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[ CAS No. 452-77-7 ] {[proInfo.proName]}

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Chemical Structure| 452-77-7
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Product Details of [ 452-77-7 ]

CAS No. :452-77-7 MDL No. :MFCD00007762
Formula : C7H8FN Boiling Point : -
Linear Structure Formula :- InChI Key :MGRHBBRSAFPBIN-UHFFFAOYSA-N
M.W : 125.14 Pubchem ID :9957
Synonyms :

Calculated chemistry of [ 452-77-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.77
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 0.92
Log Po/w (WLOGP) : 2.14
Log Po/w (MLOGP) : 2.24
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.69
Solubility : 2.56 mg/ml ; 0.0205 mol/l
Class : Very soluble
Log S (Ali) : -1.05
Solubility : 11.1 mg/ml ; 0.0887 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.273 mg/ml ; 0.00218 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 452-77-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H300-H312+H332-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 452-77-7 ]

* 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 [ 452-77-7 ]
  • Downstream synthetic route of [ 452-77-7 ]

[ 452-77-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 452-77-7 ]
  • [ 452-78-8 ]
YieldReaction ConditionsOperation in experiment
44.8% at 0 - 80℃; for 6 h; Preparation of 3-fluoro-4-methylphenol: 3-Fluoro-4-methylaniline (5g, 39.95 lmmol) was dissolved in 10percent sulfuric acid aqueous solution (100ml). Thereafter, the temperature was lowered to O°C. thereto sodium nitrate (5.5g, 79.902mmol) was added, and the reaction mixture was stirred at same temperature for 30 minutes. Then the reaction mixture was stirred at 500C for 30 minutes, and the last time, stirred at 8O°C for 5 hours. Ice water was added to quench the reaction, and aqueous layer was extracted with ethyl acetate. Combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (n-hexane:ethyl acetate = 8:1) to give 2.26g (yield: 44.8percent, colorless oil) of the target compound.1H NMR(400MHz, CDCl3): 6.98(t, J=8.6Hz, IH), 6.52(m, 2H), 5.82(br, IH),2.12(s, 3H).
Reference: [1] Patent: WO2007/8037, 2007, A1, . Location in patent: Page/Page column 34-35
[2] Journal of the Chemical Society, 1949, p. Spl. 113
[3] Journal of the American Chemical Society, 1950, vol. 72, p. 1806
  • 2
  • [ 372-19-0 ]
  • [ 593-53-3 ]
  • [ 443-86-7 ]
  • [ 367-29-3 ]
  • [ 452-77-7 ]
Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, p. 1556 - 1561
  • 3
  • [ 452-77-7 ]
  • [ 405-06-1 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 1806
  • 4
  • [ 106-49-0 ]
  • [ 452-80-2 ]
  • [ 452-77-7 ]
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 4, p. 661 - 667
  • 5
  • [ 372-19-0 ]
  • [ 593-53-3 ]
  • [ 443-86-7 ]
  • [ 367-29-3 ]
  • [ 452-77-7 ]
Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, p. 1556 - 1561
  • 6
  • [ 1427-07-2 ]
  • [ 452-77-7 ]
YieldReaction ConditionsOperation in experiment
74% With indium (III) iodide; 1,1,3,3-Tetramethyldisiloxane In toluene at 60℃; for 6 h; Inert atmosphere; Sealed tube General procedure: To a screw top vial (5 mL) under N2 containing freshly distilled toluene (0.6 mL) were successively added an aromatic nitro compound (0.60 mmol), InI3 (14.9 mg, 0.030 mmol), and TMDS (318 μL, 1.80 mmol). After the vial was sealed with a cap that contained a PTFE septum, the mixture was stirred at 60 °C (bath temperature), and monitored via TLC analysis. Sat. aq NaHCO3 solution (5 mL) was added to the resultant mixture, which was then extracted with EtOAc (3 × 6 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane–EtOAc, 9:1 to 4:1) to afford the corresponding aniline derivative.
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 42, p. 7783 - 7787
[2] Synthesis (Germany), 2015, vol. 47, # 20, p. 3179 - 3185
[3] Journal of the American Chemical Society, 1950, vol. 72, p. 1806
[4] Monatshefte fuer Chemie, 1959, vol. 90, p. 683,687
[5] Journal of the Chemical Society, 1949, p. Spl. 113
[6] Journal of the American Chemical Society, 1944, vol. 66, p. 1631
[7] Tetrahedron Letters, 2010, vol. 51, # 32, p. 4250 - 4252
  • 7
  • [ 88-72-2 ]
  • [ 452-77-7 ]
Reference: [1] Patent: US6020379, 2000, A,
  • 8
  • [ 452-75-5 ]
  • [ 452-77-7 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 6, p. 2131 - 2141
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 24, p. 4071 - 4074
  • 9
  • [ 372-19-0 ]
  • [ 593-53-3 ]
  • [ 443-86-7 ]
  • [ 367-29-3 ]
  • [ 452-77-7 ]
Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, p. 1556 - 1561
  • 10
  • [ 106-49-0 ]
  • [ 452-80-2 ]
  • [ 452-77-7 ]
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 4, p. 661 - 667
  • 11
  • [ 452-77-7 ]
  • [ 446-31-1 ]
Reference: [1] Journal of the American Chemical Society, 1944, vol. 66, p. 1631
  • 12
