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[ CAS No. 18672-03-2 ] {[proInfo.proName]}

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Chemical Structure| 18672-03-2
Chemical Structure| 18672-03-2
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Product Details of [ 18672-03-2 ]

CAS No. :18672-03-2 MDL No. :MFCD08234602
Formula : C7H5Cl2N3 Boiling Point : -
Linear Structure Formula :- InChI Key :HAADRTMPUSJNOI-UHFFFAOYSA-N
M.W : 202.04 Pubchem ID :466016
Synonyms :

Calculated chemistry of [ 18672-03-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.52
TPSA : 54.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : 2.51
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 1.96
Log Po/w (SILICOS-IT) : 2.57
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.119 mg/ml ; 0.00059 mol/l
Class : Soluble
Log S (Ali) : -3.3
Solubility : 0.1 mg/ml ; 0.000496 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.79
Solubility : 0.0328 mg/ml ; 0.000163 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 18672-03-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18672-03-2 ]

* 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 [ 18672-03-2 ]
  • Downstream synthetic route of [ 18672-03-2 ]

[ 18672-03-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 5348-42-5 ]
  • [ 506-68-3 ]
  • [ 18672-03-2 ]
YieldReaction ConditionsOperation in experiment
50% at 0 - 20℃; for 14 h; EXAMPLE 138; Synthesis of N4-(5-bromo-2-methylphenyl)-N5-(5,6-dichloro-lH-benzimidazol-2- yl)-lH-imidazole-4,5-dicarboxamide; Synthesis of 5,6-dichloro-lH-benzo[d]imidazol-2-aminc; [00392] 4,5-Dichlorobenzene-l,2-diamine (0.81 g, 0.562 mmol, commercially available from Aldrich) in acetonitrile (10 mL) and water (2 ml) at 0 °C was treated with cyanogen bromide (0.063 g, 0.6 mmol). The reaction mixture was allowed to warm to room temperature, and then stirred for 14 hours. The reaction mixture was then treated with saturated aqueous sodium hydrogen carbonate solution (50 ml) and shaken. The resulting solid was filtered off, washed with water, and dried under reduced pressure to give 0.43 g of 5,6-difluoro-lH-benzo[d]imidazol-2-amine (yield, 50percent). MS (EI): 203 (MH+).
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 4098 - 4105
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 8, p. 1252 - 1262
[3] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 16, p. 2221 - 2224
[4] Patent: WO2008/42282, 2008, A2, . Location in patent: Page/Page column 208
[5] Angewandte Chemie - International Edition, 2012, vol. 51, # 41, p. 10364 - 10367
[6] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 2842 - 2845
[7] European Journal of Medicinal Chemistry, 2009, vol. 44, # 3, p. 1024 - 1033
[8] Organic Letters, 2017, vol. 19, # 18, p. 4726 - 4729
  • 2
  • [ 934-32-7 ]
  • [ 18672-03-2 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride; dihydrogen peroxide In water EXAMPLE 5
5,6-Dichloro-2-aminobenzimidazole was prepared by a modification of the method of N. J.
Leonard et al., J. Am. Chem. Soc., 69, 2459 (1947) for 2-amino-5-chlorobenzimidazole.
To 77.2 g. (0.58 mole) of 2-aminobenzimidazole dissolved in 500 ml. of water and 50 ml. of 12N hydrochloric acid was added an additional 900 ml. of concentrated hydrochloric acid.
The solution was stirred during the addition of 120 ml. of 30percent hydrogen peroxide (sp.gr. 1.10) and for 2 hours following the addition.
After evaporation to dryness at reduced pressure, the residual solid was taken up in 500 ml. of water and made alkaline by addition of conc. NH4 OH.
After the solution had been boiled it was cooled to 20° C., the precipitated solid was collected by filtration and washed with water to afford 104.5 g. (89percent yield) of crude product.
Upon recrystallization from ethanol it melted at 252°-254° C.
Reference: [1] Patent: US4002623, 1977, A,
  • 3
  • [ 5348-42-5 ]
  • [ 506-68-3 ]
  • [ 7440-44-0 ]
  • [ 18672-03-2 ]
Reference: [1] Patent: US5360795, 1994, A,
[2] Patent: US5574058, 1996, A,
  • 4
  • [ 6641-64-1 ]
  • [ 18672-03-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 8, p. 1252 - 1262
  • 5
  • [ 18672-03-2 ]
  • [ 16865-11-5 ]
YieldReaction ConditionsOperation in experiment
49.5% With sodium nitrite In methanol; chloroform; water Method B
A CuCl2 saturated aqueous solution (15 ml) was diluted to 25 ml with water.
Sodium nitrite (1.035 g, 5 mmole) was dissolved in 5 ml of water and slowly added to the CuCl2 solution.
After two minutes, 2-amino-5,6-dichlorobenzimidazole (0.935 g, 5 mmole) was slowly added in small portions.
The mixture was stirred at room temperature for 1 hr.
Excess CuCl2 solution was added and the mixture was heated on a steam bath for 1 hr.
The aqueous solution was then extracted with ethyl acetate (3*50 ml) and the organic layer was washed with brine, dried with MgSO4, concentrated, and separated on a silica column using 2percent MeOH/CHCl3 to afford 545 mg (49.5percent) of 2,5,6-trichlorobenzimidazole.
1 H NMR, TLC, and MS analysis were identical to the same compound obtained by Method A.
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 4098 - 4105
[2] Patent: US5248672, 1993, A,
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