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[ CAS No. 3034-42-2 ] {[proInfo.proName]}

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Chemical Structure| 3034-42-2
Chemical Structure| 3034-42-2
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Product Details of [ 3034-42-2 ]

CAS No. :3034-42-2 MDL No. :MFCD00126968
Formula : C4H5N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JLZXSFPSJJMRIX-UHFFFAOYSA-N
M.W : 127.10 Pubchem ID :18210
Synonyms :

Calculated chemistry of [ 3034-42-2 ]      Expand+

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 : 0.0
Molar Refractivity : 32.31
TPSA : 63.64 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) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.93
Log Po/w (XLOGP3) : 0.16
Log Po/w (WLOGP) : 0.33
Log Po/w (MLOGP) : -1.16
Log Po/w (SILICOS-IT) : -1.67
Consensus Log Po/w : -0.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.07
Solubility : 10.7 mg/ml ; 0.0843 mol/l
Class : Very soluble
Log S (Ali) : -1.05
Solubility : 11.2 mg/ml ; 0.0884 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.14
Solubility : 92.5 mg/ml ; 0.728 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 3034-42-2 ]

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 [ 3034-42-2 ]

* 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 [ 3034-42-2 ]
  • Downstream synthetic route of [ 3034-42-2 ]

[ 3034-42-2 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 3034-38-6 ]
  • [ 77-78-1 ]
  • [ 3034-42-2 ]
YieldReaction ConditionsOperation in experiment
82% for 2 h; Reflux 5-Nitroimidazole (2) (1 g, 8.85 mmol) and dimethyl sulfate (1.2 mL) were added in dioxane (5 mL). Reaction mixture was refluxed for 2 h. The solvent was then evaporated under vacuum, and the oily acidic residue was neutralized by a NaHCO3 saturated aqueous solution. The formed solid and the aqueous solution were extracted with dichloromethane (3 x 5 mL). Mixture was dried with magnesium sulfate and organic solvent evaporated on vacuum, crude was purified using flash column chromatography (dichloromethane/ethylacetate; 97:3) to obtained 1-Methyl-5-nitro-1H-imidazole (4a) (0.92 g, 82percent); m.p. 60 °C.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1015 - 1018
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1274 - 1278
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 427 - 440
  • 2
  • [ 3034-38-6 ]
  • [ 3034-42-2 ]
YieldReaction ConditionsOperation in experiment
82% With dimethyl sulfate In formic acid; water EXAMPLE 2
202 parts of 5-nitroimidazole is dissolved in 600 parts of formic acid (90percent by weight), 250 parts of dimethyl sulfate is added and the whole is heated for 6 hours.
The formic acid is distilled off in vacuo.
420 parts of water is added to the residue, the whole cooled to from 0° to 5° C. and the unreacted 5-nitroimidazole (60 parts) is centrifuged off.
The mixture is adjusted to pH 10 with aqueous ammonia solution (25percent by weight) and the precipitate is separated at 0° to 5° C. 130 parts of 1-methyl-5-nitroimidazole having a melting point of 58° to 60° C. is obtained; this is equivalent to a yield of 82percent of theory based on reacted 4(5)-nitroimidazole.
Reference: [1] Patent: US4021442, 1977, A,
  • 3
  • [ 3034-38-6 ]
  • [ 80-48-8 ]
  • [ 3034-42-2 ]
Reference: [1] Patent: US4010176, 1977, A,
  • 4
  • [ 553-90-2 ]
  • [ 3034-38-6 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 18, p. 1957 - 1960
  • 5
  • [ 5709-48-8 ]
  • [ 3034-42-2 ]
Reference: [1] Patent: US4925949, 1990, A,
  • 6
  • [ 3034-38-6 ]
  • [ 74-88-4 ]
  • [ 3034-42-2 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 13, p. 3983 - 3993
  • 7
  • [ 616-47-7 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 1434
[2] Synthesis, 2011, # 17, p. 2859 - 2864
  • 8
  • [ 3034-38-6 ]
  • [ 77-78-1 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Liebigs Annalen der Chemie, 1987, p. 77 - 80
[2] Journal of the Chemical Society, 1925, vol. 127, p. 576
[3] Tetrahedron Letters, 1984, vol. 25, # 18, p. 1957 - 1960
  • 9
  • [ 616-47-7 ]
  • [ 3034-42-2 ]
  • [ 19183-15-4 ]
Reference: [1] Synthesis, 2011, # 17, p. 2859 - 2864
  • 10
  • [ 616-47-7 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
  • [ 19183-15-4 ]
Reference: [1] Synthesis, 2011, # 17, p. 2859 - 2864
  • 11
  • [ 3034-38-6 ]
  • [ 77-78-1 ]
  • [ 3034-42-2 ]
Reference: [1] New Journal of Chemistry, 2006, vol. 30, # 3, p. 349 - 358
[2] Antimicrobial Agents and Chemotherapy, 2003, vol. 47, # 1, p. 302 - 308
[3] Journal of the Chemical Society, 1924, vol. 125, p. 1434
  • 12
  • [ 13182-96-2 ]
  • [ 77-78-1 ]
  • [ 3034-42-2 ]
Reference: [1] Synthesis, 1995, # 9, p. 1183 - 1189
  • 13
  • [ 77-78-1 ]
  • [ 3034-42-2 ]
Reference: [1] Synthesis, 1995, # 9, p. 1183 - 1189
  • 14
  • [ 3034-38-6 ]
  • [ 3034-42-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2819 - 2828
  • 15
  • [ 212248-40-3 ]
  • [ 74-88-4 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 1997, vol. 33, # 12, p. 1764 - 1766
  • 16
  • [ 109540-97-8 ]
  • [ 3034-42-2 ]
Reference: [1] Journal of the Chemical Society, vol. 232, p. 236
  • 17
  • [ 186581-53-3 ]
  • [ 60-29-7 ]
  • [ 3034-38-6 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 576
  • 18
  • [ 3034-38-6 ]
  • [ 77-78-1 ]
  • [ 3034-41-1 ]
  • [ 3034-42-2 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 576
  • 19
  • [ 50-00-0 ]
  • [ 3034-42-2 ]
  • [ 936-05-0 ]
YieldReaction ConditionsOperation in experiment
62% at 140℃; for 48 h; In a sealed glass tube, formaldehyde (1 g, 33.54 mmol) and 1-Methyl-5-nitro-1H-imidazole (4a) (1 g, 7.8 mmol) solution were added in DMSO (5 mL). The tube was heated at 140 °C for 48 h. After that solution was poured into water (5 mL) and extracted with ethyl acetate (3 x 5 mL). Then mixture was dried (MgSO4) and solvent evaporation under vacuum, gave crude in the form of solid, which was recrystallized (THF/heptane, 1:1) and product (5a) was isolated (0.76 g, 62percent yield) as white powder; m.p. 117 °C.
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2819 - 2828
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1015 - 1018
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 427 - 440
[4] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[5] Patent: WO2014/205414, 2014, A1, . Location in patent: Paragraph 0298
  • 20
  • [ 3034-42-2 ]
  • [ 936-05-0 ]
Reference: [1] Patent: US4010176, 1977, A,
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