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Chemical Structure| 626-01-7
Chemical Structure| 626-01-7
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Product Details of [ 626-01-7 ]

CAS No. :626-01-7 MDL No. :MFCD00007781
Formula : C6H6IN Boiling Point : -
Linear Structure Formula :- InChI Key :FFCSRWGYGMRBGD-UHFFFAOYSA-N
M.W : 219.02 Pubchem ID :12271
Synonyms :

Calculated chemistry of [ 626-01-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
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 : 43.56
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 2.86
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 2.41
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 2.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.55
Solubility : 0.0611 mg/ml ; 0.000279 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.188 mg/ml ; 0.00086 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.222 mg/ml ; 0.00101 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 626-01-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 626-01-7 ]

* 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 [ 626-01-7 ]
  • Downstream synthetic route of [ 626-01-7 ]

[ 626-01-7 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 109-04-6 ]
  • [ 626-01-7 ]
  • [ 15889-32-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 2, p. 286 - 297
  • 2
  • [ 626-01-7 ]
  • [ 15889-32-4 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 50, p. 6985 - 6988
[2] Tetrahedron, 2010, vol. 66, # 17, p. 3135 - 3146
  • 3
  • [ 220565-63-9 ]
  • [ 626-01-7 ]
  • [ 57976-57-5 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 17, p. 3135 - 3146
  • 4
  • [ 626-01-7 ]
  • [ 22200-50-6 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 3236
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 113,115
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 18, p. 5170 - 5173
  • 5
  • [ 626-01-7 ]
  • [ 20780-75-0 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 25, p. 6082 - 6087
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 935 - 946
[3] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 370 - 378
[4] Patent: WO2017/211303, 2017, A1,
[5] Patent: WO2017/211303, 2017, A1,
  • 6
  • [ 645-00-1 ]
  • [ 626-01-7 ]
YieldReaction ConditionsOperation in experiment
93% With sodium tetrahydroborate In ethanol; water at 20℃; for 1.5 h; General procedure: TAPEHA-Pd (0.015 g) was added to a solution of nitroarenes (1.0 mmol) in EtOH/water (1/1) (20 mL). After NaBH4 (4.0 mmol) was slowly added to the mixture, the color of the reaction mixture turned gradually black in a few minutes, resulting in the formation of palladium nanoparticles (TAPEHA-PdNPs). 42 After being stirredfor 1.5 h at room temperature and atmospheric pressure, the catalyst was removed by ltering and the fitrate was extracted with 3 30 mL of EtOAc. The combined organic layers were dried over MgSO4 and concentrated in a vacuum.
91% 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.
82% With sodium tetrahydroborate In ethanol; water at 5℃; for 4 h; General procedure: SAC (300mg) and NaBH4 (4.0mmol) were added to a solution of nitroarenes (1.0mmol) in EtOH/water (1/1) (20ml). The reaction mixture was stirred for 4h at the temperature indicated in Table3. At the end of the reaction, the catalyst was removed by filtering and the filtrate was extracted with 3×70ml EtOAc. The combined organic layers were dried over MgSO4 and concentrated in a vacuum.
92 %Chromat. With hydrogen In ethanol; water at 110℃; for 16 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.

