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Chemical Structure| 573-17-1
Chemical Structure| 573-17-1
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Product Details of [ 573-17-1 ]

CAS No. :573-17-1 MDL No. :MFCD00001174
Formula : C14H9Br Boiling Point : -
Linear Structure Formula :- InChI Key :RSQXKVWKJVUZDG-UHFFFAOYSA-N
M.W : 257.13 Pubchem ID :11309
Synonyms :

Calculated chemistry of [ 573-17-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 69.15
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.72
Log Po/w (XLOGP3) : 4.93
Log Po/w (WLOGP) : 4.76
Log Po/w (MLOGP) : 4.9
Log Po/w (SILICOS-IT) : 4.72
Consensus Log Po/w : 4.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.23
Solubility : 0.00151 mg/ml ; 0.00000588 mol/l
Class : Moderately soluble
Log S (Ali) : -4.67
Solubility : 0.00553 mg/ml ; 0.0000215 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.6
Solubility : 0.000064 mg/ml ; 0.000000249 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 573-17-1 ]

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 [ 573-17-1 ]

* 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 [ 573-17-1 ]
  • Downstream synthetic route of [ 573-17-1 ]

[ 573-17-1 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 573-17-1 ]
  • [ 68-12-2 ]
  • [ 4707-71-5 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 43, p. 14599 - 14614
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 44, p. 14593 - 14596[3] Angew. Chem., 2018, vol. 130, # 44, p. 14801 - 14805,5
[4] Bulletin of the Chemical Society of Japan, 1971, vol. 44, p. 2237 - 2248
  • 2
  • [ 573-17-1 ]
  • [ 100-10-7 ]
  • [ 4707-71-5 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, # 10, p. 1691 - 1693
  • 3
  • [ 85-01-8 ]
  • [ 573-17-1 ]
YieldReaction ConditionsOperation in experiment
91% With acetic acid; potassium bromide In water at 40℃; for 4.5 h; In a 50ml round bottom flask equipped of a magnetic successively added acetic acid: water = 9:1 solvent (10ml), and(514 mg, 2 mmol) and KBr (215 mg, 1.8 mmol) were added and dissolved under magnetic stirring.1.2 gZnAl-BrO3 - LDHs (1.2 mmol BrO3-) were slowly added in batches over half an hour and the reaction temperature was controlled at 40 ° C for 4 hours. TLC was followed by monitoring the reaction process with ethyl acetate-petroleum ether (v / v = 1: 15) developing solvent. After completion of the reaction, the mixture was extracted with dichloromethane (3 x 10 mL) and the combined organic phases were washed again with distilled water (3 x 10 mL). And finally dried with anhydrous sodium sulfate, filtered and chromatographed (eluent ratio: petroleum ether to ethyl acetate volume ratio of 15: 1) to obtain white crystals in 91percent yiel
Reference: [1] Organic Letters, 2003, vol. 5, # 18, p. 3317 - 3319
[2] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 2093 - 2094
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2005, vol. 180, # 2, p. 533 - 536
[4] Patent: CN107151197, 2017, A, . Location in patent: Paragraph 0018; 0019; 0021-0024; 0025-0028
[5] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 7, p. 1918 - 1921
[6] Helvetica Chimica Acta, 2003, vol. 86, # 1, p. 164 - 168
[7] Journal of Organic Chemistry, 1992, vol. 57, # 9, p. 2740 - 2741
[8] Tetrahedron Letters, 1994, vol. 35, # 40, p. 7429 - 7432
[9] Tetrahedron Letters, 1998, vol. 39, # 44, p. 8163 - 8166
[10] Justus Liebigs Annalen der Chemie, 1944, vol. 556, p. 1,7
[11] Journal of the American Chemical Society, 1936, vol. 58, p. 2101
[12] Organic Syntheses, 1958, vol. Coll. Vol. III, p. 134
[13] Zhurnal Obshchei Khimii, 1951, vol. 21, p. 1517,1523; engl. Ausg. S. 1659, 1664
[14] Journal of the Chemical Society, 1923, vol. 123, p. 3097,3099
[15] Journal of the Chemical Society, 1923, vol. 123, p. 3097,3099
