temperature, slowly add 2-methylimidazole 5.0g,After starting to heat up, the temperature of the reaction liquid reaches 150°C.Slowly add concentrated nitric acid 5ml,The reaction was incubated for 2 hours after the addition.After the end of the reaction, it is cooled to 80°C and 5 ml of water is added.Ammonia water is used to adjust the pH to 3-4 and a large amount of solids precipitates.Filter, dry at 60°C,2-trifluoromethyl-5-nitroimidazole 3.8 g was obtained.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1274 - 1278
[2] Journal of the Chemical Society, 1919, vol. 115, p. 250
[3] Pharmaceutical Chemistry Journal, 1989, vol. 23, # 10, p. 861 - 863[4] Khimiko-Farmatsevticheskii Zhurnal, 1989, vol. 23, # 10, p. 1246 - 1248
[5] Patent: CN107556304, 2018, A, . Location in patent: Paragraph 0022
  • 4
  • [ 693-98-1 ]
  • [ 696-23-1 ]
  • [ 696-23-1 ]
Reference: [1] Patent: WO2015/198107, 2015, A1, . Location in patent: Page/Page column 3
  • 5
  • [ 443-48-1 ]
  • [ 696-23-1 ]
  • [ 84145-87-9 ]
  • [ 1615-15-2 ]
Reference: [1] Journal of Molecular Liquids, 2016, vol. 224, p. 589 - 598
  • 6
  • [ 693-98-1 ]
  • [ 696-23-1 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 38, p. 11525 - 11536
  • 7
  • [ 693-98-1 ]
  • [ 696-23-1 ]
  • [ 214191-53-4 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 38, p. 11525 - 11536
  • 8
  • [ 696-23-1 ]
  • [ 551-92-8 ]
Reference: [1] Patent: US4021442, 1977, A,
  • 9
  • [ 696-23-1 ]
  • [ 77-78-1 ]
  • [ 551-92-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1274 - 1278
  • 10
  • [ 696-23-1 ]
  • [ 77-78-1 ]
  • [ 13230-04-1 ]
  • [ 551-92-8 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1835
  • 11
  • [ 696-23-1 ]
  • [ 77-78-1 ]
  • [ 13230-04-1 ]
  • [ 551-92-8 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1835
  • 12
  • [ 75-21-8 ]
  • [ 696-23-1 ]
  • [ 443-48-1 ]
YieldReaction ConditionsOperation in experiment
88% at 80℃; for 12 h; (1) with a thermometer,Stirrer and airway in the reaction vessel were added formic acid 100mg,Concentrated sulfuric acid 20mg,Prepared into mixed acid solution,To the mixed acid solution was added 2-methyl-5-nitroimidazole (25 mg)Another take a couple of reaction bottles,Add 5 ml of ethylene oxide,Unicom reaction system, the reaction vessel slowly into the ethylene oxide,After reaction at 80 ° C for 12 h,Add the appropriate amount of 1M sodium hydroxide solution to the reaction solution to adjust the pH to 8,Add 5ml ethyl acetate solvent extraction three times, combined withThe phases were dried over anhydrous sodium sulfate and filtered,The filtrate was evaporated under reduced pressure to give metronidazole 29.5 mg in a yield of 88percent.
Reference: [1] Patent: CN106674123, 2017, A, . Location in patent: Paragraph 0044; 0045
[2] Pharmaceutical Chemistry Journal, 1989, vol. 23, # 10, p. 861 - 863[3] Khimiko-Farmatsevticheskii Zhurnal, 1989, vol. 23, # 10, p. 1246 - 1248
[4] Patent: CN105348200, 2016, A, . Location in patent: Paragraph 0040; 0041; 0047; 0048
[5] Patent: CN104177297, 2016, B, . Location in patent: Paragraph 0030-0070
  • 13
  • [ 696-23-1 ]
  • [ 107-07-3 ]
  • [ 443-48-1 ]
YieldReaction ConditionsOperation in experiment
3.5 g With potassium carbonate In ethanol at 75 - 80℃; (1) Synthesis reaction: 2.5 g of 2-methyl-5-nitroimidazole, 73 ml of anhydrous ethanol, 2 g of 2-chloroethanol, and 5 g of K2CO3 were placed in a reaction tank, and the temperature was raised at 75 ° C to start the heat preservation. The reaction was stopped at 75-80 ° C for 8-10 hours.(2), hot filtration, filter cake as a by-product potassium chloride, the filtrate is evaporated to dryness, dissolved in dichloromethane at 40 ° C, let cool, clear crystals, filtered, dried, that is, metronidazole 3.5 g.
