Home Cart 0 Sign in  

[ CAS No. 19812-93-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 19812-93-2
Chemical Structure| 19812-93-2
Structure of 19812-93-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 19812-93-2 ]

Related Doc. of [ 19812-93-2 ]

Alternatived Products of [ 19812-93-2 ]

Product Details of [ 19812-93-2 ]

CAS No. :19812-93-2 MDL No. :MFCD00059625
Formula : C13H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :ZRMIETZFPZGBEB-UHFFFAOYSA-N
M.W : 195.22 Pubchem ID :140610
Synonyms :

Calculated chemistry of [ 19812-93-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.62
TPSA : 44.02 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) : -5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 2.92
Log Po/w (WLOGP) : 2.93
Log Po/w (MLOGP) : 2.34
Log Po/w (SILICOS-IT) : 3.02
Consensus Log Po/w : 2.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.42
Solubility : 0.0749 mg/ml ; 0.000384 mol/l
Class : Soluble
Log S (Ali) : -3.51
Solubility : 0.0609 mg/ml ; 0.000312 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.43
Solubility : 0.00727 mg/ml ; 0.0000372 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 19812-93-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19812-93-2 ]

* 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 [ 19812-93-2 ]
  • Downstream synthetic route of [ 19812-93-2 ]

[ 19812-93-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 110-53-2 ]
  • [ 19812-93-2 ]
  • [ 52364-71-3 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314
  • 2
  • [ 111-25-1 ]
  • [ 19812-93-2 ]
  • [ 41424-11-7 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 48 h; General procedure: 4'-Hydroxybiphenyl-4-carbonitrile (1) (20.0 g, 0.1 mol), potassium carbonate (28.0 g, 0.2 mol) and DMF (600 mL) were placed in a 1000 mL flask and stirred. The corresponding alkylbromide (20.0 g for 1-bromohexane, 23.0 g for 1-bromo-octane, 0.12 mol) was added and the reaction mixture was heated at 120 °C for 48 h. The mixture was then cooled to room temperature and poured onto ice water (1000 mL) and left to stand overnight. The precipitated product was isolated by filtration and crystallized from ethanol.
Reference: [1] Tetrahedron, 2012, vol. 68, # 39, p. 8172 - 8180
[2] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195[3] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314
  • 3
  • [ 629-04-9 ]
  • [ 19812-93-2 ]
  • [ 52364-72-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314
  • 4
  • [ 111-83-1 ]
  • [ 19812-93-2 ]
  • [ 52364-73-5 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 48 h; General procedure: 4'-Hydroxybiphenyl-4-carbonitrile (1) (20.0 g, 0.1 mol), potassium carbonate (28.0 g, 0.2 mol) and DMF (600 mL) were placed in a 1000 mL flask and stirred. The corresponding alkylbromide (20.0 g for 1-bromohexane, 23.0 g for 1-bromo-octane, 0.12 mol) was added and the reaction mixture was heated at 120 °C for 48 h. The mixture was then cooled to room temperature and poured onto ice water (1000 mL) and left to stand overnight. The precipitated product was isolated by filtration and crystallized from ethanol.
Reference: [1] Molecular Crystals and Liquid Crystals, 2008, vol. 480, # 1, p. 287 - 294
[2] Tetrahedron, 2012, vol. 68, # 39, p. 8172 - 8180
[3] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 268, p. 21 - 44
[4] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195[5] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314
[6] Journal of the Brazilian Chemical Society, 2014, vol. 25, # 8, p. 1493 - 1503
  • 5
  • [ 109-65-9 ]
  • [ 19812-93-2 ]
  • [ 52709-87-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314
  • 6
  • [ 542-69-8 ]
  • [ 19812-93-2 ]
  • [ 52709-87-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3271 - 3281
  • 7
  • [ 19812-93-2 ]
  • [ 106-94-5 ]
  • [ 52709-86-1 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314
  • 8
  • [ 74-96-4 ]
  • [ 19812-93-2 ]
  • [ 58743-78-5 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate In acetone for 6.5 h; Reflux To a solution of 4’-hydroxy-4-biphenylcarbonitrile (500 mg, 2.48 mmol) in acetone (50 mL) was added bromoethane (0.47 mL, 6.2 mmol) and K2CO3 (684 mg, 4.96 mmol). The resulting mixture was stirred at reflux for 6.5 h. The white solid was filtered off and the filtrate was concentrated in vacuo to give light yellow solid, which was purified by gravity chromatography with 20percent EtOAc/hexane to get white solid, which was further recrystallized from EtOAc to give 6 as white crystalline (386 mg, 70percent). 1H NMR (300 MHz, CDCl3) δ 7.68-7.59 (m, 4H), 7.54-7.48 (m, 2H), 7.07-6.96 (m, 2H), 4.07 (q, J = 6.9 Hz, 2H), 1.44 (t, J = 6.9 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ 159.66, 145.28, 132.60, 131.30, 128.38, 127.10, 119.19, 115.11, 110.06, 63.66, 14.86 ppm. MS-ESI (m/z): calcd for C15H13NO, [M+H]+ 224.1; found 224.1.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 20, p. 6521 - 6524
