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[ CAS No. 872-49-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 872-49-1
Chemical Structure| 872-49-1
Chemical Structure| 872-49-1
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Product Details of [ 872-49-1 ]

CAS No. :872-49-1 MDL No. :MFCD00014505
Formula : C4H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :NYDGOZPYEABERA-UHFFFAOYSA-N
M.W : 116.55 Pubchem ID :70105
Synonyms :

Calculated chemistry of [ 872-49-1 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 28.5
TPSA : 17.82 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) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 0.97
Log Po/w (WLOGP) : 1.07
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 1.1
Consensus Log Po/w : 0.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.7
Solubility : 2.31 mg/ml ; 0.0198 mol/l
Class : Very soluble
Log S (Ali) : -0.93
Solubility : 13.6 mg/ml ; 0.117 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.36
Solubility : 5.1 mg/ml ; 0.0438 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 872-49-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 872-49-1 ]

* 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 [ 872-49-1 ]
  • Downstream synthetic route of [ 872-49-1 ]

[ 872-49-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 615-35-0 ]
  • [ 872-49-1 ]
YieldReaction ConditionsOperation in experiment
46% for 2 h; Phosphorus pentachloride (383.2 g, 1.8 mol) was added to methyl oxamide (116.1 g, 1.0 mol) and heated. A melt was created at 60° C. accompanied by the formation of foam. The mixture was stirred for 2 h between 85° C.-95° C., then the resulting POCl3 was distilled. The dark-brown residue was dissolved in 700 ml H2O and set to pH 8 with 915 g 12.75percent KOH solution. The solution was extracted 4 times with 500 ml DCM, the combined organic extracts were dried over sodium sulfate, reduced and the obtained red-brown liquid subjected to a vacuum distillation. 1-methyl-5-chlorimidazole was obtained as a colorless liquid (53.1 g, 46percent). Flash point: 85-86° C. at 22 mbar 1H NMR (400 MHz, d6-DMSO): δ=7.33 (s, 1H, 4-H), 6.80 (s, 1H, 2-H), 3.47 (s, 3H, CH3) 13C NMR (100 MHz, d6-DMSO): δ=137.4 (C-2), 126.0 (C-4), 118.4 (C-5), 31.6 (CH3).
Reference: [1] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 5, p. 391 - 396
[2] Patent: US2017/281501, 2017, A1, . Location in patent: Paragraph 0272-0276
[3] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1047 - 1060
[4] Archiv der Pharmazie, 1988, vol. 321, # 4, p. 193 - 197
[5] Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2690 - 2695
  • 2
  • [ 15965-31-8 ]
  • [ 74-88-4 ]
  • [ 872-49-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 1, p. 16 - 19
  • 3
  • [ 34495-37-9 ]
  • [ 872-49-1 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1990, vol. 24, # 5, p. 374 - 375[2] Khimiko-Farmatsevticheskii Zhurnal, 1990, vol. 24, # 5, p. 56 - 57
  • 4
  • [ 600-39-5 ]
  • [ 872-49-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1877, vol. 184, p. 51
[2] Justus Liebigs Annalen der Chemie, 1882, vol. 214, p. 297
  • 5
  • [ 872-49-1 ]
  • [ 50-00-0 ]
  • [ 334893-99-1 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 956
[2] Helvetica Chimica Acta, 1923, vol. 6, p. 380
[3] Journal of the Chemical Society, 1927, p. 3132
  • 6
  • [ 872-49-1 ]
  • [ 4897-25-0 ]
YieldReaction ConditionsOperation in experiment
62% at 100℃; for 3.41667 h; Inert atmosphere; Cooling with ice A solution of 1-methyl-5-chlorimidazole (57.0 g, 0.50 mol) and diluted nitric acid (690 ml, 1.15 mol) was concentrated to dryness. The obtained light-yellow oil (131.40 g) was added dropwise over 85 min in a nitrogen atmosphere to 214 ml ice-cold, concentrated sulfuric acid. Stirring subsequently took place for 2 h at 100° C. in a nitrogen atmosphere. The reaction solution was poured onto 21 of ice and the resultant precipitate was sucked out. This was washed neutral with ice water. 1-methyl-5-chloro-4-nitro-imidazole was obtained as white crystals (45.3 g, 62percent). Melting point: 147.5-148.9° C. 1H NMR (400 MHz, d6-DMSO): δ=7.50 (s, 1H, 2-H), 3.72 (s, 3H, CH3) 13C NMR (100 MHz, d6-DMSO): δ=142.4 (C-4), 134.6 (C-2), 119.6 (C-5), 32.9 (CH3).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1369 - 1375
[2] Patent: US2017/281501, 2017, A1, . Location in patent: Paragraph 0277-0280
[3] Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2690 - 2695
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1440 - 1444
[5] Patent: EP1066286, 2009, B1, . Location in patent: Page/Page column 39-40
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