[16] Synthesis, 1976, p. 621 - 623
[17] Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 1047 - 1057
[18] Journal of Organic Chemistry, 1970, vol. 35, p. 25 - 30
[19] Journal of the American Chemical Society, 1966, vol. 88, # 24, p. 5837 - 5845
[20] Journal of Organic Chemistry, 1962, vol. 27, p. 2520 - 2522
[21] Mendeleev Communications, 2014, vol. 24, # 2, p. 117 - 118
  • 4
  • [ 85-01-8 ]
  • [ 573-17-1 ]
Reference: [1] Organic Letters, 2008, vol. 10, # 19, p. 4155 - 4158
[2] Organic Letters, 2008, vol. 10, # 19, p. 4155 - 4158
  • 5
  • [ 17024-12-3 ]
  • [ 573-17-1 ]
Reference: [1] Chemical Science, 2013, vol. 4, # 12, p. 4434 - 4439
  • 6
  • [ 85-01-8 ]
  • [ 573-17-1 ]
  • [ 947-72-8 ]
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 2, p. 147 - 150
  • 7
  • [ 776-35-2 ]
  • [ 573-17-1 ]
  • [ 85-01-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2002, vol. 75, # 4, p. 769 - 771
  • 8
  • [ 17533-18-5 ]
  • [ 573-17-1 ]
  • [ 10035-10-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 167, p. 180
  • 9
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 85-01-8 ]
  • [ 573-17-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1944, vol. 556, p. 1,7
  • 10
  • [ 17533-18-5 ]
  • [ 563-63-3 ]
  • [ 64-19-7 ]
  • [ 573-17-1 ]
Reference: [1] Chemische Berichte, 1878, vol. 11, p. 1219
  • 11
  • [ 17533-18-5 ]
  • [ 7732-18-5 ]
  • [ 573-17-1 ]
  • [ 10035-10-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 167, p. 180
  • 12
  • [ 573-17-1 ]
  • [ 17024-12-3 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; for 0.25 h; Inert atmosphere
General procedure: Aryl bromide (10 mmol) was dissolved in dry THF (30 mL) and cooled to -78 °C under anargon atmosphere. n-Butyllithium (1.6 M in n-hexane; 7.5 mL; 12 mmol) was addeddropwise. After 15 minutes a solution of I2 (3.81 g; 15 mmol) in dry THF (10 mL) was addedand the reaction mixture was allowed to warm to room temperature overnight.For workup the reaction mixture was concentrated in vacuo. H2O was added to the residueand it was extracted with DCM (3x). The combined organic phases were washed withsaturated Na2S2O5 solution and H2O. After drying over MgSO4 and concentration underreduced pressure, the crude product was purified by column chromatography.
Reference: [1] Synlett, 2013, vol. 24, # 20, p. 2730 - 2734
[2] Synthesis, 1986, # 1, p. 121 - 122
[3] Journal of Organic Chemistry, 2009, vol. 74, # 12, p. 4650 - 4653
[4] Tetrahedron Letters, 1999, vol. 40, # 36, p. 6671 - 6672
[5] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1499 - 1503
[6] Journal of Organic Chemistry, 1983, vol. 48, # 26, p. 5273 - 5280
[7] Patent: EP1559706, 2005, A1, . Location in patent: Page/Page column 36-37
[8] Journal of Organic Chemistry, 2011, vol. 76, # 18, p. 7563 - 7568
  • 13
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  • [ 573-17-1 ]
  • [ 68572-87-2 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 12 h; Inert atmosphere
Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5 h; Inert atmosphere
Under nitrogen, 2.57 g (10 mmol) of 9-bromophenanthrene was dissolved in 40 ml of anhydrous THF, the temperature of the reaction was lowered to -78 ° C,After slowly adding 4 ml of 2.5 M n-BuLi dropwise, the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reactionAfter lowering to -78 deg. C, 12.47 g (12 mmol) of trimethylborate was added dropwise, and the mixture was stirred at room temperature for 12 hours. The reactionAfter completion of the reaction, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether.Water in the organic layer was removed with anhydrous MgSO 4, filtered under reduced pressure, and then the organic solvent was concentrated to obtain a compound, Hex: EA = 4:1 to obtain 1.82 g (82percent) of Intermediate-3.
