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[ CAS No. 4887-83-6 ] {[proInfo.proName]}

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Chemical Structure| 4887-83-6
Chemical Structure| 4887-83-6
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Product Details of [ 4887-83-6 ]

CAS No. :4887-83-6 MDL No. :MFCD09842603
Formula : C8H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :QCXGJTGMGJOYDP-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :1519341
Synonyms :

Calculated chemistry of [ 4887-83-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.06
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 : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.21
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 2.53
Consensus Log Po/w : 1.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.427 mg/ml ; 0.00323 mol/l
Class : Soluble
Log S (Ali) : -2.07
Solubility : 1.12 mg/ml ; 0.00845 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0721 mg/ml ; 0.000546 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.08

Safety of [ 4887-83-6 ]

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 [ 4887-83-6 ]

* 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 [ 4887-83-6 ]
  • Downstream synthetic route of [ 4887-83-6 ]

[ 4887-83-6 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 122-51-0 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
72% With iodine In acetonitrile at 20℃; EXAMPLE 17; N'-(3,4-Dimethoxybenzylidene)-3-(4-methyl-lH-benzo[d]imidazol-l- yl)propanehydrazide; [0523] (a) 4-Methyl-lH-benzo[d]imidazole: 3-Methylbenzene-l,2-diamine(400 mg, 3.27 mmol), triethylorthoformate (0.65 mL, 3.92 mmol) and I2 (83 mg, 0.327 mmol) were combined in MeCN (10 mL) and stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3 and dried (Na2SO4). Purification on silica gel using EtOAc -hexane (0 to 80percent) gave the desired product (310 mg, 72percent).
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 7, p. 1154 - 1159
[2] Monatshefte fur Chemie, 2007, vol. 138, # 1, p. 89 - 94
[3] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 6, p. 1509 - 1512
[4] Patent: WO2010/132615, 2010, A1, . Location in patent: Page/Page column 113
  • 2
  • [ 73902-60-0 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
99% With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 20 h; Inert atmosphere General procedure: A 16 mL vial with a PTFE/silicone septum and a nitrogen-bubbler line was charged with N-benzylbenzimidazole (208.1 mg, 1.0 mmol), Pd/C (10 wt percent, dry powder, reduced) (20 mg) and THF (5 mL). The mixture was treated at rt with triethylsilane (320 µL, 2.0 mmol) and then stirred under nitrogen for 14 h at rt. The mixture was filtered through a 0.45 µM PTFE syringe filter and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (0 to 10percent MeOH/ dichloromethane) to afford benzimidazole as a colorless solid (117.6 mg, 0.996 mmol 99percent). The reactions generally exhibit an induction period of 5 to 30 min as indicated by the initiation of gas release (i.e., bubbling) from the reaction mixture. The use of Pd/C on a dry matrix is imperative as wet Pd/C results in decreased yield or no reaction.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 21, p. 2688 - 2690
  • 3
  • [ 570-24-1 ]
  • [ 1758-73-2 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
57% With sodium hydroxide In ethanol; water at 70℃; for 2 h; Green chemistry General procedure: TUD (20 mmol) was added in batches to a solution of substituted 2‑nitroanilines (5 mmol) and NaOH (20 mmol) in H2O (15 mL) and EtOH (5 mL) at 70 °C. The reaction mixture was stirred for a certain period of time as required to complete the reaction (monitored byTLC). After cooling, 10percent NaOH solutions were added until pH = 9–10, the precipitated solid was filtered off and washed with water to obtain crude product. The crude product was recrystallised from water to give a white solid. The physical and spectra data of the compounds 2a–h were as follows.
Reference: [1] Journal of Chemical Research, 2014, vol. 38, # 2, p. 118 - 120
  • 4
  • [ 73902-59-7 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