[2] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195[3] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314
  • 9
  • [ 19812-93-2 ]
  • [ 460746-47-8 ]
YieldReaction ConditionsOperation in experiment
53% With sodium hydroxide; sodium hypochlorite; sodium iodide In methanol 4'-hydroxy-3'-iodo [1,1'-biphenyl]-4-carbonitrile
To a solution of 4-hydroxy-4'-cyanobiphenyl (6.00 g, 30.8 mmol), sodium iodide (4.61 g, 30.8 mmol) and sodium hydroxide (1.23 g, 30.8 mmol) in methanol (90 mL) at 0° C. was added an aqueous solution of sodium hypochlorite (47 mL of 5.25percent Clorox.(TM)., 2.29 g, 30.8 mmol) over 45 minutes.
The mixture was stirred cold for 1 hour, warmed to ambient temperature and diluted with sodium thiosulfate solution (10 mL), water (80 mL) and adjusted to a pH of 7 by addition of sodium dihydrogen phosphate.
The mixture was extracted with dichloromethane (2*90 mL).
The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to give a white powder.
The solid was crystallized from dichloroethane/hexane and chromatographed on silica with dichloromethane to give the titled compound (5.19 g, 53percent). MS (DCI) m/z 339[M+NH4+]+.
53% With sodium hydroxide; sodium hypochlorite; sodium iodide In methanol EXAMPLE 1A
4'-hydroxy-3'-iodo[1,1'-biphenyl]-4-carbonitrile
To a solution of 4-hydroxy-4'-cyanobiphenyl (6.00 g, 30.8 mmol), sodium iodide (4.61 g, 30.8 mmol) and sodium hydroxide (1.23 g, 30.8 mmol) in methanol (90 mL) at 0° C. was added an aqueous solution of sodium hypochlorite (47 mL of 5.25percent Clorox.(TM)., 2.29 g, 30.8 mmol) over 45 minutes.
The mixture was stirred cold for 1 hour, warmed to ambient temperature and diluted with sodium thiosulfate solution (10 mL), water (80 mL) and adjusted to a pH of 7 by addition of sodium dihydrogen phosphate.
The mixture was extracted with dichloromethane (2*90 mL).
The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to give a white powder.
The solid was crystallized from dichloroethane/hexane and chromatographed on silica with dichloromethane to give the titled compound (5.19 g, 53percent). MS (DCI) m/z 339[M+NH4+]+.
53% With sodium hydroxide; sodium hypochlorite; sodium iodide In methanol Example 1A
4'-hydroxy-3'-iodo[1,1'-biphenyl]-4-carbonitrile
To a solution of 4-hydroxy-4'-cyanobiphenyl (6.00 g, 30.8 mmol), sodium iodide (4.61 g, 30.8 mmol) and sodium hydroxide (1.23 g, 30.8 mmol) in methanol (90 mL) at 0° C. was added an aqueous solution of sodium hypochlorite (47 mL of 5.25percent Clorox.(TM)., 2.29 g, 30.8 mmol) over 45 minutes.
The mixture was stirred cold for 1 hour, warmed to ambient temperature and diluted with sodium thiosulfate solution (10 mL), water (80 mL) and adjusted to a pH of 7 by addition of sodium dihydrogen phosphate.
The mixture was extracted with dichloromethane (2*90 mL).
The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to give a white powder.
The solid was crystallized from dichloroethane/hexane and chromatographed on silica with dichloromethane to give the titled compound (5.19 g, 53percent). MS (DCI) m/z 339[M+NH4+]+;
53% With sodium hydroxide; sodium hypochlorite; sodium iodide In methanol Example 1A
4'-hydroxy-3'-iodo[1,1'-biphenyl]-4-carbonitrile
To a solution of 4-hydroxy-4'-cyanobiphenyl (6.00 g, 30.8 mmol), sodium iodide (4.61 g, 30.8 mmol) and sodium hydroxide (1.23 g, 30.8 mmol) in methanol (90 mL) at 0° C. was added an aqueous solution of sodium hypochlorite (47 mL of 5.25percent Clorox.(TM)., 2.29 g, 30.8 mmol) over 45 minutes.
The mixture was stirred cold for 1 hour, warmed to ambient temperature and diluted with sodium thiosulfate solution (10 mL), water (80 mL) and adjusted to a pH of 7 by addition of sodium dihydrogen phosphate.
The mixture was extracted with dichloromethane (2*90 mL).
The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to give a white powder.
The solid was crystallized from dichloroethane/hexane and chromatographed on silica with dichloromethane to give the titled compound (5.19 g, 53percent). MS (DCI) m/z 339[M+NH4+]+;

