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[ CAS No. 5851-46-7 ] {[proInfo.proName]}

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Chemical Structure| 5851-46-7
Chemical Structure| 5851-46-7
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Product Details of [ 5851-46-7 ]

CAS No. :5851-46-7 MDL No. :MFCD00628961
Formula : C12H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :OYGJENONTDCXGW-UHFFFAOYSA-N
M.W : 188.27 Pubchem ID :22123
Synonyms :

Calculated chemistry of [ 5851-46-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.42
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.29
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 3.85
Log Po/w (WLOGP) : 3.3
Log Po/w (MLOGP) : 2.51
Log Po/w (SILICOS-IT) : 3.81
Consensus Log Po/w : 3.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.64
Solubility : 0.0427 mg/ml ; 0.000227 mol/l
Class : Soluble
Log S (Ali) : -4.15
Solubility : 0.0134 mg/ml ; 0.000071 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.92
Solubility : 0.00227 mg/ml ; 0.0000121 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.88

Safety of [ 5851-46-7 ]

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

Application In Synthesis of [ 5851-46-7 ]

* 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 [ 5851-46-7 ]
  • Downstream synthetic route of [ 5851-46-7 ]

[ 5851-46-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 66-25-1 ]
  • [ 95-54-5 ]
  • [ 5851-46-7 ]
YieldReaction ConditionsOperation in experiment
85% With oxygen; cobalt(II) hydroxide In ethanol at 20℃; for 4 h; General procedure: To a mixture of 1,2-phenylenediamine (1.0 mmol) and aldehyde (1.2 mmol) in ethanol (3 mL) under open oxygen atmosphere, 10 mol percent of the catalysts were added. The resulting mixture was stirred at room temperature for appropriate time (refPreviewPlaceHolderTable 2). After completion of the reaction, as monitored by TLC, the reaction mixture was diluted with ethanol (20 mL) and the catalyst was separated by filtration. The organic layer was concentrated under reduced pressure and the crude product was purified by silicagel column chromatography using ethyl acetate-n-hexane (1:9) as eluent to afford pure benzimidazole product. The spectral data are in full agreement with the data reported in literature.refPreviewPlaceHolder [48] , refPreviewPlaceHolder[54] and refPreviewPlaceHolder[55] Some of the compounds' spectral data are given below.
82% With tris(pentafluorophenyl)borate In ethanol at 20℃; for 0.75 h; General procedure: A mixture of benzaldehyde 1 (1 mmol), o-phenylenediamine 5a (1 mmol) in EtOH (10 mL) was stirred magnetically at room temperature in the presence of B(C6F5)3 [5 mol percent]. After completion of reaction, as indicated by TLC analysis, the solid obtained was filtered, washed with ethanol, dried and re-crystallize from ethanol to give pure product (6a). The assigned structures of the products were established from their spectral and physical properties and also by comparison with available literature data.
73% at 20℃; for 0.583333 h; Green chemistry General procedure: Aldehyde (1 mmol) and o-phenylenediamine (1 mmol) were mechanically mixed in 25 percent Co/Ce-ZrO2 nano fine particles (0.1 g), at room temperature for appropriate time (monitored by TLC). Upon completion of the reaction, boiling ethanol (10 ml) was added, the catalyst was filtered off and the product was recovered at ambient temperature. For more purification, the solid residue recrystallized using ethanol/water and benzimidazoles were obtained in high yields. All compounds were fully characterised by melting point apparatus, IR and 1H NMR spectroscopy and were compared by those of authentic sample.
Reference: [1] Synthetic Communications, 2011, vol. 41, # 1, p. 58 - 62
[2] Tetrahedron Letters, 2011, vol. 52, # 43, p. 5575 - 5580
