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[ CAS No. 14235-81-5 ] {[proInfo.proName]}

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Chemical Structure| 14235-81-5
Chemical Structure| 14235-81-5
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Product Details of [ 14235-81-5 ]

CAS No. :14235-81-5 MDL No. :MFCD00168824
Formula : C8H7N Boiling Point : -
Linear Structure Formula :- InChI Key :JXYITCJMBRETQX-UHFFFAOYSA-N
M.W : 117.15 Pubchem ID :3760025
Synonyms :

Calculated chemistry of [ 14235-81-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.78
TPSA : 26.02 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) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.86
Solubility : 1.62 mg/ml ; 0.0138 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 4.5 mg/ml ; 0.0384 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.07
Solubility : 1.0 mg/ml ; 0.00855 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 14235-81-5 ]

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 [ 14235-81-5 ]

* 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 [ 14235-81-5 ]
  • Downstream synthetic route of [ 14235-81-5 ]

[ 14235-81-5 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 75867-39-9 ]
  • [ 14235-81-5 ]
YieldReaction ConditionsOperation in experiment
98% With potassium hydroxide In tetrahydrofuran; methanolReflux To a stirred solution of potassium hydroxide (1.34 g, 23.8 mmol) in 6 mL methanol, 4-(Trimethylsilylethynyl)aniline (1.10 g, 0.86 mmol) in tetrahydrofuran (5 mL) was added, and the solution was refluxed overnight. Upon cooling to room temperature, the product was filtered to remove insoluble substance, and the solvent was removed under vacuum. The residue was dissolved in CH2Cl2 (50 mL), filtered, dried over anhydrous MgSO4, and concentrated under reduced pressure providing the product as a yellow solid. Yield: 98percent. 1H NMR (400 MHz; CDCl3; Me4Si): δ (ppm) 7.32 (d, J=2.4 Hz, 2H), 6.61 (d, J=2.4 Hz, 2H), 3.83 (s, 2H), 2.98 (s, 1H). 13C NMR (100 MHz, CDCl3): δ (ppm) 147.0, 133.5, 114.6, 111.3, 84.4, 77.4, 77.1, 76.7, 74.9.
81% With tetrabutyl ammonium fluoride In tetrahydrofuran at 35℃; for 16 h; Compound 20g (423 mg, 2.2 mmol) in THF (100 mL) wasstirred with Bu4NF in THF (1.0 M, 6.7 mL) for 16 h at 35°C. Saturated aq. NaHCO3 was added. The mixture was extracted (Et2O,3 ). Drying and chromatography (petroleumether / EtOAc 1:3) gave 21g (230 mg, 81percent) as a pale green powder: mp81-85°C (lit.11 mp 88-90°C): IR nmax 3486, 3388, 2095, 1619, 1513 cm-1;1H NMR (CDCl3) d 2.95 (1 H, s, CCH), 3.79 (2 H, s, NH2), 6.58 (2 H,d, J = 7.6 Hz, 2,6-H2),7.28 (2 H, d, J = 7.7 Hz, 3,5-H2);13C NMR (CDCl3) d 74.79 (ethyne 2-C), 84.32 (ethyne 1-C), 111.34 (4-C), 114.52 (2,6-C2),133.41 (3,5-C2), 146.95 (1-C).
79% With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 0.5 h; The obtained 4-(trimethylsilyl)ethynylaniline (1.5 g, 7.94 mmol, 1.0 eq.) was dissolved in 10 ml of tetrahydrofuran, after stirring for 10 minutes at 0 °C, was added tetrabutylammonium fluoride (2 g, 23.8 mmol, 3.0 eq.) after half an hour at room temperature, the reaction solution was extracted with ethyl acetate and water to give washing the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and then the rotation evaporation concentrated dryness. Concentrated shrink after the product after silica gel column chromatography to give a white solid of p-aminophenylacetylene (0.7 g, yield: 79percent).
77% With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; To a round bottom flask was added compound 1, followed by 20 ml TBAF (Tetrabutylammoniumfluoride, 1.0 M in THF), and 6 ml THF. The mixture allowed to stirr overnight at room temperature. Solvent removed and residue run down a column of silica in 1:1 ethylacetate:hexanes.1.81 g recovered for a yield of 77percent from theoretical H(at) nmr (CDC13) No.; 7.26 (2 H, d), 6.56 (2 H , d), 4.10 (2 H, d).
1.2 g With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃; Inert atmosphere General procedure: In a glovebox were combined aryl bromide, Pd(PPh3)2Cl2 (5 molpercent), triphenylphosphine (10 molpercent), THF (50 mL), and triethylamine (10 mL). After stirring 3 min, CuI (5 molpercent) was added and the solution was stirred another 1 min. TMS-acetylene (1.5 eq.) was then added and the reaction vessel was sealed and heated to 60 °C for 18 h. The reaction mixture was cooled, concentrated, and the residue was purified by silica gel chromatography. The obtained intermediate was then dissolved in THF (50 mL), methanol (25 mL), and a 20 percent KOH solution (aq, 15 mL) in 250 mL round bottom flask and stirred overnight at room temperature. The solution was diluted with ethyl ether (150 mL) and extracted twice with brine (50 mL). The organic layer was collected and concentrated to give a residue that was purified by silica gel chromatography.