81% With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 13.5 h; Inert atmosphere After tetra-hydro furan gave 500ml put the 9-bromo-phenanthrene 50g (194mmol) in a round bottom flask containing a nitrogen atmosphere the temperature was adjusted to -78 . Slowly added dropwise to 146ml of n-butyllithium (233mmol) in 30 minutes, which was then slowly added dropwise trimethyl borate 28.3g (274mmol) After 1 hour, the temperature was raised to room temperature. After stirring for about 12 hours at room temperature, and then, extraction was collected by distillation under reduced pressure and the organic layer was added dropwise to the reaction solution until the acid is a hydrochloric acid solution 2N (n). After the nucleic acid has a normal filter to dry the recrystallized result, to obtain an intermediate a-20 (35g, yield 81percent) as a white solid.
81.1%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: at 20℃; for 12 h; Inert atmosphere
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 0℃; Inert atmosphere
In a three-necked 1.0 L flask 30.0 g (116.7 mmol) of 9-bromophenanthrene are added and dissolved in 292 mL of THF under a nitrogen atmosphere. After cooling the reaction temperature to -78°C, 56.0 mL (140.0 mmol) of 2.5 M n-BuLi solution was slowly added dropwise and stirred.After the dropwise addition was completed, the mixture was stirred at -78 °C for 1 hour, 18.3 mL (163.3 mmol) of trimethylborate was slowly added dropwise.After the temperature was raised to room temperature, the mixture was stirred for 12 hours. After the temperature was lowered to 0 °C, 20 mL of 2 N HCl was added. After adding 500 mL of dichloromethane and 300 mL of H2O,The organic layer was separated and washed with water and brine. Dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The resulting concentrate was solidified and purified by using a solvent to obtain 21.0 g (yield: 81.1percent) of a white solid compound (intermediate (5)).
42%
Stage #1: With n-butyllithium In tetrahydrofuran at -76℃; for 0.166667 h; Inert atmosphere
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 1 h; Inert atmosphere
In a 500 ml round-bottom flask, 10 g of 9-bromophenanthrene (38.89 mmol) was added and dissolved in150 ml of anhydrous tetrahydrofuran (THF) before stirring.The reaction temperature was maintained at −76° C,and 25.28 ml of 2.0 M n-butyllithium (50.59 mmol) was slowly added to the reaction vessel. After about 10 minutes, 6.07 ml of trimethyl borate (54.45 mmol) was added to the reaction vessel. Once the reaction temperature increased to room temperature after about 1 hour, 7.12 ml of 12 M HCl (85.56 mmol) was added. After the reaction,the mixture was extracted using ethyl acetate (EA)and distilled water. Water remaining in the organic layer was dried with MgSO4. The mixture was concentrated byreduced pressure and re-precipitated with THF and hexane to obtain white solid. The yield was 42percent. 1H-NMR (300 MHz, Chloroform) (ppm): 8.75–8.71(t, 2H), 8.56–8.53 (d, 1H), 8.04 (s , 1H), 7.88–7.85(d, 1H), 7.61–7.52 (m, 6H), 5.79 (s, 3H).

Reference: [1] Patent: KR2017/49295, 2017, A, . Location in patent: Paragraph 0123-0121
[2] Patent: KR101515814, 2015, B1, . Location in patent: Paragraph 0424-0428
[3] Patent: KR101652325, 2016, B1, . Location in patent: Paragraph 0092-0094
[4] Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 2, p. 1748 - 1751
  • 14
  • [ 5419-55-6 ]
  • [ 573-17-1 ]
  • [ 68572-87-2 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexanes at -20 - 18℃; for 1 h;
Compound 42e.; Step a: Preparation of 9-phenanthrene boronic acid; A solution of 9-bromophenanthrene (1 g, 3.9 mmol) and triisopropylborate (1.35 ml, 1.1 g, 5.85 mmol) in absolute THF (30 ml) was cooled down to -78°C and stirred under argon. Then n-BuLi (1.6 M in hexanes, 2.9 ml, 4.68 mmol) was added dropwise to the solution over a period of 1 hour and it was stirred at -78°C for 1 hour. The solution was then warmed to -200C and 2 M HCl (20 ml) was added, then the mixture was warmed to 18 "C and stirred at that temperature for 1 hour. Diethyl ether (300 ml) was then added and it was washed with H2O (2 x 100 ml). The organic phase was dried over MgSO4, filtered and the solvent was removed under reduced pressure to give 9-phenanthrene boronic acid (770 mg, 89percent) as a white solid which was used without further purification.