6% With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 20 h; Inert atmosphere General procedure: A 16 mL vial with a PTFE/silicone septum and a nitrogen-bubbler line was charged with N-benzylbenzimidazole (208.1 mg, 1.0 mmol), Pd/C (10 wt percent, dry powder, reduced) (20 mg) and THF (5 mL). The mixture was treated at rt with triethylsilane (320 µL, 2.0 mmol) and then stirred under nitrogen for 14 h at rt. The mixture was filtered through a 0.45 µM PTFE syringe filter and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (0 to 10percent MeOH/ dichloromethane) to afford benzimidazole as a colorless solid (117.6 mg, 0.996 mmol 99percent). The reactions generally exhibit an induction period of 5 to 30 min as indicated by the initiation of gas release (i.e., bubbling) from the reaction mixture. The use of Pd/C on a dry matrix is imperative as wet Pd/C results in decreased yield or no reaction.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 21, p. 2688 - 2690
  • 5
  • [ 4885-02-3 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In tetrahydrofuran A.
4-Methyl-1H-benzimidazole
2,3 Diaminotoluene (675 mg, 5.53 mmol) was dissolved in 10 mL of dry tetrahydrofuran and triethylamine (0.77 mL, 5.53 mmol) was added.
The mixture was cooled to 0° C. and 1,1-dichloromethyl methyl ether (0.50 mL, 5.53 mmol) was added and the reaction was allowed to warm to room temperature.
After 20 hours, the reaction was quenched with sodium bicarbonate.
The aqueous phase was extracted with ethyl acetate, dried over magnesium sulfate, filtered and the solvent removed to yield 730 mg (100percent) of a brown solid.
Reference: [1] Patent: US5212177, 1993, A,
[2] Patent: US5374615, 1994, A,
  • 6
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; formic acid In water Part B.
4-Methyl-1H-benzimidazole (Compound XVIII)
A mixture of 3-methyl-1,2-benzenediamine (11.9 g) and formic acid (150 mL) was heated at 70° C. for 15 minutes.
The solvent was removed under reduced pressure and the residual oil was stirred with water (100 mL) and sodium hydroxide solution (65 mL of 4.0 N) was added until the solution was just basic.
The precipitate was filtered off, washed with water, and air dried to give 11.6 g (90percent) of 4-methyl-1H-benzimidazole, mp 141°-145° C.
Reference: [1] Patent: US5273975, 1993, A,
  • 7
  • [ 1445-45-0 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
Reference: [1] Journal of Fluorine Chemistry, 2010, vol. 131, # 12, p. 1377 - 1381
  • 8
  • [ 2687-25-4 ]
  • [ 149-73-5 ]
  • [ 4887-83-6 ]
Reference: [1] Journal of Fluorine Chemistry, 2010, vol. 131, # 12, p. 1377 - 1381
  • 9
  • [ 64-18-6 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 1, p. 700 - 706
[2] Chemische Berichte, 1919, vol. 52, p. 1083
[3] Chemische Berichte, 1919, vol. 52, p. 1083
[4] Patent: US2006/211720, 2006, A1, . Location in patent: Page/Page column 79
  • 10
  • [ 78-84-2 ]
  • [ 4887-83-6 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 22, p. 3425 - 3439
  • 11
  • [ 255064-10-9 ]
  • [ 4887-83-6 ]
Reference: [1] Chemische Berichte, 1884, vol. 17, p. 776
  • 12
  • [ 20353-93-9 ]
  • [ 2687-25-4 ]
  • [ 4887-83-6 ]
Reference: [1] Synthetic Communications, 1986, vol. 16, # 3, p. 365 - 376
  • 13
  • [ 570-24-1 ]
  • [ 4887-83-6 ]
Reference: [1] Chemische Berichte, 1919, vol. 52, p. 1083
  • 14
  • [ 120-66-1 ]
  • [ 4887-83-6 ]
Reference: [1] Chemische Berichte, 1919, vol. 52, p. 1083
  • 15
  • [ 76153-06-5 ]
  • [ 4887-83-6 ]
Reference: [1] Chemische Berichte, 1884, vol. 17, p. 776
  • 16
  • [ 77811-44-0 ]
  • [ 4887-83-6 ]
Reference: [1] Chemische Berichte, 1884, vol. 17, p. 776
  • 17
  • [ 4887-83-6 ]
  • [ 32863-32-4 ]
Reference: [1] Patent: CN102285978, 2016, B,
  • 18
  • [ 4887-83-6 ]
  • [ 32863-30-2 ]
YieldReaction ConditionsOperation in experiment
77.6% at 80 - 85℃; 4-methylbenzimidazol (13. 4 g, 100 mmol)Was dissolved in carbon tetrachloride (150 ml) and addedNBS (23.5 g, 132 mmol)And Bz202 (0.29 g, 1.2 mmol),The mixture was warmed to 80-85 ° C. After the reaction was completed, the reaction system was reduced to 40 ° C. The mixture was filtered, washed with chloroform and the solvent was evaporated under reduced pressure to give the crude product (25. 6 g). Recrystallization from petroleum ether- A pale yellow needle-like crystals, 4-bromomethylbenzene bark (15. 3g). The yield was 77.6percent mp 94-95 ° C.
Reference: [1] Patent: CN102285978, 2016, B, . Location in patent: Paragraph 0028-0030
  • 19
  • [ 4887-83-6 ]
  • [ 132873-77-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1076 - 1092
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