Reference: [1] Organic Process Research and Development, 2005, vol. 9, # 1, p. 45 - 50
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 3, p. 689 - 693
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 38 - 55
[4] Patent: US2003/153548, 2003, A1,
[5] Patent: US2003/134835, 2003, A1,
[6] Patent: US2002/169188, 2002, A1,
[7] Patent: US2002/183309, 2002, A1,
[8] Patent: US2004/54185, 2004, A1, . Location in patent: Page 9
  • 10
  • [ 19812-93-2 ]
  • [ 460746-47-8 ]
YieldReaction ConditionsOperation in experiment
40% With sodium hydroxide; sodium iodide In methanol EXAMPLE 169A
4'-hydroxy-3'-iodo-1,1'-biphenyl-4-carbonitrile
4'-Hydroxy-1,1'-biphenyl-4-carbonitrile (25.0 g, 128 mmol), purchased commercially, NaI (19.19 g, 128 mmol), and sodium hydroxide (5.12g, 128 mmol) were combined in methanol (500 mL) at 0° C. and treated with bleach (5.25percent, 181.0 g) dropwise over 1 hour.
After stirring at 0° C. for 1 hour, the mixture was treated with 10percent aqueous sodium thiosulfate (250 mL).
The mixture was adjusted to pH 6.8 with 10percent aqueous HCl and then the mixture was filtered.
The filter cake was crystallized from hot CH2Cl2/hexane to provide the title compound (40percent yield).
1H-NMR (300 MHz, CDCl3) δ 5.40 (s, 1H), 7.10 (m, 1H), 7.50 (m, 1H), 7.60 (m, 2H), 7.77(m, 2H), 7.90 (m, 1H); MS (CDI) m/z 339 (M+NH4)+.
40% With sodium hydroxide; sodium iodide In methanol EXAMPLE 169A
4'-hydroxy-3'-iodo-1,1'-biphenyl-4-carbonitrile
4'-Hydroxy-1,1'-biphenyl-4-carbonitrile (25.0 g, 128 mmol), purchased commercially, NaI (19.19 g, 128 mmol), and sodium hydroxide (5.12g, 128 mmol) were combined in methanol (500 mL) at 0° C. and treated with bleach (5.25percent, 181.0 g) dropwise over 1 hour.
After stirring at 0° C. for 1 hour, the mixture was treated with 10percent aqueous sodium thiosulfate (250 mL).
The mixture was adjusted to pH 6.8 with 10percent aqueous HCl and then the mixture was filtered.
The filter cake was crystallized from hot CH2Cl2/hexane to provide the title compound (40percent yield).
1H-NMR (300 MHz, CDCl3) δ5.40 (s, 1H), 7.10 (m, 1H), 7.50 (m, 1H), 7.60 (m, 2H), 7.77(m, 2H), 7.90 (m, 1H); MS (CDI) m/z 339 (M+NH4)+.
Reference: [1] Patent: US2002/137931, 2002, A1,
[2] Patent: US6620839, 2003, B2,
Same Skeleton Products
Historical Records