Home Cart 0 Sign in  
X

[ CAS No. 14143-26-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 14143-26-1
Chemical Structure| 14143-26-1
Chemical Structure| 14143-26-1
Structure of 14143-26-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 14143-26-1 ]

Related Doc. of [ 14143-26-1 ]

Alternatived Products of [ 14143-26-1 ]

Product Details of [ 14143-26-1 ]

CAS No. :14143-26-1 MDL No. :MFCD16997502
Formula : C8H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :PNQUZYVEQUGPPO-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :308741
Synonyms :

Calculated chemistry of [ 14143-26-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.15
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 : Yes
Log Kp (skin permeation) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 0.98
Log Po/w (WLOGP) : 1.57
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.73
Solubility : 2.5 mg/ml ; 0.0188 mol/l
Class : Very soluble
Log S (Ali) : -1.49
Solubility : 4.28 mg/ml ; 0.0322 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.26
Solubility : 0.73 mg/ml ; 0.00548 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 14143-26-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P273-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14143-26-1 ]

* 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 [ 14143-26-1 ]
  • Downstream synthetic route of [ 14143-26-1 ]

[ 14143-26-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 7677-24-9 ]
  • [ 553-97-9 ]
  • [ 15777-70-5 ]
  • [ 14143-26-1 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 43, p. 7901 - 7904
  • 2
  • [ 21883-13-6 ]
  • [ 14143-26-1 ]
YieldReaction ConditionsOperation in experiment
96% With boron dimethyl-trifluoro sulphide In dichloromethane at 0 - 20℃; for 16 h; To a dry flask of dichloromethane (34 mL) was added 4-methoxy-2-methylbenzonitrile (14, 1.5 g, 10.2 mmol). Boron trifluoride-dimethyl sulfide complex(10.7 mL, 102 mmol) was then added slowly to the reaction mixture over 5 minutes. The reaction was allowed to stir 16 hours at room temperature. The reaction was quenched by the addition of water, and was allowed to stir for 15 minutes until fuming stopped. The reaction was diluted with EtOAc (~100 mL) and partitioned via separatory funnel. The aqueous layer was extracted 2 more times with EtOAc, then the combined organic extract was washed with water 2x and brine. The organic layer was isolated, dried over MgSO4, vacuum filtered and concentrated in vacuo to a light pink solid (1.305 g, 96percent yield over 2 steps). This phenol intermediate was combined with dry DMF (1.7mL) in a flask at room temperature. Imidazole (1.67 g, 24.5 mmol) and TBS-Cl (1.77 g, 11.8 mmol) were added,and the reaction was allowed to stir for 16h. The reaction mixture was thenpoured into diethyl ether and washed 3x with water and 1x with brine. The organic layer was isolated, dried over MgSO4, vacuum filtered, and concentrated in vacuo to a transparent red oil. After further solvent removal via vacuum pump, the resulting oil (2.41g, 96percent yield over 2 steps) was carried on without further purification.
68%
Stage #1: With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78 - 20℃; for 2.08333 h;
Stage #2: With water In dichloromethane for 0.5 h; Cooling with ice
Boron trichloride in dichloromethane (61.2 ml_, 1 M) was added slowly todichloromethane (93 ml.) and cooled to -78 degrees Celsius. To this was added a solution of 4-methoxy-2-methylbenzonitrile (3.00 g, 20.4 mmol) andtetrabutylammonium iodide (7.17 g, 61.2 mmol) in dichloromethane (20 ml_). The reaction mixture was allowed to stir at -78 degrees Celsius for 5 minutes. The reaction mixture was then gradually warmed to room temperature and stirred for 2 hours. An ice slurry was slowly added to quench the reaction. The reaction was allowed to stir for 30 minutes and the layers were separated. The aqueous layer was extracted with dichloromethane (2x) and the combined organic extracts were passed through a phase separated cartridge and concentrated in vacuo. The crude mixture was purified by flash chromatography eluting with 0percent to 60percent ethyl acetate in pentane to give the target compound as a yellow solid (1.85 g, 68 percent). 1 H NMR deuteromethanol delta ppm 7.40 (d, 1 H), 6.80 (s, 1 H), 6.70 (d, 1 H), 2.40 (s, 3H); GCMS (CI method) ES+= 133 [M] AP+ = 133 [M].
36.4%
Stage #1: With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78 - 20℃; for 16 h;
Stage #2: With water In dichloromethane at 10℃;
Boron trichloride (1M in dichloromethane, 747 ml, 747 mmol) was added dropwise, at -78° C., to a suspension of commercially available 4-methoxy-2-methyl-benzonitrile (44 g, 298 mmol) and tetrabutylammonium iodide (121 g, 327 mmol) in dichloromethane (750 ml), under nitrogen, over 40 minutes. Once the addition was complete, the yellow solution was warmed to room temperature and stirred for 16 hours at room temperature. The reaction mixture was then quenched by dropwise addition of water maintaining the internal at temperature below 10° C. The mixture was then filtered through Arbocel.(TM)., and the layers were separated. The aqueous layers were extracted with dichloromethane (250 ml). The organic layers were combined, washed with a sodium thiosulphate solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a thick yellow oil. Trituration of the oil in dichloromethane, followed by filtration, provided a first crop of the title compound (10.85 g, 27:4percent) as a white solid. The filtrate was evaporated and purified by flash chromatography on silica gel, eluting with pentane:ethyl acetate (70:30, by volume) to provide more of the title compound as a white solid (14.44 g, 36.4percent). 1H-NMR (400 MHz, CDCl3): δ=2.46 (s, 3H), 6.68 (d, 1H), 6.72 (s, 1H), 7.45 (d, 1H); LRMS: APCl-: m/z 132 [M-H]-.
36%
Stage #1: With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78 - 20℃; for 16.6667 h;
Stage #2: With water In dichloromethane at 10℃;
Preparation 42
4-Hydroxy-2-methyl benzonitrile
Boron trichloride (1M in dichloromethane, 747 ml, 747 mmol) was added dropwise, at -78° C., to a suspension of commercially available 4-methoxy-2-methyl-benzonitrile (44 g, 298 mmol) and tetrabutylammonium iodide (121 g, 327 mmol) in dichloromethane (750 ml), under nitrogen, over 40 minutes.
Once the addition was complete, the yellow solution was warmed to room temperature and stirred for 16 hours at room temperature.
The reaction mixture was then quenched by dropwise addition of water maintaining the internal temperature below 10° C.
The mixture was filtered through Arbocel.(TM). and the layers were separated.
The aqueous layers were extracted again with dichloromethane (250 ml).
The organic layers were combined, washed with a sodium thiosulphate solution (150 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to give thick yellow oil.
Trituration of the oil in dichloromethane, followed by filtration, provided a first crop of the title compound (10.8 g, 27percent) as a white solid.
The filtrate was evaporated and purified by flash chromatography on silica gel, eluding with pentane:ethyl acetate (70:30, by volume) to provide more of the title compound as a white solid (14.4 g, 36percent).
1H-NMR (400 MHz, CDCl3): δ=2.46 (s, 3H), 6.68 (d, 1H), 6.72 (s, 1H), 7.45 (d, 1H); LRMS: APCl-: m/z 132 [M-H]-.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1538 - 1544
[2] Patent: WO2012/69948, 2012, A1, . Location in patent: Page/Page column 70-71
[3] Patent: US2006/241125, 2006, A1, . Location in patent: Page/Page column 20
[4] Patent: US2007/105909, 2007, A1, . Location in patent: Page/Page column 26
[5] Patent: US2010/234346, 2010, A1, . Location in patent: Page/Page column 16
[6] Patent: US2010/261702, 2010, A1, . Location in patent: Page/Page column 13
[7] Patent: WO2010/148650, 2010, A1, . Location in patent: Page/Page column 38-39
[8] Patent: WO2013/19621, 2013, A1, . Location in patent: Page/Page column 81
[9] Patent: WO2009/109904, 2009, A1, . Location in patent: Page/Page column 31
  • 3
  • [ 67832-11-5 ]
  • [ 14143-26-1 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 3, p. 708 - 711
  • 4
  • [ 50712-68-0 ]
  • [ 14143-26-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1968 - 1972[2] Angew. Chem., 2018, vol. 130, p. 1986 - 1990,5
  • 5
  • [ 122-46-3 ]
  • [ 14143-26-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 8, p. 2186 - 2189[2] Angew. Chem., 2014, vol. 53, # 8, p. 2218 - 2221,4
  • 6
  • [ 578-39-2 ]
  • [ 14143-26-1 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 667 - 672
  • 7
  • [ 134837-20-0 ]
  • [ 14143-26-1 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 17, p. 1921 - 1924
  • 8
  • [ 855612-74-7 ]
  • [ 14143-26-1 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 885,889
  • 9
  • [ 7677-24-9 ]
  • [ 553-97-9 ]
  • [ 15777-70-5 ]
  • [ 14143-26-1 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 43, p. 7901 - 7904
  • 10
  • [ 41438-18-0 ]
  • [ 14143-26-1 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 885,889
  • 11
  • [ 155912-29-1 ]
  • [ 14143-26-1 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 885,889
  • 12
  • [ 134837-24-4 ]
  • [ 14143-26-1 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 17, p. 1921 - 1924
  • 13
  • [ 67-56-1 ]
  • [ 14143-26-1 ]
  • [ 57556-31-7 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 2127 - 2133
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 14143-26-1 ]

