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[ CAS No. 2221-00-3 ] {[proInfo.proName]}

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Product Details of [ 2221-00-3 ]

CAS No. :2221-00-3 MDL No. :MFCD01074865
Formula : C9H9N3 Boiling Point : -
Linear Structure Formula :- InChI Key :LVOASPZGXNAHJI-UHFFFAOYSA-N
M.W : 159.19 Pubchem ID :320165
Synonyms :

Calculated chemistry of [ 2221-00-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.97
TPSA : 43.84 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) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 0.99
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 0.71
Log Po/w (SILICOS-IT) : 0.82
Consensus Log Po/w : 1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.06
Solubility : 1.38 mg/ml ; 0.00865 mol/l
Class : Soluble
Log S (Ali) : -1.5
Solubility : 5.04 mg/ml ; 0.0317 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.56
Solubility : 0.444 mg/ml ; 0.00279 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 2221-00-3 ]

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 [ 2221-00-3 ]

* 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 [ 2221-00-3 ]
  • Downstream synthetic route of [ 2221-00-3 ]

[ 2221-00-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 288-32-4 ]
  • [ 106-40-1 ]
  • [ 2221-00-3 ]
YieldReaction ConditionsOperation in experiment
88% With C40H34CuIN6O6; sodium hydroxide In dimethyl sulfoxide at 100℃; for 4 h; Sealed tube General procedure: For the catalysis reaction, the catalyst C1 (12 mg,0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 °C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.
78% With potassium hydroxide In dimethyl sulfoxide at 100℃; for 10 h; General procedure: A mixture of aryl iodide (1.0 mmol), Het-NH (1.2 mmol), KOH (2 mmol), nanomagnetic Fe3O4-TiO2/Cu2O (0.010 g equal to 1.4 molpercent Cu2O) and anhydrous DMSO (2 mL) was stirred at 100 °C. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and diluted by ethyl acetate and the catalyst was separated by an external magnet from the mixture, washed with acetone, dried in an oven at 80 °C for 3 h and re-used for a consecutive run under the same reaction conditions. The combined ethyl acetate layer was washed with water and dried over anhydrous MgSO4. The residue was purified by recrystallization or short column chromatography on silica gel to afford the target products in excellent yield.
75% With potassium hydroxide In dimethyl sulfoxide at 100℃; for 9 h; General procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), Cu2O/nano-CuFe2O4 magnetic composite (0.010 g) and anhydrous DMSO (2 mL) was stirred at 100 °C. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and with diluted ethyl acetate and the catalyst was separated by an external magnet from the mixture, washed with acetone, dried in an oven at 80 °C for 3 h and re-used for a consecutive run under the same reaction conditions. The combined ethyl acetate layer was washed with water, dried over anhydrous MgSO4, The residue was purified by recrystallization or short column chromatography on silica gel to afford the target products in excellent yield.
75 %Chromat. With C16H12ClN3OPdS; potassium hydroxide In dimethyl sulfoxide at 110℃; for 10 h; General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 Mpercent) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.

Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 13, p. 4101 - 4114
[2] Journal of the Chinese Chemical Society, 2013, vol. 60, # 8, p. 1007 - 1013
[3] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2018, vol. 57A, # 2, p. 181 - 185
[4] Journal of the American Chemical Society, 2007, vol. 129, # 45, p. 13879 - 13886
[5] Advanced Synthesis and Catalysis, 2017, vol. 359, # 10, p. 1631 - 1636
[6] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4386 - 4389
[7] Chinese Journal of Chemistry, 2012, vol. 30, # 10, p. 2394 - 2400
[8] Tetrahedron, 2008, vol. 64, # 19, p. 4254 - 4259
[9] Journal of Organic Chemistry, 2007, vol. 72, # 8, p. 2737 - 2743
[10] Synthesis, 2010, # 9, p. 1505 - 1511
[11] Journal of Organic Chemistry, 2007, vol. 72, # 22, p. 8535 - 8538
[12] Chinese Journal of Chemistry, 2013, vol. 31, # 2, p. 267 - 270
[13] Journal of Organic Chemistry, 2008, vol. 73, # 21, p. 8639 - 8642
[14] Green Chemistry, 2012, vol. 14, # 5, p. 1268 - 1271
[15] Research on Chemical Intermediates, 2016, vol. 42, # 10, p. 7611 - 7624
[16] Chemistry Letters, 2016, vol. 45, # 2, p. 223 - 225
[17] Monatshefte fur Chemie, 2010, vol. 141, # 9, p. 1009 - 1013
[18] Chemistry - A European Journal, 2009, vol. 15, # 36, p. 8971 - 8974
[19] Synthetic Communications, 2012, vol. 42, # 2, p. 279 - 284
[20] Organic Letters, 2009, vol. 11, # 15, p. 3294 - 3297
[21] Soft Matter, 2012, vol. 8, # 7, p. 2274 - 2285
[22] Journal of Coordination Chemistry, 2015, vol. 68, # 19, p. 3537 - 3550
  • 2
  • [ 288-32-4 ]
  • [ 540-37-4 ]
  • [ 2221-00-3 ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) chloride; sodium hydroxide; 3-(diphenylphosphino)propionic acid In dimethyl sulfoxide at 120℃; for 14 h; Inert atmosphere; Sealed tube General procedure: NH-containing heterocycle (1.4 mmol) and DMF (2.0 mL) were added to a mixture of CuCl (15.0 molpercent) and ligand 1 (20.0 molpercent) in DMF (2.0 mL), aryl iodide (1.0 mmol), NaOH (2.0 mmol). The mixture was vigorously stirred at 120 °C for 14 h under a dry nitrogen atmosphere. After completion of the reaction (as monitored by TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine and dried over MgSO4. The solution was filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography. The purity of the compounds was checked by 1H NMR and yields are based on aryl iodide. All the products are known and the spectroscopic data (FT‑IR and NMR) and melting points were consistent with those reported in the literature.
80 %Chromat. With C16H12ClN3OPdS; potassium hydroxide In dimethyl sulfoxide at 110℃; for 10 h; General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 Mpercent) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.
Reference: [1] Green Chemistry, 2013, vol. 15, # 2, p. 336 - 340
[2] Journal of the Chinese Chemical Society, 2013, vol. 60, # 8, p. 1007 - 1013
[3] RSC Advances, 2014, vol. 4, # 14, p. 7321 - 7329
[4] New Journal of Chemistry, 2015, vol. 39, # 4, p. 2901 - 2907
[5] Chemistry - An Asian Journal, 2014, vol. 9, # 12, p. 3418 - 3430
[6] Journal of Chemical Research, 2014, vol. 38, # 2, p. 128 - 129
[7] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 2200 - 2202
[8] RSC Advances, 2015, vol. 5, # 2, p. 1522 - 1528
[9] Tetrahedron, 2006, vol. 62, # 18, p. 4435 - 4443
[10] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2136 - 2145
[11] RSC Advances, 2014, vol. 4, # 29, p. 15122 - 15130
[12] Journal of Coordination Chemistry, 2015, vol. 68, # 19, p. 3537 - 3550
  • 3
  • [ 2301-25-9 ]
  • [ 2221-00-3 ]
YieldReaction ConditionsOperation in experiment