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[3] Tetrahedron, 2011, vol. 67, # 37, p. 7096 - 7100
[4] Chemical Communications, 2013, vol. 49, # 80, p. 9197 - 9199
[5] Dalton Transactions, 2013, vol. 42, # 2, p. 338 - 341
[6] Electrochimica Acta, 2010, vol. 56, # 1, p. 454 - 462
[7] Organic Letters, 2003, vol. 5, # 12, p. 2099 - 2102
[8] Organic Letters, 2014, vol. 16, # 3, p. 948 - 951
[9] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032
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[11] Patent: CN105622638, 2016, A, . Location in patent: Paragraph 0282
[12] Patent: WO2005/97209, 2005, A1, . Location in patent: Page/Page column 55-57
[13] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
[14] Dyes and Pigments, 2012, vol. 94, # 1, p. 60 - 65
[15] Tetrahedron, 1996, vol. 52, # 15, p. 5495 - 5504
[16] Journal of Organic Chemistry, 2003, vol. 68, # 6, p. 2167 - 2174
[17] Chemistry - A European Journal, 2005, vol. 11, # 4, p. 1181 - 1190
[18] European Journal of Organic Chemistry, 2006, # 14, p. 3125 - 3139
[19] Organic Letters, 2001, vol. 3, # 7, p. 993 - 995
[20] Organometallics, 2010, vol. 29, # 12, p. 2783 - 2788
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[22] European Journal of Medicinal Chemistry, 2014, vol. 76, p. 369 - 375
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[24] Tetrahedron, 2017, vol. 73, # 44, p. 6386 - 6391
  • 2
  • [ 937-31-5 ]
  • [ 14235-81-5 ]
YieldReaction ConditionsOperation in experiment
81% With hydrazine hydrate In ethanol at 80℃; for 1 h; Inert atmosphere General procedure: Hydrazine hydrate was chosen as the hydrogen donor for the low emission of pollutants. In a typical procedure, hydrazine hydrate (4 equiv) was added into the reactor which containing fresh prepared catalyst as described above. Then the reactor was put into a preheated oil bath with a stirring speed of 500 rpm, and the substrate (1 mmol)dissolved in 1 mL ethanol was added drop-wisely under argon. The reactions were monitored by TLC. After the reaction, the reaction mixture was vacuum filtered through a pad of silica on a glass-fritted funnel and an additional 15 mL of ethyl acetate (5 mL portions) was used to rinse the product from the silica, the filtrate was concentrated in vacuum and analyzed by GC. Products were purified by column chromatography and identified by 1H NMR and 13C NMR.
93 %Chromat. With carbon monoxide; water In tetrahydrofuran at 125℃; for 24 h; Inert atmosphere; Autoclave General procedure: Into a reaction glass vial fitted with a magnetic stirring bar anda septum cap penetrated with a syringe needle was added theCo3O4/NGrC-catalyst (2 molpercent, 3 wtpercent Co-phenanthroline oncarbon, 20 mg) followed by the nitro arene (0.5 mmol), theinternal standard (hexadecane, 100 μL), THF (2 mL), and H2O(200 μL). The reaction vial was then placed into a 300 mL autoclave.The autoclave was flushed twice with nitrogen, pressurized with CO at 30 bar pressure. Finally, the autoclave was usedat 60 bar by adding nitrogen and placed into an aluminiumblock, which was preheated at 125 °C. After 24 h the autoclavewas placed into a water bath and cooled to r.t. Finally, theremaining gas was discharged, and the samples were removedfrom the autoclave, diluted with EtOAc and analyzed by GC. Todetermine the yield of isolated products, the general procedurewas scaled up by the factor of two, and no internal standard wasadded. After the reaction was completed, the catalyst was filteredoff, and the filtrate was concentrated and purified by silicagel column chromatography (n-heptane–EtOAc mixtures) togive the corresponding anilines.
