Home Cart 0 Sign in  

[ CAS No. 63082-45-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 63082-45-1
Chemical Structure| 63082-45-1
Structure of 63082-45-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 63082-45-1 ]

Related Doc. of [ 63082-45-1 ]

Alternatived Products of [ 63082-45-1 ]

Product Details of [ 63082-45-1 ]

CAS No. :63082-45-1 MDL No. :MFCD02261764
Formula : C8H7FO Boiling Point : -
Linear Structure Formula :- InChI Key :ADCFIKGEGWFWEA-UHFFFAOYSA-N
M.W : 138.14 Pubchem ID :2783217
Synonyms :

Calculated chemistry of [ 63082-45-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.75
TPSA : 17.07 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) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 2.37
Log Po/w (MLOGP) : 2.21
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.795 mg/ml ; 0.00575 mol/l
Class : Soluble
Log S (Ali) : -1.83
Solubility : 2.05 mg/ml ; 0.0148 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.98
Solubility : 0.144 mg/ml ; 0.00104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.06

Safety of [ 63082-45-1 ]

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 [ 63082-45-1 ]

* 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 [ 63082-45-1 ]
  • Downstream synthetic route of [ 63082-45-1 ]

[ 63082-45-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 452-63-1 ]
  • [ 68-12-2 ]
  • [ 63082-45-1 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667 h;
Stage #2: for 1 h;
Intermediate 2:; 4-Fluoro-2-methvl-benzaldehvde; 2-Bromo-5-fluorotoluene (15.0 g, 79.3 mmol) was dissolved in anhydrous THF andcooled to -78°C in an acetone/dry ice bath. N-butyl-lithium (48.0 mL, 119 mmol) was addeddropwise down the side of the reaction flask and the resulting solution was stirred for 10 min. 64.0 ml of anhydrous DMF (793 mmol) was then added in the same fashion. After 1 hour, the reaction was quenched with cold aqueous NH4CI and diluted with 500 mL Et2O and washed with water (3x 300 mL)., The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude material was then equipped with a distillation apparatus and the oil bath was heated to 110 °C. Product containing fractions were collected to give a colorless oil, (10.0 g , 72.4 mmol, 92percent yield); LRMS m/z (APCI+) 139 [M+ H]; 400 MHz 1HNMR (CDCI3) 8 10.91 (s, 1H); 7.81 (dd, J=6.2, 2.5 Hz, 1H); 7.03 (ddd, J=8.2, 8.2, 2.5 Hz, 1H); 6.95 (ddd, J=9.5, 2.5, 0.0 Hz, 1H); 2.67 (s, 3H).
71% With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Example 38

3- {2-Methyl-4- [3-methyl-5- (2-pyridin-3-yl-4-trifluoromethyl-phenoxy)-phenoxy]- phenyl}-propionic acid Step A 4-Fluoro-2-methyl-benzaldehyde A-78 °C solution of 2-bromo-5-fluorotoluene (12.0 g, 63.5 mmol) in dry THF (60 mL) is treated with a 1.6 M hexanes solution Of 77-butyl lithium (59.5 mL, 95.3 mmol) and then stirred for 15 minutes at-78 °C under N2. The mixture is then treated with DMF (27.8 g, 0.381 mol) and warmed to rt. The reaction is acidified with 1 N HCI, diluted with Et20 and extracted with water. The organic layer is dried (Na2SO4), and the solvent removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 5/1 to 3/1 to hexanes/ethyl acetate to afford 6.24 g (71percent) of the title compound. Rf= 0.49 (2/1 hexanes/EtOAc).'H NMR (400 MHz, CDCl3).
68.4%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78 - -75℃; for 0.833333 h;
Stage #2: at -78 - 15℃; for 2.43333 h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexanes at 15 - 20℃; for 0.0833333 h;
Example 1; This example illustrates a process for preparing 4-fluoro-2-methylbenzaldehyde (Fig. III, Scheme I); 2-Bromo-5-fluorotoluene (37.5 mL, 56.1 g, 297 mmol) was dissolved in 500 mL of dry THF and the solution was cooled to -78° C. Butyllithium in hexanes (2.5 M) (119 mL, 297 mmol, 1.0 equiv) was added at -75 to -78° C. over 35 minutes, and the resulting mixture was stirred at -78° C. for 20 minutes. Dry N,N-dimethylformamide (27.6 mL, 26.0 g, 356 mmol, 1.2 equiv) was added over 26 minutes at -75 to -78° C. The resulting solution was stirred at -78° C. for 60 minutes then allowed to warm to 15° C. over 2 hours. Ammonium chloride (100 g of 15.9percent aqueous solution) was added over 5 minutes at 15-20° C. The solution was concentrated by fractional distillation (597 mL collected at 50-61° C.). The distillation pot layers were separated. The aqueous layer was extracted three times with 25 m]L of methyl tert-butyl ether (i.e., MTBE). The organic layers were combined, washed with 50 mL of brine, dried (MgSO4), filtered, and fractionally distilled (b.p. 54-62° C.) to yield 59.3 g of yellow oil. The oil was fractionally distilled (b.p. 60-62° C. at 1.6-2.0 mmHg of pressure) to afford 28.041 g (68.4percent) of a colorless oil.
66%
Stage #1: With magnesium In tetrahydrofuran at 10 - 35℃; for 0.5 h;
Stage #2: at 0 - 35℃; for 1 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran
Reference Example 56
4-fluoro-2-methylbenzaldehyde
To a mixture of magnesium (3.36 g) and tetrahydrofuran (10 mL) was slowly added dropwise a solution of 1-bromo-4-fluoro-2-methylbenzene (24.8 g) in tetrahydrofuran (200 mL).
After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 30 min.
To the obtained solution was added a solution (10 mL) of N,N-dimethylformamide (15.0 mL) in tetrahydrofuran at 0°C.
The reaction mixture was stirred at room temperature for 1 hr. 1N Hydrochloric acid and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate.
The extract was washed with 1N hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
The residue was distilled under reduced pressure (66-68°C/6 mmHg) to give the title compound as a colorless oil (yield 12.1 g, yield 66percent).
1H-NMR (CDCl3) δ: 2.68 (3H, s), 6.93-7.06 (2H, m), 7.79-7.84 (1H, m), 10.18 (1H, s).