  • [ 452-77-7 ]
  • [ 394-42-3 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 1806
  • 13
  • [ 452-77-7 ]
  • [ 202865-78-9 ]
YieldReaction ConditionsOperation in experiment
100% With bromine; potassium carbonate In dichloromethane at -15℃; for 1 h; Example 28; Preparation of Intermediate Compound 28G; 28G; Step A - Synthesis of Compound 9B; 28A 28B; A mixture of compound 28A (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 0C in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15 0C for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to provide compound 28B (11.0 g, quant.), which was used without further purification.
100% With bromine; potassium carbonate In dichloromethane at -15℃; for 1 h; Example 9; Preparation of Intermediate Compound 9G; 9G; Step A - Synthesis of Compound 9B; A mixture of compound 9A (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 0C in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15 0C for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to provide compound 9B (11.0 g, quant.), which was used without further purification.
100% With bromine; potassium carbonate In dichloromethane at -15℃; for 1 h; Example 28; Preparation of Intermediate Compound 28G <n="200"/>; 28G; Step A - Synthesis of Compound 28B; 28A 28B; A mixture of compound 28 A (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 0C in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15 0C for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to provide compound 28B (11.0 g, quant.), which was used without further purification.
100% With bromine In dichloromethane at -15℃; for 1 h; Cooling with salt-ice A mixture of compound SA (6,00 g, 47.9 mrnol) and anhydrous potassium carbonate (6.70 g, 48.5 mmoi) in anhydrous dichloromethane (130 mL) was cooled to -15 0C in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15 0C for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to provide compound SB (1 1.0 g. quant. ). which was used without further purification.
100% With bromine; potassium carbonate In dichloromethane at -15℃; for 1 h; Example 9; Preparation of Intermediate Compound AA7; Step A - Synthesis of Compound AA2; A mixture of compound AAl (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 0C in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15 0C for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to provide compound AA2 (11.0 g, quant.), which was used without further purification.
100% With bromine; potassium carbonate In dichloromethane at -15℃; for 1 h; Example 19; Preparation of Intermediate Compound AA7; Step A - Synthesis of Compound AA2; A mixture of compound AAl (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 0C in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15 0C for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to provide compound AA2 (11.0 g, quant.), which was used without further purification.
100% With bromine; potassium carbonate In dichloromethane at -15℃; A mixture of compound AA1 (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15° C. in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15° C. for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2.x.100 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to provide compound AA2 (11.0 g, quant.), which was used without further purification.
33% With bromine; potassium carbonate In dichloromethane at -15℃; for 1 h; To a suspension of 3-fluoro-4-methylaniline (6.0 g, 48mmol) and K2C03 (6.6 g, 48 mmol) in DCM (80 mL) at -15 °C was added Br2 (2.4 mL, 48mmol) in DCM (20 mL) slowly. The reaction mixture was stirred at -15 °C for 1 h. Themixture was then quenched with ice water (30 mL), diluted with water (80 mL), andextracted with DCM (3 x 50 mL), dried and concentrated. The residue was purified via silica gel chromatography (0 - 10 percent EtOAc in petroleum ether) to give the title compound (3.2 g, 33percent) as a white solid. MS (ES+) C7H7BrFN requires: 203, found: 204 [M+Hf’

Reference: [1] Patent: WO2009/32123, 2009, A2, . Location in patent: Page/Page column 158
[2] Patent: WO2009/32125, 2009, A1, . Location in patent: Page/Page column 98
[3] Patent: WO2009/32124, 2009, A1, . Location in patent: Page/Page column 198-199
[4] Patent: WO2009/152200, 2009, A1, . Location in patent: Page/Page column 65
[5] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 3, p. 244 - 248
[6] Patent: WO2008/82488, 2008, A1, . Location in patent: Page/Page column 153
[7] Patent: WO2008/82484, 2008, A1, . Location in patent: Page/Page column 194-195
[8] Patent: US2010/322901, 2010, A1, . Location in patent: Page/Page column 64
[9] Patent: WO2018/81276, 2018, A1, . Location in patent: Page/Page column 159
[10] Journal of the American Chemical Society, 2016, vol. 138, # 40, p. 13147 - 13150
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