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[ CAS No. 78881-21-7 ] {[proInfo.proName]}

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Chemical Structure| 78881-21-7
Chemical Structure| 78881-21-7
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Product Details of [ 78881-21-7 ]

CAS No. :78881-21-7 MDL No. :MFCD02093969
Formula : C8H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :MBZDCUMFFPWLTJ-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :7010316
Synonyms :

Calculated chemistry of [ 78881-21-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.53
TPSA : 49.81 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 : Yes
Log Kp (skin permeation) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.48
Log Po/w (XLOGP3) : 0.98
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.72
Solubility : 2.51 mg/ml ; 0.019 mol/l
Class : Very soluble
Log S (Ali) : -1.61
Solubility : 3.21 mg/ml ; 0.0243 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.442 mg/ml ; 0.00334 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 78881-21-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P405 UN#:3439
Hazard Statements:H301-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 78881-21-7 ]

* 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 [ 78881-21-7 ]
  • Downstream synthetic route of [ 78881-21-7 ]

[ 78881-21-7 ] Synthesis Path-Upstream   1~23

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Reference: [1] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 2127 - 2133
  • 2
  • [ 146308-26-1 ]
  • [ 7697-28-1 ]
  • [ 78881-21-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 24, p. 3439 - 3450
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 24, p. 3439 - 3450
  • 3
  • [ 78881-21-7 ]
  • [ 42113-13-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 2127 - 2133
  • 4
  • [ 96784-54-2 ]
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YieldReaction ConditionsOperation in experiment
93% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol at 20℃; To a stirring 100 mL solution of THF at room temperature, added 9.89 g (61 mmol, 1 eq) of the benzonitrile. Then added 1 g palladium over 10percent carbon. Then added 25 mL of methanol. The system was then put under 50 psi of pressure in a hydrogenator. After no more hydrogen consumption was observed, the reaction was stopped and filtered over celite. Performed column chromatography using 1:1 hexane:dichloromethane as the mobile phase. Obtained 7.5 g of a beige powder. Yield was 93percent. 1H-NMR (DMSO): δ 2.27 (3H, s), 6.06 (2H, s), 6.41 (1H, d), 6.46 (1H, s), 7.30 (1H, d).
92% With hydrogenchloride; tin(ll) chloride In water; acetic acid for 3 h; 4-Cyano-2-methylaniline was synthesized as previously described (J. Med. Chem. (1991), 34, 3295): To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.34 mmol) in acetic acid (20 L) was added dropwise a solution of SnCl2 (9.6 g, 49.38 mmol) in conc. HCl (20 mL). After stirring for 3 h, the mixture was added carefully to a saturated NH4OH solution (120 mL) at 0° C. The resulting mixture was extracted with EtOAc (4.x.30 mL). The combined organic layers were sequentially washed with H2O (30 mL) and a saturated NaCl solution (30 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (10percent EtOAc/hex) to give 4-cyano-2-methylaniline as a white solid (1.48 g, 92percent): TLC (30percent EtOAc in hexane) Rf0.23. This material was used without further purification
92% at 20℃; for 14.1667 h; 4-Amino-3-methyl-benzonitrile: To a solution of 3-methyl-4-nitro-benzonitrile (20 g, 0.123 mol) in HOAc (200 mL) was added iron powder (17.55 g, 0.309 mol). After 10 min, the reaction was exothermic and turned to dark color. The reaction mixture was allowed to stir at room temperature for 14 h and then diluted with EtOAc (200 mL). The brown precipitate was filtered through a pad of celite and the filtercake was rinsed with EtOAc. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (40percent EtOAc/hexane) to yield the title compound (15.3 g, 92percent). 1H NMR (300 MHz, CDCl3) δ 7.30-7.34 (2H, m), 6.64 (1H, d, J=8.7 Hz), 2.16 (3H, s). LCMS (M+H)+m/z 133 (t=0.93 min).
92% at 20℃; for 14 h; To a solution of 3-methyl-4-nitro-benzonitrile (20 g, 0.123 mol) in HOAc (200 mL) was added iron powder (17.55 g, 0.309 mol). After 10 min, the reaction was exothermic and turned to dark color. The reaction mixture was allowed to stir at room temperature for 14 h and then diluted with EtOAc (200 mL). The brown precipitate was filtered through a pad of celite and the filtercake was rinsed with EtOAc. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (40percent EtOAc/hexane) to yield the title compound (15.3 g, 92percent). 1H NMR (300 MHz, CDCl3) δ 7.30-7.34 (2H, m), 6.64 (1H, d, J=8.7 Hz), 2.16 (3H, s). LCMS (M+H)+ m/z 133 (t=0.93 min).
61% With ammonium hydroxide In hydrogenchloride; acetic acid C.
To a stirred, 25° C. solution of 3-methyl-4-nitrobenzonitrile (24 g, 0.148 mol) in acetic acid (250 mL) under nitrogen was added dropwise a solution of SnCl2.2H2 O (133.57 g., 0.592 mol) in concentrated HCl (250 mL).
After stirring for 3 hours, the reaction mixture was added carefully to excess cold ammonium hydroxide.
The reaction mixture was extracted several times with ethyl ether.
The organic extracts were then combined, dried (Na2 SO4) and evaporated under reduced pressure to afford 12 g (61percent) of the title compound, 4-cyano-2-methylaniline, as a white solid; m.p. 64°-66° C.

Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 18, p. 3572 - 3587
[2] Patent: US2017/44373, 2017, A1, . Location in patent: Paragraph 0227; 0228
[3] Patent: US6353006, 2002, B1, . Location in patent: Page column 23
[4] Patent: US2005/54655, 2005, A1, . Location in patent: Page/Page column 15
[5] Patent: US2004/44203, 2004, A1, . Location in patent: Page 27
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3072 - 3076
[7] Journal of Medicinal Chemistry, 1991, vol. 34, # 11, p. 3295 - 3301
[8] Chemische Berichte, 1919, vol. 52, p. 1083
[9] Patent: US6034093, 2000, A,
[10] Patent: US6034093, 2000, A,
[11] Patent: US5731315, 1998, A,
[12] Patent: US5034410, 1991, A,
  • 5
  • [ 81018-29-3 ]
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YieldReaction ConditionsOperation in experiment
87% With hydrogenchloride; water In methanol for 8 h; Reflux General procedure: 12 mL of 3 m/L HCl was added to a solution of compound 3 (1.1 g, 5.7 mmol) in 30 mL methanol, the reaction was heated and refluxed for 8 h. When the reaction was completed, concentrated, added some water, and basified the mixture with NaHCO3 to PH 7 or 8, and extracted with ethyl acetate (EA).
The dried organic layer was evaporated in vacuum and the residue was purified on silica gel eluding with petroleum-ethyl acetate and 1j was obtained
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 22, p. 6366 - 6379
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
  • 6
  • [ 13194-68-8 ]
  • [ 78881-21-7 ]
YieldReaction ConditionsOperation in experiment
69.34% at 150 - 160℃; for 12 h; 4-iodo-2-methylaniline (2000mg, 8.58mmol) and cyanide(1.15g, 12.87mmol, 1.5eq)were added to pyridine. A reaction mixture was heated to 150~160 °C and stirred for 12hrs. A reaction mixture was diluted with methylene chloride. A diluted solution was washed with copper sulfate for several times. A mixture was washed with H2O (2 times) and brine, and then dried over Na2SO4. A residue was purified with column chromatography (n-Hexane : EtOAc =2 : 1) to yield a solid (786.5mg, 69.34percent). Mp: 78-80 °C; IR(NaCl neat, cm-1): 3403, 3335, 3220, 2942, 2220; 1H NMR(400MHz, CDCl3): 7.24(m, 2H), 6.57(d, 1 H, J=8.4Hz), 4.03(bs, 2H), 2.08(s, 9H).
Reference: [1] Patent: EP1862454, 2007, A1, . Location in patent: Page/Page column 17
  • 7
  • [ 13194-68-8 ]
  • [ 544-92-3 ]
  • [ 78881-21-7 ]
YieldReaction ConditionsOperation in experiment
69.34% at 150 - 160℃; for 12 h; Example 8: N-{4-[3-(4-tert-Butyl-benzyl)-ureidomethyl]-2-methyl-6-vinyl-phenyl}-methanesulfonamide; EPO <DP n="91"/>Step 1 : 4-Amino-3-methylbenzonitrile; 4-iodo-2-methylaniline (2000mg, 8.58mmol) and cyanide(1.15g, 12.87mmol, 1.5eq)were added pyridine. A reaction mixture was heated to 150~160°C , stirred for 12hr. A reaction mixture was diluted with methylene chloride. A diluted solution was washed with copper sulfate for several times. A mixture was washed with H2O (2 times) and b.rine, and then dried with Na2SO4. A residue was purified with column chromatography (n-Hexane: EtOAc =2 : 1 ) to yield solid (786.5mg, 69.34percent).mp: 78-80 °C ;IR(NaCI neat, cm"1) : 3403, 3335, 3220, 2942, 2220;1H NMR(400MHz, CDCI3): 7.24(m, 2H), 6.57(d, 1H, J=8.4Hz), 4.03(bs, 2H), 2.08(s, 9H).
Reference: [1] Patent: WO2006/101318, 2006, A1, . Location in patent: Page/Page column 90
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Reference: [1] Patent: US2012/196824, 2012, A1,
  • 9
  • [ 95-69-2 ]
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Reference: [1] Advanced Synthesis and Catalysis, 2009, vol. 351, # 4, p. 643 - 648
  • 10
  • [ 583-75-5 ]
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Reference: [1] Patent: WO2011/86377, 2011, A1, . Location in patent: Page/Page column 25-26
[2] Patent: US2013/72499, 2013, A1, . Location in patent: Paragraph 0176-0178
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  • [ 583-75-5 ]
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Reference: [1] Patent: WO2012/98400, 2012, A1, . Location in patent: Page/Page column 33
  • 12
  • [ 146308-26-1 ]
  • [ 7697-28-1 ]
  • [ 78881-21-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 24, p. 3439 - 3450
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 24, p. 3439 - 3450
  • 13
  • [ 120-66-1 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
  • 14
  • [ 24106-05-6 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
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  • [ 95-69-2 ]
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 1, p. 67 - 70
  • 16
  • [ 41963-20-6 ]
  • [ 78881-21-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 24, p. 3439 - 3450
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 24, p. 3439 - 3450
  • 17
  • [ 41963-20-6 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 24, p. 3439 - 3450
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 24, p. 3439 - 3450
  • 18
  • [ 676-58-4 ]
  • [ 619-72-7 ]
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Reference: [1] Tetrahedron, 1987, vol. 43, # 18, p. 4221 - 4226
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Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 22, p. 6366 - 6379
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  • [ 88990-57-2 ]
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Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 22, p. 6366 - 6379
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Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 22, p. 6366 - 6379
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Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 22, p. 6366 - 6379
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Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 22, p. 6366 - 6379
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