93 %Chromat. With hydrogen In methanol at 100℃; for 4 h; Autoclave General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15molpercent Co/C–N–X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC–MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).
95 %Chromat. With hydrogen In water at 20℃; for 12 h; Schlenk technique General procedure: Hydrogen was chosen as hydrogen donor for the hydrogenation of nitroarenes. The hydrogenation reactions were carried out in a Schlenk tube. Typically, the reactant and catalysts were dispersed into the solvent, then the Schlenk tube was purged with H2 four times to replace air. Then the mixture was stirred at room temperature for a desired period. After reaction, the reaction mixture was extracted by ethyl acetate. The product and unreacted reactant were analyzed by GC–MS. The catalysts were separated by centrifugation and washed with ethyl acetate (3 ×15 ml), deionized water (3 ×15 ml) and then used in the next cycle.
90 %Chromat. With hydrogen In ethanol; water at 110℃; for 18 h; Autoclave General procedure: In an 8mL glass vial fitted with a magnetic stirring bar and a septum cap, the catalyst (the amount depends on the catalyst) was added followed by the nitroarene (0.5mmol), the internal standard (hexadecane, 20mg) and the solvent (2mL). A needle was inserted in the septum cap, which allows dihydrogen to enter. The vials (up to 7) were placed into a 300mL steel Parr autoclave which was flushed twice with dihydrogen at 20bar and then pressurized to 50bar. Then the autoclave was placed into an aluminum block pre-heated at 110°C. At the end of the reaction, the autoclave was quickly cooled down at room temperature with an ice bath and vented. Finally, the samples were removed from the autoclave, diluted with a suitable solvent, filtered using a Pasteur pipette filled with Celite® (6cm pad) and analyzed by GC using n-hexadecane as an internal standard. Control experiments showed that the position of the vial inside the autoclave is not influential. The same outcome was obtained when the reaction was repeated by moving a vial from a peripheral to a central position.
80 %Chromat. With carbon monoxide; triethylamine In tetrahydrofuran; water at 125℃; for 24 h; Autoclave General procedure: An 8 mL glass vial (: 14 mm, height 50 mm) equipped with a Tefloncoated oval magnetic stirring bar (8 5 mm) and a plastic screw cap was charged with the corresponding nitroarene 1 (0.5 mmol, 1.0 equiv), Fe2O3/NGr(at)C catalyst (50 mg, 4.0 molpercent Fe), Et3N (70 μL, 0.5 mmol, 1.0 equiv), THF (2 mL), and deionized H2O (0.2 mL). The silicone septum was punctured with a 26 gauge syringe needle (0.45 12 mm) and the vial was placed in an aluminum plate, which was then transferred into the 300 mL autoclave. Once sealed, the autoclave was placed into an aluminum block and purged 3 times with CO (at 5-10 bar). Then it was pressurized with CO to 30 bar, followed by additional 20 bar of N2. The aluminum block was heated up to 125 °C under thorough stirring (700 rpm). After 24 h, the autoclave was removed from the aluminum block and cooled to r.t. in a water bath. The remaining gases were discharged and the vials containing reaction products were removed from the autoclave. The reaction mixture was filtered through a Celite pad (~1 cm), concentrated, and analyzed by GC and NMR spectroscoopy (Table 2).

