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[ CAS No. 16773-42-5 ] {[proInfo.proName]}

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Chemical Structure| 16773-42-5
Chemical Structure| 16773-42-5
Structure of 16773-42-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16773-42-5 ]

CAS No. :16773-42-5 MDL No. :MFCD00057960
Formula : C7H10ClN3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :IPWKIXLWTCNBKN-UHFFFAOYSA-N
M.W : 219.63 Pubchem ID :28061
Synonyms :
Ro 7-0207;NSC 95075;Tiberal;(±)-Ornidazole

Calculated chemistry of [ 16773-42-5 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.57
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.85
TPSA : 83.87 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) : -7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 0.6
Log Po/w (WLOGP) : 0.7
Log Po/w (MLOGP) : -0.1
Log Po/w (SILICOS-IT) : -0.92
Consensus Log Po/w : 0.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.58
Solubility : 5.78 mg/ml ; 0.0263 mol/l
Class : Very soluble
Log S (Ali) : -1.94
Solubility : 2.55 mg/ml ; 0.0116 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.08
Solubility : 18.1 mg/ml ; 0.0822 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.92

Safety of [ 16773-42-5 ]

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 [ 16773-42-5 ]

* 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 [ 16773-42-5 ]
  • Downstream synthetic route of [ 16773-42-5 ]

[ 16773-42-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 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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