[3] Tetrahedron Letters, 2015, vol. 56, # 48, p. 6795 - 6799
[4] Tetrahedron Letters, 2007, vol. 48, # 1, p. 61 - 64
[5] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 1, p. 153 - 155
[6] Tetrahedron Letters, 2010, vol. 51, # 39, p. 5195 - 5199
[7] RSC Advances, 2016, vol. 6, # 58, p. 53596 - 53601
[8] Synlett, 2004, # 10, p. 1832 - 1834
[9] Chinese Journal of Chemistry, 2010, vol. 28, # 11, p. 2249 - 2254
[10] Catalysis Letters, 2014, vol. 144, # 12, p. 2184 - 2190
[11] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 5, p. 1499 - 1502
[12] Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 7, p. 1011 - 1017[13] Khim. Geterotsikl. Soedin., 2012, vol. 48, # 7, p. 1088 - 1094,7
[14] Green Chemistry, 2012, vol. 14, # 12, p. 3273 - 3276
  • 2
  • [ 95-54-5 ]
  • [ 142-62-1 ]
  • [ 5851-46-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 110℃; for 3 h;
Stage #2: at 140℃; for 1.5 h;
A 50 ml reaction flask equipped with a mechanical stirrer, thermometer, manifold and reflux condenser was charged with 9.6 g (82.5 mmol) of n-hexanoic acid and 0.12 g (1.47 mmol) of natrium, and heated to 110 ° C with stirring. Which added o-phenylenediamine 8. lg.The temperature was raised to 140 ° C and the reaction was carried out for 1.5 hours. The reaction progress was monitored by TLC and the end point of the reaction (developing solvent Volume ratio of ethyl acetate: petroleum ether = 1: 1, Rf = 0.43). The reactants were neutralized with 8 wtpercent Na0H solution and stirred until the pH was 7.0 ~ 8.5; filter, washed with water to neutral crude, with ethanol - water mixed solvent recrystallization (volume ratio of 1: 2 ~ 1: 3), filtration, drying in pure product 12. 7g, the yield was 90. 0percent, m. Ρ. 160 ~ 161 ° C.
Reference: [1] Synthetic Communications, 2007, vol. 37, # 15, p. 2457 - 2460
[2] Patent: CN103483266, 2016, B, . Location in patent: Paragraph 0041; 0042; 0043; 0044
[3] Annales Pharmaceutiques Francaises, 2003, vol. 61, # 1, p. 57 - 61
[4] Synthetic Communications, 2002, vol. 32, # 24, p. 3703 - 3709
[5] New Journal of Chemistry, 2007, vol. 31, # 8, p. 1417 - 1420
[6] Journal of the Chemical Society, 1937, p. 1699
[7] Monatshefte fuer Chemie, 1931, vol. 57, p. 97,104
[8] Journal of the American Chemical Society, 1937, vol. 59, p. 178
  • 3
  • [ 102-86-3 ]
  • [ 95-54-5 ]
  • [ 5851-46-7 ]
YieldReaction ConditionsOperation in experiment
57% With 5%-palladium/activated carbon In water; toluene at 110℃; for 20 h; Inert atmosphere General procedure: A mixture of o-phenylenediamine (1) (0.108 g, 1 mmol), tributylamine (2a) (0.185g, 1 mmol), 5percent Pd/C (0.106 g, 0.05 mmol) and toluene/H2O (10 mL/0.5 mL) was placed in 25 mL round bottom flask. After the system was flushed with Ar from an Ar balloon connected to the flask via a reflux condenser, the reaction mixture was allowed to react at 110 oC for 20 h. The reaction mixture was filtered through a short silica gel column (ethylacetate-hexane mixture) to eliminate catalyst residue. Removal of the solvent left a crude mixture, which was separated by thin layer chromatography (silica gel, ethyl acetate-hexanemixture = 1/1) to give 2-propylbenzimidazole (3a) (0.115 g,72percent). All products are known and several selected spectroscopic data are shown below.
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 4188 - 4190
  • 4
  • [ 143-16-8 ]
  • [ 95-54-5 ]
  • [ 5851-46-7 ]
YieldReaction ConditionsOperation in experiment