Reference: [1] Patent: CN108276340, 2018, A, . Location in patent: Paragraph 0013-0014
  • 14
  • [ 19686-73-8 ]
  • [ 696-23-1 ]
  • [ 3366-95-8 ]
YieldReaction ConditionsOperation in experiment
89.1% With potassium carbonate In acetone at 70℃; for 5 h; In a 10L of Glass Reactor add 2-methyl-5-nitroimidazole, 1-bromo-2-propanol, potassium carbonate, acetone with molar ratio of 1 :3 :3 :20. Wherein, the mass of 2-methyl-5-nitroimidazole mass is 635g,, the mass of 1-bromo-2-propanol is 2070g, , the mass of Potassium carbonate is 2114g and volume of acetone is 7.1L. Under stirring, the reaction was refluxed for 5 hours and the reaction temperature was at 70 ° C; According to TLC analysis(Expand Condition: GF254 silica gel plate, developing solvent chloroform: ethanol = 85: 15) The end point ofthe reaction to obtain a reaction mixture A. A recovered acetone from the reaction mixture to A obtain a reaction mixture B; in reaction mixture B add 9L of water and  reaction mixture B through cooled   to 0 °C,centrifuged wet product; Clean water and stir 3 hours of The wet product with a temperatureof 1 ° C again Again centrifuged toobtain secnidazole crude. Thecrude product was added into 5L ofreactor then 40percent ethanol 3L was added and Activated Carbon 30g; It was heated upto 70 ° C, under reflux to dissolve and filtered to obtain a filtrate;The filtrate was cooled down to 0 ° C and crystallization three hours; Centrifugation, and dried in vacuum at 40 ° C to obtain Secnidazole. After weighing and calculation, the obtained quality of secnidazoles 820g, a total yield of 89.1percent.
Reference: [1] Patent: CN103772289, 2016, B, . Location in patent: Paragraph 0036-0042
  • 15
  • [ 696-23-1 ]
  • [ 106-89-8 ]
  • [ 16773-42-5 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With aluminum (III) chloride In ethyl acetate at 0℃; for 0.25 h;
A mixture of 2-methyl-4/5-nitro-1H-imidazole (1, 39.37mmol) and anhydrous aluminium chloride (39.37mmol) were dissolved in ethylacetate (50mL) at 0°C and stirred for 15min then added (±)-epichlorohydrin (78.74mmol) to the above reaction mixture and contents were further stirred for 15–20h. After completion of reaction (as monitored by TLC) 30mL of distilled water was added and further continued the stirring for 30min and stopped the reaction. Then EtOAc (20mL) and excess water (3×30mL) was added to the reaction mixture and organic layer was separated, dried (anhyd. Na2SO4), concentrated under reduced pressure. The crude obtained was further purified by column chromatography over silica (60–120 mesh) with methanol/chloroform as eluent to get the title compounds 2 in 79percent yield as white solid. mp: 84–86°C; IR (KBr) ν (cm−1): 3400, 3110, 1540, 1360, 1150, 771; 1H NMR (400MHz, CDCl3): δ 7.72 (s, 1H), 4.92 (s, 1H), 4.63–4.60 (m, 1H), 4.19–4.16 (m, 2H), 3.73–3.63 (m, 2H), 2.45 (s, 3H); 13C (100MHz, CDCl3): δ 151.9, 138.3, 132.2, 69.8, 49.7, 46.9, 14.4; ESI-MS: m/z 220 (M+H+).
4.8 g With aluminum (III) chloride In ethyl acetate at 0℃; Take 2-methyl-5-nitroimidazole 10g,After adding ethyl acetate 200ml dissolved,Then add anhydrous aluminum trichloride 10g, stirring and cooling,After cooling to 0°C, epichlorohydrin 20g was added dropwise.Insulation reaction,After the reaction is completed, the reaction solution is slowly added to water and hydrolyzed.Separate the ethyl acetate layerThe ethyl acetate layer was extracted with a 10percent hydrochloric acid solution.Finally, the acid-water layer was adjusted to pH 7 with ammonia, and a solid precipitated.Filter and dry to obtain compound 2 4.8g.
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 820 - 839
[2] Patent: CN107556304, 2018, A, . Location in patent: Paragraph 0024
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