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Chemical Structure| 50672-84-9
Chemical Structure| 50672-84-9
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Product Details of [ 50672-84-9 ]

CAS No. :50672-84-9 MDL No. :MFCD11101026
Formula : C11H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :SESASPRCAIMYLA-UHFFFAOYSA-N
M.W : 235.08 Pubchem ID :4640413
Synonyms :

Calculated chemistry of [ 50672-84-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.04
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 3.33
Log Po/w (WLOGP) : 3.41
Log Po/w (MLOGP) : 3.17
Log Po/w (SILICOS-IT) : 3.79
Consensus Log Po/w : 3.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.9
Solubility : 0.0297 mg/ml ; 0.000126 mol/l
Class : Soluble
Log S (Ali) : -3.37
Solubility : 0.101 mg/ml ; 0.000431 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.88
Solubility : 0.00309 mg/ml ; 0.0000132 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 50672-84-9 ]

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 [ 50672-84-9 ]

* 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 [ 50672-84-9 ]
  • Downstream synthetic route of [ 50672-84-9 ]

[ 50672-84-9 ] Synthesis Path-Upstream   1~11

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Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 5, p. 1986 - 1991
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YieldReaction ConditionsOperation in experiment
80.4% With 1,6-Hexanediamine; acetic acid In water at 100℃; for 3 h; A 3 L three-necked flask was charged with 318 g of 4-bromo-1-bromomethylnaphthalene (II)371.5 g of hexamethylenediamine,795g glacial acetic acid,795g water,100 ° C reflux reaction 3h,Point plate, the reaction is completed,Rapid dropwise addition of 636 g concentrated hydrochloric acid,Drop back 0.5h.Cooling to room temperature,Add 4L of water,Stir for 3 h.filter,Filter cake and then 2L water beating 2h,Filter,Filter cake washed twice with water,Drained,40 ° C drying.Adding 318 g of ethanol to recrystallize,Dried to give 200.4 g of 4-bromo-1-naphthaldehyde (III)Yield 80.4percent.Wherein the molar ratio of 4-bromo-1-bromomethylnaphthalene (II) to hexamethylenetetramine is 1: 2.5,
Reference: [1] European Journal of Organic Chemistry, 2006, # 10, p. 2329 - 2335
[2] Patent: CN106366018, 2017, A, . Location in patent: Paragraph 0040; 0041; 0042; 0043
[3] Inorganic Chemistry, 2016, vol. 55, # 5, p. 1986 - 1991
[4] Chemische Berichte, 1922, vol. 55, p. 1854
[5] Organic Letters, 2008, vol. 10, # 14, p. 3105 - 3108
[6] Patent: WO2010/79077, 2010, A1, . Location in patent: Page/Page column 34
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YieldReaction ConditionsOperation in experiment
62%
Stage #1: With n-butyllithium In diethyl ether; hexane at 0℃; for 0.333333 h;
Stage #2: at 0 - 20℃; for 1 h;
To a 150 ml flask was added 1,4-dibromonaphthalene (2.0 g, 7.0 mmol) and anhydrous ether (50 ml). After cooling to 0 °C n-BuLi (3.1 ml of 2.5 M in hexanes, 7.7 mmol) was added dropwise and stirred for 20 minutes after which anhydrous DMF (1.62 ml, 21 mmol) was added. The reaction was then warmed to ambient temperature and after 1 h the reaction was quenched with water (10 ml), stirred for 10 minutes, and extracted with ether (3x). The ether layer was dried over anhydrous NA2S04, passed through a silica plug, and concentrated to afford 1.02 g (62percent) of product as a pure off- white solid : LH NMR (300 MHz, DMSO-D6) : 8 7.80-7. 85 (2H, m), 8.10 (1H, d, J = 7.7 Hz), 8.20 (1H, d, J = 7.7 Hz), 8. 32 (1H, m). 9.24 (1H, m), 10.42 (1H, s). Anal. for CIIH7BRO : Calc'd: C: 56.20 H: 3.00 Found: C: 56.13 H: 2.98
62%
Stage #1: With n-butyllithium In diethyl ether; hexane at 0℃; for 0.333333 h;
Stage #2: at 20℃; for 1 h;
Step 1: 4-Bromo-1 -naphthaldehyde (P20a)To a solution of 1,4-dibromonaphthalene (2.0 g, 7.0 mmol) in dry Et20 (50 mL) was added n5 BuLi (2.5M in hexanes, 3.1 mL, 7.7 mmol) at 0°C and the solution was stirred for 20 mm. ThenDMF (1.62 mL, 21 mmol) was added and the solution was warmed to rt and stirred at this temperature for 1 h, quenched with water and extracted with Et20 (3x). The combined organic layers were washed with brine, dried over Na2504, filtered, concentrated and purified by CC (PE/EA = 50/1) to give compound P20a (1.02 g, 62percent) as an off- white solid.