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[8] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 258, p. 1 - 14
[9] Chemical Communications, 2011, vol. 47, # 39, p. 10972 - 10974
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[22] Patent: CN107216255, 2017, A, . Location in patent: Paragraph 0014
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  • 3
  • [ 1453814-00-0 ]
  • [ 14235-81-5 ]
YieldReaction ConditionsOperation in experiment
50% With potassium hydroxide In toluene at 110℃; for 10 h; Inert atmosphere; UV-irradiation General procedure: 1 (100 mg,624 μmol) was dissolved intoluene (10 mL) under nitrogen conditions. KOH powder (700 mg,12.5 mmol) was added and the reaction mixture stirred under reflux (110°C)and irradiation with a UV-lamp (365 nm, 200 μWatt/cm2) for 16 h. Thereaction was quenched by the addition of water. The crude product was extractedwith DCM (3 x 30 mL), dried over MgSO4, filtered off andconcentrated under reduced pressure. The product was purified by flashchromatography to remove the side product 2-nitrosobenzaldehyde. (yield: 45 mg,70percent)
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5426 - 5429
  • 4
  • [ 82815-75-6 ]
  • [ 14235-81-5 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 5, p. 1057 - 1059[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1184 - 1186
[3] Tetrahedron, 1997, vol. 53, # 20, p. 6835 - 6846
[4] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1988, vol. 42, # 7, p. 448 - 454
[5] Tetrahedron, 2009, vol. 65, # 18, p. 3728 - 3732
[6] Organic Letters, 2013, vol. 15, # 3, p. 492 - 495
  • 5
  • [ 540-37-4 ]
  • [ 74-86-2 ]
  • [ 14235-81-5 ]
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[2] Arkivoc, 2014, vol. 2014, # 5, p. 145 - 157
  • 6
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Reference: [1] Chemistry - A European Journal, 2005, vol. 11, # 4, p. 1181 - 1190
[2] Organic Letters, 2003, vol. 5, # 12, p. 2099 - 2102
[3] Journal of Organic Chemistry, 2003, vol. 68, # 6, p. 2167 - 2174
[4] Journal of Medicinal Chemistry, 2000, vol. 43, # 23, p. 4488 - 4498
[5] Organic Letters, 2001, vol. 3, # 7, p. 993 - 995
[6] Tetrahedron, 1997, vol. 53, # 20, p. 6835 - 6846
[7] Tetrahedron, 1996, vol. 52, # 15, p. 5495 - 5504
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[10] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 5, p. 1057 - 1059[11] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1184 - 1186
[12] Synthesis, 1980, # 8, p. 627 - 630
[13] Tetrahedron, 2011, vol. 67, # 37, p. 7096 - 7100
[14] Dyes and Pigments, 2012, vol. 94, # 1, p. 60 - 65
[15] Journal of Fluorine Chemistry, 2012, vol. 135, p. 231 - 239
[16] Dalton Transactions, 2013, vol. 42, # 2, p. 338 - 341
[17] Organic Letters, 2013, vol. 15, # 3, p. 492 - 495
[18] Chemical Communications, 2013, vol. 49, # 80, p. 9197 - 9199
[19] Organic Letters, 2014, vol. 16, # 3, p. 948 - 951
[20] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032
[21] Patent: CN105622638, 2016, A,
[22] RSC Advances, 2016, vol. 6, # 95, p. 92845 - 92851
  • 7
  • [ 158074-65-8 ]
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  • 8
  • [ 540-37-4 ]
  • [ 1066-54-2 ]
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  • 9
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  • 10
  • [ 937-31-5 ]
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  • 11
  • [ 126063-08-9 ]
  • [ 14235-81-5 ]
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[2] Journal of Organic Chemistry, 1994, vol. 59, # 19, p. 5818 - 5821
  • 12
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  • [ 14235-81-5 ]
Reference: [1] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
[2] Tetrahedron Letters, 2015, vol. 56, # 51, p. 7105 - 7107
  • 13
  • [ 882-06-4 ]
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  • 14
  • [ 937-31-5 ]
  • [ 92792-15-9 ]
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  • [ 1520-21-4 ]
  • [ 14235-81-5 ]
  • [ 589-16-2 ]
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  • 15
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  • [ 99-92-3 ]
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  • 16
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  • 17
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  • [ 766-99-4 ]
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  • 18
  • [ 14235-81-5 ]
  • [ 326002-92-0 ]
  • [ 118727-34-7 ]
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