31% With 5%-palladium/activated carbon In water; toluene at 110℃; for 40 h; Inert atmosphere General procedure: A mixture of o-phenylenediamine (1) (0.108 g, 1 mmol), tributylamine (2a) (0.185g, 1 mmol), 5percent Pd/C (0.106 g, 0.05 mmol) and toluene/H2O (10 mL/0.5 mL) was placed in 25 mL round bottom flask. After the system was flushed with Ar from an Ar balloon connected to the flask via a reflux condenser, the reaction mixture was allowed to react at 110 oC for 20 h. The reaction mixture was filtered through a short silica gel column (ethylacetate-hexane mixture) to eliminate catalyst residue. Removal of the solvent left a crude mixture, which was separated by thin layer chromatography (silica gel, ethyl acetate-hexanemixture = 1/1) to give 2-propylbenzimidazole (3a) (0.115 g,72percent). All products are known and several selected spectroscopic data are shown below.
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 4188 - 4190
  • 5
  • [ 95-54-5 ]
  • [ 111-27-3 ]
  • [ 5851-46-7 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 11, p. 7456 - 7460
[2] ChemCatChem, 2018, vol. 10, # 7, p. 1607 - 1613
[3] Chemistry - A European Journal, 2014, vol. 20, # 19, p. 5569 - 5572
[4] Dalton Transactions, 2017, vol. 46, # 43, p. 15012 - 15022
[5] Organic Preparations and Procedures International, 2008, vol. 40, # 1, p. 101 - 105
[6] Chemische Berichte, 1936, vol. 69, p. 2263,2270
  • 6
  • [ 111-26-2 ]
  • [ 95-54-5 ]
  • [ 5851-46-7 ]
YieldReaction ConditionsOperation in experiment
6% With 5%-palladium/activated carbon In water; toluene at 110℃; for 40 h; Inert atmosphere General procedure: A mixture of o-phenylenediamine (1) (0.108 g, 1 mmol), tributylamine (2a) (0.185g, 1 mmol), 5percent Pd/C (0.106 g, 0.05 mmol) and toluene/H2O (10 mL/0.5 mL) was placed in 25 mL round bottom flask. After the system was flushed with Ar from an Ar balloon connected to the flask via a reflux condenser, the reaction mixture was allowed to react at 110 oC for 20 h. The reaction mixture was filtered through a short silica gel column (ethylacetate-hexane mixture) to eliminate catalyst residue. Removal of the solvent left a crude mixture, which was separated by thin layer chromatography (silica gel, ethyl acetate-hexanemixture = 1/1) to give 2-propylbenzimidazole (3a) (0.115 g,72percent). All products are known and several selected spectroscopic data are shown below.
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 4188 - 4190
  • 7
  • [ 95-54-5 ]
  • [ 10488-95-6 ]
  • [ 5851-46-7 ]
Reference: [1] Chinese Journal of Chemistry, 2011, vol. 29, # 9, p. 1880 - 1886
  • 8
  • [ 95-54-5 ]
  • [ 693-02-7 ]
  • [ 5851-46-7 ]
Reference: [1] Synlett, 2009, # 12, p. 2023 - 2027
  • 9
  • [ 142-61-0 ]
  • [ 95-54-5 ]
  • [ 5851-46-7 ]
YieldReaction ConditionsOperation in experiment
63% Reflux General procedure: To0.5 g (4.62 mmol) of 1,2-phenylendiamine were addeddropwise the respective acyl chloride (9.25 mmol) withstirring. The mixture was subsequently heated to reflux until the solutionbecame clear. After 2h, the reaction is finished and the product was purifiedby column chromatography on silica gel with methylene chloride/methanol (9:1) andrecrystallization from diethyl ether/methanol.
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 138 - 152
  • 10
  • [ 95-54-5 ]
  • [ 111-27-3 ]
  • [ 5851-46-7 ]
  • [ 144991-21-9 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 11, p. 7456 - 7460
  • 11
  • [ 111-26-2 ]
  • [ 62-53-3 ]
  • [ 5851-46-7 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 8, p. 3227 - 3234
  • 12
  • [ 123-66-0 ]
  • [ 615-28-1 ]
  • [ 5851-46-7 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 18, p. 2597 - 2601
  • 13
  • [ 123-66-0 ]
  • [ 95-54-5 ]
  • [ 5851-46-7 ]
  • [ 34840-34-1 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 67, # 1-2, p. 16 - 20
  • 14
  • [ 106-70-7 ]
  • [ 95-54-5 ]
  • [ 5851-46-7 ]
  • [ 34840-34-1 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 67, # 1-2, p. 16 - 20
  • 15
  • [ 628-73-9 ]
  • [ 95-54-5 ]
  • [ 5851-46-7 ]
Reference: [1] Journal of Organic Chemistry, 1944, vol. 9, p. 31,33, 42
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