Reference: [1] RSC Advances, 2014, vol. 4, # 63, p. 33474 - 33477
[2] Patent: WO2004/103941, 2004, A2, . Location in patent: Page 16
[3] Patent: WO2013/178362, 2013, A1, . Location in patent: Page/Page column 107
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13094 - 13098[5] Angew. Chem., 2017, vol. 56, p. 13274 - 13278,5
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 4, p. 902 - 906
[7] Patent: EP2159217, 2010, A1, . Location in patent: Page/Page column 58
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YieldReaction ConditionsOperation in experiment
85% With silica gel; pyridinium chlorochromate In dichloromethane at 20 - 25℃; for 2 h; Step 2.
4-bromonaphthalene-1-carbaldehyde
Into a 250-mL round-bottom flask, was placed dichloromethane (150 mL), (4-bromonaphthalen-1-yl)methanol (6.3 g, 26.57 mmol, 1.00 equiv), PCC (11.4 g, 183.72 mmol, 2.00 equiv) and 20 g Silicon dioxide.
The resulting solution was stirred for 2 h at room temperature.
The resulting mixture was concentrated under vacuum.
The residue was applied onto a silica gel column and washed with ethyl acetate/petroleum ether (1/10-1/5).
This resulted in 5.3 g (85percent) of 4-bromonaphthalene-1-carbaldehyde as a white solid.
Reference: [1] Patent: US2015/126523, 2015, A1, . Location in patent: Paragraph 1749; 1750
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YieldReaction ConditionsOperation in experiment
15% at 80℃; for 4 h; 1-Bromo-4-methylnaphthalene (1.06 g, 4.79 mmol) was dissolved in a 50percent acetic acid aqueous solution (100 ml). Diammonium cerium nitrate (7.61 g, 13.9 mmol) was added, and the mixture was stirred at 80°C for four hours. The reaction solution was cooled to room temperature and then water (300 mL) was added, followed by extraction with ethyl acetate (300 mL). The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 10/1) to give the target compound (173 mg, yield: 15percent) as a light yellow solid. 1H-NMR (CDCl3, 400MHz):δ ppm: 7.69-7.78 (2H, m), 7.82 (1H, d, J=7.8Hz), 7.99 (1H,d,J=7.8Hz),8.38(1H,d,J=8.4Hz),9.29(1H,d,J=8.4Hz),10.38(1H,s). MS (EI) m/z: 233.9679 (M+)
Reference: [1] Patent: EP1914229, 2008, A1, . Location in patent: Page/Page column 88
[2] European Journal of Organic Chemistry, 2006, # 10, p. 2329 - 2335
[3] Inorganic Chemistry, 2016, vol. 55, # 5, p. 1986 - 1991
[4] Patent: CN106366018, 2017, A,
[5] Patent: WO2010/79077, 2010, A1,
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YieldReaction ConditionsOperation in experiment
56% With n-butyllithium In tetrahydrofuran; <i>N</i>-methyl-acetamide; water Example 39
Preparation of 5,6-dichloro-2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]naphth-1-yl]benzimidazole
To a solution of 1,4-dibromonaphthalene (1.00 g, 3.50 mmol) in tetrahydrofuran (15 mL) were added n-butyllithium (1.6 mol/L; 3.1 mL) and dimethylformamide (0.54 mL, 7.0 mmol) sequentially at =78° C. under nitrogen atmosphere, and the mixture was stirred for 15 min.
Water was added, and the mixture was extracted with ethyl acetate.
The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate.
The solvent was removed under reduced pressure, and the residue was purified by column chromatography (8:1 hexane/ethyl acetate) to afford 4-bromo-1-naphthalenecarboxaldehyde (458 mg, 56percent).
1H NMR (400 MHz, CDCl3) δ (ppm) 7.6-7.8 (m, 2H), 7.78 (d, J=7.8 Hz, 1H), 7.94 (d, J=7.8 Hz, 1H), 8.34 (dd, J=8.2, 1.6 Hz, 1H), 9.25 (dd, J=8.2,1.6 Hz, 1H), 10.3 (s, 1H)
Reference: [1] Patent: US2002/120144, 2002, A1,
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Reference: [1] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 89; 90
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Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1854
[2] Patent: CN106366018, 2017, A,
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Reference: [1] Patent: US2015/126523, 2015, A1,
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Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1854
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Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 8, p. 2628 - 2636
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