Aryls

Chemical Structure| 58537-99-8

[ 58537-99-8 ]

4-Hydroxy-2,6-dimethylbenzonitrile

Similarity: 0.97

Chemical Structure| 55289-04-8

[ 55289-04-8 ]

3-Hydroxy-2-methylbenzonitrile

Similarity: 0.95

Chemical Structure| 73289-66-4

[ 73289-66-4 ]

2-Hydroxy-6-methylbenzonitrile

Similarity: 0.92

Chemical Structure| 95658-81-4

[ 95658-81-4 ]

3-Hydroxy-5-methylbenzonitrile

Similarity: 0.92

Chemical Structure| 873-62-1

[ 873-62-1 ]

3-Cyanophenol

Similarity: 0.92

Nitriles

Chemical Structure| 58537-99-8

[ 58537-99-8 ]

4-Hydroxy-2,6-dimethylbenzonitrile

Similarity: 0.97

Chemical Structure| 55289-04-8

[ 55289-04-8 ]

3-Hydroxy-2-methylbenzonitrile

Similarity: 0.95

Chemical Structure| 73289-66-4

[ 73289-66-4 ]

2-Hydroxy-6-methylbenzonitrile

Similarity: 0.92

Chemical Structure| 95658-81-4

[ 95658-81-4 ]

3-Hydroxy-5-methylbenzonitrile

Similarity: 0.92

Chemical Structure| 873-62-1

[ 873-62-1 ]

3-Cyanophenol

Similarity: 0.92