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[ CAS No. 4766-33-0 ] {[proInfo.proName]}

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Chemical Structure| 4766-33-0
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Product Details of [ 4766-33-0 ]

CAS No. :4766-33-0 MDL No. :MFCD07369883
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :VNPCNUAYDOLBDR-UHFFFAOYSA-N
M.W : 222.08 Pubchem ID :19044893
Synonyms :

Calculated chemistry of [ 4766-33-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.05
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 2.26
Log Po/w (WLOGP) : 3.19
Log Po/w (MLOGP) : 3.24
Log Po/w (SILICOS-IT) : 2.92
Consensus Log Po/w : 2.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.26
Solubility : 0.123 mg/ml ; 0.000553 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.801 mg/ml ; 0.00361 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.57
Solubility : 0.00594 mg/ml ; 0.0000267 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 4766-33-0 ]

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

Application In Synthesis of [ 4766-33-0 ]

* 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 [ 4766-33-0 ]
  • Downstream synthetic route of [ 4766-33-0 ]

[ 4766-33-0 ] Synthesis Path-Upstream   1~7

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  • [ 52927-23-8 ]
Reference: [1] Journal of the Chemical Society, 1937, p. 1619,1621
  • 2
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YieldReaction ConditionsOperation in experiment
97% With hydrogenchloride In 1,4-dioxane; ethanol; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetic acid 5-Amino-1-bromonaphthalene (B).
To the solution of 5-nitro-1-bromonaphthalene (A) (2.5 g, 10 mmol) in EtOH/AcOH /Dioxane/H2O (2:2:2:1) (30 mL) was added Fe (5.6 g, 100 mmol) and 2 drops of 2 N HCl.
The reaction mixture was stirred at 100° C. for 2 hrs.
After evaporation of solvent, the residue was dissolved in 100 mL DCM and washed with 5percent NaHCO3 (3*30 mL) and dried over Na2SO4.
After evaporation of solvent, the crude mixture was purified on a silica gel column, eluding with DCM/hexanes (1:1), to give compound B as a white powder (3.0 g, 97percent).
mp 65-66° C.; 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=8.8 Hz, 1H), 7.76 (d, J=8.0, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.39 (t, J=7.6 Hz, 1H), 7.28 (t, J=7.2 Hz, 1H), 6.83 (d, J=7.2 Hz, 1 H), 4.18 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 142.5, 133.0, 130.4, 128.0, 125.1, 125.0, 123.9, 121.0, 118.4, 110.9; ESI-MS (m/z) calcd. for C10H9BrN222.0 (M+H)+, found 222.1. Anal. Calcd for C10H8BrN: C, 54.08; H, 3.63; N, 6.31. Found: C, 53.81; H, 3.46; N, 6.11.
84% With iron; ammonium chloride In ethanol; water at 75℃; To a suspension of 1-bromo-5-nitronaphthalene (2 g, 7.94 mmol) in EtOH (50 mL), a solution of NH4Cl (2.2 g, 41.1 mmol) in water (20 mL) was added, followed by iron powder (1.33 g, 23.82 mmol). The resulting mixture was stirred at 75° C. (bath temperature) for 1.5 h. Celite (3 g) was added, and the mixture was allowed to cool down to rt, diluted with CH2Cl2 (100 mL), filtered through a plug of Celite, washing with CH2Cl2 (150 mL). The filtrate was washed with brine and dried over Na2SO4. Upon evaporation of the filtrate, the crude material was redissolved in CH2Cl2 (20 mL), transferred on top of a 80 g SiO2 column, and ran with 20percent to 80percent EtOAc/hexane gradient. The fractions containing the product were evaporated to viscous light brown oil that quickly crystallized. Yield of 5-bromo-1-aminonaphthalene [West, R. W. J. Chem. Soc. 1925, 127, 494] 1.48 g (84percent). 