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[44] Journal of Catalysis, 2016, vol. 340, p. 1 - 9
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  • 7
  • [ 645-00-1 ]
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  • [ 23377-21-1 ]
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2015, vol. 400, p. 14 - 21
  • 8
  • [ 645-00-1 ]
  • [ 62-53-3 ]
  • [ 626-01-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2689 - 2694
[2] Journal of Catalysis, 2008, vol. 255, # 2, p. 335 - 342
[3] Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1260 - 1264
[4] RSC Advances, 2017, vol. 7, # 2, p. 751 - 757
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 33, p. 9747 - 9751[6] Angew. Chem., 2017, vol. 129, p. 9879 - 9883,5
  • 9
  • [ 54467-96-8 ]
  • [ 626-01-7 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 8, p. 1787 - 1789
  • 10
  • [ 166826-92-2 ]
  • [ 626-01-7 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 16, p. 2793 - 2794
  • 11
  • [ 1244651-40-8 ]
  • [ 118427-09-1 ]
  • [ 626-01-7 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437
  • 12
  • [ 618-51-9 ]
  • [ 626-01-7 ]
Reference: [1] Journal of the Chemical Society, 1943, p. 421,422
[2] Synthesis, 1990, # 12, p. 1143 - 1144
  • 13
  • [ 408340-16-9 ]
  • [ 118427-09-1 ]
  • [ 626-01-7 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437
  • 14
  • [ 863870-73-9 ]
  • [ 118427-09-1 ]
  • [ 626-01-7 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437
  • 15
  • [ 863870-82-0 ]
  • [ 118427-09-1 ]
  • [ 626-01-7 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437
  • 16
  • [ 1287791-71-2 ]
  • [ 118427-09-1 ]
  • [ 626-01-7 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437
  • 17
  • [ 88-74-4 ]
  • [ 626-01-7 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 2761[2] Justus Liebigs Annalen der Chemie, 1907, vol. 354, p. 197
  • 18
  • [ 99-09-2 ]
  • [ 626-01-7 ]
Reference: [1] Zeitschrift fuer Chemie, 1866, p. 218
  • 19
  • [ 457658-05-8 ]
  • [ 62-53-3 ]
  • [ 603-54-3 ]
  • [ 7664-41-7 ]
  • [ 626-01-7 ]
Reference: [1] Monatshefte fuer Chemie, 1904, vol. 25, p. 944
  • 20
  • [ 626-01-7 ]
  • [ 591-18-4 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 21
  • [ 626-01-7 ]
  • [ 625-99-0 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1900, vol. <2> 61, p. 322
  • 22
  • [ 626-01-7 ]
  • [ 626-02-8 ]
YieldReaction ConditionsOperation in experiment
92.5% at 10 - 88℃; At room temperature, a 25percent sulfuric acid solution was pumped into a Straight Static Mixer A at a rate of 50.2 g / min using an electromagnetic metering pump and the meta-iodoaniline was pumped into a straight stationary Mixer A,Straight static mixer A heat conducting oil temperature is set to 10.0 , 30percent of the sodium nitrite solution with Hanbon-NP7010C high-performance liquid pump at a rate of 6g / min pumped into the heart static mixer B, The temperature of the heat-conducting oil of the B was set to 10.0 ° C,The reaction results in a diazonium salt solution. The temperature of the HTF in the heart tube reactor was set to 88 ° C while the diazonium salt aqueous solution was pumped into the heart tube reactor at a rate of 1 ml / min using a Hanbon-NP7010C HPLC pump,After the reaction solution into the heartType oil-water separator, collecting 120min, finally get11.4 g of m-iodophenol, purity 99.1percent, yield 92.5percent.
Reference: [1] Patent: CN106905096, 2017, A, . Location in patent: Paragraph 0053; 0054
[2] Chemische Berichte, 1887, vol. 20, p. 3019
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1866, vol. 63, p. 566[4] Zeitschrift fuer Chemie, 1866, p. 662,731
[5] Justus Liebigs Annalen der Chemie, 1904, vol. 332, p. 62
  • 23
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  • [ 1121-86-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9896 - 9900[2] Angew. Chem., 2018, vol. 130, p. 10044 - 10048,5
  • 24
  • [ 626-01-7 ]
  • [ 591-27-5 ]
  • [ 15268-07-2 ]
YieldReaction ConditionsOperation in experiment