70% With ammonium hydroxide; sodium dithionite In water for 0.25 h; Reflux General procedure: To a solution of 1-(substituted) 4-nitrobenzene IVa,b,e,f(0.01 mol) in NH4OH (20 mL, 30percent), a solution of sodium dithionite(7 g, 0.04 mol) in water (30 mL) was quickly added, the reactionmixture was refluxed for 15 min. After cooling, the crude productwas filtered, washed and crystallized from methylene chloride toyield target compounds Va,b,e,f. 4-(1H-imidazol-1-yl) aniline Va
Yield 70percent as gray solid, mp 147 °C, (as reported) [64,65].
96% With hydrogenchloride In ethanol; water b
4-(Imidazol-1-yl)aniline. Dihydrochloride
A mixture of 4-(imidazol-1-yl)nitrobenzene (89.60 g, 0.474 mol) and 10percent palladium on carbon (4.50 g) in ethanol (1200 ml) and 5N HCl (189 ml) was hydrogenated in two batches at 40 psi for 80 minutes.
Water (450 ml) was then added to dissolve the product and the catalyst was removed by filtration.
washing with more water, and the combined filtrates were evaporated in vacuo, using finally a freeze drier, to give 105.4 g (96percent) of the title compound as a cream solid. δH (250 MHz, D2 O) 7.22 (2H, d, J=8.8 Hz), 7.35 (1H, t, J=2.1 Hz), 7.44 (2H, d, J=9.0 Hz).
7.59 (1H, t, J=1.8 Hz), 8.89 (1H, t, J=1.5 Hz).
96% With hydrogenchloride In ethanol; water 2.
4-(Imidazol-1-yl)aniline. Dihydrochloride.
A mixture of 4-(imidazol-1-yl)nitrobenzene (89.60 g, 0.474 mol) and 10percent palladium on carbon (4.50 g) in ethanol (1200 ml) and 5N HCl (189 ml) was hydrogenated in two batches at 40 psi for 80 minutes.
Water (450 ml) was then added to dissolve the product and the catalyst was removed by filtration, washing with more water, and the combined filtrates were evaporated in vacuo, using finally a freeze drier, to give 105.4 g (96percent) of the title compound as a cream solid. δH (250 MHz, D2 O) 7.22 (2H, d, J=8.8 Hz), 7.35 (1H, t, J=2.1 Hz), 7.44 (2H, d, J=9.0 Hz), 7.59 (1H, t, J=1.8 Hz), 8.89 (1H, t, J=1.5 Hz).
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[2] Patent: US6335445, 2002, B1, . Location in patent: Page column 84
[3] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 12, p. 1935 - 1946
[4] Bioorganic Chemistry, 2014, vol. 57, p. 65 - 82
[5] Applied Spectroscopy, 1995, vol. 49, # 8, p. 1111 - 1119
[6] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1221 - 1227
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[8] Patent: EP698024, 1997, B1,
[9] Patent: US2003/78420, 2003, A1,
[10] Patent: US6600037, 2003, B1,
[11] Patent: US5981529, 1999, A,
[12] Patent: US6020357, 2000, A,
[13] Patent: US5854268, 1998, A,
[14] Patent: US6809088, 2004, B2,
[15] Patent: EP1950255, 2008, A1, . Location in patent: Page/Page column 52-53
[16] Patent: EP946508, 2009, B1, . Location in patent: Page/Page column 39
[17] Patent: EP1612204, 2006, A1, . Location in patent: Page/Page column 19-20
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[19] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5505 - 5512
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[21] Patent: US5532236, 1996, A,
  • 4
  • [ 51581-54-5 ]
  • [ 2221-00-3 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 23, p. 5934 - 5937
[2] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737
  • 5
  • [ 350-46-9 ]
  • [ 2221-00-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 21, p. 5263 - 5267
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1221 - 1227
[3] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 12, p. 1935 - 1946
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 5, p. 731 - 738
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5505 - 5512
[6] Patent: US5532236, 1996, A,
  • 6
  • [ 2301-25-9 ]
  • [ 7772-99-8 ]
  • [ 2221-00-3 ]
Reference: [1] Patent: US5965743, 1999, A,
  • 7
  • [ 100-00-5 ]
  • [ 2221-00-3 ]
Reference: [1] Bioorganic Chemistry, 2014, vol. 57, p. 65 - 82
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