5-Bromo-1-aminonaphthalene (1.37 g, 6.17 mmol) was dissolved in trimethyl phosphate (760 μL, 6.5 mmol) in a 50 mL round-bottom flask, equipped with an air condenser and a CaCl2 drying tube, the apparatus was flushed with nitrogen, and the mixture was heated at 200° C. (bath temperature) for 1.5 h. The flask was then allowed to cool below 100° C., 1 N NaOH (20 mL) was added, the resulting suspension was sonicated briefly and stirred at rt overnight. The mixture was diluted with brine, extracted with CH2Cl2 (3×50 mL), the combined extracts were dried over Na2SO4. The product was isolated by column chromatography (100 g of SiO2, gradient 10percent to 50percent CH2Cl2/hexane) to yield 1-bromo-5-(dimethylamino)naphthalene 28a [West, R. W. J. Chem. Soc. 1925, 127, 494] as a light-orange viscous oil (1.29 g, 84percent). 1H NMR (301 MHz, CDCl3): δ 8.26 (dt, J=8.6, 1.0 Hz, 1H), 7.95 (dt, J=8.6, 0.9 Hz, 1H), 7.78 (dt, J=7.4, 1.0 Hz, 1H), 7.51 (ddd, J=8.5, 7.5, 0.7 Hz, 1H), 7.32 (ddd, J=8.4, 7.3, 0.7 Hz, 1H), 7.14 (dd, J=7.6, 1.0 Hz, 1H), 2.90 (s, 6H) ppm. 13C NMR (76 MHz, CDCl3): δ 151.3, 133.4, 130.4, 130.1, 127.3, 125.4, 124.3, 123.3, 122.0, 115.0, 45.5.
Reference: [1] New Journal of Chemistry, 2005, vol. 29, # 4, p. 579 - 586
[2] Patent: US2007/274922, 2007, A1,
[3] Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3873 - 3879
[4] Organic Letters, 2018, vol. 20, # 4, p. 1261 - 1264
[5] Patent: US2018/223102, 2018, A1, . Location in patent: Paragraph 0260-0262
[6] Organic Letters, 2017, vol. 19, # 23, p. 6380 - 6383
[7] Angewandte Chemie - International Edition, 2008, vol. 47, # 32, p. 6062 - 6064
[8] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 283[9] Gazzetta Chimica Italiana, 1886, vol. 16, p. 151
[10] Chemische Berichte, 1902, vol. 35, p. 2810
[11] Chemische Berichte, 1924, vol. 57, p. 507
[12] Journal of the Chemical Society, 1927, p. 3104
[13] Journal of the American Chemical Society, 1946, vol. 68, p. 1602,1603
[14] Chemische Berichte, 1924, vol. 57, p. 507
[15] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3356 - 3366
[16] Chemistry Letters, 2015, vol. 44, # 6, p. 743 - 745
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  • [ 86-57-7 ]
  • [ 4766-33-0 ]
Reference: [1] New Journal of Chemistry, 2005, vol. 29, # 4, p. 579 - 586
[2] Journal of the Chemical Society, 1927, p. 3104
[3] Journal of the Chemical Society, 1937, p. 1619,1621
[4] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 283[5] Gazzetta Chimica Italiana, 1886, vol. 16, p. 151
[6] Chemistry Letters, 2015, vol. 44, # 6, p. 743 - 745
[7] Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3873 - 3879
  • 4
  • [ 16726-67-3 ]
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Reference: [1] Journal of the American Chemical Society, 1976, vol. 98, p. 1701 - 1711
[2] Magnetic Resonance in Chemistry, 1996, vol. 34, # 4, p. 301 - 310
[3] Tetrahedron Letters, 2007, vol. 48, # 31, p. 5539 - 5541
  • 5
  • [ 86-55-5 ]
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Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 31, p. 5539 - 5541
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Reference: [1] Journal of the Chemical Society, 1937, p. 1619,1621
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  • [ 77332-64-0 ]
Reference: [1] Journal of Organic Chemistry, 1957, vol. 22, p. 161,165
[2] Monatshefte fuer Chemie, 1950, vol. 81, p. 850,854
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