70% With n-butyllithium In tetrahydrofuran at -100℃; for 2 h; Inert atmosphere In the nitrogen,Clean and dry 1000ml three-mouth bottle,Add 9-bromophenanthrene,Triisopropyl borate,THF, cool down to -100°C,Lithium butyl lithium was added dropwise, and the insulation was kept for 2 hours.Hydrochloric acid, washed,Desiccant solvent, toluene beating, 9-phenanthrene boric acid;HPLC: 99.9percent, yield: 70percent;
55%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: for 1 h;
9-bromophenanthrene (13.26 g, 38.74 mmol) was added to a three-necked flask,Added THF200mL, nitrogen protection,-78 ° C for 30 minutes,N-Butyllithium (2.5 M / 21 mL) was added and reacted for 1 hour.Triisopropyl borate (14 g) was further added,Low temperature reaction for 1 hour, gradually return to room temperature.After the treatment process, add 2M hydrochloric acid to make the solution PH value of 4-5,Quiescent liquid,The aqueous layer was extracted once more with ethyl acetate, the combined organic layers were spin-dried,6-A (6.55 g, y = 55percent).
Reference: [1] Patent: WO2006/135973, 2006, A1, . Location in patent: Page/Page column 31
[2] Patent: CN107652224, 2018, A, . Location in patent: Paragraph 0086; 0089-0091
[3] Patent: CN107382748, 2017, A, . Location in patent: Paragraph 0037; 0038; 0039; 0040
  • 15
  • [ 121-43-7 ]
  • [ 573-17-1 ]
  • [ 7732-18-5 ]
  • [ 68572-87-2 ]
YieldReaction ConditionsOperation in experiment
81.1%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 12 h; Inert atmosphere
Stage #3: With hydrogenchloride In tetrahydrofuran; dichloromethane at 0℃; Inert atmosphere
Add 30.0 g (116.7 mmol) of 9-bromophenanthrene to a three-necked 1.0 L flask and dissolve in 292 mL of THF under a nitrogen atmosphere. After cooling the reaction temperature to -78 ° C, 56.0 mL (140.0 mmol) of 2.5 M n-BuLi solution was slowly added dropwise and stirred.After the dropwise addition was completed, the mixture was stirred at -78 ° C for 1 hour, and 18.3 mL (163.3 mmol) of trimethylborate was slowly added dropwise. After the temperature was raised to room temperature, the mixture was stirred for 12 hours. After the temperature was lowered to 0 ° C, 20 mL of 2 N HCl was added.After adding 500 mL of dichloromethane and 300 mL of H2O, the organic layer was separated and washed with water and brine. Dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure.The resulting concentrate was solidified and purified by using a solvent to obtain 21.0 g (yield: 81.1percent) of a white solid compound (intermediate (5)
Reference: [1] Patent: KR101652323, 2016, B1, . Location in patent: Paragraph 0105-0107
  • 16
  • [ 688-74-4 ]
  • [ 573-17-1 ]
  • [ 68572-87-2 ]
Reference: [1] Patent: CN106749094, 2017, A, . Location in patent: Paragraph 0040; 0044
  • 17
  • [ 573-17-1 ]
  • [ 68572-87-2 ]
Reference: [1] New Journal of Chemistry, 2008, vol. 32, # 11, p. 1847 - 1849
[2] Journal of Nanoscience and Nanotechnology, 2010, vol. 10, # 8, p. 5153 - 5160
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