Reference: [1] Patent: WO2004/110996, 2004, A1, . Location in patent: Page/Page column 17-18
[2] Patent: WO2005/37763, 2005, A1, . Location in patent: Page/Page column 82
[3] Patent: US2006/14959, 2006, A1, . Location in patent: Page/Page column 10
[4] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1157 - 1166
[5] Patent: EP1787991, 2007, A1, . Location in patent: Page/Page column 45
  • 2
  • [ 202865-83-6 ]
  • [ 68-12-2 ]
  • [ 63082-45-1 ]
YieldReaction ConditionsOperation in experiment
41.09%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78 - -75℃; for 0.833333 h;
Stage #2: at -78 - 18℃;
Intermediate 157: 4-Fluoro-2-methyl-benzaldehvde; A solution of 10 g of 5-Bromo-3-fluorotoluene (0.05 mole) in 500 mL of THF was cooled to -780C. Then, 32 mL of a solution of n-Butyl lithium in hexanes (2.5 M, 0.08 mole) were added to the mixture keeping the internal temperature between -75°C and -78°C. The resulting mixture was stirred at -780C for 50 min. 43 mL of Dry DMF (0.53 mole) were added over 1 h to the mixture. The mixture was allowed to warm to RT (about 180C) and stirred overnight. The reaction was quenched with 20 mL of a saturated solution of NH4CI. <n="172"/>The mixture was washed with water (5x100 mL) and the organic layer was washed with a 50 mL of a saturated aqueous solution of NaHCO3, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by a column chromatography on silica gel (PE/AcOEt=50/1 ) to give the title compound as light yellow liquid (3.0Og, 41.09percent).
Reference: [1] Patent: WO2008/148853, 2008, A1, . Location in patent: Page/Page column 169-170
  • 3
  • [ 95-52-3 ]
  • [ 201230-82-2 ]
  • [ 63082-45-1 ]
  • [ 146137-80-6 ]
Reference: [1] Patent: EP1544189, 2005, A1, . Location in patent: Page/Page column 6
  • 4
  • [ 80141-91-9 ]
  • [ 63082-45-1 ]
Reference: [1] ChemSusChem, 2017, vol. 10, # 17, p. 3497 - 3505
  • 5
  • [ 452-71-1 ]
  • [ 63082-45-1 ]
Reference: [1] Australian Journal of Chemistry, 1977, vol. 30, p. 543 - 551
  • 6
  • [ 95-52-3 ]
  • [ 201230-82-2 ]
  • [ 63082-45-1 ]
  • [ 146137-80-6 ]
Reference: [1] Patent: EP1544189, 2005, A1, . Location in patent: Page/Page column 6
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 63082-45-1 ]

Fluorinated Building Blocks

Chemical Structure| 147624-13-3

[ 147624-13-3 ]

3-Fluoro-2-methylbenzaldehyde

Similarity: 0.94

Chemical Structure| 459-57-4

[ 459-57-4 ]

4-Fluorobenzaldehyde

Similarity: 0.94

Chemical Structure| 1378525-21-3

[ 1378525-21-3 ]

3,6-Difluoro-2-methylbenzaldehyde

Similarity: 0.92

Chemical Structure| 189628-39-5

[ 189628-39-5 ]

3-Fluoro-5-methylbenzaldehyde

Similarity: 0.91

Chemical Structure| 456-48-4

[ 456-48-4 ]

3-Fluorobenzaldehyde

Similarity: 0.91

Aryls

Chemical Structure| 147624-13-3

[ 147624-13-3 ]

3-Fluoro-2-methylbenzaldehyde

Similarity: 0.94

Chemical Structure| 459-57-4

[ 459-57-4 ]

4-Fluorobenzaldehyde

Similarity: 0.94

Chemical Structure| 1378525-21-3

[ 1378525-21-3 ]

3,6-Difluoro-2-methylbenzaldehyde

Similarity: 0.92

Chemical Structure| 189628-39-5

[ 189628-39-5 ]

3-Fluoro-5-methylbenzaldehyde

Similarity: 0.91

Chemical Structure| 456-48-4

[ 456-48-4 ]

3-Fluorobenzaldehyde

Similarity: 0.91

Aldehydes

Chemical Structure| 147624-13-3

[ 147624-13-3 ]

3-Fluoro-2-methylbenzaldehyde

Similarity: 0.94

Chemical Structure| 459-57-4

[ 459-57-4 ]

4-Fluorobenzaldehyde

Similarity: 0.94

Chemical Structure| 1378525-21-3

[ 1378525-21-3 ]

3,6-Difluoro-2-methylbenzaldehyde

Similarity: 0.92

Chemical Structure| 189628-39-5

[ 189628-39-5 ]

3-Fluoro-5-methylbenzaldehyde

Similarity: 0.91

Chemical Structure| 456-48-4

[ 456-48-4 ]

3-Fluorobenzaldehyde

Similarity: 0.91