79% With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 15 h; 3-Aminophenol (6.0 g, 54.8 mmol), 3-iodoaniline (10.0 g, 45.7 mmol), picolinic acid (0.56 g, 4.6 mmol), copper(I) iodide and potassium phosphate (19.4 g, 91 mmol) were added to DMSO (100 mL) and the reaction mixture degassed by bubbling nitrogen into the mixture for 1 hour. The reaction flask was then placed into a preheated 80° C. oil bath and stirred for 15 hours before cooling to room temperature. The reaction mixture was then poured into 150 mL of water and extracted with 3×50 mL EtOAc. The combined organics were washed with 50 mL water, 50 mL brine, dried and evaporated. The crude oil was chromatographed on silica with 80/20 hexane/EtOAc (v/v) followed by 50/50 hexane/EtOAc (v/v) to give 7.2 g (79percent) of 3,3′-oxydianiline as a white solid. The product was confirmed by GC/MS and NMR.
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 2, p. 650 - 654[2] Angew. Chem., 2013, vol. 125, # 2, p. 678 - 682,5
[3] Patent: US9461254, 2016, B2, . Location in patent: Page/Page column 195-196
[4] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17423 - 17429
  • 25
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  • [ 4445-43-6 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 25, p. 6082 - 6087
  • 26
  • [ 626-01-7 ]
  • [ 1066-54-2 ]
  • [ 110598-30-6 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4165 - 4169
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  • 27
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YieldReaction ConditionsOperation in experiment
48% With morpholine In isopropyl alcohol at 90℃; for 18 h; Example 39: (3-Momholin-4-vl-phenvl)-( 5-thiophen-3-vl-pvrimidin-2-vl)-amine; A 5-mL reaction vial equipped with a magnetic stirrer was charged with 3-lodo-phenylamine (438 mg, 2.00 mmol), morpholine (348 mg, 4.00 mmol), copper iodide (38 mg, 0.20 mmol), potassium phosphate (850 mg, 4.0 mmol), ethylene glycol (248 mg, 4.00 mmol), and isopropanol (2.0 mL). After stirring at 90 °C for 18 h the reaction was concentrated under reduced pressure, dissolved in methylene chloride (3.0 mL) and washed with water (3.0 mL). The organic layer was then dried over sodium sulfate, filtered, concentrated under reduced pressure and the residue purified by column chromatography (methanol/methylene chloride) affording a 48percent yield (172 mg) of 3-morpholin-4-yl-phenylamine as a colorless oil.
Reference: [1] Patent: WO2005/113548, 2005, A1, . Location in patent: Page/Page column 46
  • 28
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  • [ 184098-19-9 ]
Reference: [1] Patent: WO2002/8199, 2002, A2, . Location in patent: Page 32
[2] Patent: US2002/99225, 2002, A1,
  • 29
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  • [ 959236-72-7 ]
Reference: [1] Patent: WO2008/86462, 2008, A2,
  • 30
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  • [ 626-01-7 ]
  • [ 626248-56-4 ]
  • [ 16279-73-5 ]
YieldReaction ConditionsOperation in experiment
68% With potassium phosphate; copper(l) iodide; ethylenediamine In 1,4-dioxane; dimethyl sulfoxide for 72 h; Reflux The mixture of 3-iodoaniline (3.70 g, 16.9 mmol), 1,2,3-triazole (3.91 mL, 67.6 mmol), K3PO4 (7.17 g, 33.8 mmol), fine powder Cul (1.61 g, 8.45 mmol), ethylenediamine (0.60 mL, 8.45 mmol) in 30 mL dioxane and 15 mL DMSO were refluxed for three days to yield major product 3-(2H-l,2,3-triazol-2-yl)aniline and minor product 3-(lH-l,2,3-triazol-l-yl)aniline in ratio of about 3:1. The mixture was diluted with 400 mL EtOAc, vigorously stirred, filtered through celite, washed with brine twice, concentrated in vacuo, and subjected to flash column to isolate 3-(2H-l,2,3-triazol-2-yl)aniline (1.86 g, 68percent yield).
68% With potassium phosphate; copper(l) iodide; ethylenediamine In 1,4-dioxane; dimethyl sulfoxideReflux The mixture of 3-iodoaniline (3.70 g, 16.9 mmol), 1,2,3-triazole (3.91 mL, 67.6 mmol), K3P04 (7.17 g, 33.8 mmol), fine powder CuT (1.61 g, 8.45 mmol), ethylenediamine (0.60 mL, 8.45 mmol) in 30 mL dioxane and 15 mL DMSO were refluxed for three days to yield as the major product 3-(2H-1,2,3-triazol-2-yl)aniline and as the minor product 3-(1H- 1,2,3 -triazol- 1 -yl)aniline in ratio of about 3:1. The mixture was diluted with 400 mL EtOAc, vigorously stirred, filtered through celite, washed with brine twice, concentrated in vacuo, and subjected to flash column to isolate 3-(2H-1,2,3-triazol-2-yl)aniline (1.86 g, 68percent yield).
Reference: [1] Patent: WO2013/78468, 2013, A1, . Location in patent: Paragraph 0314; 0315
[2] Patent: WO2014/152768, 2014, A1, . Location in patent: Paragraph 0124
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